Welcome to Sabbatical — where we help ambitious people like you take a mid-career break. Since last issue, 5 people have signed up. Woo!

I’m on TikTok!

Hi, it’s me: an elder millennial on TikTok. I’ve been posting things like a guide to thin-sliced retirement (12K views!), avoiding “domestic propaganda”, and detailed breakdowns on topics like “How to Pay For Your Sabbatical” (below)

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The four ways people afford sabbaticals. Still curious? Drop a comment and ill make sure I get you an answer when I do my next batch of ... See more

How I Took a Working Parent Sabbatical

In her 20s, environmental sociologist Ashley Colby spent some time nannying for a wealthy Chicago family. The parents were successful by traditional measures, but they rarely saw their children. 

The experience was one that galvanized Ashley. 

She and her husband then planned what can only be described as a “working parent sabbatical” to ensure they would be both fully present for the young lives of their future children. 

Three kids later, the family moved to Uruguay and built a house on land they had purchased years earlier. There, the low cost of living allowed both Ashley and her husband to parent nearly full-time until all of their children were older than four.

They’ve recently returned to the States, so we reflected on her family’s sabbatical and explored the often impossible balance between careerism and family.

We cover…

• …why she moved her entire family to Uruguay for years and how she planned such a bold move.

• …what it looks like to live your life intentionally.

• …how accepting Americans have become of not seeing their kids.

• …the right time to take a sabbatical with your kids.

• …why young parents should deprioritize work.

You’ll enjoy Ashley’s story if you…

• …don’t have kids yet, but want to ensure you can still travel and be adventurous as a parent.

• …don’t identify with the “busy working parent” archetype.

• …would like to find a way to spend more time with your family. 

• …are considering homeschooling.

Example #4519 of “Living Your Life in Seasons”

Twitter tweet

(Submit your sabbatical story for a future issue here.)

Welcome to Sabbatical — where we help ambitious people like you take a mid-career break. Since last issue, 20 people have signed up. Woo!

The Collapse of Retirement (And Why That’s a Good Thing)

The retirement enjoyed by baby boomers and older generations is fading from view. You know, the whole “work for 30 years and then retire to somewhere warm” approach that was the expectation for years.

This week I talk to Richard Banfield. At 54, he views retirement as “self-imposed imprisonment” and is taking a different approach. One he calls “thin-sliced retirement” (see the three types of retirement here).

Our conversation continues a theme of Sabbatical: you have more control over your life and path than you may think. Born in South Africa, Richard is a widower and father of two young children, and he’s taking this next act of his life to embracing what he calls his “second harvest.”

We cover…

• How to embrace “thin-sliced” retirement and remove “what ifs” from your mind.

• Earning money in the U.S. and spending it in Europe.

• The agency we have when something bad happens to us.

• How Richard’s approach to life results in an unconventional educational experience for his two children.

You’ll enjoy Richard’s story if you have…

• …seen success in your field, but are ready to change the role work has in your life.

• …doubts about the idea of conventional retirement and want some other options.

• …children and want to bring them along for sabbatical adventures.

• …just moved to the other side of 40.

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(Submit your sabbatical story for a future issue here.)

Welcome to Sabbatical — where we help ambitious people like you take a mid-career break. Sent every other week. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 28 totally chill people have signed up. That's 254 subscribers. Woo!

Considering a sabbatical? I can help.

I’m trying a fun thing: Are you considering a sabbatical? Willing to test out some of the upcoming content and resources I’m working on? Let’s chat! We can discuss:

• Learnings from 15+ interviews with people who have taken career breaks.

• Frameworks, books, and exercises to consider depending on the type of sabbatical you’re taking.

• How to best recover from burnout.

• Fun places and adventures to consider.

Totally free and no-pressure. What do you have to lose?

The Interview: Greg Portnoy

This one is for all of your startup folks. Greg spent years hustling for early-stage startups. The rewards came, but so did a feeling that he was getting away from his values. This is the story about how he got back on track.

(Read this in your browser, here)

Greg in Sedona, his first stop on sabbatical.

Tell me about your sabbatical.

It was 2021, and I built the partner program at Attentive through the Series A investment round all the way to Series E. It was hyper growth in its truest form, from $20 million in revenue to hundred-plus. 

When I left there, I was hired to do a PE turnaround on a distressed SaaS startup. It was supposed to be a years-long project but it ended up being a 10 month turnaround. So, that was absolutely nuts.

From those two crazy startup experiences, I was super burned out. I didn't have a breakdown or anything like that. But I just said, “You know what? I'm done with tech, I'm done with e-commerce, I'm done with all this. I'm going to go figure something else out.” 

In December 2021, I stopped posting on LinkedIn. I left tech. I left all of that the whole the thing I've been doing for over a decade. And I didn’t come back until September 2022.

How did you approach this recharge period?

It wasn't planned. I had a nice outcome from both Attentive and from the turnaround. Nothing life changing, but I was in a very solid financial position and decided I didn't need to jump into something else. 

I went on a spiritual retreat to Sedona and did that whole thing and I was just trying to figure out what I wanted to do and reconnect with my inner self. You know, you just kinda lose track of that when you're doing startup stuff. 

With that empty space, what started to bubble up?

My number one reason to be successful is to take care of my family. My number two reason is to have a positive impact. And I felt like I had completely lost sight of number two. While I was just taking some time off I started to think about something that always bothered me: homelessness. 

So I started volunteering at a center for homeless youth downtown. I started walking on the street and talking to homeless people and learning about their stories and lives and trying to help them out. I thought, “maybe nobody has come from a private sector background and has tried to solve this problem. Let me see if I can figure out a way to help.” 

I networked with all the top executives and thought leaders around the problem nationally, and I read a bunch of books. I was really trying to come up with a private sector, tech-enabled approach to addressing homelessness. 

That sounds like incredibly hard work, how did that affect your burnout? 

I wasn't working as hard as you would work at a startup, but I was doing stuff every single day. To be honest, I really wanted it to go somewhere. I really do think it's a terrible problem, but the short version is that I realized that it was such a deeply systemic issue. 

Because of the systemic nature of the problem, the organizations created to address the symptoms of homelessness had become part of the issue and they were actually perpetuating the problem. Ultimately, I had to abandon that. It was a bit too much hubris in thinking that I could fix it. 

But it was the kind of mental break that I needed. And then I started returning to my previous industry, doing consulting and partnerships. I saw this massive gap that I'm now filling with my company, Euler. 

But as far as I knew it, if you had talked to me in the middle of that experience, I would have been like, “Yeah, I'm done with tech. I'm done with the private sector.”

What was it like having to leave behind the thing you thought would be your next move? 

I have ADHD and people with ADHD have a tendency to not finish things that they start. I also grew up with parents that kind of harped on finishing what you started. I knew that it was not going to go anywhere long before I abandoned it. 

And I'm sure you didn't want to prove people right who thought you didn't finish things.

It’s more that I didn't want to abandon an important issue. I didn't wanna feel like I was giving up on something like that, because it felt important. But I also knew in my heart of hearts that I wasn't going to be able to figure this out, at least not in any kind of reasonable amount of time.

In what ways do you feel it worked out? What are the positives to come out of that experience?

It was valuable to learn more about why this is an issue. And honestly, it was a positive to reconnect with human empathy and with those who are in a not a great position. It also was a much needed reset for my brain, I had been working at high-growth startups since 2013.

I had just been in “get shit done” mode for so long in a very specific context of privately-owned startups that I didn't know anything else at that point. All of my mental paths and grooves felt so deeply worn. This break provided a much needed reset and a kind of reality check.

When I came back to working and started a company, it actually took me a while to get back into what is now a pretty obscene level of productivity on a daily basis. I had to ramp back up to juggling a million different things and constantly switch contexts like you do as a startup founder. It took a while for my brain to get back there, but I think that I am better for it.

I think I'm able to perform better and with a clearer mind and with less professional baggage or operational baggage than I would have otherwise if I had just gone from one startup to the next. I would have just still been in those same habits.

What do you mean by “professional baggage”? 

I just had ways of working that had served me for a long time. My brain is very well suited to being entrepreneurial and I kept pushing that aside most of my life because it wasn’t valued by the companies I worked for.

When you work for someone else, they tell you what to do, when to do it, how to do it, and what not to do. It very much pigeonholed me into a particular way of thinking and working and doing. I was able to shed that and come back to working on my company Euler with a set of fresh eyes. I was able to attack it without that baggage of “This is the way I'm supposed to think or this is the way I'm supposed to work.”

A lot of ambitious people are afraid to stop because they fear they can't start again. Or that they will never be as good at their jobs as when they left. I'm curious what you would say to someone who has that exact doubt before taking a break 

I can only speak to my experience. If you're a day trader or doing something that's extremely technical, maybe coming back you’ll see that the game has changed and you don't have that same edge. I don't know about that. 

My experience has been in high growth startups and, in those companies, if you're a very ambitious person it's very easy to burn yourself out because a high-growth startup is a succubus. Anything that you have to give, it will try to suck out of you. And if you want to give, it'll suck even more. You give it an inch, it'll take a mile. For ambitious folks that are working in an environment that really wants to get the most out of their people, sometimes to a very unfair balance, it's very easy to burn out and give too much. 

But I am, by a wide margin, less stressed than I was working for other people in other people's companies than I am for myself — even though I am definitely working way harder than I ever worked before.

I think it's more about a level of motivation and passion and making sure your work aligns with your personality and your values. And you need to be very honest about this with yourself. 

For me, working for other people, especially other people that very often did not appreciate the effort that was being made, didn’t work for me. Doing it for myself and being my own boss and pushing myself harder than I've ever been pushed — but doing it in a context where I know that every incremental bit of effort will have an incremental benefit and outcome for me — is a very different kind of motivational structure.

It sounds like you said, “I need to better connect my work with my values.” One of those values led to tackling the homeless issue you cared about. And while that didn't work, you are still connecting with your values as a founder: It’s just the values are entrepreneurship and self-sufficiency. 

Absolutely. And look, in full transparency, I’ve also had some very bad luck with managers. My wife has had phenomenal managers, they were very supportive and empowering and appreciative. I have had one good one, ever, and the rest of them sucked (laughs). 

I'm not trying to self-aggrandize in any way here, but honestly it felt like I was a wild stallion that had been basically made to go race around a track. While I was good and I was successful, I was forced to do one very simple thing the way that somebody else wanted, when somebody else wanted. When I took the saddle off of myself, I became able to just open up and go exactly where I want, how fast I want, when I want. 

It's just a very, very different experience.

There had to be a period where you quit everything and then you're looking at nothing. There's nothing there. You have nothing planned, you have nothing going on. And that is a terrifying thing for an ambitious person to see because you lose a little bit of your identity. What was that like for you?

I was like a fish out of water and definitely uncomfortable. I remember when people used to ask me “Well, what are you doing? What are you working on?” And I'm like, “I'm just figuring it out.” Even though I had earned the right to just figure it out, it felt underwhelming and somewhat lazy like I was somehow taking it too easy. I grew up in an immigrant family. It was always a mindset of “If you're not working hard, if you're not grinding it out, you're not doing enough.” 

After a while I did settle into it and it was nice to not feel that overwhelming pressure and anxiety. But I did feel kind of unmoored at times.

Being a child of immigrants, were you at Thanksgiving or something, and your family's like, “Everyone here is busting their ass, Greg, and you're going to spiritual retreats in Sonoma, what the hell, man?” 

So the nice thing is that they were supportive. I had three toxic environments in a row and it just changed who I was. I was snippy, I was stressed, I was no fun to be around. And so I think that by the time I took that time off, I remember my mom saying, “that's amazing. I'm so happy.” Which for the record did still surprise me that she said that!

If you're at a bar with a friend who you respect and they ask you, “Should I do what you did? Should I just drop everything and figure it out?” What would you say to them?

Give yourself the grace to sit in your own thoughts and reconnect with yourself. Going on that spiritual retreat was so helpful. 

If you're an ambitious person, you're also very self-aware. It's very rare that we just sit in the quiet and connect with our thoughts or go on a silent retreat or a spiritual retreat. 

For ambitious people, it's very hard to get to that point where your brain is actually out of its day-to-day habits. Just take time to really disconnect and then take time to really listen to yourself on a deep level. Between all of our devices and all of our work, I don't think that we find any time to do that at all.

Welcome to Sabbatical — where we help ambitious people like you take a mid-career break. Sent every other week. (Submit your sabbatical story for a future issue here.)

See last issue here. Since then, 35 totally chill people have signed up. That's 223 subscribers. Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

The 6 Types of Sabbaticals (With Examples)

When you think of taking your sabbatical, what does it look like? Are you surrounded by your family? Are you in a brand new place with a brand new circle of friends? Or is it more of an internal journey, one filled with reading, writing, and journaling? The only “right” approach is the approach that works for you. To inspire, I organized the sabbaticals I’ve profiled thus far into 6 categories with examples:

Living Your Life in Seasons, An Explainer

Longtime Sabbatical readers have seen the theme of “living your life in seasons” emerge across those who have taken a career break. But, what does that mean?

To live your life in seasons is to acknowledge that we are different people at different points in our life. Each season demands different levels of focus on your career, your community, your health, etc.

And it’s uniquely possible now thanks to some macro-economic trends.

Want to be featured? I’m in search of:

• People whose companies have sabbatical programs

• People who have taken a sabbatical

• Experts on specific countries or cities for a guide to their place

Hit “reply” and lmk - I respond to everything.

In this issue:

• New website!

• A behind-the-scenes note

• Amanda Mohlenhoff: The Life-Changing Magic of a Cr …

Welcome to a very special and very new Sabbatical! In celebration of crossing the 200 subscriber mark, there’s now a totally relaunched and reimagined Sabbatical website!

New website!

Oooooo fancy

Here’s what you’ll find:

• Every Sabbatical interview I’ve ever done all in one place with all of the advice and candor you’ve come to expect.

• Every essay including the difference between digital nomads and sabbaticals, the benefits of a modular career, and more.

• A sneak peek at some of the comprehensive research and guides I’m working on — vote for the one you want first!

With a new site comes more goodies: this newsletter will now be sent every other Wednesday, alternating interviews and essays.

A behind-the-scenes note

Our lives and careers are full of stops and starts and explorations that help us figure out the best path for us. Sabbatical has embraced this spirit — exploring without knowing exactly where it's headed.

But now, some clarity that’s come from more than 20 interviews and 7 issues of this newsletter: Sabbatical is for ambitious people. I mean that in two senses:

Ambitious in your career. So much of our career discourse teeters on a kind of nihilism that views hard work as something to be totally avoided. Best to “quiet quit”, FIRE, or start some business from your laptop with the goal of working 5 hours a week in Thailand or something. Sabbatical embraces that it’s one of the joys of life to work hard on a problem you care about with people you respect. We take sabbaticals not to avoid, but to recharge.

Ambitious with your life. I have an ongoing text thread with some dads in my life where we just forward social media advice posts (usually from men in the 30s) that totally ignore that their advice is impractical if you are raising a family.

Surely you’ve seen videos of the super jacked dude who has optimized every hour of his day in the name of health. Or the travel influencer who bops from country to country endlessly. There’s a kind of advice-industrial complex that acts as if commitment to anyone other than yourself is not worth it. Or, as Derek states below, there is no one in your life worth sacrificing anything for.

Twitter tweet

Sabbatical acknowledges that it’s fun to be a parent. Or to commit yourself your local community. Or any of the other things that fulfill us. Our lives rarely have a singular focus.

Speaking of, let’s get to this week’s interview:

Amanda Mohlenhoff: The Life-Changing Magic of a Creative Sabbatical

There are many types of sabbaticals, and in this interview, we explore the creative kind. Amanda was working for a tech company when she was so burned out she couldn’t even look at her laptop anymore. During COVID, she left and began a journey that included:

• Producing her own show complete with costumes, music, and dance.

• Learning how to be a self-starter again and structure her time

• Getting back in touch with her creative side through a series of collabs with friends

• Exploring the work that would energize her, rather than exhaust her, returning to the same industry with a new approach — she even got her new company to cover a career coach!

Choice quotes:

• “I was really seeking novelty. I knew that the antidote to boredom and depression is newness and learning new skills and building this confidence and allowing myself to be afraid.”

• “I thought maybe I became exhausted because I was working for someone else's dream. And so then I produced my own, I wrote a musical and it was really successful.“

• “Sometimes it's time to focus on other aspects of your life, your one life that you have before you die forever.”

👇 I think you’ll like it

Welcome to Sabbatical — an exploration of the future of work, designing your life, and travel. Sent every month-ish. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 36 totally chill people have signed up. That's 182 subscribers. Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

Programming note: I’ve left my full-time job to focus on creative pursuits like this newsletter and spinning up a publishing house to publish more cool stuff online. The feedback about these lil’ issues has been amazing and subscribers like you were part of the reason I felt comfortable making the move. ❤️ 

Now let’s get to the issue, it’s a fun one.

Today's Itinerary

• The Note: Living Your Life in Seasons

• The Debrief: Frances Benjamin

The Note: Living Your Life in Seasons

Take a second and imagine the trajectory of your life. Which direction does it go?

No, literally, the direction? Is it going left? right? out? up?

Chances are you see your life as something that progresses linearly. Something that builds on itself. There’s a reason we climb career ladders. We aspire to marry up. We want to build a life by setting a solid foundation.

In 2024, life and careers don’t work that way. A framework used by several past interviewees that I find myself using: you’re living your life in seasons. Each phase of your life serves a different end. Sometimes it is a restful season. Other times, it is a season to work and amass wealth and knowledge. Sometimes you are focusing on family. Other times, yourself.

The key is knowing what season you are in and why you are in it. Be purposeful and unapologetic about what season of your life you are in. This means getting FOMO and letting people “pass you” while you are resting. Sabbaticals can be difficult when you see your peers getting promotions or accolades that, deep inside, you think you could have had.

It also means missing out on some things you would find short term fulfilling in service of some larger goal. Most entrepreneurs of massive businesses point to birthdays missed, health sacrificed, and hobbies left unexplored.

In this issue, we profile Frances who thought she was in one season, but was quickly pulled into another.

She worked in hospitality during the pandemic. She raised a daughter as a single mom and she was the sibling that lived closest to her elderly parents.

But just as she was getting underway for her long-planned sabbatical, her family was rocked by tragedy, and she was pulled back home. She began to question her plans, her place in her family, and whether she was “too late” to take the trip of her dreams.

She had every reason to restart her “old life” — but she pushed on. And on the other side was a “lightness” that began her newest phase, one centered around flexibility and family. 

In this Debrief, we see yet another example that hitting pause on your life may not go exactly as you planned it.

The Debrief: Frances Benjamin

Frances at a cooking class in Thailand

Tell us about your sabbatical. When was it and why did you do it?

I tell people all the time that the pandemic was a blessing to me. In 2020, I was the general manager and also an HR director of a casino and two small hotels in the Virgin Islands. I was also a single parent to a high schooler.

And basically I had three jobs: two at work and one at home. When the world stopped, everybody stopped working, but I didn't. The infrastructure of my company still had to keep going. The bills still had to be paid. So I still worked and I still got paid. 

My daughter was in 10th grade at the time, and I knew obviously that in the next couple of years she would be leaving and going off to college. And so I decided at that time to take a sabbatical, while I have the luxury of still earning an income and the flexibility of being able to travel with my daughter. 

I got really serious and I hunkered down and I paid off all my debt except for my mortgage. I saved as much as I could. At one point, I was saving about 50% of my income. And on June 3rd, 2022, I left my job.

Did you wait for your daughter to move out of the house before doing this?

I wanted her to experience some of it with me. When she finished high school in June of 2022, we signed her up to start university the following January. So instead of spending the Fall semester at school, she traveled with me.

You very easily could have just dialed back your responsibilities or found another job or moved and kept working. What was appealing to you about taking this break?

It's just important to take a break. And I don't mean take PTO or take a vacation, because it's not the same. You know, a break really needs to focus on you and what you want for yourself and not for an employer.

I wanted to travel and experience different cultures and different environments. I come from a very small island community [in the Virgin Islands]. And travel has always been very important to me, especially having a child. I felt, and I believe still do, that travel is a big educator. And so I always wanted to not only do that with my daughter, but also for myself. 

Tell me about how you approached your trip. 

Initially, because my daughter was going to be with me for the remainder of 2022. We had a dog that we couldn’t take on the trip. And so we flew to Atlanta, dropped the dog off with my sister.

Then my daughter and I went to Mexico and traveled to a few places in Mexico for a while. And the plan was after we left Mexico, we did some house sitting in California, and then she wanted to go to New Orleans and Colombia before she started school in January. 

How did being a single parent impact your planning here? 

The world of your kids is greater than where they happen to live.

The biggest part of their education and their growth is through the experiences that they get. Those experiences are outside of the bubble that you're in or they're in in their schools and stuff like that. 

I look at it as the experience, not only for myself, but the experience and the education that I’m giving to my child and exposing them to the world outside of where they live.

You said “the plan was” like it didn’t work out that way.

It didn’t. We left Mexico, I believe, in September, and when we were housesitting in California I got a call that my mom was on life support. We had to go back.

The day after we landed home, we had to take her off of life support and she passed away. So the trip ended. As difficult as it was, it gave me the opportunity to spend a lot of time with my 83-year-old father and to make sure that he was okay.

I struggled a lot. Do I continue what I had started? Or do I stay and make sure that my father is okay? And so ultimately, I decided that I would stay until the end of the year. I knew the holidays were coming. I didn't want him to be alone on the holidays and stuff like that. I knew my daughter would be going off to college in January.

In January, my father and I dropped her off in Savannah. And we went back to the Virgin Islands. 

And the feeling came back again. It's like, “Are you gonna not continue this journey that you started out? What are you gonna do?” 

I have this promise to myself, where every year on my birthday I have to wake up in a place that I have never been before. My birthday is in February. And so now here we are in the beginning of the year and I'm like: What am I going to do? Am I going to continue? Am I going to stay? 

And then my dad said, “What are you talking about? You have to go, you have been planning this thing for two years and you know I can take care of myself.” It was difficult for me. I still struggle because he and my mom were joined at the hip, and now I'm leaving him alone. He was like “No, you gotta go.” And so on January 31st, I got on a plane to Thailand.

I had to start over.

How did losing a parent while you're thinking of this journey affect the way you approach it? 

One of the things that I had to remind myself of is that I had done a lot to prepare for this moment and I had shared it with my parents and they were aware and they knew how important it was to me. 

It made me feel like “it's time for you to start thinking about you and what you want because all this time as a single parent you've always taken care of someone else.” 

But as my parents aged, I questioned myself. But since these people that I care for: my daughter, my parents, know how important this is to me and know that this is something that I want to do. 

I just kept wondering, when are you going to stop and put yourself first?

What’s interesting is that, the very moment you're ready to expand your horizons, you have this moment where you actually have to come back home and focus on family. But once everyone else was settled I bet returning to your journey felt … lighter?

100 percent, much lighter. It was like weight lifted off. Absolutely.

So let's talk about the fun breezy light period where you're gallivanting all around the globe. How did you think about it? How long did you intend to go?

I started out making a list of places that I wanted to go. Not necessarily planning strictly like April I'm going to go here, May I'm going, you know what I mean? After a month in Thailand I headed home, stopping in Doha to take advantage of their stop over program, and I came home to check on my dad and he was okay. So I left again.

I went to Paris, it was okay. And then I went to Morocco. I had been to Morocco before and I really liked it. And I ended up doing a group trip and I met a bunch of women. It was great. But then I had an accident.

What was the accident?

We were on a tour of a museum in Morocco, and I misstepped at a fountain and I fell. It was awful. I was freaking out because I thought I had messed my knee up again. I ended up having to get the doctor to come into the hotel and I was put on crutches.

Luckily for me, I was surrounded by other women that just really stepped up and took care of me. I was preparing to go to Lisbon, and it turned out that a lot of the women I met were going to Lisbon as well. And they took care of me. I don't know if you've been to Lisbon, but it's a lot of hills and a lot of cobblestones so that was a little difficult.

Frances with one of her “angels” in Morocco that helped her travel after being injured

They pushed the wheelchair and they carried my bags. One of them went with me to the ER. I mean, it was amazing. Luckily it turned out not to be anything serious. 

Tell me about the end. When did you decide to stop traveling and how?

I called it at the end of 2023. When I got back to Atlanta, I decided that I would travel more within the US. And one of the things that I started doing when this whole thing jumped off was house sitting, so I would book house sits in different parts of the US. I booked some sits in Miami. I booked sits in Savannah. 

I booked a three-week sit in NYC that allowed me to catch up with friends, hang out, and take in the city vibes without having to pay for accommodation. Housesitting is the ultimate travel hack!

How does housesitting work? How did you find houses? How did you get introduced to this?

It's amazing. I use Trusted House Sitters. House sitting is huge in places like the UK and Australia. Those are probably the biggest areas. People post that they need a house sitter in this location for this amount of time. Some of the house sits that don't include pets. They can be dogs, cats, horses, whatever. You have a video interview and then if there’s a match they hire you. 

You have to the location on your own. But once you get there, you don't have to pay for accommodation. You water their plants, you walk their dogs. And I'm a dog lover, so it just kind of was a natural thing for me.

How did you fund this trip?

I saved a lot of money and I sold a lot of my stuff, like my car. I created buckets of savings, and I had money specifically for travel. I had a bucket of money just to pay my mortgage. I had a bucket for courses I wanted to take. I did not work, but my house became a huge income generator because I rented it. And a third of the rental covers my mortgage. So the rest of it is mine. So that was a big help. 

Initially, I thought I would spend, I don't know, maybe 60 grand for the year? And I ended up spending less. 

Most people come home because they run out of cash, but it feels like you came home because you were ready. So tell me about what it felt like to be ready.

One of the things that made me feel ready was that I was kind of tired of living out of a suitcase. I wanted to get back the feeling of sleeping in my own bed and cooking with my own pots and stuff that weren't mine. 

Because, again, my daughter was in Savannah so I chose to settle there. It kind of reminds me a little bit of where I'm from. I am very winter averse [laughs].

How did your life change post-sabbatical?

I am not a typical sabbatical age, as you can probably tell [points to gray hairs].

I knew there was no way that I could go back to work and living life as I knew it for the past 30 years. And so it was never really my intention to go back to that full-time hospitality business.

Recently, in the last couple of months, I have taken a step back into that world and started HR consulting and started consulting other women about taking a career break. And so I'm building that for myself now, but with no intention of going back to the old life.

So it's not quite a retirement. It's not even a semi-retirement. It's kind of like you're still working as much as your capacity allows. It's just that flexibility seems to be the most important thing.

Flexibility is of the utmost importance. My dad is still back home. And so I need to be able to get there if I need to get there. And I know that working a nine to five for whomever would not always give me that flexibility. My dad is 85 and he lives alone. If I need to get there, I gotta get there.

Travel is also very important to me. There are so many places still on my list so having portable work is a must.

Given your focus on taking care of your family, you alluded to having a little voice in your head saying, “You’re being selfish!” How did you handle that?

For me, what I had to tell myself was, “You've taken care of people all your life. You've done it. Take something for yourself. Keep something for yourself. You are worth it.” 

You made the sacrifices. At what point are you going to reward yourself?

Welcome to the sixth issue of Sabbatical — an exploration of the future of work, modern life, and travel. Sent every month-ish. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 26 totally chill people have signed up. That's 146 subscribers. Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

I’ve also started posting Sabbatical videos! See the first one on LinkedIn here — more to come.

Today's Itinerary

• The Debrief: Len Markidan, COO of Podia

The Debrief: Len Markidan, COO of Podia

This debrief is a bit different than previous issues. Yes, Len took a sabbatical — but that’s not the main reason we’re speaking to him today. Len is the COO of Podia, a platform for creators and small online businesses. And his company has the most generous sabbatical policy I’ve ever seen: fully paid month after your first three years. After that employees get a sabbatical every two years.

Today, we’re taking a look at sabbaticals from the employee side of the equation. Hopefully, this helps you build a similar program at your company.

We spoke about why his company is so bullish on taking extended breaks and why they’re not worried about employe attrition.

-

Why did you take your sabbatical?

Podia had a pretty standard PTO policy since its founding. But then in 2020, the pandemic happened.

There were many layers to how that impacted the mental health of our employees — of all of us. And a lot of people had kids at home and had obligations outside of work that were draining on their time. I don't have to rehash that though, because we all lived through it.

So in 2022, inspired by some other companies, we rolled out a sabbatical policy. In the summer of 2023, I went on a one month sabbatical where I traveled with my wife and son. We went to visit some friends and family in San Francisco and then we visited Vancouver and the beautiful US state of Alaska.

A view from Len’s Alaskan cruise

Why instill a sabbatical policy? I’m sure some would think, “Why am I paying for a month off of an employee? They could just leave!” What was the logic at the leadership level?

You want the long version or the short version?

Long. Let’s get into it.

There are three real benefits to a company for having sabbaticals. The first is energy. The second is perspective. The third is resilience. 

Energy is the most obvious one. When you take PTO you’re not recharging. You're getting a hall pass to skip work for other obligations. You're going to weddings, you're taking days off because your kid's school is closed. I took a few days off earlier this month to move. 

What most people are left with is this small handful of vacation days that actually belong to you and that are actually being used for anything resembling a vacation. A sabbatical creates space for rest. A sabbatical is just this rare opportunity to not have to fit your life around work. You can, you can handle the life stuff, yes, but still recharge you with the rest of the time. And you come back rested and energized and not exhausted the way that almost everybody comes back from a three or four day vacation. 

And benefit number two?

The perspective that you get from such a dramatic pattern interruption in your life. Most of us spend most of our work day on tasks. And it turns out the brain can do some really neat stuff when it's not focused on a task. About two weeks into my sabbatical, my thoughts did drift back to work. More in a zoomed out, “Hm, maybe I've been thinking about this thing wrong the whole time” kind of way.

You have these thoughts, you can't really act on them because you're off work, but that's part of the beauty of it. Your ideas have space and time to just sit and develop and change and grow. And when you come back to work, you see it differently and that can make a really big positive impact.

This sounds like a weird thing for a manager to say, but we've had situations where someone comes back from sabbatical and says, “You know, after giving us a lot of thought, I've decided I actually want to take my career in a different direction.” And they left. And that's great. 

There is no long-term good that comes from two people being in a relationship that one of them doesn't want to be in. And in a lot of cases, without the sabbatical, those feelings of dissatisfaction or of being in the wrong place, they sit under the surface because there's no time and there's a space for them. And they just grow and fester and get worse and worse until the person just really hates their job, and resents their boss. 

People will often change jobs just because they think the grass is greener. They just want a change of scenery or they're bored or they're burned out. But when they go on sabbatical, they discover that they really just needed a recharge. It's a great way to give people that perspective without them having to actually leave their job to find it. 

We have energy and perspective. What’s number three?

You build a much more resilient organization. Of course there's the cultural strengthening that happens when people have this shared experience of planning on and going on their sabbaticals. They get excited about these experiences and they come back and they share photos and stories and they get their teammates thinking about what they want to do on their sabbaticals. 

But then there's a less obvious strengthening of the organization. And that comes from forcing gaps in the resources that are available to the team. In programming, there's this concept of “chaos engineering.” Where you force failure into a system to build resiliency and companies have done this in a bunch of different ways, but probably my favorite example and maybe the most prominent example is Netflix. 

Their team built a program they called “chaos monkey”. It essentially just unplugged servers at random to ensure that the system was resilient enough to deal with the consequences of that happening. And that caused them to build and to strengthen their infrastructure to basically be sure that the things still function when those critical resources went offline. 

That's not so different from what happens when an organization has somebody go away for four weeks. It can just make it very clear where you have fragility in your workflows, in your process, in your business. And because the pain isn't going to go away while that person that you think you need is away, it motivates the team to fix things on their own. And that is a very, very powerful skill to build in a team. 

How long has this been in place at Podia? 

We implemented the system in 2021 and the first person took a sabbatical the next year. The policy was that you get a sabbatical every three years with the company. After this first kind of cohort of sabbaticals in 2023, we got together and we said, “Wow, that was extremely powerful”. So much so for both employees and the organization that we increased it. 

Now you get a sabbatical after three years and then it's every two years after that.

I’ve seen companies do four or five year sabbatical cadences but never two. Is that a testament to something unique about either Podia or remote work or knowledge work?

I don’t mean this in a derogatory way, but most companies in our industry are on this kind of venture capital track of, “We're going to raise tons of money. We're going to spend it as quickly as possible to test this model and then scale it.” 

What you're effectively doing, even though you're not deliberately saying it, is admitting that employees are basically fungible. There's going to be some expectation that if we hire X number of people, we're going to have Y percent attrition, either voluntary or involuntary. And we want to hit some total headcount number over time. 

Podia is very different. We have not taken that path. We raised a seed round, but for the last four years, have effectively been operating as a bootstrapped company. We decided when the pandemic hit, we're just gonna go for profitability. We're gonna try to be as sustainable as possible, and build an enduring business and not really worry about the rat race. I can count on one hand, the number of people who have voluntarily left Podia in my memory since I joined in 2017. 

For a lot of companies, if somebody is really burnt out and tired and needs a break, they'd rather just have that person leave and replace them than pay them for four weeks off every couple of years. 

If a Podia employee who was about to embark on their sabbatical asked you for advice, what would you tell them?

Don’t have a goal.

I did not say, “I'm not touching my laptop for four weeks”, or “I'm completing X personal project during the sabbatical.” Because if I had a goal and then I didn't achieve it, then I would have failed sabbatical. And can you imagine anything more demoralizing than failing at rest?

You can have a loose plan. Do not have a goal. Anything you accomplish on your sabbatical is, you know, that's frosting on the cake, but please do not set yourself a goal that you can fail.

What do you say to your fellow founders, executives, and people who are responsible for setting a sabbatical policy? What would your suggestion be for them to pursue this thoughtfully? 

Make sure your most experienced employees are your guinea pigs for this. Those are the employees who, whether you think they're happy or not, are probably the most likely to be getting emails from recruiters. To be looking at other jobs, to be interviewing for other things. 

Very few of them will come back and say “I thought about it and I'd like to figure something else out.” Most of them will come back and say, “Wow, this was exactly what I needed. I am more focused, more productive and more excited to get back to work. It's almost like coming back and starting a new job all over again.”

If you love something, let it go. 

Welcome to the fifth issue of Sabbatical — an exploration of the future of work, modern life, and travel. Sent every month-ish. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 10 totally chill people have signed up. That's 120 subscribers. Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

Today's Itinerary

• The Note: Important Things Are Hard

• The Debrief: Melissa Dorsch

• The Recommendation: Food Tours as Stop #1

The Note: Important Things Are Hard

Social media can feel like the world’s most obnoxious upselling salesman.

“Oh did you look up running shoes? HERE ARE VIDEOS OF ULTRA MARATHONS.”

“Did you research that new Spiderman movie? HERE’S EVERYTHING YOU NEVER WANTED TO KNOW ABOUT TOM HOLLAND AND ZENDAYA OVER AND OVER AGAIN”

When it comes to designing your life, the phenomenon becomes particularly frustrating. If you’re interested in starting a business it won’t be long before you are served a steady stream of people who claim to run one-person businesses making millions. If you want some parenting advice, it won’t be long before some dude with 11 kids on a farm will be telling you how to create Cheerios from scratch. And if you look into taking a sabbatical, you’ll see a steady stream of people who tell you how easy and fun it all was.

But nothing important is easy. Sabbaticals make for great social media content. But the act of removing everything from your day-to-day life and putting it back together can come with some pain.

It’s in that context I’m happy to share Melissa’s story. Don’t worry, her story has a positive ending, but the path to get there was not what she expected when she set out on her journey. There was some unfortunate timing, like when she returned just as the deepest recession in her industry’s history began (aka the “software as a service (SaaS) recession”).

That blue line is an index of SaaS companies.
Melissa’s sabbatical ended at the bottom of the market.

So goes risky uncertain things like entrepreneurship. Or quitting one’s job to travel without something lined up on the other side. This stuff is not as reckless as most people think, but there is risk. It is difficult.

Sabbaticals demand that your life open up to new experiences. Though there’s no guarantee those experiences are always pleasant. Or predictable.

Important things are hard, and a sabbatical can be the most impactful period of your life. Expect some bumps.

The Debrief: Melissa Dorsch

Melissa Dorsch in 🇫🇷

Melissa took nearly one and a half years between full-time gigs. But that wasn’t necessarily the plan. First, there was the canceled wedding and then there was the historic contraction in her industry. See how she navigated all of this and ended up better off on the other side.

Why take the break?

I was at my previous company for five and a half years doing workplace operations, events, and culture work. It was one of the fastest-growing startups at that time. I loved it. It was amazing. But the pandemic really threw a wrench in all of our workplace plans. 

I was sort of a one man show doing way too much by myself. It just felt like time. On top of that, I was also planning a wedding. I had some trips planned over the summer. I was about to enter my last big employee stock vesting window and so I was like, “This is my time. I'm so ready to go”.

Where did you go?

I left the company on April 1, 2022 and almost immediately went to Costa Rica for two weeks with my friends and my partner — that was amazing. Then we had a month-long trip to Italy planned for later that Summer. The first few weeks I just kept thinking, “This is great! How nice! I can sleep in! I can take my dogs on walks whenever!”

But then it started to have an impact on my relationship. A lot of my identity was tied up in my day-to-day work ethic and I was starting to be a little bit depressed.

Three months into the sabbatical, we broke up.

How did that impact the sabbatical?

I wanted to distract myself. I wanted to take advantage of the money that I had saved, and ended up on my “Eat, Pray, Love” journey. I went to the south of France and Monaco by myself. Visited some friends and went to places like New York, San Francisco, and New Orleans. I would come home for a few days and then go on another trip. 

I didn't feel like I was running away from my problems, this is what I wanted to do anyway. I just thought I would have been doing it with a partner. But by January 2023, nine months into the break, I felt like I was finally ready and in the right mental health space to start looking for work. And that's about when the tech market plummeted. 

We saw so many layoffs, so many people are looking for work in the Workplace and Events industry. I ran my own event planning business for a while, but I missed being a part of a team so I started looking into full-time work. I finally landed myself in, I think, exactly where I was supposed to be, with a startup called Circ in October 2023.

Why did you take the break versus just hopping into your next thing?

I've been working since I was 14 years old. I moved out when I was 17. I didn’t go to college. I worked really hard to get here. Why not do this while I'm young enough and before I have children? Why not take this time to sort of evaluate my next step, see what I want to do, take what I felt was a well-deserved break? 

I wanted to see what fell into my lap, and what the next steps were. Especially because work has such a huge bearing on the rest of your life.

Melissa Dorsch in Hawaii

How has the role of work in your life changed before you went into this versus after? 

I used to be the kind of person that was accessible 24/7. In facility management, that is going to be a thing and you're going to be working after hours to an extent. But I was too reachable.

I'm now better about setting boundaries. I now say things like, ”I'm going to get to this on Monday” rather than working on a weekend, for example. I have been in a way better headspace since. 

Do you feel like the break and allowing all that stuff space to breathe resulted in all these latent things coming to the service? Maybe you realized your relationship with work wasn't what you wanted it to be? Or the relationship with your partner wasn't what you wanted it to be? We can all paper over our issues by staying busy each day.

I think once you have space from anything, you're going to be able to see a lot of the things you maybe didn't see before. I had a really hard reset on life after that breakup. My mental health really plummeted and I definitely attribute that to the change in my career and not having something that's distracting me all the time. 

I can’t stress this enough, it's really important to take a step back sometimes. It doesn’t have to mean that you're changing careers or taking a sabbatical. But take a mental health day every once in a while when you need it. Not everyone struggles with mental health, but a lot of people struggle and don't even realize it.

How did you pay for your sabbatical? 

I started at the previous company pretty early on, and did really well as a result when they went public. I put a lot into savings at first and then hired a financial advisor to help me do some goal-setting. I also had previously purchased some real estate and sold a house right around this same time for a healthy profit. So when it was time to leave, my financial advisor and I had planned for what that would mean financially. 

But, I also thought my sabbatical was going to be a little bit shorter, so I definitely tapped way more into those savings than I wanted to. But luckily, I didn’t have to sell my house to travel or anything. 

You ate into that savings a little more than you would have liked, but you weren't, like, panicking up against the wall necessarily yet?

If you plan to take a sabbatical, be very weary of the market, of whatever you're working in. So if you're working in housing and there's a housing crisis, or if you're working in tech and tech takes a nosedive, it can be a little bit tough. 

If I could have changed one thing, it would have maybe been nice to have something lined up already, just slightly further into the future.

If someone were to come to you and say “Melissa, I’m fried. I want to take a break like you did.” What would you say?

Don't be scared to take a little bit of time off, and don't get scared by my story.

If you're not going to do it now, you probably won't ever do it. Take the leap. Just set budgets, goals, and expectations, not only for yourself but for your family or the people around you, and have good resources around you, say for example if you do end up needing to move in with friends because you couldn't find another job. Don't isolate yourself during the time off because work is such a social thing.

It was freeing to take this break. My stress levels got better, my skin got better, my hormones evened out. I was just so much less stressed on a daily basis. 

Did you do anything purposeful like meditation or a journal or checking in with friends?

I did journal, I did meditate, I do Pilates, I was able to just enjoy the sunshine. 

I listened to a million podcasts, and kind of stayed up to date on LinkedIn. I wanted to know what people were doing. I was still networking to an extent, I didn't want to completely fall off the earth, especially because mine was such an extended time off that I wanted to still stay relevant. 

Don't worry about a gap on your resume. If you can explain it in any way, anything from travel to being a caretaker for someone to spending time with your family, I think it's super important to do those things and hopefully companies with similar values will be totally on board with that as well.

Yeah, in a purely tractional way, when I’m hiring someone and I see they’ve taken a break, it’s relieving. I now know they won’t up and leave because they have taken their big trip already.

I was so ready to hit the ground running and just do good work and just get back into the workforce again and be a part of a team. I don't think it would have been the case had I gone straight from my last job into something else. I came back refreshed and rejuvenated, for sure — and I was just excited to work again.

The Recommendation: Food Tours as Stop #1

When you arrive in a new city, how do you get a lay of the land? Consider starting with a food tour. It’s a quick way to get oriented, meet several locals, and get additional historical and cultural context about the place you are about to explore.

Also, it’s delicious.

🎟️ Next time you’re in Nice, Melissa recommends this one.

Welcome to the fourth issue of Sabbatical — an exploration of the future of work, modern life, and travel. Sent every month-ish. (Submit your sabbatical story for a future issue here.)

See last month’s issue here. Since then, 14 totally chill people have signed up. That’s more than 100 subscribers! Woo! If you dig these issues, please forward along to any travel-loving, career-pondering friends!

Today's Itinerary

• The Note: It’s Never Too Late

• The Recommendation: Hut-to-hut in Switzerland

• The Debrief: Rachel Bicha

The Note: It’s Never Too Late

When we are early in our careers, our knowledge of what our working (and non-working) lives can look like is limited. We lack context.

If your mother was a freelance graphic designer, you’ll be more aware of what it is like to work for yourself than, say, the person with two parents who had a “traditional” corporate 9-to-5. If your father was a powerful CEO, you have a better idea of what it takes to climb the ladder (and the costs and benefits of doing so). Steph Curry has natural talent, but surely having the context of his dad playing 16 years in the NBA helped him realize what was possible. 

As we advance in our careers, we meet different kinds of people. We cross paths with different sectors of the economy. We gain an awareness of what is possible. 

When I talk to people about taking sabbaticals, they sometimes lament that they “missed their window” or that they’re too deep into their careers to press pause. On the contrary, the bigger the contextual gap between when you started your career and where you are now, the more helpful a sabbatical can be.

Taking a sabbatical later in your career means you are more aware of what is possible. Whether you want to change course or hop back into your previous career, your cumulative connections and talents make it possible.

Sure it’s difficult to press pause mid-career with “more to lose” and more to manage. But we’ve seen already that you can take your entire family on sabbatical. You can do it as an entrepreneur (see below). You can leave a promotion on the table.

The more career experience you have, the more fruitful your break will be.

📍 The Recommendation: Hut-to-Hut in Switzerland 

If you’re craving peace and a few days to sit with your thoughts, consider a multi-day hike in the Swiss Alps. The mountains are dotted with huts where you can spend the night — so whether you need two days or two weeks to fully unwind, plan the route that works for you. Just be sure to book your huts ahead of time to make sure you have a spot.

Twirling around like Julie Andrews is optional but encouraged.

🎟️ Book your huts.
🗺️ See example routes.

The Debrief: Rachel Bicha

Rachel Bicha in 🇨🇭

Rachel Bicha’s five-week sabbatical was an end rather than a means. The solopreneur started her own business in part to allow her to take extended breaks. We touch on how we’re not as indispensable as we think (and why that’s a good thing).  

Let’s start with just the overall shape of your sabbatical. Where'd you go? What'd you do? 

One of my big goals working for myself was to be able to take a sabbatical, just because I'd never done it before. I started planning it in February 2023 and I took five weeks off in August 2023. 

The first week, I was just settling in. I went to Switzerland and Austria for two weeks, and then I had a week where I was traveling in New England. And then the first week of September was kind of like reflecting, getting ready to go back to work to Boston.

When I got back, I pretty much went back to the same thing I was doing before. But I feel like I had a different outlook on it in terms of how I wanted to structure my days, and what kind of projects I wanted to take on.

Why was taking a sabbatical an important part of being self-employed? 

I felt like I fell into my career. When I graduated college six or seven years ago, I got a marketing internship. And after a few weeks there, they offered me a full-time position. I took it and liked it so much that I stayed there for four years. It was at a travel company, which was awesome — until Covid happened.

I then switched to this B2B tech company, which wasn't a good fit for many reasons. And then I thought I needed to work for myself. I’d fallen into these different roles based on what I thought I needed at different points, and a lot of it had to do with factors external to myself. 

I wanted to take time to figure out what I wanted to do, separate from these external things. Of course, money is always a factor. Of course, the economy is always a factor. But what are the factors that I'm bringing to the table? And then, obviously, it also just sounded really awesome. [laughs]

So it's almost like this passive career versus an active career, right? 

Especially in the tech space, I think there's a lot of pressure to always be growing and always be moving up the ladder. Maybe taking five weeks off is more important than an extra $10k. 

Did you have any kind of process going into the sabbatical?

I didn’t want to think about work at all. I just let everything run in the background and tried not to overthink it too much. I went to Austria and Switzerland. I did a hut-to-hut hike for two weeks (see “The Recommendation” above). It was more than 70 miles. No wifi, no cell service. I had a little satellite phone to tell my mom, “I'm okay, I made it!” 

That true disconnection was important. And I tried to hold on to that. Before I left I felt like, “Oh, my gosh, what if everything burns to the ground and I don't even realize I'm not even there?” And of course, I came back and nothing had happened. Maybe, unsurprisingly, when I came back the second week of September and I sat down, I kind of felt like, “Yeah, I know what I want. I want more time that feels like THAT.”

Did you have any moment of doubt? Like, “Am I doing this the right way?”

We spend a lot of time having other people tell us what they think we should do. Part of this was clearing a space where I could hear my own thoughts without somebody else's voice. If nothing else happens, at least I'll have done that. 

Your sabbatical is particularly interesting because it wasn't such a dramatic outward change. You resumed your business when you returned. It seems like it was more of an inward change. So what was that change?

There’s something that happened to me that stuck with me during that multi-day hike. I noticed after a week or so that I'm up in the morning and I'm trying to get out the door as fast as I can. I'm packing up, I'm eating breakfast, I'm getting my shoes on. 

And I'm watching all these other people around me, Germans and Swiss, and they're just like sitting on the porch drinking coffee in the sunrise. After a week or so, I kind of started to feel like,” Hey, how come I'm the only one in a rush to get out the door here? Are they only hiking five miles a day? What am I doing wrong?”

After I kind of realized that, I said to myself, “Okay, tomorrow I'm not going to rush. I'm going to go this German route. I'm going to sit on the porch and have my coffee.”

And I just didn't look at the clock, and I just tried to slow it way down. I had my leisurely breakfast, and I got my shoes. And when I finally got out the door, I looked at the clock, and it was only 15 minutes later than all the other mornings when I had to rush and try to get out the door. And that was such a light bulb moment for me. 

I wasn't even saving any time. I was just stressed the whole time. And when I came back, I thought “Oh, my God, this is my whole life rushing around, being stressed, trying to get these deliverables out, and do I even need to be stressed about it? I could just do everything at a leisurely pace and it would be okay.” So that was a really big takeaway for me. 

How did that filter into your day-to-day work?

Now, when I work, I try more to accomplish two tasks. I have two priorities or goals for the day and that's it. And if I finish them at 2 p.m. That's great, then I just stop. 

I also thought a lot about the types of work that I wanted to do. I realized little things like having a balance between the strategy offering and the writing offering allow me to create the kind of pace that I want. I realized that there were a couple of clients I had taken on because I was concerned about the finances or how it would look in my portfolio, and I wasn't enjoying working on them. 

Why did I start my own business if I'm going to keep on doing work I don't enjoy? Wasn't the point to be able to pick work that I like to do? 

I didn't blow up my life or move somewhere else or do something crazy, but I think probably for a lot of people, it's those little mindset things that kind of change the direction of your ship over time.

Much like adjacent dreams, you were adjacent to control of your time and your stress. But you didn't quite commit. Sounds like it took a little bit of reflecting to do that.

It's easy to be self-employed but to carry over that employee mindset. Having the sabbatical shook me out of that. I can take five weeks off in a row, what else can I do? What other options are available to me that I just haven't considered or haven't even seen as a possibility? What if I took six months off in a row? Who says I can't? Who's going to stop me? 

How did you pay for your sabbatical?

My base expenses like rent and utilities were about $3,500 a month. I needed to have that banked specifically for August. So as I was planning out my spring, I just took on that much more work to cover it.

The whole trip was probably, $2,200 to $2,300, including flights. So I needed $5,500 for the month. In the beginning, it felt like, “How can I not make any money for a month?” But then when I broke it down, it came down to just taking one additional strategy consultation. Turns out, one strategy consult equaled a sabbatical. 

What advice do you have for people considering this?

There’s a desire to optimize a break like this. You’ll ask yourself, “How do I get the most out of this time? How do I make this the most productive sabbatical I've ever had?” That desire is just so deeply ingrained in us. Don't try to make it productive. 

Don't try to be an ultra-journaler and figure out your whole life. Do something unproductive. Waste some time. Spend three weeks learning how to play the accordion or go on a really long walk. Whatever! Waste some time and see how it feels to not be productive and see how that changes you. We need a little bit more of that. 

Welcome to the third issue of Sabbatical — an exploration of the future of work, modern life, and travel. Sent every month-ish. (Submit your Sabbatical story for a future issue here.) 

See last month’s issue here. Since then, 11 totally chill people have signed up. Sabbatical is so close to 100 subscribers! If you dig these issues, please forward to any travel-loving, career-pondering friends!

Today's Itinerary

• The Note: Everything is a Lego Brick

• The Recommendation: El Nido to Coron, Philippines …

• The Debrief: Janice Karbachinskiy

The Note: Everything is a Lego Brick

Several factors make sabbaticals more possible than ever. Sure, we have remote work and widespread broadband connections. But there’s also a cultural component — an acceptance of the modular nature of our working lives. Consider:

• The rise of “fractional” executives: part-time leaders who often lead multiple teams across multiple companies. The number of people looking for fractional roles far exceeds the opportunities available.¹

• Work on Zoom? Or Slack? What is the practical difference between working with a freelancer, a full-time colleague, or someone 12 hours away?

• 45% of millennials have done freelance work in the past year.

The upside of this is a modular career, one where you can assemble a “portfolio” of jobs, freelance gigs, or contracts to assemble the life and workload you want. That leads to control and flexibility — a career that can better bend to your needs and interests.

Of course, there are downsides, which we’ll address in other issues. But the modular career is like Legos in more ways than one.

Sure it’s more work to build something brick by brick with no guide. But once it’s complete, it’s uniquely you — and a little more satisfying than making something according to the instructions.

📍The Recommendation: El Nido to Coron, Philippines 🇵🇭 

Introducing The Recommendation, a section for travel suggestions assembled from people who’ve been around the world.

via @Tao Phillippines

Our interview subject today embarked on a year-long trip that spanned 17 countries. One of the highlights was this boat trip across the Philippines

“It was five days/four nights and we sailed from El Nido to Coron, spending the days on the boat, snorkeling, playing volleyball, and sleeping in tents on different islands.”

To book this recommendation, visit https://www.taophilippines.com/. Tell them Janice and Sabbatical sent you.

The Debrief: Janice Karbachinskiy

After getting married, Janice and her husband left their jobs (a recruiter at a fast-paced startup and a physical therapist in the army, respectively) to figure out what the next chapter of their life would be. We explore how to use the time to ask your spouse the deep questions that underpin a great marriage + her perspective as a recruiter on resume gaps.

Janice in Guatemala. 🇬🇹 

Why did you drop everything and take a sabbatical?

I was at a hypergrowth startup and it was the best thing that ever happened to my career. I learned so much in a very short amount of time. I loved the pace and the people, but after three-and-a-half years I got to a great point to take a break. I realized I wasn’t ready to jump back into something, I needed a breather.

My husband and I were both up for very big promotions around the time we were considering taking the time off. Our lease in Tel Aviv was ending. The timing lined up. 

Sounds like you had to decide whether you need a break from the industry or that particular job. And it took going away to parse that.

During the trip, I had an open mind. I thought, “Maybe I'll switch careers, industries or not be in a startup” — just to keep it open-ended. But when I got back, I realized I loved what I do. I just need to find the next right place for it. 

How did you balance leaving money and prestige on the table that a promotion would have given you?

It was so hard to make that decision because these are our growth years. These are the years when we can dedicate everything to our careers. We have very few responsibilities. We don't have kids. Our expenses are very low. 

On the other hand, we knew that taking the career opportunities also meant that we would be delaying the trip by a year, or even a few years. Who knew if we would ever actually do it. So it came down to, “If not now, when?” 

So we put our stuff in storage, packed two backpacks, and booked a one-way ticket to Vietnam!

Leaving for the trip

Now that you’re back, has your relationship with work changed?

I cannot wait to get back to work. I am so excited. I'm rejuvenated for what it is that I want to do, and I want to throw myself in 100%. I love my work ethic. I worked very hard. But I worked too long, too many hours. And I want to focus on the “too long” part. My goal is to incorporate that balance, and I think I can find that company.

I imagine during COVID when all these companies were hiring a million people, it had to be hard work to fill those seats in your role as a recruiter.

It was exciting. Our company was in hypergrowth. During COVID I was working so much, taking breaks for meals, but straight back to work in the evenings. And I loved it, but it just is not sustainable.

Let’s talk about the finances of your sabbatical. How did you make it work?

We budgeted in prep for the trip to make sure we saved enough so that we didn't feel limited financially. But we also set expectations that weren't going to stay in luxury places. We also chose Southeast Asia, which we knew was much less expensive. 

We decided not to work while traveling, so we dipped into our savings and we took a couple of risks on the investment front while we were traveling and it ended up working out for us. 

We had just gotten married a few months before we started the trip. We knew that we were going to use the bulk of the gifts we received to travel. So we kind of knew that there was some maybe, I don't know if you can say “unearned money” that would help us enjoy.

Jana and her husband in Malaysia 🇲🇾 

The expected thing to do is put it toward a house or car or furniture. You chose this

Yes. Again it was a hard decision because it went against the “traditional” path but we just were willing to accept the consequences of that financial decision and budgeted to decrease the burden on the way back. While we were planning out our trip we also budgeted to make sure that we had a cushion of three months when we returned. 

What was your process like for figuring out what was next?

At the end of each day, we would do voice notes where we would leave the phone recording and talk to each other about our day.

One day, we’ll listen back to them, but the process was so helpful.

What were those conversations like?

We talked about everything that happened throughout the day but also asked a lot of really big questions because we had time to answer them. We would give our gut reaction, we would reflect on what each other said, and then we would circle back to that question. 

What are our shared values? What is our vision for the future? What's important? 

We also started talking to other people to ask those big questions — often to absolute strangers. We met this chef in Cambodia who already had two kids who were about 12 and 14 years old. He established his career as a chef and teacher and we asked him those big questions. We had the chance to get to know a woman who was 26 and an entrepreneur in a super small town in Vietnam. 

We had the chance to ask people from different cultures our big questions as well as ask fellow travelers. Traveling in the style that we did, where we took a decent amount of time in each place, we really got to connect with so many people as well as so many places. It was cool to be in an environment where you can jump into those conversations as we engaged with the world.

Can you share an example of one of those questions?

Our family is spread around the world. So one of our questions is always, “Where do we live?” We value family so much. We also love the careers we established in Tel Aviv.  We value our time together. How can we balance all of it? That was the biggest question.

What’s your advice for people considering a trip like this?

When I talk to friends, the biggest question they have is the financial element. At first, we monitored every single expense that we had. We wrote it down. And then we got a sense for cost. We had an app that helped us manage it, TravelSpend, we knew more or less how much we were spending each month. 

Also, it’s important to set your expectations. It's not amazing, awesome fun every single day. Sometimes you're tired and you just want a break, and you just want to sit down and you want to unpack. But at the same time, you're like, “Wait, but I'm in Indonesia, and I'm never going to be here again at this time or this place.” Know that it's okay to take some of the things from your old life and slow down. It’s ok to “miss out” on some things. You don't need to become a new person when you're traveling. 

Anything more tactical that you find yourself sharing?

Don't ever pay for a hotel before you see the room! Always book free cancellations. Make sure that you have your apps and you're getting your points. We had the Chase Sapphire card, which helped us a lot with budgeting because we were able to use a lot of points. In Asia, we were working with booking in Agoda and Booking.com so we got tons of points and deals. Do a quick Google of your activity on YouTube or travel influencers for discount codes

One of the biggest things that I learned during the trip is that someone has done this before and you don't need to reinvent the wheel. It's okay to follow someone else's path, but also to make it your own. I think what's important is kind of like to leave breadcrumbs for the next person who comes after you and to help make the path a little nicer, a little smoother. I don't like telling people too much about certain places because I want to leave it for them to experience it and have it but guidance from someone who has done is helped us avoid a lot of mistakes. We got a lot of guidance that helped us to have very good experiences. I want to pass it along. 

That was another lesson I learned - I don’t need to know everything ahead of time, it’s ok to make mistakes but most importantly you should ask for help! People are so willing to help but you have to be open to ask.

Yeah, if you’re traveling somewhere and you know the beats, what are you doing?

No shade from me there. There were times, I'll be super honest with you, when we were judging people's travel choices. And, you know what? Sometimes we said “Let’s try what they are doing. Let's challenge our assumptions. Let's follow the path step by step and see why people are doing that.” 

Is there a time when that surprised you?

In Japan, a lot of the things that you do are on a set path. It's very much like, “Go here, walk five steps, go to the next thing, make sure to go to this exhibit.” And we were very anti, we wanted to to do it our way. 

And we went and we realized, this was a highly curated experience, let’s lean into it and we ended up loving it. It was awesome to let go in that sense. 

You are a recruiter, how do people in your position look at breaks like this?

Now that I'm interviewing and on the other side, I actually haven’t felt any concerns. Maybe because more people are doing it. Maybe it's become more accepted? I see taking a sabbatical as such a huge advantage and it seems a lot of people in the industry are also seeing it in a better light. 

It was a huge concern on my mind. I wondered “Is anyone going to hire me? Are they going to look down on me?” I'm not finding that materialized.

And it didn’t. After this interview, Janice started a new position in January.

(Submit your Sabbatical story for a future issue here.)

1 - The source of this is a fractional work marketplace — which may skew the results a tad higher. Even so, I thought the 50-60 to 1 was notable.

Welcome to the second issue of Sabbatical — an exploration of the future of work, modern life, and travel. Sent every month-ish. We start every issue with a note and end with a story of someone who stopped everything to figure out what’s next.  

See last month’s issue here. Since then, 25 totally chill people have signed up. Today’s itinerary: The emptiness of being a digital nomad and Anna Redmile shows us how families can take sabbaticals too. 

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Today’s Note: Digital Nomad vs Sabbatical

Few books have poisoned the minds of (mostly) millennials than The Four-Hour Work Week. The book, first published in 2009, argued that thanks to the internet, we can work anywhere and lean on new software and outsourcing to run tiny but profitable businesses.  

Long before COVID threw millions into the remote workforce, the book was of a movement that inspired a wave of people to “escape corporate life” and live the “nomadic” lifestyle, traveling from place to place and working on their laptops for as few hours as possible.

The more books you have, the more hours you’re working.

The digital nomad lifestyle framed labor as something to be hacked. Your surroundings are something you observe but not something you participate in. To the nomad, optionality is everything. Stay free to chase the next business idea, live in the next town, and make the next set of friends. It’s thrilling, good for social media fodder, and makes for a good story. 

Most nomads call it quits eventually. They stop moving and lay down roots. Or they stop viewing labor as a thing to avoid and instead, as a tool to affect change, however small.

Things worth doing are difficult. They take commitment. They require you to sacrifice optionality. (You know, the kind of things that make one sound like an old crank.)

But as I get older, I realize it’s the stuff life is made of. It’s the homecooked meal from a friend versus the Doordash order. It’s walking down the street and making small talk with one neighbor versus 100 likes on your LinkedIn posts. It’s jumping in and improving your neighborhood versus moving to the next town when things get boring or difficult. 

There’s a hollowness to the digital nomad movement - because it exists largely in opposition to something. When your life design is geared toward running AWAY from something, you’ll come to the crashing realization that you eventually need to run TO something.

A sabbatical is an absence of normal to figure out what your next version of normal should be. It’s removing things that don’t work so you can add things that do. In issue one, Tam Pham talked about his pivot from the nomad life to “slow living” picking three cities to rotate between. That’s running TO something.

The point of all this is to have a day-to-day life that you don’t want to run away from — whatever that means for you.

_

Sabbatical Story Time: Anna Redmile’s family sabbatical

In the name of seizing adventure when and where you can, Anna Redmile and her family of four took a 13-month sabbatical that concluded just before COVID. We explore the benefits of taking a Sabbatical with children and the role ego plays in our work.

Why did you take these 13 months?

It's something my husband and I had been thinking about for a while. We had been working hard for a long time and had a hankering for a break and some adventure. Then my husband's brother died unexpectedly at the age of 45. That really put things into perspective and motivated us to go for it. You just don't know what's ‘round the corner. 

Our kids were four and seven and it felt like a great time to do it - they were still at an age where they actually enjoyed spending time with us! And we were keen to bank the experiences and memories with them now.

How did you handle pulling your seven-year-old out of school?

When I went to the school to tell them we were doing this and taking him out, I thought they would shut it down and say “What on earth are you thinking? What a ridiculous idea!” But they actually said, “Wow this is a really amazing opportunity!” 

In Australia, a lot of people don’t know this, but the government supports distance learning. Even before COVID. So they gave me all the resources I needed to homeschool. That was the moment the sabbatical changed from an idea to a reality.

Why did you take the break? Were you burned out or tired? Or was it more personal than that?

My husband was burned out a little bit, bearing in mind what happened to his brother. For me, it was about the adventure and spending time with the kids.

Between our planning and leaving, my husband and I were both offered promotions and it was tempting to put the trip on hold. The promotions would not make a meaningful difference to our lives, so we stayed true to our plan, grabbed the bull by the horns, and went for it.

One of the benefits of staying in the same town and community is the deep roots that your children benefit from. How did you balance showing them the world with the stability and continuity kids often need?

When we were away for the year and came back, we picked right back up where we were. The kids were re-enrolled in their school, picked up their friendships and within a few weeks it was like we'd never even left! 

Whilst we were traveling, the homeschooling gave us structure to our days, which were otherwise very varied. We moved every 3 to 5 days which meant we were constantly doing and seeing new things. We tended to do 3 to 4 hours of homeschooling in the mornings, then would head out to do something cool in the afternoon. The schedule was super flexible, but it gave us a sense of structure and stability.

They weren't concerned about friends or missing out on things whilst we were traveling because we were always doing such cool stuff ourselves, and because they had their support network traveling with them. What's more, they had our undivided attention

To your point about laying down roots, since traveling we relocated from Sydney to London. Now that has been hard. The traveling for the year was not hard at all.

I’d love to talk about finances. Did you work while abroad? Did you save money?

We probably spent about $100k AUD all up over the 13 months. We saved money before we went, and rented our house out whilst we were away. 

We didn't travel on a strict budget, but we stayed in hostels, took public transport, ate at local places, and traveled overland where possible.

We generally tried to book accommodation for $50 a night for the 4 of us - in Central & South America that was ideal, but in Europe it was tricky. It's another benefit of going when the kids are younger: With the kids smaller, it was easier to all fit into smaller rooms or buy three meals for four people.

How did your perspective on work change after you returned?

I came back really revived from the trip. It was important to me that I find a job that I would find fulfilling as we spend so many hours a week working, you might as well make it count. I like a sense of achievement and I like being able to add value in a meaningful way.

My identity was no longer tied to my work or my role, and my sense of ego had also diminished. Work was no longer about me climbing the ladder because it fans my ego, it was about a sense of fulfillment, purpose, and earning money which is an enabler to do cool things.

So I returned pumped and ready to go but with some subtle differences around my key motivators.

How did your perspective on parenting change?

I wanted our kids to see how lucky they were living in Sydney in this bubble where most people look the same and everyone is doing fairly well in life. When they came back, they did appreciate that.

While we were traveling, they gave me a lesson: All of the things that I think make them “lucky”? They didn’t even notice that it was gone. It was superfluous to them. They didn’t care they didn't have those things while traveling. 

I remember we were in Turkey, and there was a guy by the river who had a tarp, a tap for water, and a pallet with some rocks around it so he could sit. That’s it. And my son said. “That’s a nice setup he has.” 

And I said “Is it really?  It's not as good as an actual kitchen.” 

And he said “He’s got running water, he can fish, he has shelter and he even has a table. He has everything that he needs.” 

His learning was that as long as you have your basic needs met, you’re covered. And that made me realize many of the things we showered on our kids were superfluous. 

That’s a proud parenting moment!

It was one of the moments when I knew the trip was the right thing to do. I appreciated how they interacted with people and learned languages. They had no baggage and preconceived notions. They befriended people they couldn't communicate with. They learned and experienced so much.

I want to be real here though, you had to have some moments that were tough with the kids on the road. How did you handle tough moments on the road vs at home?

The most challenging thing was home-schooling. Thankfully it was only one child. My husband and I shared the load and tag-teamed when we needed to. We learned to recognize when to call it a day, or switch it up and not just carry on banging your head against a brick wall!

We had to set some clear boundaries and expectations which was tough at first, but we stuck with it and it got easier. My son actually got incredibly efficient at getting his work done so we could crack on with the fun stuff. 

What do people get wrong when they think about taking a break like this?

People think it’s a high-risk situation for their career. But it isn’t. We quit our jobs and came back into COVID. We resumed our lives. Same friends. We slotted back in and picked up our things. A year sounds like a long time, but people don't forget you in a year. Your network is there when you return. 

Is it fair to say it altered your path but it didn’t “set you back”?

Yes. It saw me move into a partnerships role (which was an exciting new challenge) for an EdTech company which was strategically a strong sector to be in during COVID. Again, relocating from Sydney to the UK has been a lot more disruptive than this trip.

What is your advice to other parents considering a trip like this?

I would strongly advocate doing a trip like this (or something totally different) if it is an option open to you. You have to plan for it, but don't wait forever! We have a gift of time, but we don't know how long it will last or how our circumstances might change. 

It was the most incredible thing I have done, and it was such a gift to spend that much time with our children, having fun and shaping them into responsible, open-minded global citizens. I don't believe you have to choose between doing this and having a career.

We would stay at hostels alongside people in their twenties and thirties. And they were often surprised to see a family there. People would tell me they were traveling to “get it out of their system” before they had to “settle down”. You don’t have to live your life that way.

(Submit your Sabbatical story for a future issue here.)

Welcome to the first issue of Sabbatical — an exploration of the future of work, modern life, and travel. You likely signed up for this in the past two months when I posted about this on Threads or LinkedIn.

This newsletter was born from dozens of conversations with ambitious people in my life who were reconsidering the roles work, family, and place have in their lives. These periods of reflection are often punctuated by a sabbatical, an extended break from normal routine to reflect on one’s life. In many (but not all) cases, what comes after the sabbatical looks nothing like what came before.

The mission of this newsletter (and whatever sprouts from it) is to create a guidebook for the modern sabbatical. To use the experience of those who came before to come out on the other side with a life and career that aligns with you, whoever you are. Consider these newsletters never-ending chapters to a book. 

Each monthly-ish issue will start with a note and end with a story of someone who stopped everything to figure out what’s next. 

Today’s itinerary: The beliefs underpinning this project + Tam Pham’s sabbatical and “Adjacent dreams”. 

Today’s Note: What’s going on?

Calling our lives before 2020 the “before times” went from clever joke to cliche. But like most cliches, there’s some truth there. Careers, travel, community, and work are all in a state of change.

These trends are difficult to quantify, as one can find research, surveys, and coverage that both supports and counters them. Instead, after conducting roughly 15 interviews (and counting!) with people who have taken sabbaticals, I’ve noticed several common reasons people are slamming the pause button. 

Reason #1: Remote workers are feeling disconnected

When many white-collar jobs went fully remote in 2020, the general response was positive. Workers loved no longer having a commute, having more time with family, and gaining a more flexible work schedule.

Three years later, the cons are starting to catch up with the pros, especially for those who prioritized their careers as a source of fulfillment (“live to work” rather than “work to live”). A sort of existential panic sets in when one realizes they hustled for years only to spend all day talking to talking heads in boxes on a screen. It’s 2024’s version of the Office Space cubicle. In many industries, you never meet your customers, coworkers, or managers. Is the flexible working style worth the isolation?

Reason #2: Tech and startups are less appealing to the ambitious

If you worked in tech startups in the aughts or earlier, you sacrificed salary and prestige for massive upside if your company was successful or exited. To work for a startup was to toil for 12+ hour days for years. But something changed in the 2010s. Tech startups offered upside and best-in-market salaries. Young people prioritizing money exchanged finance jobs for tech jobs.

After an unprecedented bull run, growth tech companies are getting hammered with layoffs and sinking valuations. If you never really cared about technology or the problems they solved and were in it for the money, you may have a bit of a career crisis on your hands right now. 

Reason #3: The nature of “place” and “home” are changing

Prior to COVID, ambitious college grads often moved away from family to a handful of cities (as profiled in books like The Big Sort and The Rise of the Creative Class). When work was decoupled from location, that naturally left many folks wondering why they were living where they were — to say nothing of the ever-increasing price of buying a home and putting down roots.

Reason #4: The increasing focus on mental health

The reasons vary from “I watched my parents burn the candle at both ends for their career” to “I’ve been going to therapy for years and know how to navigate this” but if you’re under the age of 40, you’ve probably been well-versed in the treatments and culture around protecting your mental health. “Burnout”, “quiet quitting”, “emotional labor”, and “work/life balance” are common phrases I’ve heard when discussing this. When it’s time to reconsider our options, we’re all much better equipped to talk candidly about how we’re feeling and what we need.

Reason #5: Traveling arbitrage is still possible (for now)

Someone once told me that the best plan is to earn your money in America but spend it in Europe. Consider this reddit thread asking what do Americans even do with all of that money. Or that the money that Americans spend shopping for the holidays would rank 19th largest in GDP. Despite decades of globalization, those with high-earning jobs in advanced economies can still derive great value by taking their money elsewhere. One month of a tech/finance/law salary can pay for a three-month sabbatical. 

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Sabbatical Story Time: Tam Pham and Adjacent Dreams

Tam Pham has taken two sabbaticals, one ended up being about getting better at chess and the other to learn (and eventually teach) Bachata. He’s about to start his own business teaching the latin dance style — something he attributed to his sabbaticals.

Tam Pham takes on a challenger

You’ve taken two sabbaticals. Why did you take your first break?

After trying for a long time, I landed what I thought was my dream job in marketing. And I thought, “This is amazing! I’m working with one of my role models!” And then, guess what? I'm still the same old person. Nothing in my life changed in a dramatic fashion.

Second, I was living the remote work digital nomad life. And after I was done work, I had a lot of time on my hands working in an off-timezone from North America. I had to figure out how not to get bored when my coworkers were sleeping and I was in a new place by myself.

What did you do?

One of the things I started doing was playing chess. I fully immersed myself in playing and experimenting, not expecting that I was going to have a sabbatical just for chess. I leaned into it and, holy crap, I'm addicted. I got really passionate about it, and it felt like I was a kid again back in high school when I was competing in my chess club and stuff. I took a break to focus just on that.

How did this change your approach to your career after? 

That sabbatical reminded me that I've always been a great learner. But I've always thought I should learn things within the realm of work. I had to learn digital marketing or I have to learn coding, etc. And I realized, “Oh, wow, there are actually a lot of things I can learn outside of work that can challenge me.” 

So a few years after your first chess sabbatical, you took another break.

It was a bit of an accident because I got sick. I had long COVID, and I didn't have any energy to do anything. My work visa in Canada also expired. And I knew I needed a vacation. As I was resting, I wanted to rest in Mexico. And it just so happened that as got better, I started to lean into the things that were available around me, which was learning Spanish and dancing.

And now you’re starting your own business based on dancing?

Yes. I took a “one-week retreat” in Oaxaca. I spent a week there by myself to see what thoughts come up. And the biggest realization I had was that, deep inside, I've always wanted to start my own business. But instead, I've been taking adjacent jobs as, like, a chief of staff role an operations role or marketing lead role. Because those jobs felt safe. They were all very adjacent to the entrepreneurship goal without taking my own risks.

My setup is great. But if I'm thinking about it long term, that'll be my life for 30 more years. And if I'm going to do that for 30 more years, I might as well tackle the dream I know I have sooner rather than later.

Right. It can be easy to do the safe version of our ambitious goals, so if it doesn’t work out, no one faults you.

Yes, and it’s seen as a good thing by your peers too. They’ll say “Wow you have a job working working with your role model!” or “You know this entrepreneur that I’ve heard of!”

So how did you create that blank space in Oxaca to allow that revelation to come in?

I was burnt out. But I knew with enough space, things would naturally come up. My mind is always running. And so just journaling and not having any distractions I can dive deeper into what's actually under the surface in my own mind. 

I didn't do any drugs, but some people might recommend shrooms or something similar. For me, it was just yoga twice a day, walking on the beach for an hour or so, and then watching the sunset by myself and just seeing how that was. My life was quite overstimulated before that and it was really helpful.

So what’s next?

In February, I’m going to go full-time on my own business teaching Bachata. I haven’t felt this aligned in a while. All of my other jobs were adjacent to my dream. But I’m putting myself on the line for this. I already gave my notice to my full-time job.

Tell me about the finances of these breaks you’ve taken for chess and bachata.

I would have done things very differently for my first sabbatical knowing what I know now. I went broke after my chess one. I had to borrow money from friends to move to my next job. I remember Keith Ferrazzi writing, “Learn in your 20s, earn in your 30s.” I was totally investing in learning. 

With my Bachata one, I moved to Mexico where I could extend my runway. I was also very confident I could get a job whenever I wanted. That speaks to some privilege of having marketable skills. My friends tell me it was risky but I don’t think that at all.

Why?

I could find another job. I could live on my parents’ couch. I could live in a cheap city if I needed to. I could borrow money from friends. I have options. Not everyone is as fortunate as I am, I know.

How do you deal with the lack of community that can come from being a nomad and moving often?

This year I tried something new that I call “slow living”, I was like, “You know what? Let me just have a few home bases around the world and go to those places the most often.  So for this year, I spent six months in Mexico City, three months in Toronto, where I used to live, and then a month in California with my family, and then with the other two months I went where I wanted.

The difference between a digital nomad and slow living is community. When I go back to Mexico City, I feel like I have made more friends here in the last two years than anywhere in the world.

Of course, there are trade-offs. But for now, at least in this stage of my life, I think it's quite cool. I learn new things through people. 

What’s your advice to people considering a sabbatical or designing their life in the way you have?

I hope anyone considering a sabbatical truly does things for themselves and not for clout or accomplishment. Just doing it for the love of doing something, learning a skill, and having an experience you’ll remember forever.

My hope for people is that they take sabbaticals and they aren't outcome-driven. Sabbaticals are personal and special to each of us.

(Submit your Sabbatical story for a future issue here.)