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Hello friends and welcome back Life Reimagined, a weekly elixir designed to make you feel good and live better.

If you’re new here or missed the last newsletter, I’ve been releasing parts of a new essay, Letting Go of Ambition, for the last couple of weeks. This week, I’m excited to share the final part of the essay, which you can find below.

If you want to read the full essay from soup to nuts, you can do so here:

📍Letting Go of Ambition

While it’s not perfect, I think this essay is the closest I’ve come to explaining how I’ve landed at much of my current perspective in life. It details a hard-earned lesson that led to the most enjoyable period of my life so far.

Letting Go of Ambition #3

Six months after the Bali trip, I woke up in an Airbnb in San Diego. My friends were still sleeping off a late night of drinking. I downed a banana and two cups of coffee before scrambling out the door with a wetsuit, surfboard, and container filled with my mom’s ashes.

It was my 30th birthday and the sixth anniversary of my mom’s death. For the last two years, I had envisioned this day as a special moment where I would be surrounded by loved ones and holding a copy of my first book as I entered my third decade of life. 

But there was no book to hold, and I was forced to confront the gap between my expectations and reality on the bleary-eyed drive to a new surf break.

I thought back to what happened after my depression loosened its grip on the coffee plantation in Bali. I had returned home feeling like myself again and with a renewed vigor to write the book from a more informed and grounded place.

I started by re-reading my original manuscript, concluding that the story I had tried to tell was too big and would take years to make it good. I decided to discard most of that draft and write a smaller chunk of the story in a more descriptive, emotionally resonant way.

To improve my memoir-writing skills, I devoured niche memoirs and took notes on the type of writing I liked. As I put those lessons into practice, I asked other writers for feedback. Not only did these people help me improve my work, but they made writing a more fun and less isolating pursuit than it had previously been.

I also started writing a prescriptive self-help book. That gave me another book to pour my energy into when the memoir became difficult. And because the writing style was similar to how I had blogged for years, the words came more easily.

All of this effort gave me a sense that I was moving somewhere, that within a short period, I would certainly be able to finish one book if not two. That sense of progress was motivating and filled me with the confidence I had lost after the manuscript review with Linda.

Reflecting on the “progress” from the last six months on the drive to the surf, I realized that all I had to show for my efforts was a discarded manuscript and fragments of new book ideas. I had done many things, but my dispersed efforts left me no real pathway to finishing anything.

And now that I had arrived at my 30th birthday, my deadline for being a real writer with a published book, with no book in hand, it was hard to deny the reality of the situation. I wasn’t on the cusp of finishing a book. I was a flailing writer who talked about writing a book and who had no clear path to actually finishing one. In fact, I felt less certain about what I was doing than when I started two years earlier.

When I arrived at the surf break, I got out of the car with a heavy feeling in my face and chest. As I put my wetsuit on in the cool December air, my head throbbed from the previous night’s activities and the weight of the realization about where I was in my quest to finish the book.

I grabbed my board and mom’s ashes and made my way down the beach. As my bare feet hit the cool Pacific Ocean, I closed my eyes and imagined my mom’s spirit joining me on the surf that I hoped would cleanse me of the disaster that the book had become. I sprinkled her ashes into the ocean, set the empty container on the beach, and began paddling out. I may not be an author, but at least I had my mom with me in the Pacific.

On my way to the lineup of this punchy beach break, wall after wall of whitewater halted my efforts. I paddled for 10 minutes without making much progress and began to wonder if I was going to catch a wave today. I took a breath and looked to my right. Two other surfers were cruising out without much effort. Ah, there’s a rip. I paddled twenty yards to my right, found my way into the rip current, and arrived at the lineup without taking any more waves on the head.

As a surfer, you learn to look out for rip currents, which are powerful bands of water that pull you out to sea. If you’re caught in a rip current that you don’t want to be in, your instinct is to try to paddle against it. But resisting the rip is unwise. Since the sea is stronger than you, fighting it only burns your limited energy and increases your chances of drowning.

Instead of fighting the rip, it’s better to let it take you until it ends or to swim parallel to the shoreline until you’re out of it. Then you can go about business as usual.

While the rip zipped me to the lineup on my 30th birthday surf, I realized that for many reasons, writing the book had become like paddling against a rip current. As I paddled harder, I thought I was inching closer to my dream of being a published author. But I was wrong. 

I was stuck in a rip, and the more I fought the insurmountable force, the more exhausted I became. My depression before Bali was a warning sign. And the last six months of effort were my last bits of energy. I was exhausted and had lost sense of what I was doing.

Writing the book was not the dream I thought it would be. As the rip of becoming an author tired me out, the book became a constant source of anxiety and insecurity. Whatever confidence I had in myself as a writer had dissolved into a not-so-subtle self-doubt. 

Continuing along the same path was only to lead to peril, not the outcome I had hoped for. It took me getting to my deadline without a book in hand to wake up to what was happening.

By this point, I knew what I had to do. I had to let the book go and surrender to the rip. That way, I could make it back to shore without drowning. 

But I was scared to give up on the book. I had quit my job, poured two years into writing, and told all of my friends that I would be an author. My ego and identity were wrapped up in an ambition that I had failed to fulfill. 

What did it say about me if I gave up?

I wasn’t sure, but it was the only path forward. I had exhausted myself into surrender.

Rethinking Ambition

A few weeks after my birthday, I stopped working on any of the book ideas and stopped telling people I was writing a book. Giving up on the book was not so much a decision as it was a slow acceptance that I no longer had the will or strength to fight. Perhaps I would return to the project someday, but for now, I needed to take an indefinite break and move on with my life.

For the next few months, I deliberately avoided setting goals or expectations for myself. I was afraid of what would happen without my core ambition, but wanted to live life as it came and see what emerged. I wasn’t ready to attach myself to a new professional pursuit.

What emerged first was an intensifying love story with surfing. Each session left me feeling healthy, content, and liberated from the pressure I had put on myself with writing. Spending weekdays chasing lines of energy in the Pacific Ocean transported me back to the freedom of childhood. Sunshine, birds, and warm showers suddenly seemed profound.

Surfing was fascinating, in part, because I had no idea where it was taking me. I knew I had fun, enjoyed improving, and felt better when I did it, but there was no finish line to cross or external achievement that I could show to other people. It was inherently rewarding, like writing a journal entry that you know no one else will ever read. And that was enough reason to keep doing it.

My relationships outside of surfing also began to flourish during this period. With more time and energy on my hands, I said “yes” to all invites from new and existing friends. As my social web grew wider and deeper, I realized how much of my life satisfaction came from the people around me. I began to value good laughs with friends more than even creative work.

When friends or strangers asked me what I did with my days, I now said I was a flaneur, a surfer, or a house husband. I got used to the unimpressed looks I received in rooms where people were gushing about their big ambitions. I was happy to be happy and living a simple life without any orientation other than enjoying the day at hand.

The only thing that made me uneasy during this period was how happy I seemed to be without any particular ambition driving my life forward. It was unfamiliar and odd to feel satisfied without any external purpose to hold onto.

Up until this point in my life, ambition was my driving force. Growing up, ambition meant studying hard to get into the best school possible. Once I did that, it meant excelling in college so that I could get a high-paying job in finance. When I did that, it meant saving money and finding meaningful work.

These shifting ambitions were my source of fuel. They motivated me to work hard and gave me a sense of direction when life turned dark. And when I accomplished what I set out to do, I grew more confident in my ability to build the life I wanted.

But then the ambition of writing the book came, and unlike my other ambitions, the toil did not lead to the spoils. It led to disappointment and depression. I struggled to make sense of the situation while it was happening, though I knew there was no one to blame but myself.

As far as I was concerned, there was no legitimate excuse for not finishing. I had everything I needed to complete the mission and still came up short. It felt like an unforgivable and indulgent waste of two years that destroyed my self-confidence and filled me with self-loathing. The only reason I let go was because I had exhausted myself into surrender, not because I wanted to do it.

I expected the post-book life to be difficult, but then something unexpected happened. In the months following the surrender, the striving and judgmental layer of my mind began to soften. I no longer berated myself for being a failed author. Through surfing, being with friends, and navigating the world without any real direction, I had unintentionally found a pathway to the equanimity I thought the book would bring me.

Letting go of my dream was, in a weird way, exactly what I needed to enter a new season of life. And that new season seemed to have less to do with hard-charging ambition than it did with realizing that my satisfaction came from non-ambitious places.

Today, as an example, I woke up to the sounds of birds, surfed for three hours, and worked on this essay at a new cafe. I picked up groceries at Costco, sat in traffic, and video-chatted with friends before cooking dinner for my wife. Honestly, it felt like a perfect day.

And today was not a reprieve from an otherwise busy life. It followed the rhythm of how I’ve lived for the last 18 months. I wake up without any firm plans and try to map my activities to the evolving needs of my mind and body as the day progresses. Repeating this cycle leaves me feeling relatively happy and relaxed most of the time.

Almost nothing I do is ambitious in any classical sense, nor will it lead to any impressive creations, large financial returns, or invitations to come on podcasts. And while I’m okay with this, for now, my formerly ambitious self still has unanswered questions about this path:

Am I wasting my potential? How long can I keep this up? Is this enough?

Basically, despite feeling pretty good, part of me still wonders if I’ve become a hedonistic man-child who is throwing his life away. It’s a fair question, though I’ve come to see that this questioning comes from the narrow scripts we have about what it means to live well.

In Turning Pro, the writing hero Steven Pressfield who advised me to “plunge right in” to my book, offers a take on ambition that resonates with the part of me that’s suspicious about my current path,

When I started my blog seven years ago, I would gobble up this type of self-help hype talk. I loved well-packaged ideas and distilling life into its essential truths. But now, I look at Pressfield’s idea of ambition and wonder what I found so profound. 

His words now sound less like Truth than they do some clever prose that makes ambition out to be the God that it certainly is not. For some people or seasons of life, feeling big ambition and acting on it may be a good move. But if I’ve learned anything since giving up the book, it’s that you can be perfectly happy without striving for anything other than to take care of your basic needs.

My ambition, if you want to call it that, seems to have shifted away from external goals and toward listening to the whims of a given day. Some days, I want to be a better surfer. Other days, I want to be as healthy as I can. Other days, I want to be a great husband and friend. 

The throughline of these shifting desires, though, is that I want to enjoy my life. And my pathway to doing so is not aiming toward some goal, but rather living a fluid existence filled with activities I enjoy and people I love.

In Gift From the Sea, Anne Morrow Lindbergh shares a view that counters Pressfield’s and that helps explain some of the change that’s happened in my relationship with ambition,

I think Lindberg is on to something. Perhaps all of my former ambitions, including the book, were armor that protected me in a world obsessed with achievement. And once I let go of the book, my primary armor, without replacing it, I began to become more of myself.

And that self, it turns out, is not the Ivy leaguer, Wall Street Banker, Startup Grinder, Great Book Author I’ve been or tried to be at various points of my life. Those were simply masks I wore, and now that they’re gone, it turns out I’m a simpler and less ambitious guy than I fancied myself to be at one point. Failing to finish the book helped me see and accept that surprising truth.

If I have any ambition these days, it has no specific aim. Rather, it’s an orientation toward living fully, without really knowing what that means, that is helping me let go of all of the false ambitions that have driven me up to this point. 

And like a tide that goes out and reveals the contours of a previously hidden and vibrant reef, perhaps I’m finally starting to see what’s underneath all of that armor that I carried for so long.

The reef, I know, is not yet fully exposed. Maybe that will happen with time; maybe it won’t. I’m okay either way. I’ve grown to enjoy walking this weird and unpredictable path in the dark.

— Cal

🙏 Want to Support Life Reimagined?

If you enjoyed this week’s essay, help me spread the message by sharing your favorite bits on Twitter. You can tag me @calvin_rosser to kick off the conversation.

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

👋

Hello friends and welcome back Life Reimagined, a weekly elixir designed to make you feel good and live better.

I’ve been away for two weeks tending to family matters, but am back to the usual programming this week!

If you’re new here or missed the last newsletter, I’m releasing a new essay, Letting Go of Ambition, in three parts. This week, I’m excited to share Part 2 of the essay, which you can find below.

In case you missed Part 1 or need a refresher, you can read it here.

Letting Go of Ambition #2

After the busted surf session, I was stuck in a groove of misery, lacking the insight, energy, or confidence to find my way out. Depression, I realized, was not a problem I could solve with my mind alone. That’s because my mind was the source of the problem. Instead of offering solutions, it whispered a terrifying suggestion: you can end this.

Losing control of my mind and will to live was terrifying, like being trapped in a car with no brakes on a twisting mountain road. If I was going to stop the car safely, I needed to tap into the part of me that recoiled at the word suicide being etched in my gravestone.

From living through my mom’s descent into the darkness, I knew that suicide was a selfish act. When you end your life, it’s the ones you love who pay the price. They’re left with the burden of grief, unanswerable questions, and guilt while you rest peacefully in the grave.

I didn’t want my friends and family to pay that price, but I also wondered if I had a choice. Both my mom and grandfather had committed suicide. Was I destined to follow the same path?

If anything was clear, it was that I needed a hard reset. My usual coping techniques like surfing, exercise, journaling, and meditation were not enough. I needed to find something potent enough to pull me out of this groove.

Having watched my mom battle depression for 10 years, I was deeply skeptical of the traditional solutions offered by the mental health system — pharmacological interventions, past-focused therapy, electroshock treatments, and psych wards. While these interventions worked for some people, they accelerated my mom’s demise. I couldn’t risk having a similar experience.

Unconventional healing modalities held more appeal. A friend had recently found his way out of a similar rut with a few months of ketamine therapy. While I thought ketamine was likely to help, the high cost of treatment and my lack of a stable income made this path unfeasible.

As I grappled with the pros and cons of various paths forward, I realized that I would never escape this rut by continuing my same routine in Southern California. What I needed was a change of scenery, a reminder that joy, beauty, and meaning were still possible.

I told Steph that I wanted to take a trip to see if it would help restore my sense of self. We decided that Bali was a good place to go. It was far away, fun, and perhaps the medicine I needed.

Bottoming Out

Traveling 8,700 miles across the globe was not the miraculous remedy I had hoped it would be. That first week in Bali, I remained the same lost, exhausted, and frustrated person I had been in Encinitas. Apparently, Confucius was right: Wherever you go, there you are.

At this point though, I was used to my depressed state. It seemed like the new normal, and so what if it continued for a few more weeks or months?

This line of thinking would have been fine if I had been the only person on the trip. But Steph was in Bali too, and she wanted to have an enjoyable reunion with the place she used to call home.

For as much as she wanted me to get better, her patience with my negative state was waning. I understood where she was coming from. Not only had I been a downer at home, but I was now the type of travel companion that I would advise people to avoid at all costs.

Still, I had no idea how to get better and felt like my biggest supporter was abandoning me when I needed her the most.

We decided to travel north to stay at a resort in the jungle. Perhaps a few days outside the busyness of Canggu may bring us together. But that first night, we got into a shouting match that made me think that there was a good chance that I would lose myself and my partner to this depression.

I went to breakfast alone the next morning, hoping that the sunshine and plate of tropical fruit would wash away the tension from the previous night. As I was about to leave, I was relieved to see Steph arrive. We were supposed to tour the organic coffee plantation on the property, and I wasn’t sure if she would join me.

The tour featured a bubbly Balinese guide who led us through lush, jungle-like fields as he discussed the origins and operations of the plantation. On our walk to the roasting facility where we would sample the local coffee, we strolled into a small, open-aired room.

Two women with grey hair and deep wrinkles sat on the floor in front of a wooden table, their nimble fingers sifting through thousands of coffee beans with surprising speed. I asked the guide what they were doing. He explained that all exported coffee beans needed to look perfect. Otherwise, foreign buyers (like me) would not be satisfied. 

Made with Midjourney

The women were examining each bean and sorting them into two piles: those that were good enough for foreigners and those that would go to locals who weren’t so concerned about the shape of their beans.

While Steph and the rest of the group moved on to the coffee tasting, I felt compelled to stay behind and watch the women work. Despite their tedious task and buzzing flies, subtle smiles graced their sun-worn faces. One of the women looked up at me and beamed, making me feel welcome in a place where I was nothing but a gawking intruder.

I thought about all of the lattes I had consumed so mindlessly over the years. Never once had I paused to think about everything that had to happen for me to enjoy my morning coffee. And now the truth was here in front of me: every single bean I had consumed had been hand-sorted by people like these women, who likely earned less in a year than I did on my best days.

As I watched their hands move effortlessly through the never-ending pile of beans, I sighed and felt the tension in my neck release. The room brightened, and a small smile washed over my face. For the first time in months, the darkness that had engulfed me began to dissipate.

I thought about how lucky I was to be born where I was, to have received a good education, and to be able to do work that mattered to me. I thought about the book, my white whale, and how it hadn’t unfolded as I had hoped. It suddenly seemed silly how much pressure I had put on myself and how miserable I had become in failing to meet my arbitrary expectations.

Buddhist Pema Chodron says, “The most difficiult times for many of us are the ones we give ourselves.” 

Is that what was happening to me? Did all of my misery stem from some unnecessary story I created about how my life and the world should be? And could I simply revise that story and move on with my life?

I waved goodbye to the two women and headed to the coffee tasting, feeling a glimmer of hope about the future. My self-loathing still had a strong grip on me, but the pressure had decreased just enough so that I could start breathing again.

And as hope-infused oxygen began to enter my lungs, I knew the worst part of this depression was over. I had no idea what would happen with the book or my life, but I at least felt like everything would eventually be okay. The task was now to find a way to hold on to that feeling.

That's all for now. Don’t forget to tune in for Part 3 next Sunday!

— Cal

🙏 Want to Support Life Reimagined?

If you enjoyed this week’s essay, help me spread the message by sharing your favorite bits on Twitter. You can tag me @calvin_rosser to kick off the conversation.

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back Life Reimagined, a free weekly elixir designed to make you feel good and live better.

I’m trying something new and CRAZY this week 🤪. I’ve been working on an essay that is somehow getting longer and longer (usually it’s the opposite). Apparently, I have a lot to say about the topic and don’t want to rush it by glossing over some of the details that make the story tick.

Instead of releasing the growing beast all at once, I’ve decided to share it as a series of posts over the next few weeks. Think of it like a Netflix show that airs every Sunday, instead of all at once.

I may also update each part of the series as the full piece comes together. So if you have anything that you really like, find boring, or are confused by, just reply to this email and let me know :).

OK that’s enough jabbering for now.

You can find the first part of Letting Go of Ambition below.

Letting Go of Ambition

At 28 years old, I was terrified that I would never become a real writer.

I had spent my post-college years as a growth marketer while blogging on the side. Growth marketing paid the bills, but writing was my calling, and I often wondered if I would ever have the guts to stop dabbling and pursue it seriously.

I had already tried going full-time with my blog when I was twenty-five, but it wasn't enough. In my mind, real writers didn’t churn out essays and newsletters; they wrote books. 

With my twenties slipping away, writing a book became my white whale. I didn't need to write a bestseller; I just wanted to write something I was proud to hold and share with others.

For years, I had pushed my writing dreams aside in favor of a stable career. But my fear of not achieving my ambitions began to outweigh my desire for financial security. 

In part, that’s because I couldn't shake the irrational suspicion that I might not make it to my 30th birthday. If that were true, I had less than two years to write my book. Otherwise, I would end up on my deathbed filled with morphine and regret. And I only wanted the morphine.

So, I made the leap. I left my job to write a good book before I turned thirty.

On the first day of my new path, I printed out an email exchange with author Steven Pressfield, who had given me feedback on my book idea. I smiled when I read his final piece of advice:

“Sometimes it's best to plunge right in.”

Beneath the email, I placed a photo of a penguin diving into frigid waters. I was excited and optimistic about taking my own plunge.

I just wish I had known what was waiting for me in the waters below.

Free Fall

A year later, wine and laughs flowed freely between me and my partner Steph. We were celebrating the 80,000-word book draft I submitted to a developmental editor. 

We talked about how the draft had taken longer than expected, concluding that all of the time I spent trading options, watching television, and researching was not a wasted effort. Those activities were simply the tax I paid for learning how to navigate the oddities of the writer’s life. And now that I had a full draft and this wisdom, finishing the book before my 30th birthday would be no problem.

The next step was to review the draft with Linda, an editor specializing in memoirs. In the hours leading up to the call, I nervously watched Linda’s icon race through the manuscript containing raw accounts of my life’s most difficult experiences. What would she think, and could she help me finish this thing?

After we introduced ourselves, Linda shared her initial impressions:

“You have some interesting plot points. But…it’s really flat. This is not going to change lives. It doesn’t speak to anyone. I think you should write an entirely different book.”

As Linda spoke, I felt my chest constrict. Her words were landing like a precision strike on my psyche, rather than the constructive feedback I was expecting. I felt a sudden, sickening sense of vertigo, as if the ground beneath me had given way. The manuscript I had poured my heart into, the dream I so desperately desired, was crumbling before me.

I wanted to shut my laptop and run. What did LINDA know anyway? But I also knew that running away would not help me finish the book. And I needed to finish. So as I learned to do as a kid, I suppressed my emotions, pretended to be okay, and listened to what she had to say.

Linda explained that I had two paths. The first path was to continue working on the memoir I set out to write. This path involved nuking all but one good chapter in my draft and learning how to write in a more descriptive style that would resonate with readers. This would probably take at least another year, and even with that work, the book may not land.

The second path was to write an entirely different book. Linda pointed out that I’m good at finding and sharing nuggets of wisdom. My existing blog audience comes to me for these nuggets, not my life story, and I would be better off offering readers a prescriptive self-help book.

Steph asked me how the call went. I told her that I didn’t feel great about what Linda said, but thought her feedback was directionally correct. As a next step, I would work on the two paths she gave me in parallel before deciding which one to take. There was still a lot more work to be done — a lot more than I had expected — but this was just part of the journey.

She knew I was hurting and disappointed, but respected my need to believe I could power my way through this setback. But over the next few weeks, it became clear that the hard-nosed pragmatism that had helped me navigate many of life’s setbacks would not work here.

One problem was that I was confused. I thought I was writing one book, but now I was being advised to write another. If I continued with my first idea, was I going to end up with a shitty and embarrassing memoir? Was I okay with that outcome? And if I went down the second route, did I have to let go of a year’s worth of work and begin again? That seemed impossible.

And then there was the fact that every time I sat down to write, I felt numb. All my optimism, excitement, and confidence about the project had faded. I wanted to watch television and drink wine and forget that I had ever tried to write a book. But it was too late to give up now. I had already told so many people about the book and built my identity around becoming an author.

Noticing my confusion and the rapid decline in my spirits, Steph suggested that I take a break from the book. I could always pick it back up once I felt better. Her suggestion — like almost everything about my life since the book review call — irritated me. Didn’t she know that I had to finish the book? How would taking a break solve the problem? I just needed to keep going.

I didn’t appreciate how bad my inner world had become until I went surfing on a warm spring day. Surfing had been my zendo for the last few years. I could enter the water angry and distraught and emerge with a zen-like appreciation for the simple beauty of a grain of sand. There was no emotional problem that could not be solved by a vigorous surf session.

I paddled out to the lineup and sat on my board, a leaden heaviness sitting on my eyes. As waves rolled in, I felt no motivation to chase them. The heaviness spread to my chest and arms, as if invisible weights were pinning me to my board. I wondered why I was out in this stupid ocean, doing this pointless sport I sucked at. 

I looked at the other surfers, desperately wanting to inhabit their lives, convinced their struggles couldn't compare to mine. I sat, waiting for the healing powers of the ocean and sun to cleanse me. But relief never came.

Instead, the corners of my mouth dropped downward, and I wept. 

As tears raced down my cold cheeks, I held my breath and looked around me, hoping the other surfers would not notice a loser like me in the lineup. My mind chimed in: “How pathetic. You’re surfing and have a great life, and you’re crying and feeling sorry for yourself. What a joke.”

I gave up on catching waves and rode a wall of whitewater on my belly until I reached the shore. As I sat on the beach, I could no longer deny the truth: I was depressed. Not even surfing, my silver bullet for emotional regulation, could bring levity and light back into my life. 

No, this was a different beast. It was the same one that led my mom to take her own life a few years earlier. I was in uncharted territory, facing a darkness I had never known before. Stoicism, pragmatism, and the other isms that had worked so well in the past were no match for this beast. I had no idea what to do in the face of such a formidable opponent. 

I realized that whatever was happening was about more than my confusion and frustration about the book. The review call may have sent me over the precipice, but it was not the cause of this depression. I had been walking toward the edge for at least a year, and now I was in free fall.

As I moved my trembling fingers through the damp sand beneath me, my fear of not finishing the book gave way to my terror about the depression that gripped me. I had to find a way through or risk losing myself entirely.

That's all for now. Don’t forget to tune in for Part 2 next Sunday!

— Cal

🙏 Want to Support Life Reimagined?

If you enjoyed this week’s essay, help me spread the message by sharing your favorite bits on Twitter. You can tag me @calvin_rosser to kick off the conversation.

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

👋

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

Before we dive in, make sure to tune into next week’s newsletter. I’ll share an essay about something I’ve been trying to make sense of for the last few years. I think it’s time to share some of what I’ve discovered with the world.

🏛️ I. Internet Archive

For years, I’ve used the Internet Archive’s Wayback Machine, a digital archive of the entire internet that allows you to go back in time and look at what websites have looked like at different moments. I use the tool for marketing and internet sleuthing work, but never thought much about who built it or what else you could do with the product outside of looking at websites over time.

Then on Friday, my wife organized a tour of the Internet Archive’s physical building in San Francisco as a community event for people who are a part of Internet Pipes, her new product that teaches people how to use the web to find, vet, and validate trends and business ideas.

The tour was heaps of fun. Here are a few things I learned:

• Archive.org started archiving the web in 1996 and has saved nearly a trillion web pages since then.

• The company hosts all of the data themselves, and they even have physical servers in the SF location that you can touch! I was glad to learn that they also have backups of the data in various locations around the world.

• Their physical building is an old Christian Science church, and they bought it because it looked like their logo. They still have the pews, organ, and many remnants from the church.

• They probably have more valuable data about the internet and users than any company in the world, and they refuse to collect or sell user data despite pressure from many people to do so.

• The organization is funded entirely by grants, donations, and partnerships with people who want to digitize their context. You can donate here if interested.

• In addition to web pages, they archive video, software, music, and even have a growing archive for television. This is pretty cool because apparently, many networks don’t keep their old content so this is the only place you can find it.

Without what Internet Archive does, you can imagine a world in which a lot of internet could be lost with time. That may not seem like a big deal, but in a sense, they’re one of the few defensive forces against the many actors who may want various parts of the web to disappear for one reason or another.

Ultimately, I came away from the tour with an appreciation for how this site is the largest, coolest, and most underrated library in the world.

I’ll leave you with a picture of our tour guide on a stage with three numbers to her right. They are old hymns converted into internet error codes. Outside of codes you may recognize, you’ll notice 451. That’s the temperature at which paper burns and is a reminder of how web pages can be taken down for legal reasons.

Internet Archive tour

The 451 reminded me of Ray Bradbury’s Fahrenheit 451, one of my favorite books as a kid that reminds us of the importance of being mindful of the forces that try to erase ideas and human creations.

P.S. If you find yourself in San Francisco, Internet Archive does free tours every Friday. Check it out if you’re a fan of the internet.

💰 II. Free Money

Gift cards at Costco

I recently found out that Costco sells gift cards for other brands at a discounted price. For example, you can buy $100 gift cards for the grocery delivery company Instacart for $80 each. If you use Instacart often like I do, this is a neat way to get 20% off your grocery purchases. It’s kind of like free money.

I was curious how this works financially: Does Costco lose money on these gift cards to attract new members, or do brands offer Costco subsidized gift cards for some reason? It appears it’s the latter. But why?

I can think of a few reasons brands would do this. Let’s use Dominos (one of the participants) as an example. Why would Domino’s give me $100 of purchasing power for only $80? Well…

Margin matters. Imagine you use your discounted gift card to buy $100 of pizza. Domino’s operates with a margin, so perhaps that pizza only costs them $60. If that were true, they would still earn $20 even though you paid $80 for $100 worth of food. It’s a win-win. And it’s an even bigger win for Domino’s if you spend more than $100 on food because they would earn their non-discounted margin on anything over $100.

More cash ahead of time: Let’s say Costco buys ten thousand $100 Domino’s gift cards from Domino’s for the discounted price of $800k on January 1st. On that day, Domino’s gets $800k in the bank. It would be irresponsible if they spent that money immediately because they still owe that amount in services to the Costco members who eventually buy and use the gift cards. BUT they can put that $800k into treasuries or similar instruments and earn a good yield until consumers buy and redeem their cards.

Unused gift cards: Outside of earning yield, there is another benefit. Apparently, something like 6% of people never use their gift cards. They lose them, forget about them, or don’t spend the entire balance. Domino’s technically still owes these people the services they can buy with the unused funds, but they can probably safely assume that some percentage of gift card funds will never be used. In theory, they could let that expected amount earn yield forever or use that money to fund other operations.

Distribution: Costco has a bazillion members, and if you’re a brand that’s less well-known than Domino’s, you may benefit from having your name in front of the Costco members who will discover you via a gift card. Something like the Brazilian steakhouse Fogo de Chao is a good example. It’s one of the Costco gift cards offered, and while it’s not an entirely unknown restaurant, it may benefit from all of the Costco members who have never eaten there and decide to give it a shot for the first time thanks to the gift card discount. Not only do brands like this get awareness, but it’s likely people spend more than the gift card amount when they go. If these people like their experience, they may return with others or recommend the restaurant to a friend. More wins!

I’m sure there are other reasons for the existence of these gift cards, but this is what came to mind when I started thinking about why this “free money” is so readily available by just being a Costco member.

Outside of Fogo de Chao and Instacart, I also got a gift card for Southwest Airlines ($500 worth of credit for $450). If you're curious to see what brands participate, you can see all of the offers here.

Just don’t forget to use your gift card if you get one!

🎬 III. A Series I LOVED

While in Costa Rica in December, a friend introduced me to Fargo, a 1996 black comedy film that’s bizarre and definitely worth watching.

I didn’t think much about the film until I learned there was a television series that loosely follows the style and plot of the movie. Each of the five seasons in the series can be watched independently as they all have a different story and set of characters that echo the style and loose plot of the original Fargo.

Based on a recommendation, I started with Fargo Season 2. And oh boy was that a mistake! It was so good that I binged it in an embarrassingly small amount of time. I then went on to plow through to three of the other seasons.

All of them were pretty good, but Season 2 was excellent. It’s definitely one of the top five series I’ve ever watched.

If you have some time to laze around or are willing to take a productivity hit, consider giving it a watch. But if you are in a period of life where you need to get stuff done, maybe don’t tune in until things slow down.

🧠 IV. Something I’m Thinking About

If you feel called to bring something into this world, don’t wait. The idea’s time may have come, and why shouldn’t you be the one to make it happen?

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

📚 I. Books I’ve Enjoyed

I’m reading at a good clip this year. I’ve mostly gobbled up memoirs that take me into the unfamiliar and interesting worlds of the authors who wrote them. Below are five of my favorite books from the year so far.

• Saltwater Buddha by Jaimal Yogis: A memoir about a lost teenager who finds his path in life via Zen and surfing.

• Journey to the End of the Night by Louis-Ferdinand Céline. One of the few novels that Bukowski enjoyed, this is a wild and dark tale of a European man who navigates a life of poverty.

• Gift from the Sea by Anne Morrow Lindbergh: A wonderful collection of essays from a woman reflecting on relationships, parenthood, and solitude while vacationing in Florida.

• Troubled by Rob Henderson: An American Dream story about navigating and growing up in the foster care system.

• This Boy's Life by Tobias Wolff: A phenomenally-written story that captures the uncomfortable and confusing experience of adolescence.

📦 I. Cool Company Creating the Future

I recently toured Zipline, a company creating autonomous drones that deliver goods and services to people.

The most interesting part of the experience was learning that Zipline’s drones have primarily been used in Africa to deliver blood and other life-saving medical interventions to hospitals. In some countries, they have helped reduce the number of deaths from postpartum hemorrhaging by 50%!

Outside of learning about Zipline’s progress and impact, it was awesome to be on the ground floor of a hardware company making real things. I left the facility feeling like I should leave the digital world and start working on something with more direct impact.

If you’re curious about the company, the popular Youtuber Mark Rober created a great video about what Zipline is doing and how it works.

🌊 III. A Good Description of Grief

A few weeks ago, I shared The Wave I’ll Never Forget, an essay about a paranormal experience I had while grieving the loss of my mom.

A reader reached out afterward and recommended this Reddit post from an older man who has lost “friends, best friends, acquaintances, co-workers, grandparents, mom, relatives, teachers, mentors, students, neighbors, and a host of other folks.”

It’s one of the better descriptions of grief that I’ve seen. I particularly enjoy his metaphor for the early stages of loss:

Since I write about losing my mom from time to time, many people have reached out to me over the years to ask for advice after losing their mom.

Providing “advice” on such matters feels impossible, but I still try. One universal theme in the responses is that a big loss can feel like a fight with a force far more powerful than you.

Fighting the force or trying to “solve the problem” is futile. You will only wear yourself down. Instead, you must surrender and offer yourself as much self-compassion as you can.

I think this Reddit user captures what I’ve been trying to say for years.

🎙️ IV. Podcast Worth Listening To

I enjoyed Lex Fridman’s interview with Annie Jacobsen, a journalist who writes about war, weapons, security, and secrets. Lex and Annie dive deep into what it would look like if the world entered a nuclear war. They get into the details of the nuclear capabilities of different countries, the unbelievable power of these weapons, and what would happen if they were deployed.

What they discuss is both informative and horrifying. In listening, I realized that my idea of nuclear war has always been opaque. I knew it was a primary threat to human civilization, but my thinking stopped there. This interview turned that opaque thinking into something more concrete.

On the whole, I left the interview with a deepened sense of the fragility of life and the importance of our efforts to preserve and improve the world that we have.

You can listen to the interview here.

🧠 V. Something I’m Thinking About

In This Boy’s Life, Tobias Wolff discusses the blissfully ignorant period of adolescence and your early 20s when you still believe the world is an oyster designed for you and your specialness.

For most of us, this period ends. As we mature, we realize that we are not special, or at least that we are not uniquely special. That realization can feel like a punch to the gut, but ultimately allows us to live out our small piece of the cosmic puzzle without all of the angsty egoism of youth.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, I wrote about how our endless striving to leave our mark on the world leads us to overlook the simple source from which real impact emerges.

You can read the full essay below or find it on my website here.

P.S. If you missed last week’s essay about love, loss, and encounters with the supernatural, you can read it here.

Footprints

I stumbled upon this sign the other day. 

Keep Nosara Green. Leave Only Footprints.

It reminded me of Leave No Trace, an environmental conservation philosophy that encourages people to leave nature as they found it. Basically, leave only footprints.

I trekked onward and noticed the sounds of leaves and sticks breaking beneath me. With each step, the jungle path became more matted and lifeless than it had once been. The change was almost imperceptible, but it was happening.

It occurred to me that no matter how hard we try to minimize our impact, we can never leave nature quite as we found it. Even our footprints transform the places we walk.

The impact of small actions in the natural world is obvious, hence the popularity of ideas like Leave No Trace. But we seem to forget that this dynamic also occurs outside of nature.

As we navigate careers, conversations, and the responsibilities of life, our goal is not to leave no trace. In fact, we often want to leave the biggest trace we can imagine. We strive for an impact large enough to create a positive legacy, garner adulation, and imbue our lives with meaning.

But in our relentless striving to leave our mark, we forget something important. We forget that it’s the tiny footprints we leave behind, not our grand plans, that actually change the people and world around us.

The importance of footprints became clear to me a few years ago. I was writing a memoir and interviewed friends and family to get a better understanding of myself.

At the end of the interviews, I always asked: What’s something you know about me that I don’t know about myself? 

I hoped this question would reveal my blind spots through the people who knew the best and worst parts of me. Most people said something unmemorable, but my friend Dror said something that shook me:

“You would be a great dad.”

A tight ball formed in my chest and remained long after the interview ended.

At the time, I had never seriously considered being a dad, let alone a good one. In part, that’s because I had a complicated relationship with male role models.

My biological father was a drunk gambler who disappeared when I was two years old. In his absence, my mom fell for a rotating cast of sketchy and selfish men. My grandfather is likely the only reason I didn’t end up in jail. He was a good man who showed up when it counted.

But even with my grandfather’s influence, the idea of fatherhood never sat well with me. I always assumed that I would be no better than my father or the men my mom brought around.

It’s with this backdrop that Dror offered those six penetrating words: you would be a great father. I don’t know if he remembers what he said, but he left a footprint that changed my life. 

His words opened a door that allowed me to reconsider my self-image and ideas about fatherhood. Over the next few years, I began to understand that I was not the same as my father or my mom’s other love interests. I was not destined to leave my kids in the dust or exist as an unreliable outlaw.

I could have been like these men, but I made different choices. And as Dror helped me understand, those choices mattered. Perhaps I could be a half-decent father.

I don’t have children, so the jury’s still out on the great dad thesis. But no matter what happens, it’s clear that Dror’s footprint nudged my life in a better direction.

Looking back, I can think of dozens of similar examples. Each event started with something as simple as kind words or an act of generosity from people who took their footprints seriously. And those small acts made a profoundly positive difference in my life.

Taking your footprints seriously requires you to believe that the little things count, even when you can’t see the outcome. That’s because the impact of your footprints, unlike the dollars you donate, is not measurable or predictable.

Footprints are like a gust of wind at sea. That gust can start a chain reaction of energy that moves thousands of miles across the ocean. The energy slowly builds until it has transformed into a wave that arrives to the delight of a surfer looking for his next ride. The wave crashes onto the shore, subtly changing the sandy ocean bottom and the spirit of the surfer who will re-enter land life with a smile.

Every day, we leave behind dozens of footprints that have the potential to be like this gust of wind. Those footprints could be the attitude we bring to work, the presence we offer to loved ones, or the curiosity we bring to a conversation. These subtle acts are less about what we do and more about how we show up in the world.

Trusting that how you show up matters is an act of humility and faith. No one will put you on a magazine cover for being consistently kind, patient, and generous. And you will never quite know when you change someone’s life. Yet, you show up anyway.

We’ve all heard of or met people who make a name for themselves by saying that they care about this or that cause. But behind closed doors, they are mean-spirited and uncharitable. Magazines love these people and don’t care to mention the muddy footprints they’ve left around the world.

But it’s that mud, not the praise, that will define their lives.

We all reach the end of our time at some point. It’s at this moment when the seriousness with which we took our footprints will matter most. Hooked up to a series of tubes, we will no longer be blinded by the legacy, fame, and admiration we once craved. Those desires will have faded and lived on with the young.

With clear heads, we will finally have time to think about the millions of footprints we made as we traversed the world. And hopefully, we will be satisfied with the traces we left behind.

That's all for now. See you next Sunday.

— Cal

🙏 Want to Support Life Reimagined?

If you enjoyed this week’s essay, help me spread the message by sharing your favorite bits on Twitter. You can tag me @calvin_rosser to kick off the conversation.

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back Life Reimagined, a free weekly elixir designed to make you feel good and live better.

Today would be my mom’s 56th birthday if she were still here. I spent the week writing a new essay exploring loss, love, and encounters with the supernatural. I poured my heart into this one and hope you enjoy it.

You can find the full essay below or you can read it on my website here.

The Wave I'll Never Forget

Made with Midjourney

Mom would be 56 years old today, and I wonder what her life would have become.

I like to imagine that she would be living her dream: a slow and sunny life on the sandy shores of Florida. But I can only speculate about how her story may have unfolded. She passed away six years ago after a decade of teetering on the edge of darkness.

I know that Mom would not have liked that she was nearing sixty. She was fond of being young and would have resisted the wrinkles, aches, and extra paddling of midlife.

But then again, I can’t even know this with any certainty. What if Mom’s fierce resistance to aging had loosened its grip by now? What if she had a newfound appreciation for the accumulated wisdom in each of her wrinkles? I’m again left to wonder.

Losing someone you love leaves you with many unanswered questions. You’re perpetually suspended in a state of not knowing. That’s a particularly uncomfortable place to be if you have a strong desire to control your world.

The only thing you have to grasp onto is the fading memory of who the person once was. But that memory is an imperfect glimpse at the past that offers no real answers or comfort.

Birthdays of lost loved ones are interesting moments in the grieving process. They can surface memories and questions that don’t come up on other days. And even if you want to live the day like it’s nothing special, people remind you that this day is not ordinary.

On Mom’s birthday, I receive supportive texts from friends and family. They seem to think that I will be in shambles. But so far, that has not been my experience. Mom’s birthday has felt like any other day.

With time, I’ve come to believe that grief does not walk a predictable path. Grief is more like floating down an uncharted river than hiking a well-known trail. You don’t know what will come, when it will arrive, or how long it will last. You float and hope everything turns out okay.

On some days, often when you least expect it, grief will knock on your door with angry fists. And on other days, you won’t even think about the person you lost. In such an uncertain environment, staying sane requires you to learn to let go and accept life as it unfolds.

While Mom’s birthday has not been difficult in the ways that other people expect, I still treat it as a sacred day. Instead of going about my usual routine, I go into the day without any goals, work, or pressure. My only intention is to spend the day as I want.

In a sense, her birthday is a dedicated day for me to float down the river of grief and see what emerges. A few years ago, that float took me on an unexpected ride.

On March 3, 2020, I woke up in Encinitas, California. I drank coffee, grabbed my surfboard, and walked barefoot down Neptune Avenue. I watched the waves from the top of the wooden steps that led down to Grandview, the break where I was learning to surf.

The setup was perfect — small, clean, and uncrowded waves. I zipped up my wetsuit and paddled out expecting to have a great session. The surf gods had other plans for me. I spent an hour missing waves, faceplanting, and banana peeling on the takeoff.

Leaving the dreamy surf a little frustrated, I headed to a restorative yoga class to settle down. A solo lunch and lazy afternoon of reading and looking at the wind-swept ocean followed. As the afternoon progressed, I noticed something interesting. The waves were cleaning up, opening up a window for another session. This time, I would surf without any expectations.

During the first 30 minutes of the session, I scored two beautiful, long lefts and rode them to completion. I then duffed it on a few rights but laughed it off. While waiting for the next set, a fin emerged from the water three feet in front of me. My legs curled up onto my board until I saw fins all around me. 

Dolphins. I exhaled and smiled.

There were at least six dolphins and likely more I couldn’t see. My eyes suddenly darted to the horizon where a large, dark line had formed. A set wave was moving in my direction.

I paddled toward the peak, turned around, and popped up once I felt the board lift. Stoked that I had not faceplanted, I was now racing down the face of a peeling right-hander.

Twenty feet ahead of me, I noticed a fin in the water. A dolphin had joined me for the ride! Time slowed as we cruised together in harmony for the next 20 seconds. When the wave closed out, I took a belly ride to shore while the dolphin rejoined her friends. 

As I sat on the beach, salty tears dripped down my face as little bumps formed on my arms.

I thought back to a trip Mom and I took to Clearwater Beach on the Gulf Coast of Florida. We took a boat out one day to see dolphins. Mom held my arm and giggled as a pod of dozens of dolphins followed the boat and played in its wake. It was one of the last times I saw her truly happy.

Then I thought of the blue sticky note that Mom put on her bathroom mirror a few months before she passed. It read: Clearwater Beach Surf Shop. The note was a reminder of the dream she was working toward. She wanted to work at a surf shop in Clearwater and get a shack with an extra bedroom for me to visit.

I wondered if my recent decision to move to Encinitas and spend my days surfing had anything to do with Mom’s unlived dream. I wasn’t sure. But I did know that being in the ocean made me feel more connected with her, especially when I saw dolphins.

As my mind raced between the past and the present, I knew deep in my heart and soul that it was Mom who had joined me on that wave.

That knowing was absolute. I didn’t need to believe in reincarnation, God, or anything else to know its truth. I felt Mom’s energy and strength flow through me and the body of the dolphin.

It’s been four years since that day, and I’m left to make sense of the experience.

The first question: Was it real?

It’s difficult to know. 

It felt real, but I may be like the child who confuses the shadows of the night for monsters in the closet. Just a grieving man confusing a coincidence for a paranormal connection with his late mother.

I have sympathy for this interpretation. Yet that sympathy doesn’t penetrate the part of me that knows that this experience was real. As real as anything explainable with math or physics anyway.

During my life, I’ve had a handful of experiences that follow a similar rhythm. Something happens, and that something shatters my understanding of what’s possible. As I’ve had more of these moments, I’ve learned that I can either accept or reject what happened, but I can’t explain it. Words and the limitations of the rational mind can’t capture such experiences.

I’ve also learned that knowing the “realness” of these events is not important.

Illusions or not, these experiences point toward something worth knowing. In a sense, they remind us that there is something core to life that we may never fully understand. We can begin to understand it, but not through the narrow lens of science and intellectualism. Its only with faith and humility that we can begin to understand.

Each of these experiences has occurred in wildly different ways. However, they have all given me what feels like a glimpse of the all-knowing interconnectedness that ties reality together.

People use concepts like God, mystical experiences, and consciousness to hint at this interconnectedness. But like my words, these concepts are insufficient. They are only loose approximations of what it’s like to have encounters with the ineffable.

My ability to notice these encounters seems to have accelerated on my 25th birthday. That was the day I held my mom’s hand as she took her final breath. The absurdity and pain of that day seemed to crack open a doorway to more moments like the wave at Grandview.

Before that day, I was bound by mental and spiritual shackles. I would have seen my ride with the dolphin as nothing more than an enjoyable and lucky event. But with my shackles loosened in the wake of Mom’s death, my heart opened to supernatural interpretations of these moments. And with time, I’ve begun to see the wisdom embedded within these previously off-limits interpretations.

As I’ve reflected on my ride with the dolphin, it’s become clear that it was more than a cathartic moment of reconnection with Mom. That experience, with the help of time and reflection, helped me understand that Mom’s love endures even in the absence of her physical presence.

The aftermath of that wave felt like the many times when I was afraid as a kid and received one of Mom’s hugs. Her comforting embrace reminded me that her invulnerable love would always be with me. The wave had a similar effect, reminding me that Mom didn’t need to be in this world for her love to endure.

Today, another one of Mom’s birthdays will come and go. I still don’t know how her story would have unfolded and can’t share new moments with her. I wish I could.

But thanks to that experience on the wave I will never forget, I have something that allows me to rest easy. I know, deep in my heart, that Mom’s love will always be with me.

And what more could a man without his mother ask for?

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, I wrote a new essay exploring our relationship with being alone and the hidden preciousness of periods of solitude.

You can find the full essay below, or you can read it on my website here.

Seeking Solitude on the Sandy Shores of Costa Rica

Made with Midjourney

Solitude is precious.

That’s what comes to mind as I lean back on my forearms and nuzzle my toes into the soft sand of Playa Carmen. It’s the first discernable thought I’ve had in a few hours. Now that the unbearable heat of a Costa Rican afternoon has loosened its grip, my mind is working again.

All around me, friends gather in small circles to share laughs and light beers. Surfers snag their final waves of the day, performing as much for themselves as for the land-dwellers who watch them. Cicadas buzz loudly in celebration of the sun’s descent below the horizon.

I’ve spent the last two weeks bopping down the coast of Costa Rica discovering the textures and rhythms of unfamiliar waves. Friends have appeared here and there, but I have been on a primarily solo expedition to deepen my ongoing love story with the ocean.

At least that’s what I thought when I began this trip.

But as I sit on this beach, alone and typing furiously on my phone with no desire to communicate with anyone but the voice inside my mind, it feels like there is something other than the pursuit of waves that is emerging from this trip.

I’m not unfamiliar with the rhythms of solo travel. I spent multi-month periods of my twenties hopping around foreign lands, floating like a dandelion in the wind to wherever life took me. I enjoyed that aimless and solitary period. I had no home base and was on a mission to figure out who I was and what I wanted. Solo travel was indispensable to the process of self-discovery.

But now, these self-inflicted periods of solitude seem out of place. I live in a city I enjoy, am happily married, and believe that the only thing that matters at the end of life is that we share it with loved ones. Yet from time to time, I still hear the call to hit the road and see what happens.

I often listen to that call, knowing that it’s a signal that something needs to be worked out. I’m just not always sure what that something is. The trip always reveals the answer.

Last year, the call took me to the surf-filled coast of France and Spain, where I spent two weeks exploring new waves, puttering around, and enjoying good food. 

It was only when I returned home from Europe that I realized how that trip helped me unlock a new relationship with creativity. Solitude allowed me to re-examine my stale relationship with writing, and I came back with a renewed vigor for sharing ideas. That was not the intention of the trip. It’s just what happened, and the feeling endures to this day.

But what is this Costa Rica trip all about?

On the surface, it was completely unnecessary. I had no real reason to be in Costa Rica outside of my love for surfing and distaste for the moderately cold and rainy winter days of Northern California. That reason was enough to book a plane ticket, but I was curious to see if something more profound emerged.

I think I’m starting to see what that something is, and I’m slowly finding it in the many feelings of discomfort that I’ve had while navigating life near the equator on my own.

Being alone, now that I’m married and settled in San Francisco, is not as comfortable as it used to be. When I was young and had no real home, drifting around felt more normal. Not just to me, but to people who heard my story. People don’t turn their heads when a lost soul in his twenties is basking in solitude, but some people do when you’re married. 

Oh, you’re married, why isn’t your wife with you? Is she okay with you being here?

Answering these questions isn’t difficult, but the fact that they’re now being asked reminds me that something has changed. And while I think such questions are often a projection onto me of what people believe life after marriage has to be, they are a good forcing function to make sure I’m still doing something I want to do and not repeating the wandering escapism of my youth.

The experience is also different for me. I now feel that solo trips make me miss out on things I enjoy back home. I see packs of travelers laughing and drinking and sharing stories with people they love. I watch lovers embrace during sunsets. I feel like an aging, stone-faced wallflower when I see young people enjoying the bliss of their first year on the road.

These feelings and experiences raise questions that weren’t as relevant during my earlier years: Why am I here? Should I be at home? Am I too old for these trips?

This trip has also surfaced the nagging insecurities of an earlier version of me. In some ways, I feel like I’m a new kid at school trying to navigate the oddities of a middle school lunch.

As I pass through my days, I look around awkwardly, hoping that the cool kids will welcome me to their table and tell me how glad they are that I’ve arrived. I want to feel like a person worth knowing, someone with people to see and things to do. But this type of emotional validation does not make it into my days. 

And so I’m left alone to sit with my questions and insecurities.

This experience is particularly noticeable in the surf towns I like to visit these days. I wake up at dawn to squeeze the maximum juice out of the morning surf window. It’s an unbelievably exciting and energizing period for me. I really am living my dream. But after that session is done, I eat a well-deserved meal and my thumbs start twiddling.

If you’re not surfing, tropical surf towns aren’t very exciting places. As the heat picks up around 11 am, sluggishness consumes my mind and body. All I can seem to do is sit lazily in the shade or retreat to an air-conditioned room. From there, I wait.

What am I waiting for? Mostly for the sun to set, which on some days offers a window where the wind drops and the ocean cleans up to allow another round of surfing.

But whether or not that window opens up, I’m left with hours of uncomfortable moments.

I think this discomfort is the point of this trip.

The uncomfortable quiet of my experience is something that I need to feel. For what reason? I’m not sure yet. But the awkwardness, isolation, and silence — the things that I spend so much of my life trying not to feel — appear to have good and healing properties.

I can think of a few benefits to these feelings.

The first is that they help me remember why it’s worth having loved ones and friends in this life. I realize how nice it is to have these people around. They really do make life worth living. 

Not only do they give me the sense that I am someone, but they are joint gatekeepers of the mundane, sad, and profound experiences we share. And simply having shared memories of those experiences is a deep source of joy and connection in my life.

In the absence of the people who enrich my life with meaning and purpose, another benefit of discomfort bubbles to the surface. I have the chance to explore who I am without these people and the comfort of feeling that I belong.

In Letters to a Stoic, Seneca says:

While Seneca is talking about practicing financial poverty as a reminder of how little you need, my solo expedition offers something similar. By creating an environment in which I’m forced to practice social poverty and feel all the feels of solitude, I’m remembering just how little I need to be and feel okay in the world.

While I’ve had many uncomfortable moments, they have not killed me. Nor have they stripped me of satisfaction. On most days, I wake up with a healthy dose of stoke and find myself sleeping well at night. Knowing that I can still be content living with the ups and downs of being alone in an unfamiliar place is a good reminder. Wherever I am and whoever I’m with, I am indeed okay.

Feeling gratitude for loved ones and knowing how little I need for contentment are valuable lessons, but they’re too reductive. They don’t quite get at the beating heart of this experience. There is something deeper to solitude. 

This something is difficult to describe, but it feels like entering the clear and sunny eye of a hurricane. In the chaos of the violent storm that surrounds me, I’m realizing that I can still tap into the equanimity that is always there at the core if I can just remember that it exists and muster the courage to get there.

Yes, that’s part of it. Solitude is helping me remember something fundamental to the experience of living an imperfect and sometimes difficult existence.

And remembering that has a similar effect as a vigorous surf session. After hours of intense paddling, underwater demolition, and brief moments of bliss, my body buzzes with the invulnerable knowledge that everything I need is always with me. Striving and yearning disappear as I trot like a barefooted zen zombie along the beach.

This is how I’m starting to feel as I get closer to the end of this period of solitude, and it’s similar to how I’ve felt during other such periods.

Solitude, in a weird way, is slowly washing away the accumulated muck of the life I know that has taken me far from the simple core of existence where true equanimity rests. As the muck begins to clear, I’m starting to see myself and the life I’ve built more clearly.

This process only seems to work if I surrender fully to the experience. Surrendering involves feeling it all — the lulls of the day, periods of peace, and longing for what I know.

Surrendering is not easy. When my legs start moving or the call to drink alcohol arrives or I grab for my phone, it takes courage to avoid distracting the discomfort away.

The distractions come in seemingly benign forms — a podcast I should listen to, making plans for the next day, and so on. I’ve learned with time that these distractions are a form of self-sabotage. While they may alleviate short-term discomfort with what seem like productive or harmless actions, they subtly subvert the process of rebirth and growth that solitude offers.

The most difficult part of avoiding the distractions comes when my mind starts asking hairy questions: Is anyone back home thinking of me? What am I doing here without loved ones? Why am I not a part of the friends huddled together and enjoying the sun’s final act of the day?

So far, I’ve allowed my mind to race without numbing it with distractions.

Being booze-free for the first time in my life, taking headphone-free walks, and regular meditation have helped. But no tricks or techniques can take away the small stings of discomfort. So like a meditating zen-master who ignores the fly that has landed on his eyebrow and continues to focus on the rhythms of his breath, I trudge forward knowing the discomfort is part of the experience.

Now that I’m sitting on this beach and beginning to understand what this period of solitude may be about, I can’t help but wonder if all of this was necessary. Did I need to isolate myself in a foreign land, embrace discomfort, and limit distractions to get here?

And is here even a better place than wherever I was before?

Maybe, but it’s impossible to know.

What I do know, however, is that solitude has helped me in the past and appears to continue to have some function in my new life. In a sense, these self-induced periods of being alone seem to facilitate a process that will allow me to return to the life I know with soft, still eyes. 

Like the water and sunlight of Spring help plants emerge in full stride after a harsh winter, solitude is an elixir that helps me remember my core during the many seasons of life.

For most people, I doubt it’s necessary or possible to venture to foreign lands for weeks or months at a time to experience this opening and re-alignment of mind, body, and spirit. My guess is that even a few hours or a day of solitude in the place you call home can at least nudge you in the direction I’m talking about.

And yet, how often do we create space for even an hour to explore the wisdom of solitude?

But I also know that a longer adventure, if you can make it work, certainly forces your hand. With nowhere to hide, all of the frenetic energy that tells you to be somewhere else and to cover up the acne of existence starts to melt away. In its wake, there is now room for something new.

In a world that has hijacked and monetized our attention at nearly every waking (and even sleeping) moment, we have been convinced that we must know what’s going on and constantly striving to be somewhere else and someone different. There is no escape unless we actively fight against this pressure to do anything but be alone.

It may be more difficult today than 50 or 200 years ago to be alone, but our strained relationship with solitude is not a modern problem. While writing Gift from the Sea in the 1950s, writer Anne Morrow Lindberg shares her observations about solitude from the sandy shores of Florida:

Sounds familiar, doesn’t it? Lindberg goes on to describe why she has resisted these forces and made her way to the coast of Florida for a few weeks of alone time:

Like Lindberg, whose work I discovered on the sandy shores of Costa Rica, I’m realizing that being alone is slowly helping me to reconnect with my core. Yes, that’s it.

When I return home soon, I suspect I will see the fruits of this re-connection not only in the inner stillness that has begun to replace the discomforts that solitude has surfaced but in a deeper connection with all those people who graciously allowed me to go on this adventure and re-emerge into their lives.

And perhaps that’s what this whole trip has been all about.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, I wrote a new essay about Alaskan grizzlies, letting go, and what it means to live in a fundamentally unpredictable and uncontrollable world. You can find the full essay below, or you can read it on my website here (FYI the website version has special video footage that adds to the story)

Also, I did something I don’t usually do and went on a podcast this week. You can listen to my interview with Monica Lim of the Wander podcast here. The episode captures a lot of my current thinking that I’ve yet to capture in writing.

Let Go or Be Dragged: Adventures in The Last Frontier

Made with Midjourney

I want to tell you a story about how an unexpected encounter with nature changed everything.

In the summer of 2021, my girlfriend Steph and I spent all of July working on a course designed to help people use technology to get more out of their time. By the time launch day rolled around, we were exhausted but had pocketed $20,000.

I decided that we should use those course winnings on a trip to Alaska. The Last Frontier seemed like a great place to unwind and recharge, and I planned a two-week trip that included epic hikes, a glacier tour, whale watching, salmon fishing, and good food.

As we boarded our first-class flight to Anchorage and took a sip of the free champagne, my mind fantasized about a magical Alaskan experience that would deepen our budding romance.

But as war strategists say, no plan survives contact with reality. 

The first few days of our trip were not the romantic fairy tale I had imagined. Upon landing in Anchorage, we spent our time quibbling about this and that as we drove through landscapes that belonged in a Bob Ross painting.

On the third day, we woke up at dawn to ride bikes through Denali National Park. I thought this biking adventure might turn things around, but during the first 10 miles, we continued bickering. If we had not been the only two people biking in the park, we probably would have parted ways and enjoyed the alone time.

I started wondering if we were going to have to cut our trip short, and that’s when life handed us an unplanned gift in the form of a snacking grizzly bear.

When we were five miles from the end of our bike ride, a tour bus driver stopped and rolled down the window. He said a bear was munching on berries close to the road about a quarter mile ahead. There was no way to predict how he would react to us, so he advised us to stop biking and go back. Before we could ask him the many questions we now had, he drove away and left us to fend for ourselves.

We were less than prepared for this news. While each of us had spent time in nature, we were not the type of people who carried first-aid kids, went overnight camping, or knew what the hell you do when a bear decides to eat lunch on your path.

But this little snafu proved to be the medicine we needed. As the reality of dealing with a wild grizzly bear sunk in, the tension and quarreling dissipated. With our lives on the line, we had to drop the drama and start working as a team on a mission to survive.

We agreed that we could not turn back. That involved biking 10 miles (mostly uphill), and neither of us had the water supply or quads for such an endeavor. That meant we either had to convince the next bus to let us on or that we had to bike past the bear. The team preferred the bus option.

We had no cell phone service or knowledge about the bus schedules, so while we waited for another bus to come, we moved closer to the bear to observe him. He would get sick of eating berries and move on at some point, right? Well, apparently not. This guy went on munching for the better part of an hour, ignoring our pleas for him to move on.

A bus eventually came and we waved it down. The driver said he couldn’t take us onboard, so we asked him about biking past the bear. He said it wasn’t smart, but we could give it a go and see what happens. He wished us luck and kept driving. Thanks man.

To his credit, his cheeky answer was another gift. Given our ignorance about the situation, his lack of a hard no for going past the bear gave us the confidence we needed to try it out. Steph and I hugged each other, exchanged nervous glances, and agreed not to look the bear in the eyes.

With that, we began to peddle, quickly realizing that we were moving uphill into a fierce wind. Neither of us was moving more than a few miles an hour, but we weren’t turning back now. I reached the bear first and tried not to look at him, but he looked up for the first time and gave me a long stare. I looked at him and realized just how big bears are. 

My heart thumped a little faster as I prayed that he didn’t chase me down. I looked back to see that he now had his eyes on Steph. She had fallen back quite a bit, and it wasn’t until she was a couple hundred yards past the bear that I took a breath. Mr. Bear seemed unphased and resumed his adventures in Berrylandia. We both peddled hard for a half mile and finally stopped to discuss what had happened.

We laughed about how stupid we were and how helpless we would be if the bear came after us. But he didn’t, and it was nice to feel the rush of connection that comes from dicey moments. The quibbles of the past few days already seemed like they were from another part of our lives. All that mattered was that we were together and safe.

As we prepared for the last few miles of the journey, we caught our breath and passed an apple back and forth. Right as I handed the apple to Steph for the final bite, I saw something emerge from the woods about 50 yards away. It was moving fast and toward us.

Another grizzly, much bigger and more active than the other one. Oh boy.

My eyes bulged and I told Steph to come to me. A bear was walking toward us. She giggled and told me to stop joking until she looked back and froze in silence. I considered telling her to run, but she appeared unable to move her legs. My mind turned off as my instincts took over.

My arms raised high above my head and a series of tribal-sounding chants emerged from my mouth. I don’t know where these sounds came from or what they were, but I’m sure I could not make those noises again. Upon hearing these sounds, the bear immediately changed course. He made a hard right, darting into the woods on the other side of the road. My chants continued as I watched the trees closely. A bus driver pulled up thirty seconds later.

I pleaded for him to take us on the bus, and after deliberating for too long, he relented, helped us load our bikes, and cursed us for being dumb enough to bike through the park. The bears had become a lot more active with fewer people visiting Denali during the pandemic. Didn’t we know?

I had never been so happy to enter a hot, packed bus of chatty middle-aged tourists. As I sat down, the image of that bear walking toward us remained burned in my mind. Some passengers asked me what happened, but I was not ready to speak. Steph told the story while I remained in awe about the size of the grizzly, the sounds that came out of me, and our proximity to a violent death.

Let go or be dragged

When I’m surfing and the ocean holds me underwater, I often think of the Buddhist saying: “let go or be dragged.” It’s a reminder to let go of the desire to breathe, relax, and wait for the ocean to allow me to resurface. It always does. Over time, I’ve learned to shortcircuit my desire to fight the ocean. That’s an unwinnable battle that only makes the experience worse.

While I’ve learned to let go in the water, I sometimes forget to apply this idea to land life. 

The Alaska trip is a good example. I had an idea in my head about what our trip should be. The plan was to have the BEST TRIP EVER, and when reality deviated from those expectations, I resisted. And that resistance dragged me and Steph further away from enjoying our time.

But sometimes life has a few tricks in its book that force you to let go of your expectations. In our case, that trick came in the form of two Alaskan grizzlies. While neither bear did anything other than be a bear wandering around, the experience of being that close to and helpless against a bear in the wild put everything into perspective.

I don’t — and I doubt Steph does either — remember what we were even quibbling about at the start of the trip. Almost certainly something silly. 

But I do remember the joy and gratitude that bubbled to the surface after we came out unscathed from the encounters with the bears. The opportunity to continue enjoying this life and the experience of being together, even for one more day, felt like a gift.

After the bears, all expectations went out the window. I let go of all my ideas about the trip and simply lived out the experience of being in Alaska with someone I love and everything that came with it. And once I let go of the plans and expectations and started living more fully in the moment, one of the more magical and unexpected events of our relationship played out.

At the end of the first week of our trip, I woke up groggy and exhausted. We were supposed to go on an all-day trek up to a glacier, and I didn’t feel like going. I nearly bowed out until I thought about how those bears had given us a second chance to live more fully. So I got myself together, and Steph and I headed for the trek to the Harding Icefield.

After five hours of intense hiking, we reached a stunning view of a glacier that stretched for miles and looked like it belonged to some land other than Earth. As we sat down to enjoy some snacks, I surprised us both by taking out the ring that I had carried around for the last 9 months and asked Steph to marry me.

She said yes.

Some locals sensed love in the air and followed us to take pictures of the proposal.

Making sense of the experience

Looking back on the proposal, marriage, and many good times that followed, I can’t help but consider the role of those grizzlies.

I had no plans of proposing on that trip or on the day that it happened. Sure, I carried a ring, but I figured I might use it in the next 5 years if and when the moment felt right. Even 15 minutes before the proposal, the idea had not crossed my mind.

In my attempts to make sense of it all, I like to think about what John Lennon said In “Beautiful Boy (Darling Boy):” “Life is what happens to you while you’re busy making other plans.” 

I didn’t know what he meant until the Alaskan journey that led to an unplanned proposal. You see, it was the bears that allowed me to let go of my original plan and focus on simply being present with life as it unfolded. And paying attention to the full beauty of our experience together is what gave me the courage to take the leap with Steph at that glacier.

As I noodle on that experience now, it’s humbling to realize how the random unfolding of life leads us in directions that no plans can account for.

I mean, had we started biking 20 minutes earlier on that day in Denali, maybe we would not have seen any bears. Maybe we would have been killed by a bear. Maybe we would have continued quibbling and missed the chance to start over and take our relationship to the next level.

I can’t know for sure because you can never know the counterfactual. All you know is what happened, and the rest is conjecture.

What I do know now is that regardless of how it happened, the process of letting go is what allowed us to stop getting dragged during our vacation and to embrace the unpredictable twists and turns of the experience. We needed to chill and roll with it to allow the beautiful moments to emerge.

Zooming out beyond that trip, it’s clear that so many of the most important forks of life follow a similar path. There is some plan, and while I grasp onto it with all I have, the randomness of the world causes me to lose my grip and chart a new path.

Whether that randomness comes in the form of people, things, experiences, or bears that I did not forecast, these deviations all play a role in moving life in a new direction. Sometimes that direction is a good one; other times it isn’t. And often we don’t even know whether it’s good or bad until enough time has passed for us to connect the dots backward.

What I take from these experiences is that my desire for control over my life and the world is a fool’s errand. Life does not offer certainty or control, no matter how much we want it. There are no guarantees in this world. None. And when you begin to see that this is the fundamental, unalterable nature of life, you can learn to let go and surrender to the unknown.

I think this is what Lennon meant when he said, “life is what happens to you while you’re busy making other plans.” He was reminding us that life is fundamentally unpredictable and uncontrollable. No matter how diligent we are with our planning, intentions, and goals, there will be surprises that muck it all up.

That doesn’t mean that we shouldn’t try to plan or direct our lives, but it does mean that we should remain open to the flow of life that does not care about our plans. Or at the very least, we should recognize that life becomes easier and more enjoyable when we stop resisting.

To do otherwise is no different than fighting a wave that will hold you down as long as it wants. If you’ve ever found yourself in that situation, you understand that the wave is not what will kill you; it’s the panic and fear and grasping to get to the surface that does you in.

It’s only in learning to let go that we can finally be free to exist as we were meant to be.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

📑 I. Essay Worth Reading

I enjoyed “in praise of uselessness,” a short essay by Ava of Bookbear Express about our resistance to and relationship with doing things with no agenda. It’s a well-written, thoughtful piece that gets to the heart of something that I’ve been thinking about a lot over the last two years.

In some ways, Ava communicates a large part of what I hoped to express in last week’s essay: The Case for Being Less Serious. That said, I think her piece does a better job of getting to the heart of the matter in fewer (and better) words. I especially enjoyed her interesting and surprising conclusion.

🎥 II. A Documentary I Enjoyed

I watched Ethan Newberry’s documentary WHERE DREAMS GO TO DIE - Gary Robbins and The Barkley Marathons this week.

It’s a fascinating tale about a Canadian ultrarunner’s attempts to complete The Barkley, a 100+ mile race held in Frozen Head State Park in Tennessee that has been completed by only 17 humans in its multi-decade history.

I suppose the film could motivate you to push yourself harder physically, but I mostly found it insane that people feel compelled to attempt anything like this. Looks not fun and probably not that good for you. Still interesting though.

💰 III. A Tip for Tax Season

In my old age, I’m starting to see the wisdom in using Reddit to find interesting and practical solutions for various problems. While browsing r/coolguides this week, I stumbled upon this post about how to talk to a human at the IRS.

The post is 3 years old, but if it still works, it’s a neat hack for getting in touch with the IRS if you ever need to do that.

Honestly, I wish there were a website that had simple guides like this for talking to real humans quickly across banking, healthcare, telecom, airlines, and all the other areas where it’s easy to waste a lot of time tinkering around and waiting to solve your problem.

As a side note, the r/coolguides subreddit where this post lives is full of useful picture-based references like this and is worth browsing if you have some time. You can start by sorting for the top posts from the last year.

🍝 IV. A recipe I’m trying this week

Something switched in me recently, and I’ve started to enjoy experimenting in the kitchen 👨‍🍳. This week, I attempted to make my grandma’s eggplant parmesan and decided to add some meatballs on the side. The eggplant parm was decent, but the meatballs were nothing to write home about.

I’m sure there are many ways to make good meatballs, but this week, I’m going to try a recipe from my favorite “learn how to cook person,” Myles Snider.

Twitter tweet

Outside of specific recipes, Myles is a wonderful follow on Twitter for practical advice about how to improve your cooking with simple tips and changes.

I save a bunch of his tweets, and now that I’m in the kitchen more often, he is my go-to guide for learning how to make simple, healthy meals and have fun doing so.

🧠 V. Something I’m Thinking About

I was talking to a friend this week about how I’ve noticed that many people in my life squirm at any mention of the word God. I used to be one of these people, but certain experiences have shifted my thinking.

I told my friend that I was going to write an essay about this topic soon to see if I could understand the matter better, and he told me to read Tattoos on the Heart by Gregory Boyle. My friend — who is one of the squirmers I mentioned — said that the book gave him a more balanced view of what God can mean for the world.

I listened to the book on Audible to see what my friend was talking about. It was a short read with a bunch of joyful and heartbreaking stories from Boyles’s life as a Jesuit priest and founder of Homeboy Industries, a gange-intervention program in the LA area.

The book didn’t do much to further my concept of God, though it was clear how it might do that for someone who comes to the idea of God from a certain angle.

That said, I am walking away from the read with an enhanced view of what it means to live with compassion at the center of how you operate in the world.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, I wrote about how resisting the pull toward seriousness may be a useful idea to consider as you navigate this chapter of life.

You can find the full essay below, or you can read it on my website here.

🌻 The Case Against Being Serious

Made with Midjourney

Too many adults become serious people.

Serious about work. Serious about politics. Serious about mowing their lawns. Serious about everything!

I want to make a case against being so serious, but first, I must make a distinction. I have no qualms with people who take the act of living seriously. Life is brief, and I commend anyone who tries to make the most of their time.

The seriousness I’m talking about is different. It’s a pernicious form of seriousness that emerges the day you accept the myth that life has to get harder, busier, and less enjoyable with time. This seriousness is bad news. 

It’s a wet blanket on adulthood that suffocates the childlike looseness and curiosity that makes life worth living. And it’s the loss of that looseness and curiosity that worries me.

This worry comes from direct experience, so let’s begin there.

Serious dude to mellow bumpkin

If you met me today, you might be surprised to learn that I was once a very serious guy. It was the kind of seriousness that I now resist, but that made sense at the time.

You see, my early life was heavy. Or at least it felt that way. I had to escape poverty, and that felt like serious business. I didn’t see any room for error or games in that pursuit. I only had room for focused effort, hypervigilance, and prayers for a lucky break.

For the first 25 years of my life, I felt like I was climbing a mountain and could not stop to take a breath until I had basic financial freedom. My ongoing battle with poverty meant that I never fully relaxed. I had many wonderful times, but it’s now clear that there was a limit on my joy meter.

Once I had some cash in the bank, my situation changed. The cash didn’t solve everything, but it turned the pressure down. It was as if I reached a flat spot with a beautiful vista on my climb up the mountain. I finally had time to breathe and widen my focus. 

As I enjoyed the view, something (probably a self-help charlatan) told me to stop climbing the mountain. It was time to regroup and take a look at my inner world. I could always keep climbing later on if I needed to do so.

That decision to pause upended my life, sending me into a difficult process of unlearning, decompressing, and shifting my identity. While I didn’t know it at the time, I was learning to live without the ferocious focus and seriousness that directed my youth.

Little by little, my inner and outer world began to soften. I started laughing more, connecting with a wider group of people, enjoying simple moments, and perhaps most importantly, taking myself less seriously. Collectively, these changes made nearly everything about life more enjoyable.

By my 30th birthday, my orientation toward the world had shifted radically. I was open to the random unfolding of life and felt very little connection to my past. I no longer felt obligated to do anything other than show up fully. I was at ease.

This was a strange orientation to have, especially considering where I started. For a long time, a part of me resisted this shift. It felt indulgent and unserious and like I was heading down a lame path. But at some point, the perpetually striving part of my serious self faded away and transformed into a silly curiosity that felt like enough on its own.

The other strange part of this transition away from seriousness is that I was moving in the opposite direction from many of my friends. As I started feeling more like a kid discovering the world for the first time, friends seemed to gravitate towards the more rigid and responsibility-focused idea of adulthood that everyone is always talking about.

But my own meandering experience was enough to convince me that not only is it possible to avoid the pull toward seriousness with age, but that it can be a rewarding shift if you can find a way to make it work. And that’s the next part of the equation: how does this type of loosening coexist with the unavoidable responsibilities of adulthood over time?

Can you stay loose?

These days, a lot of friends ask me when I’ll stop living like a kid and start being a real adult again. Embedded within the question is the idea that living in this way simply cannot last. At some point, one has to become serious again. Or so they seem to think.

But my answer for the moment is always the same: so far it’s working, and I don’t know if or when that will change. Why shake up a formula that’s working?

I think this question comes up a lot because it’s not immediately obvious how a loose orientation toward the world is compatible with the real and serious business of adulthood: paying the bills, working toward goals, taking care of kids, being a good partner, trying to do good in the world, and so on.

But even though it’s not obvious, it’s certainly possible. I still lead a fairly normal life where bills get paid, necessary work gets done, and responsibilities are taken care of. The difference is just in the spotlight that I put on certain areas of life.

I spend most of my days chasing waves, exchanging small talk with strangers, and avoiding self-created stress and striving. Practically speaking, that means that previous areas of focus like increasing my net worth, moving up the career ladder, and maximizing my potential have taken a lower priority.

Now, an open question is whether or not this reorientation of priorities is good for the long term. It’s certainly possible that I’m on a path that will leave me with deathbed regrets.

But while it’s possible, it doesn’t feel likely.

One guidepost I use to think about whether this path has legs is thinking about what I’ve valued most in my 31 years of life. I’m not old, but three decades of life is enough data to get a sense of what worked and what didn’t work.

And when I think about my life in those terms, what I’m most proud of are the times when I stopped striving, pulled out a big floaty, and waded down the river of life.

The moments where I had one too many drinks and lots of giggles about nonsense with friends and strangers. The endless days I’ve spent checking surf reports and flapping around the ocean. The years I’ve spent traveling without purpose and reading books. These are the moments I cherish.

Before I leaned into the looseness, the moments I cherished looked quite different. I was proud of getting into a great university, making a good living, solving problems, building systems at startups, and other classic markers of achievement. Those pursuits now feel like they were done by some other person and are no longer interesting to me.

With time, they seem more like means to an end than a representation of my life or who I am. They were mechanisms for enabling the freedom I now have to enjoy a simpler existence. And to my surprise, that simpler existence seems closer to what I want and more satisfying than my younger self would have guessed. At least for now.

As to how these ideas hold up or change over time, I have no idea. Given the magnitude of shifts in thinking and values over the last decade, I can only imagine that similar unpredictable shifts will happen over the coming years.

A thought experiment for you

By this point, I think you have a sense of why I’m in favor of taking a less serious approach than is considered normal for adulthood. And while I’ve shared my path to this conclusion, I’d like to explore how this idea of resisting the pull toward seriousness could be useful for you. Or at the very least, I’d like you to consider what rejiggering the balance between seriousness and play looks like throughout your life.

To do so, let’s imagine that you’re accompanied by a two-year-old child on a morning walk.

While you lock the front door, you hear the child cry out with joy. She’s pointing at a beautiful yellow flower near the garden. Before you get to the end of the driveway, she’s giggling at a squirrel eating a nut at the base of an oak tree. As you walk down the street, she grabs your leg firmly as she sees a cat emerge from under a car.

The entire walk is like this. Pure discovery and presence.

Now imagine that you took the same walk without the child. What would you see and think about on your walk?

If you’re in the mode of being a serious adult, perhaps by the time you get to the end of the driveway, you may have seen some weeds that need to be pulled or bird poop on the car that needs cleaning.  You may also be thinking about the many things that you have to do today.

You throw in Airpods, queue up a podcast, and go on walking to avoid further irritation.

This is a bit of a silly example, but do you see the point?

During your solo walk, you’re thinking about adult stuff. The things you need to do, the problems you need to solve, and so on. Maybe you’re thinking about good stuff too like an awesome date you had or how you’re stoked about a new promotion. It doesn’t matter.

The point is that you’re likely lost in some story in your head. You’re not in the moment, and you’re missing all of the wonderful stuff of life — the sunflower, the squirrel, and everything else the child notices. And maybe those seem like trivial observations, but I think being a person who can notice that type of thing enhances nearly every area of life.

The child is the opposite of most adults. She is not lost in some story about what her life is or what it needs to be. She’s simply living, fully present with the seemingly infinite novelty, joy, and pain that exist when you’re experiencing the world for the first time.

If there is any takeaway from this essay, it’s that you can (and may benefit from) seeing the world more like the child. Instead of being engrossed in the incessant dialogue of the adult mind, try to see the world with fresh eyes. Even if you can do it only once a week, that’s better than nothing.

The philosopher Jiddu Krishnamurti once said, “The day you teach the child the name of the bird, the child will never see that bird again.”

Krishnamurti gets to the core of my quibbles with allowing yourself to become too serious. As you navigate life, the tendency is to start to think you understand and know things. You develop ideas, names, and concepts for all that you encounter. You see a tree and it’s not interesting because it’s just a tree and who cares? You have plans, goals, and ambitions to get to. Nonsense!

You don’t need to lose your childlike curiosity as you age. And remaining loose doesn’t mean that you have to be enamored by every tree you see. But what if you could nudge yourself toward being a person who can appreciate small pleasures like a beautiful tree or a cool breeze on a sunny morning?

What might a subtle shift like that do for your life?

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

Happy New Year to everyone who celebrates. 🙃

📖 I. Book I’m re-reading

To kick off 2024 in style, I’m reading Awareness by Anthony de Mello for the third time. This short book is certified nourishment for the soul that has helped me think more clearly and productively about myself and the world. Check out my notes from the first read to get a preview.

If you decide to read it, my advice is to commit to getting through at least half of the book. It takes some time to warm up to the weird style and tone, but if you can get over the hump that flattens about 25 percent in, there’s a lot of gold that may help you see yourself and the world in life-enhancing ways.

🍷 II. Bukowski on Writing, Creativity, and Living 

If you’ve been around for a while, it will be no surprise that I’ve become a little bit of a Charles Bukowski fan. The work that hooked me on Bukowski is On Writing, a posthumously published collection of letters that Bukowski wrote to publishers, agents, writers, and friends from 1945 to 1993.

This week, I collected everything I found interesting from that book and wrote about what we can learn from Bukowski about writing, art, and life. If you’re curious, you can read the full piece here:

Charles Bukowski on Writing, Creativity, and Living Fully

P.S. This piece is an extension of a podcast Steph and I recorded last year about Bukowski and his unconventional approach to creating.

✍️ III. Books for Writers

I fancy myself a writer, and over the years, I’ve become a little bit of a junkie for books about the craft of writing and the pangs and joys of the writer’s life.

While these types of books can be a sneaky form of procrastination that stops you from actually sitting down and putting words on the blank page, I still think that they have value. Not only can they help you learn the nuances of the craft and overcome blocks, but they can also make you feel understood.

And because writing can be a difficult and lonely pursuit, feeling understood by the likes of other writers is a nice bonus on top of any practical knowledge you absorb.

Anyways, if you write or love procrastinating by reading about writing, I put together a short list of my favorite books about writing and creativity here:

12 Essential Books for Writers

P.S. If you read these types of books, I think it’s best to read widely and then select the 3-5 books that you find most helpful. Then when you feel stuck, re-read your favorite books or revisit your highlights instead of seeking out new books. This approach can help you avoid the trap of constantly looking for more information to solve whatever problem you’re facing.

🧠 IV. Something I’m Thinking About

Twitter tweet

2024 is here and you may have been thinking about the many different changes you want to make and goals you want to pursue.

In previous years, I’ve shared a structured goal-setting framework that I used for nearly a decade to direct my life. That methodology served its purpose, but these days, structured approaches to life satisfaction no longer resonate.

While I have not abandoned goal setting entirely, I am no longer trying to optimize all of the areas of my life with OKRs, frameworks, and tracking. In the place of structure, I’ve adopted a more fluid approach to living.

In part, this fluid approach now works because I have a good sense of what I want and enjoy after experimenting a lot over the last decade. And now that I spend most of my days doing stuff I enjoy, my life feels pretty complete by just leaning into those areas. For me, that roughly maps to goals that look like:

• Improve as a surfer

• Increase creative output

• Spend time with people I love

These broad objectives inform the overall structure of my life, including the work I do, my health routines, where I travel, etc. And at least for now, this simple orientation is “enough.” Perhaps that will change at some point.

So today and for the rest of this year, my challenge to you is to consider spending more time on activities you enjoy. Forget about maximizing productivity, money, spirituality, or health for a minute and think about what your life would look like if you focused on stuff that lights you up.

Of course, we all need to pay the bills, take care of responsibilities, and so on. Adulthood isn’t all fun and games. But perhaps your life could feel more like fun and games than you imagine or than you’ve experienced so far. I’m not sure.

And if you decide to tinker with this fluid approach to living, you may realize that you don’t know what you like. That’s normal and has a simple solution: experiment a bunch.

Try five new things every month and pay attention to where your energy flows. Double down on the good stuff; drop the bad and “meh” stuff. See if you can find a hobby, pursuit of mastery, or people who make your life more enjoyable.

Or if all of this sounds like woo woo childlike nonsense, stick to being a serious person with serious goals and serious focus. That can work too. Just depends on what you want and where you’re at in life.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends, and welcome back to Life Reimagined, a free weekly elixir designed to make your life more enjoyable.

Greetings from Nosara, Costa Rica. I’ve spent the last week with my laptop closed enjoying warm water surfing and sunshine ahead of the holidays.

With 2023 coming to an end, I wanted to share some of the highlights and best stuff I encountered this year across work, life, books, and more.

This will be the final newsletter of the year. I’ll be back in your inbox on January 7th. I hope you have an enjoyable and relaxing time over the holidays :).

✍️ The Blog, Essays, Podcasts, and Newsletters

I started calvinrosser.com and this newsletter 7 years ago as part of a mission to help 10 million people live a more fulfilling life. It still feels like the beginning days of what I hope to be a lifelong path of sharing ideas that nudge all of us toward more enjoyable lives. A few encouraging numbers from 2023:

• 881,213 people read the blog this year (vs. 606,458 in 2022).

• 7,500 people actively read this newsletter (vs 4,200 at the start of the year).

• Since 2020, I’ve awarded scholarships to 50+ students and helped 200+ other people create scholarships for causes they care most about.

I published four new essays this year:

• What Do You Want?

• Calvinball: The Only Game Worth Playing

• The Day I Heard the Birds Sing

• How to Make Friends as an Adult

I also published dozens of newsletters and new podcasts this year.

• You can browse an archive of the last 57 newsletters here.

• You can find all of the Sh*t You Don’t Learn podcast episodes here.

The most rewarding part of the blog and newsletter continues to be the hundreds of kind emails I receive every year from people around the world who take the time to share their thoughts on my musings.

I’m still surprised and excited by how sharing thoughts on the internet can lead to exchanges with strangers that deepen my thinking, create new friendships, and highlight the kindness and generosity of the human spirit.

In 2024, I’m planning on writing more essays than I have in the past few years and sharpening my software development chops so that I can expand my work in useful (and hopefully) more interesting ways.

Finally, if you’ve ever considered sharing your work publicly via a blog, newsletter, or social media, I’d encourage you to do so. It leads you down many very interesting roads that can enrich your life, even if it remains a silly thing you do on nights and weekends.

As far as I know, the best way to get started is to simply start and see where your explorations and interests take you. Don’t overthink it or come up with grand plans. Creating online is not a linear or predictable path. If it was, it wouldn’t be all that fun.

And if you want more tactical advice, particularly about how to think about what to write and how to reach people, I recommend checking out Doing Content Right, a phenomenal book written by my wife Steph Smith.

🧑‍🎨 Other People’s Work

Books

I finished 30 books this year and started but didn’t finish dozens more. Here are some of my favorite reads from this year.

• Harry Potter Series: In 11 reading-packed days this April, I read the Harry Potter series. As a kid, I loved these books, but never made it to the seventh one. So I started from scratch this year and had a lot of fun getting to the epic conclusion.

• Charles Bukowski’s work: The poet/writer Charles Bukowski captured my interest this year. I read Post Office in the spring, On Writing later in the year, then Ham on Rye, and concluded with a collection of his poetry. Bukowski is an odd and complicated character, but his work inspired me to get a typewriter and write the poetry that I’ve shared in this newsletter of late. Steph and I also recorded a podcast about Bukowski’s philosophy on writing and creativity.

• I devoured many memoirs this year. A Year in Provence (Mayle), One Blade of Grass (Shukman), and Do Travel Writers Go to Hell? (Kohnstamm) were some of my favorites.

• Shantaram (Roberts) was my top audiobook of the year. I also enjoyed Among the Thugs (Buford).

• Quarantine (Egan) was a mind-bending and very enjoyable sci-fi book.

• In the self-help domain, I enjoyed Wild Mind (Golberg), Tiny Beautiful Things (Strayed), and How to Get Rich (Dennis).

Essays

• The Cab Ride I'll Never Forget. Simple zen story

• Welcome to Holland. A story about surprises in life

• The Midlife Unraveling. Essay about midlife.

• What Makes You Happy. Power of expectations.

• If You Have Writer's Block, Maybe You Should Stop Lying

Movies and Series

• Tetris

• About Time

• The Marvelous Mrs. Maisel

• The Ying and Yang of Gerry Lopez

• Force Majeure

• Drops of God

• The White Lotus

New Podcasts

• The Witch Trials of J.K. Rowling. Why I liked it here.

• Tetragrammaton with Rick Rubin. Start with the Jack Johnson episode. Pair with Rubin’s book, The Creative Act, if you dig his vibe.

• How I Write by David Perell. Good for digital creators.

• In Depth - A Surfing Podcast. Mindset work for surfers.

P.S. It’s rare that I find a tweet that I think could change someone’s life, but Erik Newton’s story about his wife’s death is a beautiful one that is a particularly helpful message ahead of the holidays.

The holidays can be complicated. You may see or be around friends and family with whom you have longstanding quibbles or frustrations. Or you may be around people you love but who you don’t always appreciate.

Either way, read Erik’s story. Don’t forget to savor the time you have with the people in your life. Life is short, death is certain, and as Erik shares so beautifully, learning to love more fully is the antidote to this human conundrum.

Twitter tweet

🌊 Experiences

San Francisco. My wife and I moved from Encinitas to San Francisco this year. We talk about why we moved and how we chose SF here. Despite being uncertain about whether we would like SF, the move had a profoundly positive impact on our daily satisfaction. The main boon to happiness came from a wider and deeper community of friends in the city, and one of the key (and obvious) learnings from 2023 is that living near a higher density of friends makes everything in life better. As someone who spent most of his 20s as a nomad bopping around the world, this lesson was not yet obvious to me. But now I believe that it’s worthwhile to trade on surface-level things like climate, taxes, and so on to be near people who you want to be around.

Surfing. Surfing has been the primary domain for my ambition over the last few years, and this year, my interest in the sport deepened even more. I surfed 160+ times and took trips to France, Spain, Tofino, Mexico, and Costa Rica to explore new waves. Nomading in my 20s had burned me out on travel, but taking trips around the world to explore waves and new areas has reawakened my desire to continue exploring the world through this new lens. I can’t wait to see where this silly sport takes me next year.

David Whyte walking tour: David Whyte is one of my favorite poet/writers, and this year, I joined him and 30 other people on a week-long walking tour in the English Lakes District. The theme of the trip was “setting direction for a future life.” We explored that theme via daily poetry teachings, beautiful hikes, and conversation over good food with an impressively thoughtful group of people. Outside of being a fulfilling direct experience that birthed new friendships, the trip led to a creative spark that resulted in new essays and poetry.

Spas. I enjoy finding new ways to heal and nurture the body. This year, that interest took me to many spas, which included Ojo Caliente in Taos, Russian baths in New York, and Japanese spas in SF. I’m now visiting baths and doing cycles of sauna and cold therapy once a week. It’s particularly helpful on weeks when I’m doing heavy amounts of surfing.

Used bookstores: I experimented with buying only used books for 3 months this year. That experiment led me to explore and get hooked on the many wonderful used bookstores around the world. I’m now pretty much only shopping at these stores.

🎧 Products, Services, and Routines

Foundations training: This 12-minute routine, done twice a week, has helped me alleviate the acute and chronic back pain that has plagued me since my late teens. It’s been life-changing for helping my body manage all that I ask of it.

Typewriter: After immersing myself in the world of Charles Bukowski, I sought out a typewriter. I ended up finding a kind man in Oakland who spent 6 hours with me over two sessions to find a typewriter I enjoyed. And that typewriter has allowed me to explore new ways of creating, including poetry, letters to friends, and more. I love it and already feel like my 1945 Smith Corona is one of those possessions that I’ll want to hold onto forever.

Slim profile pillow. I got rid of all sleeping-related neck pain by shifting to this slim pillow. I tried a dozen pillows, and this was one of the cheapest and least fancy ones, but for some reason, it worked for the shape of my neck and sleeping posture. I like it so much that I bring it on travels or send one to wherever I’m going.

Butcher Box: Butcher Box is a meat subscription service that sends you a big box of various cuts of meat. I get a box every 2 months and put most of the meat in my freezer. And instead of having to go to the grocery store for meat, I can just pull something out of the freezer. Alongside using ChatGPT as a sous-chef, it’s encouraged me to cook more and order out less.

Balance pad: I have tight hip flexors that cause my lower back to seize up if I don’t stretch them daily. So a couple of times a day, I do the Couch Stretch on a wall while placing my knee on this balance pad. I think you can use the pad for other things, but I love it for this daily stretch. You can also use a pillow instead of the pad.

Bose 700 Headphones: I’m enjoying these Bose noise-canceling headphones. If I want to grind, they help me dive into my inner world with some chill indie rock music. They’re also nice on planes and if I want to go deep into a nap with binaural beats. I’m sure there are “better” headphones, but these are perfect for me. I’m using them now as I write this!

That's it for this year. See you in 2024! 🥳

— Cal

If you liked this piece, make sure to subscribe by adding your email below!

🌎 Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

The holidays are sneaking up on us so it’s time to start resting, reflecting, and enjoying the many contours of this odd time of the year.

Next week, look out for my final post of the year: The Best of 2023. I’ll share all of the best stuff I discovered this year before taking a couple of weeks off.

📰 I. No One Owes You Anything

In the wake of a divorce during which he lost custody of his 9-year-old daughter, the American writer, investor, and politician Harry Browne wrote a newspaper column that was published on Christmas of 1966.

Browne’s column is his Christmas gift to his daughter. Instead of a traditional holiday present, he shares advice that he hopes will endure beyond the holiday season.

The core message of the article (which you can find below) is that your life will be better if you accept that no one owes you anything.

I have mixed feelings about the article. On the positive side, I think Browne’s core message is useful advice for many people. If you can find a way to navigate the world without expecting much from other people, you can avoid common frustrations and take more ownership of your life.

I also like the idea of giving a timeless holiday present, something that has the potential to endure much longer than most of the gifts that we give.

However, as I read the letter and nodded along with some of the advice, I couldn’t help but think: this is a weird piece of advice to give to a young girl who is adjusting to a newly broken family and the absence of her father.

While believing that no one owes you anything may be helpful, I’m not sure if that advice should come from a parent to a young child. In some ways, the implication is that your parent does not feel that they owe you anything.

Overall, my noodling on Browne’s advice and the context behind it led me to two conclusions:

1. It’s useful for me to believe that no one owes me anything.

2. As it relates to other people, I prefer to believe that I owe them something.

Whether it’s with family, friends, or strangers, I find it helpful to believe that I owe them kindness, respect, integrity, generosity, and other foundational values that I use as a guide for how I operate in the world.

Believing that I owe these things, even when other people may not give me them in return, allows me to be more of the person I would like to be than if I simply acted on my selfish impulses.

As with all life advice, there are rarely right answers. I’ll leave you with Browne’s letter in the event you want to form your own conclusions.

📈 II. Do you need to live up to your potential?

I’ve been wondering if the well-intentioned idea of "living up to your potential," which sits in the hearts and minds of most smart and ambitious people, has done more harm than good.

On one hand, this idea motivates you to be and do more than you may have originally thought you could. It encourages you to become the best version of yourself, which is generally a good motivation.

But on the other hand, the idea encourages you to strive for some future state that does not exist. You were not born to maximize your potential, nor is there any real measurement for having done so. It's an abstract idea that can never really be achieved.

And if you continue to berate yourself internally to push harder so that you have maximized your potential and not squandered your life, you're going to be plagued by a low-grade anxiety that prevents you from ever living fully.

You'll never feel that you have done enough, and this will keep you trapped in the cycle of trading away more of today for a future you who will probably just keep moving the yardstick.

A lot of truly wonderful and accomplished people I know are stuck in this dilemma and really don't seem to appreciate that they're already a very solid and commendable version of themselves.

There's no problem with trying to improve or achieve more in different domains, but I often wonder if people would be more satisfied in day-to-day life if they simply let go of the notion that they exist to maximize their potential.

The utility of this process of letting go is contingent upon where you are in your life, but at least for some subset of people, I think it would enhance their experience of life without too much downside.

P.S. If you have thoughts on this topic, you can join the conversation on Twitter.

😒 III. Pesky Colleagues

Getting a break from work is one of the best parts of the holidays, especially if your job or someone you work with has been getting on your nerves.

But before that break and period of rest arrives, enjoy this silly Comedy Central skit that taps into one of the funny dynamics of working with other people.

Twitter tweet

🧠 IV. Something I’m Thinking About

In his new book, Same As Ever: A Guide to What Never Changes, writer Morgan Housel discusses why it’s often so difficult for us to appreciate progress.

One reason bad news gets more attention than progress is because it’s more visible. You get more eyeballs if you report on the tragic death of 10 people than talking about the millions of people who didn’t die because of specific innovations over the last 50 years. One story is visible; the other is abstract.

Another reason that progress is difficult to feel is because it happens more slowly than destruction. While bad events can happen overnight, progress is often a slow, almost imperceptible march up a hill.

If something is getting 1% better every year, it will compound to enormous improvements over 50 years. But in any given year, it’s hard to feel that 1% improvement, and is easy to discount how wonderful things may be if things keep improving a little bit every year.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, we’re going to talk about stories of suffering, art, death, and what it means to live in a world that you will never fully understand.

📚 I. Book I’m Reading

I’m reading Survival In Auschwitz, Primo Levi’s vivid account of his experience in the Auschwitz concentration camp. In addition to detailing the horrors that he and others endured, Levi discusses the implications of this unimaginable suffering for individuals and society at large.

Suffering in Auschwitz reminds me of the first half of Viktor Frankl’s Man’s Search for Meaning, a book that I first read in my early 20s and that had a profound and enduring impact on how I view the world.

If you’ve never read direct accounts of people who experienced the concentration camps, consider making one of these books your next read.

These stories will give you perspective on your own life and remind you of the importance of never allowing this type of suffering to happen again.

🦿 II. Burning Man Art Archive

Burning Man has a mixed reputation. Some people think that it’s the best place on earth; others think that it’s a hedonistic festival for privileged druggies.

Regardless of what you think about the event, one thing that’s difficult to dispute is that Burning Man has some of the coolest art in the world.

Every year, people band together to create large art installations that communicate the experience of being human, raise awareness for important social and political issues, and speak to the collective consciousness of the tens of thousands of people who venture to the Nevada desert for the event.

Every time I leave Burning Man, I’m sad that more people don’t get to experience the art. I always assumed that you have to go to the event to experience the art, but then this week, I discovered that there is a catalog with pictures and descriptions of all of the Burning Man art going back to 1992!

Of course, looking at pictures is not a replacement for the in-person experience, but it does give you a sense of what you may discover if you go.

And even if the art doesn’t inspire you to head to Burning Man, it may generate some ideas for your work or be a fun way to spend a few hours on the internet.

If you’re interested, you can see the full catalog here: Burning Man Art Archive.

Burning Man art created with Midjourney.

⚰️ III. Mortality Calculator

For as long as I can remember, I’ve thought about my own mortality. On most days, I think about death at least a few times. Some people think that’s sad or weird, but I honestly think it’s been a positive force in my life.

Regularly remembering that I and the people around me will die has allowed me to be more patient with my family, give more of my presence to friends, make “risky” career moves, forgive myself for mistakes, and operate in a way where I’m never trading too much of today for tomorrow.

In a sense, the knowledge that I’m not here forever has helped me spend my days in better alignment with how I actually want to live. I don’t think you need to think about death as much as I do to be a good director of your life, but I do think that actively considering your mortality from time to time can be helpful.

There are many ways to introduce more mortality consciousness into your life, but one of the easier entry points is to spend a few minutes on Population.io, a tool that uses actuarial tables to help you understand how much time you may have left. Hat tip to Kevin Kelly for recommending the tool.

After entering a few data points on the site, I learned that:

• On average, I’ll live for another 53 year

• 49% of the world population is younger than me

• My chance of dying in a given year is 10%+ starting at age 55

I came away feeling like I’m definitely not young anymore, but that I still have a good amount of time to experience more of what the world has to offer. And as I considered the statistical risk of dying over time, I felt motivated to continue front-loading the things I still want to do while I’m still around to do them.

This tool is obviously rudimentary and cannot tell you when you’ll actually die, but it’s still useful in giving you a sense of how much time you have left. And I think that even seeing the estimated number of years you have left may help you think more productively about how you want to spend that time.

🧠 IV. Something I’m Thinking About

I’ve spent a lot of my life trying to understand myself, others, and the world.

And while I’ve had glimpses of insight that make me feel that I know more about what this whole thing is all about, in recent years, I’ve come to believe that the answers to life’s mysteries are behind the grasp of humans.

We may have moments of understanding, but they inevitably fade into the muddy waters of the complex and ineffable nature of existence.

And it’s with this idea in mind that I wrote the poem below.

“this moment”

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

If you find yourself with friends and family this week, try to slow down and cherish those moments. You never know how much more of that time you’ll get.

🏄‍♂️ I. Wave Pools

In the 1870s, Ludwig II of Bavaria, “the Mad King,” built the Venus Grotto, an underground aquatic park featuring an electrified lake with breaking waves that soothed the king’s weary soul. This was perhaps the world’s first wave pool.

Midjourney rendition of Ludwig II chilling at the Venus Grotto

Since the time of the Venus Grotto, surfers, engineers, and other nerds have teamed up to polish the Mad King’s idea of producing breaking waves outside of the ocean. Today, there are around 20 surfable wave pools around the world.

A wave pool is basically a swimming pool that uses some mechanism to move energy through the water in ways that create waves like you would find in the ocean. Surfers flock to these artificial waves to hone their skills and surf in places far from the sea.

Last week, I headed to Waco, Texas to try my first wave pool.

My thesis for the trip was that I could accelerate my surfing skills dramatically by paying to ride a perfect wave and avoiding all of the other variables you have to worry about in the ocean — wind, swells, sea life, aggro surfers, and so on.

I only had four hours in the wave pool, but that was plenty of time to confirm the thesis. Every hour in the pool, I had about 15 perfectly shaped waves. I’m working on sharper turns, so that’s what I focused on during the sessions.

But you could use these waves to practice popping up, generating speed, or barrel riding. It’s a neat and efficient way to progress.

Me riding a left at Waco Surf

The main value of the experience is that, unlike the ocean, you’re guaranteed a high number of good waves per hour. That means that you get a lot more time to practice the board-riding part of surfing than you do in the ocean.

On the whole, the Waco wave pool experience was both fun and helpful. Not only did I have the conditions I needed to practice specific skills, but I was surrounded by other surf-obsessed souls who had the same excitement and enthusiasm for the sport.

While I plan to return to Waco and visit other wave pools, I also came away with two ideas about the limitations of these artificial experiences.

1. It’s not a substitute for learning to surf in the ocean. While wave pools can help you learn how to pop up on a board, do turns, and try different maneuvers, they can’t teach you other important parts of surfing.

If you only spent time in a wave pool, you wouldn’t know how to assess ocean and wind conditions, read waves, navigate lineups, deal with the dynamic and unpredicted nature of the ocean, control your breathing during hold-downs, and so on.

And while those are not the sexy parts of surfing, they make up about 95% of the sport. If you’re lucky, 5% of your time is spent on the board.

2. Wave pools take away surfing’s best feature. When you begin to surf, you think you’re just shredding on a board and having fun. But as you enter the ocean time and time again, you begin to see that the sport is actually a pathway for introspection, spirituality, healing, and transformation.

That may sound dramatic, but it’s true. For people who find themselves on the surfer’s path, which is most beautifully captured in William Finnegan’s Barbarian Days, the ocean becomes something more than a playground.

The ocean, in all of its variability, power, and vastness, becomes a surfer’s greatest teacher. Simply being in its presence feels like encountering the divine itself, and as you try to harness some of this divine energy to have fun on a board, many unexpected inner and outer changes emerge.

A wave pool misses this part of surfing, and if you’re crazy enough to spend a large part of your life chasing waves, it really is the best part. So while I plan to return to these wave pools to improve my craft, I’m coming away with an even deeper appreciation for my greatest teacher at the moment: the ocean.

P.S. From a business perspective, I think wave pools are still early in the innovation cycle and that there will be hundreds more created over the next few decades. One developer in Florida, for example, plans to create a few dozen wave pools across the country.

The developer’s thesis is that these pools could help make surfing an NCAA-sanctioned sport by creating places to host competitions and for land-locked people to surf. Given that surfing entered the Olympics for the first time in 2020 and continues to grow in popularity, this idea makes sense.

TBD on how this unfolds over time, but there is one thing that is guaranteed: these commercially-driven attempts to bring surfing to more people will be resisted by the droves of surfers who feel that the sport is already overrun with too many kooks.

🎞️ II. “the black-and-white photo”

I wrote a poem about an old photo that I pass on most days.

🧠 III. Something I’m Thinking About

Deep suffering is the primary catalyst for spiritual transformation.

That suffering comes in many forms: dissatisfaction in your work, watching a loved one battle a terminal illness, or a personal war with the darkness.

When the suffering cuts deep enough, it can lead you toward unexpected and uncertain paths that deviate from all that you expected life to be.

These times of transition are often scary, but if you learn to trust them, I believe you’re likely to end up closer to wherever it is that you need to go.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

This week, we’ll reflect on how life evolves in random ways, two cool artists, and a film that will remind you to focus on what matters.

🏨 I. The Bellman

I spent 10 days in New York City in October. The Big Apple is the first place I lived after college, and while I had returned a dozen times since moving away in 2016, this trip felt different.

I was now entirely untethered from my former life as a young lad taking on the world of investment banking. In fact, I had drifted so far away from the person I had been that it was hard to imagine that I had ever been that person.

When I got home to San Francisco, I sat at my typewriter and tried to make sense of my fun and reflective return to the city. “The bellman” is what emerged.

“the bellman”

👨‍🎨 II. Meet the Typewriter Artist

I’ve been sharing my love of the typewriter over the last couple of months and recently stumbled upon a guy who’s doing something pretty cool with typewriters.

James Cook, the “Typewriter Artist,” creates pictures of celebrities, nature, cities, and more with his collection of over 60 typewriters. In this video, for example, he creates a skyline in London with a 1970s typewriter.

His Instagram gives you a good flavor of what he’s been creating over the last decade, and his website is a fun rabbit hole to go down to learn more.

I have no idea how much James has earned from his typewritten art, but it seems like he has gained enough traction to make a full-time living from his creations.

James is a good example of how following your interests and mastering a craft can lead you to make a living doing something that falls outside the default path.

🐋 III. Film I Enjoyed

The Whale is a fantastic movie about an overweight writer who attempts to reconnect with his estranged daughter during his last few days of life. It’s an emotional rollercoaster that tore me to pieces.

My main takeaway from the film is that at the end of our lives, most of us simply want to feel that we did some good in the world. That good could be the friendships we had, the children we raised, the companies we built, or the strangers we helped.

In the buzz of busyness that permeates daily life, it’s easy to lose sight of these few things that will matter to us as we take our final breath. And in many ways, I think the central task of life is to find a way to see through the noise and find the courage to commit yourself to what really matters to you.

👩🏻‍🎨 IV. Yayoi Kusama

As I shared earlier this year, I discovered Yayoi Kusama’s brilliant art at the Guggenheim Museum in Bilbao, Spain. That experience led me to watch this documentary about Yayoi’s life. Steph and I then recorded a podcast about Yayoi’s life, philosophy, and work. I guess you can say I’m a fan!

Then last week, Steph and I had a chance to see the new Yayoi Kusama Infinite Love exhibit at the San Francisco Museum of Modern Art. If you’re in the Bay Area or visiting during the next year, I recommend checking it out. We had to book tickets a month in advance, so plan ahead.

If you’re familiar with Yayoi’s work, you’ll know that she likes pumpkins. I didn’t know why until I saw this quote at the exhibit. I can’t say that pumpkins have ever spoken to me in this way, but it’s always interesting to learn about the things that inspire the artists and people you admire.

Steph and I at the big pumpkin in the SF MOMA

🧠 V. Something I’m Thinking About

In their pursuit of earning, saving, and investing more, many people forget that the highest value of money is not to maximize the number in their net worth spreadsheet.

The best way to use money is to gain control over your time and to use that time on the people, activities, and random things that bring you joy.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

It’s obvious that friendship is essential to a life well-lived, yet many of us struggle to maintain a vibrant social life as adults.

This week, I wrote an essay with some ideas and techniques that have helped me make and keep friends as an adult. My hope is that some of these ideas will also be useful for you, regardless of your age or the current state of your social life.

I’ve included the full essay below, and you can also read it here.

🚶 I. How to Make Friends as an Adult

I noticed something interesting recently. Over the last decade, more and more people have been searching for “how to make friends as an adult” on Google.

I don’t know why this is happening, and I’m not here to play the blame game. Adults want more friends and need real answers, not another dissertation about the root causes of adult loneliness.

Below, I share a few ideas and techniques that have helped me build a socially vibrant life as an adult. Not everything that has helped me will help you, but I suspect that some of it will.

Okay, you get it. Let’s get to the good stuff so you can stop listening to a stranger on the internet and find more friends to share life with.

Don’t be a hermit

We played a game called “hermit” in my fraternity. If you were asked (forced) to play, you had to grab six beers, sit in a corner of the room, and stare at the wall in silence until you finished your beers. Hermit is a great game for getting drunk, but no one makes friends playing the game.

Making friends in adulthood follows a similar dynamic. Friendship is built on shared experience, and you can’t have that shared experience if you play the adult version of hermit, which is to stay at home, DoorDash your ice cream, and watch Friends for the fourth time.

So if you’re serious about making more friends, pick up a sharpie and write “I WILL NOT BE A HERMIT” on your bathroom mirror. Then, go out into the world in whatever ways you can manage.

Work from the same cafe for a week and practice chatting with the baristas. Say hello to people at the dog park. Say yes to any invitations you get. Do anything but sit in your house expecting that people will knock on your door and cure your loneliness. No one is coming to save you.

Now that you’re motivated to leave the house, let’s talk about how to be with people.

Don’t be dull

You’re a weirdo. I’m a weirdo. We’re all weirdos. Not weirdos in a creepy way, but people with beating hearts and blushing faces and eccentric beliefs and interests.

Don’t hide your quirks from people. Tell a stranger that you think Bukowski is a beast of a man, but that his poetry makes your blood pump. Let a colleague know that you want to open a food truck that serves pupusas and peanut butter pie. Don’t settle for dull, surface-level talk.

Sharing what makes you tick helps you in three ways. The first is that you can exist in the world as YOU, not some shell of a person who walks through life afraid to be who they are. The second is that you find kindred spirits. And third, sharing your interests makes you more interesting, and being interesting is worth at least 25 likeability points.

But Calvin, what if people think I’m weird? You’re going to have to get over that. Some people will think you’re weird, but who cares? We’re all heading for the grave one day. It’s better to be a weirdo with friends than dull and lonely in your brief moment on this spinning rock.

Park your ego at home

People don’t care that you went to Princeton, traveled the world, and now make a living as a fledgling writer. Let your grandma tell that tale. No one worth knowing cares about what you’ve done or what you own; they care about who you are.

Who you are is revealed by how you behave. Are you present, curious, positive, honest, kind, reliable, and overall a good lad who will show up in both the good times and the bad? If so, you’ll make more real friends than the stuffy credentialites who sip espresso martinis and ask, “So…what do you do?”

Get curious

Pretend that every person you meet is God herself. You can’t impress God. She already knows all of your good deeds and dirty secrets. The best you can do is to learn from her.

When you believe that everyone is a god who can teach you something, you will stop being a judgmental asshat and start finding points of connection with more people.

Store clerks, cab drivers, used-book store dwellers, naive youths, temporary lovers, and snoopy neighbors will suddenly become wells of wisdom and friendship.

Most of these people will not become friends, but some of them will.

Don’t fret about bad impressions

It feels crummy when you say the wrong thing at a party or are irritable and “off your game” when meeting new people. I’ve had many restless nights in bed replaying the tape in my head about how I could have done something differently in a social encounter.

However, time has revealed that almost all of my fretting about social stumbles has been a big waste of time and energy.

No one becomes your friend because you present yourself perfectly. The people who you want to stick around enjoy your company even when you’re not as charming or affable or funny or graceful as you want to be. They like you despite (and sometimes because) of your quirks.

So if you flub something up, dwell on it for a bit, but let it go as fast as you can and go on living.

Find the forums that work for you

There are endless ways to meet people, but depending on your interests and personality, you will find it easier to form friendships in some contexts than others.

Some people love meeting friends of friends; other people dig meeting strangers. Some people enjoy one-off events; others enjoy regular meetups over shared hobbies. Some people love going out for drinks; others thrive at intimate dinner parties and poetry readings.

Don’t worry about whether you’re an extrovert, introvert, or whateververt. There is no “right” or “best” way to meet new people or nurture relationships. All that matters is that you find what feels good to you.

If you don’t know what you like, pour yourself a glass of whiskey, try many activities over the next six months, and pay attention. Stop doing the stuff you don’t like, and double down on the forums that you enjoy.

Be responsive and flexible

The early stages of friendship are fragile. You and the other person are feeling each other out. If there is an initial flame, nurture it with gasoline. Respond to texts, send memes, share invites, and change your schedule to make time for the person.

Don’t be a “sorry for the delay, but I’m a bad texter and have been busy” type of person. Your lack of responsiveness will suck the air out of the flame of friendship and leave dog poo on its doorstep. And you will be left standing in the stinky ashes wondering why you still don’t have friends.

Avoid lukewarm connections

Friendship is a decision between you and another person to make the time and space to get to know the weirdest parts about each other. For this process to work, you both need to be into it.

Sadly, that’s not always the case. Sometimes you think someone is awesome, but they don’t think the same about you. Other times, someone likes you, but you’re kinda “meh” on them. And sometimes, you’re both only hanging around because it’s convenient.

Don’t waste time on any of these variations of lukewarm connections. These sluggish relationships will suck the limited time and energy you have, preventing you from building the rewarding relationships that are available if you find the courage and patience to build them.

And if someone you like doesn’t like you, don’t take it personally. You may not be their cup of tea, or they may already have a vibrant social life. The reason does not matter. What matters is that you don’t waste time with people who don’t want to have you in their lives.

Even when it’s fast, it’s slow

In college, you can make friends quickly. Making friends as an adult is different. People are busy, spread out, and often less open to letting new people into their lives.

They’re also in different stages of their lives. Some people are in grind at work mode, others are in young parent mode, and others are drifting souls who aren’t sure if they’ll be in the same town a month from now.

The complex social landscape of adulthood means that adult friendships take more time to build. It often takes at least a year to build enough trust and shared experience with a new person to call them a real friend.

So don’t get too worried if you’ve been trying for a few months and don’t have new besties. That’s normal!

Don’t forget: people are lonely as hell!

Made with Midjourney.

Do you know what this picture is? It’s the sad and lonely inner world that plagues most people in our hyper-connected and fast-moving era.

Modern life gives us free porn and burgers in bed, but it is also overwhelming and leads many of us into an isolating spiral of worry, comparison, and doubt. And if you stay in that spiral for too long, you may begin to believe that you’re the only lonely person out there.

The good news is that you’re not the only one. Not even close. Most people are spiraling and want more friends to share this crazy life with.

So as a final tip, do yourself a favor: Stop feeling bad about yourself and the current state of your social life. There is a vast world of fellow lonely souls who want to connect with people like you. If you want proof, put on some pants and interact with the real world.

Talk to 10 strangers. Host a dinner party. Organize a morning run. Take a drawing course. Just get out there. You’ll be surprised by the warm reception you’ll receive. And little by little, your social life will become more vibrant. I promise.

Alright, I’m done babbling for now. Put your phone down and get after it.

🧘‍♂️ II. Audiobook I’m Enjoying

Many people have recommended Shantaram by Gregory David Roberts over the years, and I’m finally diving into this long, beautiful story. I’ve listened to a third of the audiobook, and the story is living up to the hype.

Here’s the description from Amazon in case you’re interested:

🧠 III. Something I’m Thinking About

I believe that most of us know what we need to do. Sure, we can be blinded by numbing agents, fear, insecurity, and people that distract and paralyze us, but even then, there is a faint voice telling us what’s good and right.

The challenge of life is learning how to hear, trust, and listen to that voice. Developing this skill is important because it is the best way to avoid the painful moments in life when you realize that you have acted or not acted too late, which is the theme of Bukowski’s poem “oh yes.”

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

🎨 I. Love and Art

This week, I ambled through New York City carrying Rainer Maria Rilke’s Letters to a Young Poet in my back pocket. I took out the book when I needed a break from the intoxicating buzz of busyness, money, and ambition that covers the city.

Rilke’s letters have many insights, but there was one that struck me as important for anyone who enjoys or makes art.

If you create, don’t pay attention to or try to please the critics. Focus on the art.

And if you comment on art, be kind. Turn a shoulder to the art you don’t enjoy and don’t forget to share your love of the works that make your blood pump.

🧘‍♂️ II. A Weird Exercise to Reset

My buddy and I were waiting for a train, and he was visibly agitated about being ghosted by a romantic interest. Not only was he agitated about being ghosted, but he was also agitated about how agitated he was.

Mark Manson calls this “the feedback loop from hell.” It’s when we have negative emotions, and because we think we should not experience them, we end up spiraling even deeper into the emotion. We’re unhappy that we’re unhappy in the first place.

Instead of telling my friend to chill out or offering any advice, I asked him to close his eyes and invited him to do an exercise that we had learned earlier that day.

We took a few slow breaths, and when we opened our eyes, we imagined that we had died and were given one last chance to look around and exist in the world.

I’m not sure if my friend felt better, but I did. My irritation about waiting for the subway, being tired, and all of the rest of my petty grievances with the world felt a little less heavy now that I had imagined that I had been given a final chance to experience what it felt like to be alive.

This week, when you inevitably start to feel yourself spiral, give the exercise a try.

Even if it seems silly, imagine that you have died and that the universe has given you a final chance to be here for some more time. I’m curious to know if it works for you as it did for me.

❤️ III. You Don’t Have to Be Good

I heard Mary Oliver’s poem, “Wild Geese,” for the first time this week. It’s a wonderful poem with a timeless message, but it’s her first line, “You do not have to be good” that shook me when I first read it.

I began to think about all of the anguish I’ve experienced in social situations, in the act of creation, and in my career, simply because I didn’t feel good enough for one reason or another.

While the emotional pain of not feeling good enough has been potent fuel for improving in certain domains, it has also created a lot of unnecessary suffering.

Being “good” is not the best measure of living well, and for most things, the compassionate response is simply to remember that you do not have to be good.

Here’s Oliver’s full poem:

🗣️ IV. Ultraspeaking

I had the opportunity to participate in the Creator Cohort of Ultraspeaking this week. Ultraspeaking is an online course designed to improve your public speaking in social situations, at work, and on stages.

I’m fairly comfortable in most of the situations in which I need to speak, and I wasn’t sure if I would gain much from taking the course.

Thankfully, I was wrong. The Ultraspeaking team has created a course that is not only fun and actionable, but that introduced me to new ways and techniques for using the spoken word as I navigate the world.

It’s the best speaking training on the internet and one of the most fun, well-designed courses I've seen across any subject. And beyond the speaking insights, I came away with a thoughtful and kind group of friends who made the experience something that I looked forward to every week.

They have a variety of course options that you can check out if you’re interested here: https://ultraspeaking.com/.

🧠 V. Something I’m Thinking About

When you die, you will never regret that you were too generous. For the next day, week, or month, try to be a little more generous than you’re comfortable with and see how it goes.

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.

Hello friends and welcome back to Life Reimagined, a free weekly elixir designed to make you feel good and live better.

In case you missed it, last week we discussed lessons in life and creativity from writer Charles Bukowski and the joys of puttering around. You can read that edition here.

🧘‍♂️ I. Perfect Moments

A surprising number of readers have said that they’re enjoying my silly, typewriter-inspired poetry. So while the inspiration flows, I’ll continue sharing what emerges.

This week, I wrote a poem about an experience in a wonderful, Kyoto-style meditation garden in Northern California.

“A perfect moment”

My wife got up and captured the moment that inspired the poem.

🧐 II. Spotting Trends

The internet has a treasure trove of resources for generating business ideas, spotting trends, and seeing what the future will look like. But to benefit from the internet's wealth of knowledge, you need to know how to use it in the right ways.

In the latest episode of the Sh*t You Don’t Learn in School, Steph and I discuss four unconventional ways that you can use the internet to find good ideas for businesses and products that people actually want.

You can listen here: Opportunity is Everywhere: Using Twitter, Wikipedia, Patents, & Niche Databases to Discover Trends

💡 III. Sci-Fi Idea Bank

One of the internet resources Steph and I discuss in the Opportunity is Everywhere podcast is Not Boring’s Sci-Fi Idea Bank, which is “a spreadsheet of 3,567 sci-fi ideas lovingly pulled from Technovelgy, updated to include whether they’ve been built yet, and if so, when, by whom, and what the product is, plus some additional notes and whether they’re mainly bits or atoms.”

This spreadsheet is a fascinating look at all of the ways science fiction writers across time have imagined what the future will look like long before it has arrived.

Describing the motivation behind building the database, its creator Pack McCormick said,

“Ideas for new technologies almost always appear in sci-fi before they show up in real life. Not the exact ideas, of course, but science fiction writers are astonishingly good at sketching the outlines of technologies that will only become possible decades or even centuries in the future.”

Even if you don’t listen to the podcast, I recommend checking out the database and the accompanying article describing what the Sci-Fi Idea Bank is, why it was built, and the ways in which you can use it.

🧠 IV. Something I’m Thinking About

What if you let go of your to-do lists, plans, “shoulds,” and all attempts to control how your life unfolds? What if for one moment, one minute, one hour, or one day, you simply went out in nature and listened?

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.