Going Places

Millennials don't want to retire, we want out.

Janel Abrahami — Fri, 06 Mar 2026 10:55:00 +0000

Welcome to the 400 new subscribers to Going Places! I’m so happy you’re here. Did you know I put together an entire course called Pivot with Purpose? Think of it like a supercharged version of all the best content from this newsletter, tailored to help you nail your career goals.

Today, I want you to imagine retirement.

Go ahead and type “retirement” into the TikTok search bar.

What comes up isn’t people collecting a pension check at 65, or the Boca Raton retirement community dreamscape from Broad City.

It’s actually 30-somethings explaining why they’re trying to retire by 40, spreadsheet-obsessed FIRE (Financial Independence, Retire Early) devotees calculating their “coast number,” and a growing chorus of people admitting that the traditional version of retirement— the one we were all supposedly working toward— feels less like a goal and more like a myth.

And our Going Places community feels the same way.

I recently surveyed this newsletter audience about your career, your ambitions, and where you think all of this is headed.

When I asked what "end-of-career success" actually looks like for you, the responses stopped me in my tracks. Not because they were surprising, exactly. But because they confirmed something I'd been sensing for a while:

Retirement, as a concept, has lost its grip on our generation, and something messier, more personal, and more honest has replaced it.

Let's talk about what that is.

First, The Story in the Data

When asked about end-of-career success, the most common coded theme from Going Places readers was financial freedom — cited by nearly a third of all respondents.

Impact and legacy came in second, named by roughly one in five.

Less than one percent said end-of-career success looks like status and recognition.

Almost nobody in this audience is orienting their entire career around a corner office or a C-suite title. The prestige ladder that our parents climbed, the one we were told to want, has basically fallen off the list.

But here's what's interesting: financial freedom and retirement are not the same thing. And the way readers described financial freedom reveals a lot about what we're actually chasing.

The Retirement Dream Means Something Different Now

Some readers did want traditional retirement — early, comfortable, done:

“'Retiring by 55.”
“Early retirement.”
“Hitting my retirement savings number."
-Responses from this year’s Going Places reader survey

But for every response like that, there were two or three that described something more nuanced — less a finish line, more a feeling:

“Having enough money so that work is a choice, not a must.”
“Where my work doesn't feel like work.”
“Not working for someone.”
-Responses from this year’s Going Places reader survey

Notice the shift?

It's not necessarily, "I want to stop working."

It's more, "I want to stop working on terms that aren't mine."

That is a fundamentally different ambition, and it explains why "financial freedom" topped the list even among people who, elsewhere in the same survey, said they have no idea if they'll ever actually be able to retire.

Over half of Going Places readers — 52.7% — are under-saving for retirement or genuinely uncertain whether they're on track. And yet financial freedom still dominates as the end-goal.

Because for a lot of us millennials, financial freedom + optionality is the whole point. It's the thing that buys us the right to make a different kind of choice, whether it be early retirement, mini-retirements, or choosing to never retire because we’re having too much fun with our work (a concept!).

The People Who Rejected the Question Entirely

Some of the most telling responses were the ones that pushed back on the premise of "end-of-career" altogether:

“I have not really thought about this — I'm still trying to figure out what my 'career path' is when the concept of work while the country is falling apart is hard enough.”
“Who knows at this point. I think most of us are living rather day-to-day.”
“I never expect to fully 'retire' from the workforce or if I do, it will be very late (75+). I want to be doing aligned, interesting work until I can't anymore. Retirement feels out of reach.”
“I'm not sure what this means? Like before I retire? Working on projects I'm excited about and proud of and making more than enough money to just survive.”
-Responses from this year’s Going Places reader survey

There's something important in these responses. I see them as realistic rather than nihilistic.

A generation that entered the workforce during the Great Recession, lived through a pandemic that rewrote the rules of work entirely, and is now watching AI reshape entire industries doesn't have the luxury of a stable 40-year plan.

Day-to-day survival and long-term visioning are happening simultaneously, awkwardly, in the same body.

it would be easy to write this off as hopelessness, opting-out, or giving up, but I’m inclined to see it as something more hopeful — less linear, more iterative.

Less "this is the path" and more "this is what I want to feel."

I think me, retired, will look a lot like me at 3yo.

What We Actually Want (And Why It's Harder to Name)

Read enough of the qualitative surveyr esponses and a pattern starts to emerge.

When asked about end-of-career success, readers weren't describing a destination so much as a set of conditions:

“To still have a sense of self to go back to after years in the workforce.”
“Being able to afford the life I want without stress or worry.”
“Having learned and led along the way, while having meaningful real life experiences with people I love.”
“Knowing that I built a successful brand empowering women while staying present for my family, creatively fulfilled and financially free.”
-Responses from this year’s Going Places reader survey

Freedom. Presence. Impact. Identity. These seem more like life goals than retirement goals, no?

And the fact that they're showing up in a question about careers tells you something: for our generation, work was never supposed to be just a vehicle to fund a life we'd enjoy later.

We were told our careers would be central to who we are. And now we're reckoning with what happens when that promise collides with economic reality, with burnout, with the realization that the ladder had missing rungs all along.

The survey also showed that only 6.8% of Going Places readers describe their career as "thriving where I am."

But nearly a quarter are actively building something new.

Almost half are considering a pivot to a different industry in the next 12 months.

We are trying to redesign the whole career timeline, from the inside out, while still inside it.

So What Are We Actually Working Toward?

My read of the data: we are working toward optionality.

The ability to choose — how we spend our time, what we build, who we work for (or whether we work for anyone at all). The freedom that comes not from stopping work but from no longer being trapped by it.

And when you read the responses through that lens, even the ones that seem contradictory start to make sense together. "Retire by 55" and "I want to be doing aligned, interesting work until I can't anymore" are both expressions of the same underlying desire — to not be locked into a version of work you didn't choose.

One reader put it as cleanly as I've ever seen it:

“Coast FIRE — something where if my career ends or I'm fired I'll be ok.”

A psychological safety net, the thing that lets you take a risk, say no to something, or walk away from a job that's slowly making you someone you don't recognize.

Which, if you think about it, is what all the "starting over at 30" content is really about too. We want optionality, the ability to blow something up and still be okay on the other side.

We were handed a broken blueprint — one that promised security in exchange for loyalty, and then took the security away while keeping the loyalty requirement. Is it any wonder we stopped planning for the retirement that blueprint promised?

What This Means For How We Build Now

If optionality is the actual goal, then the moves that feel radical — building a side income, going freelance, investing in a personal brand, staying curious across industries — are actually the most rational responses to the environment we're in:

The survey bears this out too:

Among readers who are self-employed or business owners, the average work-ambition alignment score was 6.94 out of 10.
Among full-time employees, it was 5.08.
Among those between jobs, it dropped to 4.58.

Autonomy correlates with alignment. This doesn't mean everyone needs to quit their job and launch a newsletter, but it does suggest that the people who have designed more control into their work — even incrementally — feel more like themselves inside it.

Almost 9 in 10 Going Places readers are open to multiple streams of income. Over a third said "don't have a thing to sell" is what's stopping them — not a lack of desire, but a lack of clarity. That's a fixable problem.

And it's one worth solving, because the "thing you sell" is often just a packaged version of what you already know.

A Final Thought

One reader wrote: "happily retired and not thinking about 'career' at all."

Another wrote: "A Wikipedia article."

Both of those answers made me smile. Because they're both valid. Both are saying:

I want to have lived a life meaningful enough that I won't need to think about whether it was worthwhile.

The dream of retirement didn't disappear because this generation is lazy or unambitious or incapable of long-term thinking. It disappeared because the deal that underpinned it — work hard, stay loyal, receive security — got renegotiated without our input.

And now we're trying to write a new deal. One that centers on choice, contribution, and the ability to still recognize ourselves when we finally look up.

I don't think we millennials want to stop working (most days).

I think we want to stop working against ourselves.

I'm curious: what does the end of your career story look like right now — and how has that picture shifted from what you imagined even five years ago? Reply or leave a comment, I read everything!

— Janel

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Love the newsletter but want more? Did you know I put together an entire course called Pivot with Purpose? Think of it like a supercharged version of all the best content from this newsletter, tailored to help you nail your career goals.

It’s about damn time you found a career that fits!

Pivot with Purpose is a self-paced online course that has helped 100’s of mid-career millennials land competitive roles in marketing, non-profit management, venture capital, and more! Unlock customizable networking scripts, interviewing & negotiation resources— most Pivoters earn back their investment in the course with their first negotiated offer! Don’t leave clarity, confidence- or cash- on the table.

It's not corporate vs. entrepreneurship. It's way more interesting than that.

Janel Abrahami — Fri, 27 Feb 2026 10:55:00 +0000

For a long time, we were taught to think about careers in terms of “either - or”:

You can either go up or down the ladder.
You can either be a Corporate Baddie or an entrepreneurial founder with a business to pitch on Shark Tank.
You can either succeed or fail.

But, after eight years in corporate HR + going on five years of entrepreneurship– in multiple forms, across multiple income models– I don’t see careers that way anymore.

I see careers as a spectrum with tons of variability between Corporate + Entrepreneurship.

And when you’re trying to design a career that actually fits your life (not just your résumé), two variables come up again and again:

What you’re actually exchanging for money (your time or your insights)
How predictable your income is

Once you look at your career through those two lenses, a lot of confusion suddenly becomes… data.

Let’s map it. I present to you my latest brainchild: The Career Model Matrix.

⏳ 🔁 Time for Money × More Predictable Income

These roles trade the time you actually spend working (aka “butt in seat”)-- and your output during that time– for relatively stable pay. You pretty much know when that direct deposit is going to hit, but you’re still tracking a timesheet.

The career models in this quadrant are (but not limited to):

9–5 Employee: Self-explanatory. You’re paid for availability, output, and consistency.
Independent Consultant : Still time-based, but with higher autonomy and usually higher upside.
Freelancer: Project-based execution work. Flexibility goes up, predictability varies by pipeline.
Portfolio Careerist: A blend of several time-for-money streams at once (part-time roles, retainers, contracts). Stability comes from diversification, not one employer.

⏳ 🎲 Time for Money × Less Predictable Income

This is where volatility starts to show up. People are still paying you for the time you spend with them or on solving their challenges, but retainer (long-term, consistent) clients are less common, so you’re constantly trying to sign new ones.

Online Coach: Speaking from experience, this can feel like feast or famine, depending on how often you “sell” your coaching offer, client demand cycles, and your emotional stamina as much as your skill. I burnt out from this model within one year, but there are many folks for whom this works perfectly, because they genuinely like + are good at the sales/lead generation component.

🧠 🔁 Insights for Money × More Predictable Income

Here, you’re not necessarily paid for the number of hours you work, but for your expertise, leadership, judgement, scar tissue, and skill in communicating all of that to benefit others.

Fractional Leader: You’re brought in for strategic insight at a senior level, without full-time attachment. Common Fractional titles right now are Fractional CMO, COO, Head of HR/Talent Acquisition.
Digital Product Creator: You build and sell courses, templates, frameworks, and other digital tools. You typically only create them once (so you can cap your working time), and, depending on what challenges they solve for your customers, can be high-leverage and offer more predictable income once you find consistent customers. The competition here is extremely high (think Etsy sellers, Notion template sellers), so most success stories have either an existing large audience to sell to or use ads to drive traffic to their products.

🧠 🎲 Insights for Money × Less Predictable Income

High upside, high uncertainty.

IP Licensing: You’re monetizing your ideas, frameworks, or intellectual property. Revenue can be meaningful, but highly irregular. Maybe one or two clients can be enough for your annual revenue, but the sales cycle in landing those clients can be long and intense, and there is no guarantee that they’ll sign after all that courting. Other career coaches can pay me to license my Pivot With Purpose IP/ coaching framework to use in helping their own clients.
Educational Creator: I see this as different from a traditional influencer in that education content (like the kind I create) is often the top of the funnel for a more robust business model that includes consulting, speaking, brand deals, or products. Some of that work quietly pulls you back into the time-for-money quadrants.
Influencer: In my view, an influencer is different than a content creator is that their main goal is to influence you to click on/buy something that turns into a commission for them, whereas a content creator’s main goal might be to build a portfolio of content whose individual, discreet aims are not to convert to sales, but to build a larger audience that can then be monetized B2B (brand deals, consulting, etc).

How to Use This Matrix

After 14 years coaching millennial professionals, I’ve gathered that most career dissatisfaction comes from misalignment:

You might crave predictability, but your career model is volatile.
Or maybe you want leverage and freedom, but you’re stuck in time-based work.

When people say, “I don’t know what my next move is,” what they often mean is:

“I don’t know which trade-offs I’m actually willing to make.”

This spectrum helps you answer that honestly, without shame, hustle rhetoric, or one-size-fits-all advice.

Want to share the Career Model Matrix © with a friend? Tap below:

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It’s about damn time you found a career that fits!

100 Ways to Land a New Job

Janel Abrahami — Fri, 20 Feb 2026 10:55:07 +0000

Oh, hello!

Between you and me, I had a completely different issue planned for today. But being the self-proclaimed pivot queen, I decided this one felt more urgent.

Here's where I'm at: we're officially past the point of pretending there's a "right" way to find new work. Just like there's no single correct place to land on the spectrum between corporate and entrepreneurship, there's no single correct job search strategy either. The rules dissolved. The playbook got rewritten. And the people landing roles right now are just trying more things. Increasing their surface area for luck, if you will.

So, in that spirit, here are 100 different ways you could realistically find yourself a new role right now. Whether that's a 9-5, your own thing, or something the org chart doesn't have a name for yet.

And keep reading for this week's Playbook: proven tutorials for putting the best of these ideas into action. (By "proven," I mean they've resulted in actual job offers — for friends, former clients, and yes, me.)

Highlighted = tutorial in this week’s Playbook

⭐ Direct Job Search (we start here, but we don’t stay here):

Apply on LinkedIn, find the hiring manager’s email, and send them a direct follow-up email to raise your resume to the top
Apply on company career pages
Use niche job boards
Use alumni job boards, and send your alumni career center a personalized note with the role you’ve applied to asking for a warm intro the hiring manager
Use recruiter job portals
Use government job sites
Apply through referrals listed in postings
Apply directly via email to hiring manager
Submit speculative applications
Re-apply to roles after improving your résumé, and send a personalized note highlighting the improvements
Apply through staffing agencies
Apply through temp-to-perm agencies
Apply to contract roles first, like parental leave covers
Apply to internships/fellowships for pivots
Apply to rotational programs

⭐ Networking That Actually Works

Ask friends who’s hiring
Ask former coworkers for leads in your industry
Reconnect with your favorite past managers, who likely know other great managers you’d like to work with
Message second-degree LinkedIn connections
Attend industry events
Attend alumni meetups
Join professional associations, and use their job boards/find a mentor/ask for leads
Join Slack communities in your field
Join WhatsApp job groups for local networks
Join coworking spaces, and ask if they share “member of the week” spotlights. If they do, nominate yourself and include what you’re looking for in your bio.
Volunteer at industry conferences
Host your own small networking dinner
Ask for informational interviews
Ask directly: “Who should I talk to?”
Tell everyone you trust that you’re job searching + give them a “blurb” about you+ what you’re looking for that they can easily copy/paste into an email or DM to someone they know

⭐ Visibility → Opportunity Pipeline (aka, career gravity in action)

Post thought leadership on LinkedIn
Share case studies from your past work
Publish a newsletter (!!)
Start a niche blog
Create short-form video content
Speak on podcasts
Write guest articles
Present at meetups
Teach a workshop, live or virtual
Share portfolio projects publicly
Document your learning journey online
Build something new in public/share your progress and that you’re open to collaborations
Comment thoughtfully on industry leaders’ posts
Publish research or insights
Create a personal website showcasing work, and send it to the same trusted peers in #30

⭐ Recruiters, Headhunters, and Matchmakers (let someone else run the search)

Connect with in-house recruiters
Connect with agency recruiters
Join recruiter talent pools
Update LinkedIn “Open to Work” privately
Send quarterly update emails to recruiters
Ask friends to introduce you to recruiters
Attend recruiter-hosted events
Follow recruiters on LinkedIn and engage thoughtfully with their posts (don’t spam!)
Share your portfolio with recruiters
Ask recruiters what roles are opening up soon (1-2 Quarters in advance)

⭐ Skill-First Entry Points

Take a certification tied to hiring demand (here’s 50% off Coursera plus!)
Complete a portfolio project
Contribute to open-source work
Do freelance gigs for experience
Do volunteer work in target field
Join hackathons or build-a-thons
Compete in case competitions
Publish a capstone project
Shadow someone in the role
Do a short apprenticeship to strengthen key skils

⭐ Inside Moves (the easiest job to get is often inside the building you’re already in)

Apply internally at current company
Ask for cross-functional projects
Request stretch assignments
Move to a different team
Ask to backfill someone on leave
Transition from contractor → full-time
Relocate to a new office for a new role within the same company
Ask internal leaders you trust about any upcoming roles + ask to stay updated
Build a role proposal around unmet needs

⭐ Creative & Hidden-Market Strategies (turn side work into something official)

Pitch yourself for an unposted role
Audit a company and suggest improvements
Send a short Loom/walk-through video explaining how you’d help with a specific initiative
Create a 30-day action plan for a target company
Build a mock project for them
DM founders at small startups
Respond to people’s “we’re growing” posts!!
Track funding announcements and reach out
Track new leadership hires and reach out
Offer to consult first, then convert to full-time

⭐ Community → Opportunity Loops

Join cohort-based courses (I like these)
Join mastermind groups, or better yet, create your own peer cohort of your favorite former coworkers who still work in the same field but at different companies, and keep each other top of mind for leads or other creative ways to find new work
Join founder/operator communities
Participate in online forums
Attend retreats or intensives
Teach inside communities (I do this often + it almost always yields a new client or gig)
Help organize events
Become known as a connector
Share job leads with others first #careerkarma
Stay visible in recurring spaces

⭐ Portfolio Career → Job Offers (ironically, not chasing a job often creates one)

96. Start freelancing in your skill
97. Build a small client base
98. Turn a client into an employer
99. Grow a personal brand that attracts recruiters
100. Create work so valuable someone hires you to keep doing it 😉

And now, the plug-and-play steps + scripts to use to:

Find niche job boards
Apply on LinkedIn, find the hiring manager’s email, and send them a direct follow-up email to raise your resume to the top
Message second-degree LinkedIn connections
Tell everyone you trust that you’re job searching + give them a “blurb” about you+ what you’re looking for that they can easily copy/paste into an email or DM to someone they know
Connect with in-house recruiters
Send quarterly update emails to recruiters
Build a role proposal around unmet needs
Pitch yourself for an unposted role
DM founders at small startups

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4x weekly Playbooks with my exact how-to strategies, hacks, and templates for each newsletter's topic
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The Art of Corporate Espionage (the legal kind)

Janel Abrahami — Fri, 13 Feb 2026 10:55:06 +0000

Last week, we covered the 5 types of revenue streams that corporate professionals are best suited to run, how to choose the right one, what you need to get started, and where to find your first clients.

This week, we’re tackling maintenance: how to stay stable at your 9-5 while gaining momentum in your side business.

🤠 Grab your Hannah Montana wig, we’re getting the best of both worlds (kinda)!

When leading a double life, the goal is usually to not make a splash in either of them, lest one jeopardize the other.

So the following advice is meant for the nebulous space after you’ve gotten a side hustle off the ground and before you prepare to quit your full-time job. Again, read here for the how-to’s of getting started.

This time can stretch on for as long as you want/need it to, as long as your 9-5 work doesn’t suffer. Next week, we can talk about when you know it’s time to go, but first:

1️⃣ Determine your minimum + maximum time split

How many hours per week can you dedicate to your own business? What’s the minimum number of hours per week, and what’s the maximum? Are those hours on weekends, nights after work, the mornings, or somewhere in between? Schedule the hours on the calendar like a work meeting (and you can even up the accountability factor by body-doubling during those hours).

This split will change over time, so don’t get too rigid, but it’s crucial for both your sanity and forward momentum that you commit to a certain breakdown. Without clear dedicated hours to your business, it’s all too easy to spend your precious time deciding “what should I do right now? Should I do anything? Maybe I’ll wait until the weekend and do everything then.” And boom, that time rarely ever arrives, and you’re still “thinking about” starting your own thing this time next year. We don’t want that.

2️⃣ Cash, Clients, Content

When you boil it all down, any business wherein you’re trading your insights for money, you only have a business when you have revenue from clients. Duh. So, to reduce your daily decision fatigue as much as possible, stability only requires (1) growing cash, (2) serving your clients, and (3) sharing marketing content to bring in more business.

3️⃣ For cash, pick 3 RGA’s + focus there

RGA = revenue-generating activity. The stuff that can actually yield new business and build your golden parachute ($$$) out of your 9-5.

Revenue-generating activity is not:

Installing a website design template
Designing a logo in Canva
Ordering business cards
Taking a webinar on how to use your CRM

Revenue-generating activity is (for example):

Hosting your own webinar or “virtual open house” for qualified leads to learn more about your consulting method
Pitching a semi-customized project scope to a dream client
Partnering with a local business to talk about your services in front of their clients, like a registered dietician giving a 20-minute workshop on protein sources at a fitness studio before class

Even after I’d quit my corporate job to go full-time with entrepreneurship, I would spend entire days in a co-working space (an expense!) configuring Zapier automations between my booking page + email inbox. And at the end of the week I’d take stock of my bank account and wonder why it’d only grown by an inch. Because I wasn’t spending enough time on RGA’s.

4️⃣ Context-switch at your own risk

Don’t try to multitask in your business while you’re already multitasking between your day job. Choose either cash, clients, OR content to focus on on any given day.

Here’s what a typical week in my double life looked like in 2021, when I was building my career coaching business in secret while staying on top of my corporate job:

Mon: Content
Tues: Cash
Wed: Content
Thurs: Clients– stacked all my coaching calls one day of the week
Fri: Content
Sat: Cash
Sun: Try to unplug. Where was Brick back then?!

5️⃣ And finally: have an emergency brake ready in case shit hits the fan.

What does your brake look like? Maybe it's a conversation with your manager about flexibility. Maybe it's temporarily pausing client intake. Maybe it's a hard rule that if you hit a certain stress level, something gets cut. Define it now, while you're still functioning, not when you're already burned out and making decisions from a place of panic. Your future self will thank you.

Remember: the goal here is to build something real without sacrificing the stability that lets you take the risk in the first place.

Here's what most people get wrong about running a side business while working full-time: they treat the two like they're equal priorities. They're not.

This week’s playbook breaks down exactly which revenue-generating activities actually move the needle for each of the 5 C's portfolio income streams— and which ones are just busy work that make you feel productive without earning you a dime. 🙅

(Spoiler: most people are spending 80% of their time on the wrong 20% of activities.)

Inside, you'll find the exact checklists I use to stay organized in my double life, plus copy-paste scripts for cold outreach, biz dev, and pitching that actually work!

Become a paying subscriber to get access to the weekly Playbooks and other subscriber-only perks!

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4x weekly Playbooks with my exact how-to strategies, hacks, and templates for each newsletter's topic
Free admission to live career workshops

Part-Time, Contract, or Freelance Jobs to Apply to This Week

Janel Abrahami — Tue, 10 Feb 2026 23:52:06 +0000

Hey there! This list of part-time, contract, and/or freelance jobs is updated on a weekly basis. I can’t guarantee that any given job will still be available at the time you find it, but I’m rooting for you + hope this list can get you in the right direction. For more advice on building a portfolio career, check out this comprehensive article + playbook!

Jobs for week of Feb 9, 2026

⏰ Full-time, 12-month contract

📍 Los Angeles

^💰 $60-84/per hour

Event Sponsorship Sales Lead @ Running Remote →

⏰ Full-time, 3-month contract

📍 Remote (North America / EMEA preferred)

💰 20% inbound/outbound sales commission + base salary

✈️ Limited travel

Community Manager @ The What →

⏰ Part-time, contract, 20-25 hrs/week

📍 Remote

💰 ~$5,500/month

Marketing Lead @ ProMom AI →

⏰ Part-time, 10–20 hrs/week

📍 Remote

💰 $60/hr - $70/hr

UX Researcher @ Prose

⏰Part-time, 12 - 16 hrs/week

📍 Remote

💰 $65 - $90 / hr

It’s about damn time you found a career that fits!

Portfolio Careers Come in 5 C's- Which is Yours?

Janel Abrahami — Fri, 06 Feb 2026 10:55:06 +0000

A portfolio career is an approach to work where, instead of having a single full-time job, you create a "portfolio" of different clients, projects, passions.

Just like investors have portfolios of companies they invest in and creatives have portfolios of projects they’ve worked on, modern professionals like us are building portfolios of a few different titles, clients, and income streams to create an entire career.

The idea of a portfolio career might seem radical if you're used to thinking about work in traditional terms. But in many ways, it's a natural evolution of the gig economy and the increasing desire for work-life balance and professional fulfillment.

When I first encountered the concept of portfolio careers, it was like a lightbulb moment.

Suddenly, all the different aspects of my professional life – my corporate job, my coaching practice, this newsletter, and my speaking engagements – didn't feel like competing interests. Instead, they became complementary parts of a diverse, fulfilling career that no one job description could fully capture.

When you shift your mindset from path 👉portfolio, you find:

You make more money. When one job provides your entire income, everything is riding on that one job. When you diversify your career portfolio, you build a bigger financial safety net.
You find more purpose. Similarly, when one job is your only source of professional identity, how you feel about your work is determined by what's going on at that job in this moment in time: office politics; quarterly earnings; your manager's mood. When you diversify, you take meaning & fulfillment back into your own hands.
You have more social support. Have you ever had your favorite manager resign out of the blue or feel totally isolated after losing your work BFFs when you change jobs? One be-all-end-all job has a huge impact on your social wellness, for better or worse. Tapping into different work communities brings more social stability, support, and fresh perspective.

A few years ago, I started by offering 1:1 career coaching on nights and weekends after my day job in corporate HR. I used the insights and takeaways from those clients to develop my proven career pivot frameworks (the same ones you’re implementing from my newsletter + social content!), and distilled those frameworks into an online course for more people to access.

I marketed that course on social media, which slowly but surely grew my platform. Eventually, I was making a very decent income on the side of my 9-5, and I think I could have continued growing both sides of my career for a while longer.

But what happened next was a perfect illustration of the larger context we’re living in:

One week, I’d noticed that my boss at my corporate job had been ignoring my emails for a day or so, and would only give vague, non-committal responses to my Slack messages. Suddenly, some of my big projects were “on hold,” and I knew what was coming.

I could almost hear the Psycho theme music as I logged into our last-minute Zoom call titled “Quick Update”-- I was laid off.

And suddenly, my side income became my only income.

While it was super jarring at first, this plot twist ultimately reinforced my belief in the portfolio career model. But how can you tell if this path might be right for you?

Here are some signs you’d thrive with a portfolio career:

You have multiple passions or skills that don't neatly fit into one job description.
You value flexibility and variety in your work life.
You're comfortable with a degree of uncertainty and enjoy the challenge of managing multiple projects.
You're looking for ways to diversify your income streams.

Whereas side hustles can be limited to the singular gigs or projects you pick up when you want them, portfolio careers have the potential to become entire businesses with layered projects within.

And in my experience, I’ve identified 5 distinct portfolio career “models” that are easiest for someone with a bit of corporate experience who wants to exchange their insights for money (versus their time) to implement on their own.

I call them the 5 C’s– and yes, I’ve personally experimented with all of them:

Consulting: This side hustle is best for someone who’s comfortable with executive presence and pitching their work to CEOS, founders & VIPs. It’s also a great option for someone with a few successful case studies in their portfolio– prospective clients will want to see your expertise in action and how you’ve helped businesses like theirs achieve a specific result.
Coaching: It’s such a buzzword now that it’s almost lost it’s meaning– Helping individuals achieve a desired transformation through dialogue and ethical protocols. Coaching could be best for the individual who is gifted at guiding someone through a transition or transformation– you understand how to break down a process into its parts for multiple different learning styles.
Courses: Online course side hustles have popped off since the pandemic boom, because they’re relatively simple to set up. You’re basically distilling your expertise into a passive resource that others can benefit from. Creating an online course may be best for the introverted or efficiency-focused individual who wants to package what they know into a comprehensive product and then profit from it indefinitely (as opposed to meeting with clients consistently in real-time).
Content Creation: Content can be such a lucrative side hustle for corporate professionals-- whether from brand partnerships, paid content subscriptions, or other paid opportunities that emerge from your consistency (like speaking or consulting).
Community: Best for someone who thrives on dialogue and connection—you understand how to facilitate conversations that help people feel seen in their professional struggles. Unlike courses or content, community is relational and allows you to deepen relationships over time, which unlocks multiple revenue streams downstream (coaching, speaking, brand partnerships).

Today, my own portfolio looks like: consulting + content creation + course, but it’s taken years to build out a collection as robust as this. And I’ve had to decide which elements to NOT include in my portfolio career– the jobs and projects that weren’t worth the ROI of my time, marketing, and mental energy (not all money is “good” money).

Remember, this isn't about abandoning stability or taking unnecessary risks.

It's about expanding your definition of what a successful career can look like. It's about creating a professional life that allows you to express all aspects of your talents and interests, that provides multiple streams of income and opportunities for growth, and that can adapt and evolve as you do.

*Heads up! Starting next week, this practical how-to section will be a weekly bonus for paid newsletter subscribers. This is the kind of detailed plug-and-play guide you’ll get every week when you upgrade to premium!

👉 Choosing your first “C” without overthinking it

Most people get stuck before they begin because they assume their first choice revenue stream has to be permanent. They search for the perfect long-term direction, which is another way of postponing movement entirely.

But portfolio careers rarely emerge from perfect clarity.

They emerge from sequence, from trying one direction, learning something useful, and letting that learning shape the next step.

A more helpful question, then, is not “Which of the five C’s is the smartest?”

It’s closer to: “Which one already has a pulse in my real life?”

Where do people naturally come to you for help or advice?
What kind of work leaves you feeling more energized than depleted, even when you’re tired?
Which activities feel interesting in a quiet, sustainable way (not exciting for a week, but engaging over time)?
What skills do I want to develop or showcase?
How much time can I realistically commit each week?
What kind of financial return am I hoping for?

Those factors tend to matter more than prestige, and energy is often a better compass than ego, especially at the beginning.

Dig into my comprehensive “starter packs” for everything you need to launch one or more of these revenue streams in the next 30 days!!

It’s about damn time you found a career that fits!

The First Annual 'Going Places' Reader Survey

Janel Abrahami — Fri, 30 Jan 2026 10:55:05 +0000

Oh, hey! I have a fun idea for us.

See, I'm building something I wish existed when I was drowning in career confusion: real data on what's actually happening in our careers right now.

Not like the corporate employee surveys we’re all sick and skeptical of, but honest answers from mid-career folks like you who are figuring out what "going places" even means anymore.

Here's the deal:

👉 You spend approx. 7 minutes answering my questions about where you are, what's working, what's broken, and what you're trying next.

👉 I turn everyone's answers into a State of Modern Careers dashboard that shows you:

What modern careers really look like and how your peers are navigating career confusion, change, and growth
Which tools and hacks are actually making life easier
What your peers are paying for, pivoting to/from, and betting on next
The language to describe what you're going through

Ooh, fun! Let’s start the survey →

Here’s what’s inside:

✔️ The roadblocks keeping you stuck
✔️ The goals giving you energy
✔️ Your real experience with layoffs, job searching, and unemployment
✔️ Tools, systems, and productivity hacks you actually use

After the survey closes next Friday 2/6 at midnight Eastern, you’ll get:

📊 The full dashboard: Salary ranges, tool recommendations, pivot strategies, and direct quotes from people in the same boat

🎯 Early access before I share it publicly

🧠 The receipts:

Feel less alone in your struggles and sticking points
See opportunity in what others are trying
Discover which tools, apps, hidden gems are making life easier for others
Back up your career decisions with data

The catch? I need at least 500 responses to make this legit. So if you've ever thought, "I wish I knew what everyone else was doing," this is your chance to help build that answer.

Contribute to the dashboard→

My promise: None– I repeat none– of your personal info will ever be shared beyond this survey. Not with brand partners, not with organizations, and not with any of my nosey friends (jk, they’re not that nosey). Anything you choose to share (email, name, etc.) is only so I can send you the dashboard and invite you to free events or resources you'd actually want. That's it.

You give 7 minutes to get the full picture.

Let's build this together!!

Let’s jump in →

— Janel

It’s about damn time you found a career that fits!

How to Productize Your Career

Janel Abrahami — Fri, 23 Jan 2026 10:55:09 +0000

Hey, it’s Janel.

Over the past 14 months, I’ve been sitting in on juicy closed-door conversations among CFOs, investors, and other tech execs as part of my fractional role at The Circle by Founders Circle Capital.

And I’ve got to say, I wish I’d learned a specific vocabulary a lot earlier in my career: the vocabulary of Product.

When CFOs talk about their product, they talk about pricing, packaging, and positioning. Yes, marketing and branding is part of that, but what it’s really about is how value gets structured and delivered.

At some point, I realized how different this sounds from the way we’re taught to think about our careers.

Careers are still framed through identity language: titles, roles, ladders, companies, categories. We’re trained to answer “What do you do?” as a declaration of self, not as a description of function. Years of experience, pattern recognition, and skill-building get compressed into a single label, and that label slowly becomes ingrained within us as the boundary of what’s possible.

Over time, that creates a fusion (and confusion) between identity and work. Careers stop being something we do and start becoming something we are. Roles become internalized, our titles become our containers. And, consequently, changing our jobs/containers/identities feels way too big, too self-destructive.

This is why so many career pivots feel existential instead of practical: we register them as threats to our identity instead of what they really are: product design decisions.

But there’s another way to look at this:

What if a career isn’t an identity structure at all?
What if it’s a product structure?

A product isn’t who you are, it’s something you build, shape, and continue to refine. It’s a way of organizing value so it can move through the world in different forms.

Walk with me:

Your skills → product features
Your experience → the infrastructure
Your personal perspective → the product’s differentiation in the market
Your voice → product brand
Your network → the distribution channel

Job titles start to look flimsy in this context, don’t they?

One of my job titles used to be Learning & Development Manager. Sure, it was accurate to what I did at work every day, and it was nice and clean to explain to other people.

But it also barely captures the actual value (me) underneath it — job search systems, coaching methodology, public speaking, training and facilitation, HR and hiring knowledge, employer relations, content strategy, media fluency, narrative building, future-of-work research, community design, cultural analysis of ambition and identity, and systems thinking about careers and labor.

Woof.

OR, you could look at everything I just listed as the “core product stack.” And suddenly, the same core product can be packaged + delivered in many forms, to different “customers”:

A Learning & Development Manager
A career pivot course
A keynote talk
A VC community advisor role
A training program for companies
A media platform
A consulting practice
A community
or a content ecosystem.

💡 Instead of asking who you are, you start asking what you’re building.

If a career is treated as a product, different questions emerge:

What does it actually do for people?
Who is it for?
Where could it live?
What forms could it take?
What contexts would it be valuable in?
How many versions could exist at different scales?

What would it mean for you to build a career that doesn’t depend on a single institution, a single employer, a single role, or a single channel?

What would it mean for you to build something that can evolve without requiring psychological reinvention every time direction changes?

The more I sit with this, the more I think a lot of modern career anxiety isn’t about ambition or clarity. It’s about trying to use identity frameworks to solve design problems.

How to Actually Start Productizing Your Career (The Practical Part)

Alright, enough theory. Here's where you can actually start:

1: Extract Your Core Product Stack

Most of us have been trained to describe ourselves through job titles and responsibilities. But your real value lives underneath all that.

⭐ Try this:

Open a blank doc and write down everything you've genuinely gotten good at over the years— not just what's on your resume, but the invisible stuff, too. The things people come to you for. The problems you solve without thinking. The knowledge you've accumulated that feels obvious to you but isn't to everyone else.

Don't organize it yet, just brain dump.

Then, look for patterns. Are there 3-5 core capabilities that show up across different contexts? Those are your product features.

For example, mine include:

Systems thinking about how careers and identity intersect
Translating complex cultural shifts into relatable narratives
Being the “face and voice” of those cultural moments
Building trust through vulnerability and cultural analysis

Your list will look different. That's the point.

2: Identify Your "Customers"

In product speak, your customers are anyone who benefits from what you offer. But here's the thing: you probably have multiple customer segments, not just one.

⭐ Try this:

Make a list of who has benefited from your core capabilities in the past year. Include:

Your actual employer
Colleagues who've asked for your input
Friends who text you specific types of questions
Anyone who's paid you (or would pay you) for your expertise
Communities or audiences who engage with your ideas

Again, look for patterns. Are there 2-3 distinct groups that keep showing up? Those are your potential market segments.

3: Explore Your Packaging Options

Here's where it gets interesting. Your core product stack can be packaged in wildly different ways depending on who it's for and what context it's living in.

⭐Try this:

Take one of your core capabilities and brainstorm at least 5 different ways it could be delivered:

Example: If one of your core capabilities is "translating technical concepts into accessible language," you could package that as:

Internal training programs for your current company
A consulting service for tech startups who need better user documentation
A content series on LinkedIn
A workshop for bootcamp graduates entering the industry
A keynote talk about the communication gap in tech

Notice how the same underlying capability can live in completely different containers?

That's the shift from "My job is Technical Writer" to "I have a product that solves communication gaps, and it can be delivered in multiple formats."

4: Test One New Package

You don't need to quit your job or burn anything down. You just need to test whether your product has legs outside its current container.

⭐ Try this:

Pick the lowest-lift version of a new package and test it this month:

Write one LinkedIn post sharing a perspective from your expertise
Offer to give a lunch-and-learn at your company on something you know well
Have one conversation with someone in a different industry about how your skills might apply to their context
Create a simple framework or template based on something you do repeatedly

You’re not trying to build a whole new business here. You’re just trying to see if your product resonates when it's not wrapped in your job title.

5: Notice What Feels True vs. What Feels Assigned

This is the psychological work underneath the practical work.

⭐ Try this:

As you go through this exercise, pay attention to what feels like you versus what feels like the role you've been playing.

When you strip away the job title and the company name, what actually energizes you? What would you keep doing even if no one was paying you for it (yet)?

Those are the signs that your product stack is real, not just cosplay of the career you think you’re supposed to have.

So here's my question for you: If you stopped thinking about your career as "who you are" and started thinking about it as "what you're building," what would become possible?

Love the newsletter, but want more? Did you know I put together an entire course called Pivot with Purpose? Think of it like a supercharged version of all the best content from this newsletter, tailored to help you nail your career goals.

It’s about damn time you found a career that fits!

💌 SPECIAL INVITATION for January 23rd

Janel Abrahami — Fri, 16 Jan 2026 20:39:13 +0000

us next friday

Hi friend! I know you just heard from me this morning (what did you think of the newsletter), but I’m moving quickly on an idea and needed to get you the details ASAP.

SO MANY readers are relating hard to The Great Millennial Career Crisis, so I want to do something about it now.

Not to toot my own horn or anything… but in addition to being a millennial who was in a career crisis not long ago, I’m also a 10-year Human Resources girlie (worked across Recruiting, Learning & Development + Employee Engagement) and a career coach since 2011. Yes, really.

I’ve talked to thousands of high-performers who did everything “right” to set themselves up for success only to feel let down when they “arrived.” And even more who feel like they never got the chance to “arrive.”

Lots of conversations like,

“On paper, my career is fine… but something feels off.”

“I’m tired of pretending I should be grateful.”

“I don’t want to blow up my life– I just want it to make more sense.”

“I know there’s something more out there for me, but I can’t explain what it is.”

I have a few ways for you to start solving your Millennial Career Crisis, and I want to share them with you in a space that’s deeper than a TikTok series.

So, I’m throwing a virtual party next Friday + I want you to come!!

🎥 The Great Millennial Career Crisis: Now What?

🗓 Friday, January 23 (just one week away)
⏰ 12pm-1pm ET
📍Virtual on Zoom → recording available to all registrants

During this hour, I’ll walk you through 6 different ways people are actually navigating today’s career crisis– from strategic pivots and portfolio careers to redefining ambition, stability, and success in a shifting economy.

You’ll come away:

Understanding why your career feels harder than it used to
Seeing options you might not realize you already have
Reducing the panic that comes from feeling stuck without context

And just as importantly: You’ll get to connect with other smart, thoughtful people who are asking the same questions– because this moment is a lot less heavy when you realize you’re not the only one in it.

I’d love to see you there!

👉 Sign up here — we’re one week out!

Questions? Hit reply + I’ll answer you directly!

The "Ambition Dial"- Why we're choosing selective ambition

Janel Abrahami — Fri, 16 Jan 2026 15:19:15 +0000

A colorful wall + Valencia filter? On vacation? Groundbreaking.

In case you missed it, 2016 is trending on social media. Did I need the reminder of my go-to outfit combo of shoelace choker + ripped skinny jeans + “Rose All Day” tank top? Actually, yeah, it’s been fun to reflect on who we were a decade ago and who we are now!

2016 is often cited as the last year of the Millennial Optimism Era, and sometimes I really do yearn for the hopeful, active life I lived back then. To set the scene, I graduated from NYU in 2014 and worked my “big girl” entry-level media job in midtown Manhattan through 2016, before leaving for grad school.

*Read the following Day in the Life like Lady Gaga saying “bus 👏 club 👏 ‘nother club 👏 no sleep!”:

Barry’s Bootcamp on Classpass → shower + get ready in the locker room → spend 8 hours in business casual from Ann Taylor LOFT in the office → walk 20 blocks to happy hour → swing by sweetgreen for a Harvest Bowl → take the train home listening to Pandora… with ads(!).

Ah, the good ol’ days.

But there’s one thing I definitely do not miss about that era, and that’s my very rigid understanding of ambition + drive.

Back then, I believed ambition was something you either had, or you didn’t.

We were driven, or you weren’t.

You either wanted a Big Life at full speed, or you wanted a small life.

That all-or-nothing view was extremely uncharitable, but influenced by the hot media for 20-somethings at the time: Leave Your Mark, The Big Life, Girls, Lauren Conrad being chastised for choosing love over work, etc. The message was loud and clear: slowing down meant opting out.

Now, my friends and I think about ambition very differently.

Think of ambition not as something you either have or you don’t, but as a VOLUME DIAL, one that you get to adjust, based on your priorities in this chapter of your life.

Your ambition is not all or nothing. It can exist on a spectrum or move in seasons.

Three years ago, I’d been scaling my own business as a career coach, day in and day out, all on my own, and I was so lonely and burnt out. The ambitious overachiever in me was trying to pretend that everything was fine, but the human in me was exhausted. And, if I’m honest, a little ashamed that it seemed like I couldn’t “hack it” as an entrepreneur.

So I made a decision that felt radical at the time: I adjusted my Ambition Dial down just a notch. I chose to step back into a 9-5 job and give my nervous system a chance to regulate.

Now that it has, I’m in a season where I can push the Ambition Dial up a little bit more, and have more energy to play the long-game.

And now that it has, I’m in a season where I can turn the dial up again—this time with more intention, more energy, and a clearer sense of the long game I actually want to play.

Which brings me to you.

You’re finally recovering from the toxic Girl Boss era, but you’re still ambitious. You know you still have a lot of potential left to fulfill. So how do you go after that potential and make your younger self proud… without going so hard that you eventually burn out and break down?

A simple way to use the Ambition Dial today

If you want to make this idea real (not just conceptually nice), try this:

⭐ Name the chapter you’re in right now.

Not the one you wish you were in. Not the one you think you “should” be in. The one you’re actually living.

⭐ Then ask yourself three questions:

Where is my Ambition Dial currently set?
Be honest. Is it on high out of genuine excitement—or habit, pressure, or fear of falling behind?
What would happen if I turned it up or down by just one notch?

⭐ What’s one small behavior that would reflect that setting this week?

Saying no to one extra commitment
Blocking an hour for deep work instead of busywork
Reaching out to one person who represents the future you’re building
Letting yourself rest without labeling it “falling off”

Your ambition doesn’t disappear when you slow down, it just recalibrates. So when you’re ready to turn the dial back up, you’re doing it from a grounded, regulated place… not survival mode.

On a scale of 1 (all the way down) to 10 (all the way up), where is your Ambition Dial set right now?

While I regret my rigid view of ambition from back in the day, these are 3 things I did in 2016 that I'm most thankful for in 2026:

Lived at home for 2 years after college. At the time, it felt like I was sacrificing my social life at a pivotal point post-grad, but that couldn't have been further from the truth. I paid my parents some rent + saved the rest for grad school, and I still managed to make the most of being a 20-something in NYC. Shoutout NJ TRANSIT-- when it chose to run properly!

Finally got into fitness (thank you, ClassPass $99 Unlimited plan!). I'd never been a gym class hero or team sports girl, but the boutique fitness craze lowered the barrier to entry and let me experiment with different workouts until I found the ones I loved. My love affair with weight lifting + kettlebells is still going strong. (RIP my OG Outdoor Voices leggings.)

Started my career at a legacy corporate company NBCUniversal. There are pros and cons to getting your start in corporate vs. a start up, and choosing to learn the "rules" before I learned to break them was the right call for me.

What about you? Did you make similar choices back then, or did we live completely different lives?!

It’s about damn time you found a career that fits!

Big Career Changes are Happening This Year

Janel Abrahami — Fri, 09 Jan 2026 15:01:08 +0000

💖 Hello, hello to the 1,000 new members of the Going Places movement! I’m Janel, and I’m so, so happy you’re here. As a refresher, this newsletter is 100% organic writing, never from Chat 😉— there will be typos, there will be gaps in my logic at times, and there will always be my earnest mission to help you feel more empowered in how you work. I’ve been musing about millennial careers + the future of work for over five years now, and it just now feels like we’re getting vocal about out discontent.

OK, so now that we’re squarely in the Great Millennial Career Crisis conversation (not dancing around it anymore or pretending it’s not happening), I feel emboldened to share more observations I’ve made about how women work now… and how we’ll be working in the very near future.

It’s no secret that the “old rules” of work aren’t working for us anymore, but I see it manifesting in a number of specific ways than just a binary “MiLLenNiALs are f*cked” attitude.

From corporate life, to the Creator Economy, to freelancing, portfolio careers, and the AI-ification of literally everything, here are five observations on how our work lives (a full ⅓ of our entire lives) will continue to change shape over the next 12 months:

Observation #1: Women are forming "consulting collectives" (a new term I'm coining right now)

Women are creating a third option between solo freelancing and full-time corporate. They're banding together in small, specialized groups to take on bigger clients and projects than they could individually, while maintaining independence and flexibility. Think of it as the grown-up version of the group project, but everyone actually pulls their weight. These collectives share resources, split revenue, cover for each other during vacations, and bid on enterprise-level work. It's the stability of a company with the autonomy of freelancing.

Observation #2: Women are using AI to complement their EQ

While everyone's obsessing over technical AI skills, the women I’ve been speaking to are doing something smarter: they're using AI as a force multiplier for their natural emotional intelligence. They're automating the grunt work (data analysis, scheduling, first drafts) so they can spend more time on the high-EQ stuff that actually moves the needle: relationship building, strategic thinking, and creative problem-solving. Women are already ahead on this.

Observation #3: Women are scaling creator businesses

Content creation is a legitimate business model with serious revenue potential. More women are replacing men as “top creators” because they equate being a creator as being a business owner. I’m personally looking at the playbooks being built by folks like Maggie Sellers Ruem, Grace Beverly, and Jackie Asamoah who are building “sticky” audiences, monetizing core content through multiple streams (sponsorships, products, courses, consulting), and creating businesses that give them both financial security and creative control. We're watching the early days of a massive wealth transfer from traditional corporate structures to individual creators who own their own platforms.

Observation #4: Women are demanding more from corporate

I witnessed the ballsiest move by TIME CEO Jessica Sibley at Web Summit Lisbon last November: in front of an entire packed stadium of founders, leaders, and tech professionals, she called out the fact that the conference moderators forgot to introduce her before she interviewed tennis star + entrepreneur Maria Sharapova on the Main Stage. While Sibley did it with grace and humor, I saw this as a prime example of a larger sea change in Corporate America-- the leverage has shifted, and women know it. They're negotiating harder, leaving faster, and speaking up louder about what's not working. I was fucking impressed.

Observation #5: Women are angel-investing in their own self-interests

I’m stating the painfully obvious when I say that women are tired of watching male investors fund male founders building products for male customers. So they're writing their own checks to female founders, businesses solving problems women actually have, and companies with diverse leadership teams.

Even small angel investments (some starting at $1-5K) are reshaping what gets built and who gets funded. I recently attended a “Female Founders & Funders” mixer that brought in 250 women in one evening! Creator-entrepreneurs like Ruffin Mitchener are bolstering this movement by teaching other women the foundations of angel investing + the steps to writing their first checks.

I keep coming back to this idea: Most millennial (+millennial-adjacent) women I know want three things from their careers:

A career that evolves instead of escalates.
Income that isn’t tied to one source.
Work that leaves room for health, curiosity, and change.

And there is no one-size-fits-all type of job that solves those things. But even leaning into one of these five movements can help you get closer to a reality that feels more meaningful and fulfilling to you. And closer counts!

More to come as I keep pulling on these threads. -Janel

Your response to last week’s exploration of the Career Model Matrix was incredible! And, quite a few of you raised a similar question:

What’s the difference between freelancing, consulting, and fractional work?

I see these three model in particular kind of like concentric circles, so please indulge the sketch below: Freelance work is an umbrella framework for an autonomous career, or “not having one singular boss.” Within that umbrella falls the gig economy, assignment-based work like writing, photography, or graphic design, etc. You most likely collect 1099 forms for each gig (if you’re in the US).

Independent consulting is a type of freelance work, in that you’re out on your own outside of a corporate structure. You don’t have an HR team to help set up your benefits or an IT gal to troubleshoot your tech struggles. As an independent consultant, you likely work under an LLC or an S-Corp and use an EIN number for your taxes.

If you’re a Fractional Leader, you are a type of independent consultant who needs to be set up legally/financially in the same way (no 1099s or one-off invoices). Your payment comes more regularly, as agreed upon with the companies you’re stepping into, but you probably don’t receive full benefits from those companies. You’re likely still in “contractor” status.

Fractional leaders are always freelancers, but freelancers are not always fractional leaders. At least, the way I’m making sense of it! Have a different POV? Reply to this email and let’s chat about it!

literal back-of-the-napkin explainer 🙂

It’s about damn time you found a career that fits!

There’s More Than Just Corporate OR Entrepreneurship:

Janel Abrahami — Fri, 02 Jan 2026 10:55:07 +0000

For a long time, we were taught to think about careers in terms of “either - or”:

You can either go up or down the ladder.
You can either be a Corporate Baddie or an entrepreneurial founder with a business to pitch on Shark Tank.
You can either succeed or fail.

But, after eight years in corporate HR + going on five years of entrepreneurship– in multiple forms, across multiple income models– I don’t see careers that way anymore.

I see careers as a spectrum with tons of variability between Corporate + Entrepreneurship.

And when you’re trying to design a career that actually fits your life (not just your résumé), two variables come up again and again:

What you’re actually exchanging for money (your time or your insights)
How predictable your income is

Once you look at your career through those two lenses, a lot of confusion suddenly becomes… data.

Let’s map it. I present to you my latest brainchild: The Career Model Matrix©.

The Career Model Matrix ©

⏳ 🔁 Time for Money × More Predictable Income

The career models in this quadrant are (but not limited to):

9–5 Employee: Self-explanatory. You’re paid for availability, output, and consistency.
Independent Consultant : Still time-based, but with higher autonomy and usually higher upside.
Freelancer: Project-based execution work. Flexibility goes up, predictability varies by pipeline.
Portfolio Careerist: A blend of several time-for-money streams at once (part-time roles, retainers, contracts). Stability comes from diversification, not one employer.

⏳ 🎲 Time for Money × Less Predictable Income

Online Coach: Speaking from experience, this can feel like feast or famine, depending on how often you “sell” your coaching offer, client demand cycles, and your emotional stamina as much as your skill. I burnt out from this model within one year, but there are many folks for whom this works perfectly, because they genuinely like + are good at the sales/lead generation component.

🧠 🔁 Insights for Money × More Predictable Income

Here, you’re not necessarily paid for the number of hours you work, but for your expertise, leadership, judgement, scar tissue, and skill in communicating all of that to benefit others.

Fractional Leader: You’re brought in for strategic insight at a senior level, without full-time attachment. Common Fractional titles right now are Fractional CMO, COO, Head of HR/Talent Acquisition.
Digital Product Creator: You build and sell courses, templates, frameworks, and other digital tools. You typically only create them once (so you can cap your working time), and, depending on what challenges they solve for your customers, can be high-leverage and offer more predictable income once you find consistent customers. The competition here is extremely high (think Etsy sellers, Notion template sellers), so most success stories have either an existing large audience to sell to or use ads to drive traffic to their products.

🧠 🎲 Insights for Money × Less Predictable Income

High upside, but high uncertainty.

IP Licensing: You’re monetizing your ideas, frameworks, or intellectual property. Revenue can be meaningful, but highly irregular. Maybe one or two clients can be enough for your annual revenue, but the sales cycle in landing those clients can be long and intense, and there is no guarantee that they’ll sign after all that courting. Other career coaches can pay me to license my Pivot With Purpose IP/ coaching framework to use in helping their own clients.
Educational Creator: I see this as different from a traditional influencer in that education content (like the kind I create) is often the top of the funnel for a more robust business model that includes consulting, speaking, brand deals, or products. Some of that work quietly pulls you back into the time-for-money quadrants.
Influencer: In my view, an influencer is different than a content creator is that their main goal is to influence you to click on/buy something that turns into a commission for them, whereas a content creator’s main goal might be to build a portfolio of content whose individual, discreet aims are not to convert to sales, but to build a larger audience that can then be monetized B2B (brand deals, consulting, etc).

How to Use This Matrix

After 14 years coaching millennial professionals, I’ve gathered that most career dissatisfaction comes from misalignment:

You might crave predictability, but your career model is volatile.
Or maybe you want leverage and freedom, but you’re stuck in time-based work.

When people say, “I don’t know what my next move is,” what they often mean is:

“I don’t know which trade-offs I’m actually willing to make.”

This spectrum helps you answer that honestly, without shame, hustle rhetoric, or one-size-fits-all advice.

Do you need to tell your boss about your side hustle? And if so, when and how should you do it? Here’s my take, as a former HR professional, who also started her own side business while working full-time:

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It’s about damn time you found a career that fits!

Consulting Collectives are the Future of Independent Work

Janel Abrahami — Tue, 30 Dec 2025 15:32:37 +0000

Consulting Collective (noun): when 3-6 independent consultants or freelancers band together to operate as a unified business entity, without actually forming a traditional company.

You're not employees, you're not co-founders.

You're strategic partners who share clients, resources, and revenue on specific projects while maintaining your independence on others.

Like the Avengers, but for client work.

Why they’re popping off everywhere right now:

The solo consultant life is lonely and limiting. You can only take on so much work, you have no backup when you're sick or on vacation, and big clients often want teams, not individuals.

But going back to a traditional agency or corporate job means giving up your autonomy, flexibility, and probably a pay cut.

Consulting collectives are the clever middle ground no one’s talking about.

How they actually work:
Each person maintains their own client relationships and projects (your bread and butter).

But when a bigger opportunity comes along-- something that needs diverse expertise or more hands-- the collective bids on it together.

You split the revenue based on contribution, share the workload, and deliver something none of you could have done alone.

The Upsides:

Bid on enterprise-level clients who won't hire solo consultants
Share resources like software subscriptions, admin support, or office space
Cross-refer clients when someone needs skills outside your zone
Split marketing costs and amplify each other's reach
Maintain full autonomy on your own projects
Keep your own rates and client relationships

The Downsides:

Requires extreme trust + clear agreements upfront
Revenue splits can get messy if contributions aren’t defined
You need compatible working styles and values
Harder to scale than a traditional agency model
Client confusion if positioning isn't crystal clear

How to Start One:

Start small. Find 1-2 people you've worked with before and trust completely.
Run one pilot project together before you formalize anything.
Create a simple operating agreement covering: how you split revenue, how decisions get made, what happens if someone wants out, and how you handle client conflicts.
Use a shared project management tool (like Notion) and a joint bank account (or PayPal) for collective projects.
Test it for 6 months before you make it official.

The Bottom Line:

Consulting collectives aren't for everyone, but they might be the future of independent work for those who want the freedom of self-employment with the stability of a team.

If you're tired of turning down big opportunities because you're just one person, or if you're craving collaboration without ommitting to a co-founder or traditional employment, this could be your move.

Just make sure you're building it with the right people!

It’s about damn time you found a career that fits!

Is the Great Millennial Career Crisis Solvable?

Janel Abrahami — Fri, 19 Dec 2025 10:55:17 +0000

👀 Hello! Well, it’s been a doozy of a week. Another creator found massive virality by regurgitating my thoughts and ideas on the Millennial Career Crisis without credit. You can read about what happened– and my response– here. What sets me apart from this creator (and the many who have hopped onto the trend since), is that since I’ve been trying to crack the Millennial Career Crisis for 11 years and writing about it for 5 years, I already had a working thesis on how we move forward. So that’s what I’m sharing with you today!

The question: Can the Millennial Career Crisis be solved?
My answer: Yes, but it’s not just on you + me.

We solve the Millennial Career Crisis by replacing the old promise of "arrival" with a new guarantee of mobility.

Millennials were trained to hunt for the perfect job that will finally make things click, but we’ve seen that that’s a trap in a labor market built on constant churn.

The new goal should be: individual clarity + optionality.

1) You + Me: Shift from “find your one calling” to “build your career operating system”

What individuals can do (without pretending it fixes everything):

Stop using job titles as the unit of identity. Use problems you solve, conditions you need, and strengths you compound. (The Energy Resume approach is basically the antidote here: it’s a map of what actually fuels you.)
Design around constraints, not fantasies. Not “What would I do if I were fearless?” but “What would I do if I wanted to still like my life in 18 months?”
Treat the job search like a flywheel. The “try harder” narrative burns people out; the “experiment smarter” approach creates momentum.
Build a two-track plan:
- Track A: the next role that stabilizes income + builds market leverage
- Track B: the assets that reduce long-term dependence on any one employer (skills, relationships, portfolio proof, audience, products, advisory, fractional work– whatever fits). This is called a Portfolio Career.

This is the psychological shift: from “arriving” to iterating. Millennials were promised that we would eventually arrive, but instead the success metric is agency.

2) Organizational: Stop managing humans like disposable line items

Companies can’t keep preaching loyalty while operating like commitment-phobes. If we want to reduce the crisis at scale, organizations have to rebuild the employment transaction deal in ways that match modern reality.

What employers should implement (and what we can advocate for):

Transparent progression that doesn’t require management. More “expert tracks,” skill ladders, and pay bands people can actually see.
Internal talent marketplaces that work. Real mobility pathways: short-term projects, rotations, internal gigs, reskilling budgets that aren’t performative.
Layoff hygiene. If layoffs happen, treat them like a failure of forecasting (not an inevitability) and standardize severance, benefits continuation, and redeployment support.
Workload truth-telling. Stop praising “high performers” for absorbing dysfunction. Reward sustainable systems, not martyrdom.
Respect the transaction openly. The future of work is transactional; pretending it’s a family just creates betrayal. A healthy transaction is still a relationship—it’s just honest.

3) Policy and economics: Make stability possible again

You and I cannot “self-help” ourselves out of housing costs, medical risk, childcare expense, and debt burdens that shape every career choice. If we’re serious about solving the crisis, the floor has to rise.

High-impact levers that we must continue to demand:

Portable benefits (healthcare, retirement, paid leave that travel with you across jobs, contract work, and unemployment gaps)
Childcare support that actually reduces career penalties for parents (especially women)
Housing supply + affordability policy (because “career choices” don’t mean much if geography traps you)
Stronger wage growth mechanisms (bargaining power, pay transparency enforcement, fair scheduling, misclassification crackdowns)
Public investment in reskilling that’s linked to real jobs (and not just tuition funnels)
This is the macro shift: just like a climate crisis is less about “personal responsibility” to use paper straws, this Career Crisis is systemic.

4) Culture: Rewrite the meaning of success for the post-linear era

Millennials are grieving a story we were sold: that ambition is a straight line and “making it” looks the same for everyone. We need a cultural update that treats non-linearity as normal, not shameful.

Let’s build these new cultural norm:

Decouple worth from productivity. Not as a cute slogan, but as an actual practice: rest, boundaries, identity beyond output.
Normalize career “seasons.” Not everyone is in a climb season. Some are in a rebuild, care, health, exploration, or consolidation season.
Treat your ambition like a volume dial that you get to adjust based on where you are in your life, not a personality trait that you either have or you don’t.
Name the system out loud. When people understand the economic and organizational forces at play, shame loses its grip.

This is the cultural shift: from “prove yourself” to build a life.

If you’re here for this, let me know your thoughts in the polls below + hit the SUBSCRIBE + SHARE buttons. You’re not gonna want to miss what’s coming in 2026!

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It’s about damn time you found a career that fits!

F*ck your 5-Year Plan: Try this instead

Janel Abrahami — Fri, 10 Oct 2025 09:55:00 +0000

Many of my peers and I have latched onto the framework of a Five-Year Plan, whether it was reinforced through the high school-college-career pipeline or that old chestnut of an interview question, "Where do you see yourself in five years?"

In my opinion, a question that was meant to encourage us to develop a sense of vision and intentionality may have actually stunted our willingness to experiment and pivot.

We became so committed to our meticulously planned futures that we lost our ability to try something without needing it to be The Thing™ for the rest of our lives.

And in a world where entire industries can be disrupted in a matter of months, where AI is reshaping job categories faster than we can update our LinkedIn profiles, where the "rules" of work change every few years... the Five-Year Plan is actively holding us back from our most agile, adaptable, and fulfilled selves.

So, what can we do instead?

Take it Back to Middle School Science Class

Do you remember the scientific method from grade school?

Start with a question.
Form a hypothesis.
Design an experiment.
Collect data.
Analyze results.
Draw conclusions.

The whole point wasn't to prove your hypothesis was right, but to learn something, regardless of the outcome. A "failed" experiment wasn't actually a failure, it was just information.

Somewhere between our playful adolescence and perfectly-planned adulthood, we forgot this.

We stopped treating our professional lives like experiments and started treating them like commitments we had to defend. Every job became a five-year statement of intent. Every pivot looked like admitting failure and starting again from scratch.

But what if we brought the experimental mindset back?

What if instead of asking "What's my five-year plan?" we asked "What's my five-month experiment?"

Why the 5-Year Plan Framework Is Too Outdated

Let's be honest about what's changed since the Five-Year Plan became career gospel:

🏃‍♀️ The pace of change has accelerated beyond recognition.

In 2020, who could have predicted that remote work would become the norm? That an entire generation would quit their jobs in what we'd call the Great Resignation? That ChatGPT would launch in late 2022 and fundamentally shift how we think about knowledge work?

We can barely predict what skills will be in demand 18 months from now, let alone five years. The career landscape is shifting beneath our feet constantly.

🏆 The old markers of "success" have lost meaning.

Previous generations could plan: stay at the company, get promoted to manager, VP, maybe C-suite. Buy the house. Collect the pension.

But only 6% of millennials say their primary career goal is to reach a leadership position. We've collectively shrugged off the corner office, and our paths are becoming less and less linear.

🎲 The cost of being wrong is too high.

When you commit to a Five-Year Plan, you're committing before you have enough information. You're betting your next half-decade on a hypothesis you haven't tested.

And when that plan doesn't work out— when the job isn't fulfilling, when the industry shifts, when you realize you chose it because you were good at it, not because you actually wanted it— you don't just feel disappointed. You feel like you failed. Like you wasted time you can't get back.

The Five-Year Plan mindset makes every course correction feel like a crisis.

Enter: The 5-Month Experiment

Here's what I'm proposing instead: treat your career like a series of experiments, not commitments.

Five months is long enough to:

Learn something real
Build a skill
Test whether you actually enjoy something or just like the idea of it
Gather real data, not just daydreams

But it's short enough that:

You're not betting your entire future on it
Failing, or not liking it, doesn't feel catastrophic
You can pivot without the weight of a "wasted" multi-year investment
You can try multiple things in the time it would take to execute one rigid plan

Those of us who will thrive in the next decade won't be the ones with the most ironclad plans.

We'll be the ones who are comfortable experimenting, iterating, and treating our career experiences like a laboratory instead of a locked-in trajectory.

A Starter Framework: Your First 5-Month Experiment

So you've been curious about something— freelancing, content creation, a career pivot, starting a business, going back to school— but you've been paralyzed by the commitment? By the pressure to make sure it works out?

Here's how to structure it as an experiment instead:

Month 1: The Hypothesis

What are you curious about testing?
What's your actual question? (Not "Will this be my forever career?" but "Do I enjoy the day-to-day of this work?" or "Can I build this skill while keeping my current job?")
What would "success" look like for this experiment? (And remember: learning "this isn't for me" is a successful outcome)

Months 2-4: The Experiment

Take one concrete action per week that moves you closer to testing your hypothesis
This could be: taking a free course, doing freelance work on weekends, posting content 3x per week, informational interviews, shadowing someone, joining a new community
Track what you're learning— skills, yes, and how you feel doing this work
Give yourself permission to hate it. To love it. To feel confused. That's all data.

Month 5: The Analysis

What did you learn about yourself?
What surprised you?
Based on what you now know (not what you thought you knew), what's the next logical experiment?
Do you want to go deeper into this path, pivot to something adjacent, or close this chapter and test something else?

The key: You're just deciding your next move, not your entire future.

What This Actually Looks Like

Maybe your Five-Month Experiment is:

Testing freelance copywriting on weekends while keeping your marketing job
Launching a newsletter and committing to publishing weekly for five months
Enrolling in a data analytics bootcamp and building one portfolio project
Reaching out to five people in a field you're curious about and asking them what their day-to-day actually looks like
Saying yes to a stretch project at work that scares you
Starting a side business and seeing if you can get your first five clients

None of these require you to quit your job, burn it all down, or have it all figured out.

They just require you to start.

The Permission You're Waiting For

Repeat after me: “I don't need to know where this is going.”

You don't need to be sure it's going to work out.

You just need to be curious enough to run the experiment.

Because, in my opinion, the ones who are going to be the most fulfilled, the most adaptable, the most resilient in the years ahead are the ones who got comfortable not knowing, but exploring anyway.

So what's your next experiment?

What have you been curious about but too scared to fully commit to? What would change if you gave yourself permission to just test it for five months?

I want to know: reply to this email or leave a comment below with what your first experiment might be!

This week's question comes from Sarah, a nurse, on Instagram:

This is the exact reason I love the experiment framework!

Here's my rule of thumb: If you're exhausted by the work itself, that's a sign. If you're exhausted by the uncertainty, the learning curve, or the vulnerability of being new at something… that's just part of the experiment.

When I was building my coaching business, I loved the work: the conversations, the group dynamics, watching people gain clarity. But I was exhausted by the constant sales cycle, the content treadmill required to ~fill my pipeline~, and the isolation of being a team of one.

That exhaustion was data. It told me I wanted to shift from sales-focused content to reach-focused content, and eventually back to a role with a team (whether full-time or part-time).

So ask yourself: Am I tired of the work, or am I just tired of being a beginner?

If it's the former, you have your answer. If it's the latter, maybe give yourself one more month of the experiment.

Either way, it's all just information.

It’s about damn time you found a career that fits!

3 Types of Ambition: Why You Haven't Lost Your Drive, You've Just Evolved

Janel Abrahami — Fri, 03 Oct 2025 09:55:00 +0000

There are actually three different types of ambition, but we only ever talk about one of them. But acknowledging all three could make us feel a lot better about our path and more confident in our choices.

Let’s dicsuss:

1. Achievement Ambition – the one we always hear about and think being ambitious always falls into this bucket. Get into a top business school, update your job title to something higher, land a book deal, get a new shiny gold star. Nothing wrong with this one, as long as you're going after achievements that actually mean something to you, not just what you think you should be achieving.

2. Experience Ambition – the drive to live through certain things, often for the sake of the experience itself. Living abroad for a year. Giving van life a go. Pitching your work to a creative agent just to know what it feels like to put yourself out there, regardless of whether you land the deal. Rather than checking boxes, this one’s about expanding what you know is possible for yourself.

3. Process Ambition – the desire to become someone through sustained practice and learning. Starting that craft business to see what you feel like as someone who owns a craft business. Learning to grow your own food. Strengthening your financial literacy. Building sustainable healthy habits for the long term. You're motivated by the transformation that happens through the doing, not necessarily by any external marker of "arrival."

Here's why this distinction matters:

We've built an entire culture that only recognizes the first type. Our LinkedIn profiles, our dinner party conversations, our internal scorecards are all designed to track Achievement Ambition. And when you stop optimizing for those metrics, it's easy to feel like you've lost something essential about yourself.

So many of my peers and I feel like we're losing our grip on our ambitious selves just because we don't care as much about achievement-based goals as we once did.

And I'm not talking about a lazy "I've given up" kind of apathy. I'm talking about an active choice to pursue things that matter deeply but don't come with external validation. The problem is, without a framework for recognizing Experience and Process Ambition, that choice can feel like failure.

It can feel like you're becoming less admirable, less driven, less something than your past self— the one who was "going places." (Just speaking for myself.)

So what changed?

I think it's disillusionment, but not the cynical kind– the clarifying kind.

Somewhere around our early 30s, a lot of us started realizing that the achievement-based metrics we'd been chasing— the ones that looked so good on paper— weren't actually making us feel the way we thought they would. The promotion came with more stress than satisfaction. The prestigious company name on our resume didn't make us wake up excited.

We hit the milestones and found ourselves asking, "Wait, is this it?"

For some of us, especially those who stepped away from corporate environments where ambition was easier to measure, the shift has been particularly disorienting. Without those external markers, how do we know we're still becoming something? How do we know we haven't just... stopped?

I've wondered this about myself constantly. After leaving the corporate world, I chose to prioritize goals like learning to grow my own food, understanding my finances more deeply, and maintaining sustainable routines that actually stick. These things matter enormously to me. But they don't come with job titles or announcements or anyone else noticing.

And that doubt around my own ambition made me question whether I was still the person I wanted to be, or if I'd somehow become a less impressive version of myself.

But here's what I've realized:

Since I've started thinking about Experience and Process Ambition as legitimate forms of drive, I feel just as sure of my forward momentum. Maybe more sure, actually, because I'm not waiting for someone else to validate that I'm moving in the right direction. I can feel it on the inside, and that's enough.

The gold stars are still there if you want them. Achievement Ambition isn't going anywhere, and for many goals, it's exactly the right framework.

But if you've been feeling like you've lost your edge just because you're chasing different things now (things that don't fit neatly into a LinkedIn update or a toast at a dinner party), I want you to know: you haven't lost anything. You've just evolved into a different kind of ambitious.

And this version of you is still going places, too.

This week’s question comes from Ellie, a graphic designer in Austin, TX:

Yesss, Ellie! Among my cohort of freelance/consulting/fraction peers, here are the top places we find interesting gigs to stack on top of other income streams:

Generalist World newsletter
Hello Generalist
Freelancing Females
Fractional Jobs
Slack groups specific to an industry (eg. public relations, social strategy, UX designers)

It’s about damn time you found a career that fits!

Are Side Hustles Really About the Money?

Janel Abrahami — Fri, 26 Sep 2025 10:15:00 +0000

Here's a question that's been gnawing at me: if side hustles are just about making extra money, why do so many people choose the hardest possible ways to earn it?

Think about it:

You could drive for Uber, pick up shifts at a retail shop, or freelance in the skill you already get paid for at your day job. Easy money, proven demand, minimal setup.

Instead, I watch my peers launch Etsy shops that take months to turn a profit, start newsletters that might never monetize (this one included), or offer services they've never sold before. They'll spend weekends learning new platforms, evenings pouring over website design, and spare moments responding to Instagram DMs about their "little side project."

If it's just about the cash, we're doing it all wrong.

But if you feel a pang of sorrow at the above statement, like I do, then I bet it’s not just about the extra income.

So what are we really buying when we build something on the side?

The Real Currency: Identity

I had a coffee date last autumn that still lives in my head rent-free:

I sat across from my dear friend Franckie, then seven months pregnant with a full-time job in tech sales that gave her decent benefits— including 12 weeks of paid maternity leave. On paper, she was set.

But when we talked about her return-to-work plans, she said something that stuck with me:

"It's so messed up to think that I have to go back to work in order to afford someone to care for my child while I'm at work."

When I asked if she had any other income streams, her whole energy shifted.

"I've always wondered about having a photography side hustle. I'm really good with the camera, and all of my relatives use photos I've taken as their LinkedIn headshots."

Notice what happened there? The side hustle wasn't necessarily about passion or entrepreneurial spirit, but about buying back time that the American corporate world wouldn't give her.

It was also about being recognized for a skill that made her feel differentiated and useful to people she cared about.

The Identity Split

Here's what I've noticed about almost everyone I know with a side hustle: they describe their day job with resignation and their side project with animation.

The corporate marketing manager who teaches yoga on weekends doesn't just want the extra $200/week. She wants to be seen as someone who helps people find peace, not someone who optimizes click-through rates.

The software engineer who makes jewelry isn't just trying to supplement his tech salary. He's creating beauty with his hands after spending 40 hours a week debugging code.

The recruiter who writes queer romance novellas isn't necessarily chasing bestseller-type of money. They’re exercising parts of their imagination that spreadsheets can't touch.

A side hustle becomes a place where we fulfill our career fantasies.

What We're Really Purchasing

When you strip away the "passive income" promises and "be your own boss" rhetoric, most side hustles are actually expensive ways to buy three things money can't directly purchase:

Autonomy: The ability to make decisions about your work without asking permission from someone who doesn't understand what you're trying to build.
Identity: Recognition for skills and interests that don't fit into your job description but feel central to who you are.
Time: Not just more time, but time that belongs to you— time when you're building something with your name on it, instead of building someone else's dream.

The American working world has almost convinced us that these things are luxuries, nice-to-haves. But really, they're psychological necessities that traditional employment stopped providing somewhere between the death of pensions and the rise of "we're like a family here" corporate culture.

The Hidden Economics of Meaning

The most telling thing about side hustle culture, to me, isn't how much money people make— it's how little money they're willing to accept for work that feels meaningful.

I've watched people leave corporate jobs that pay six figures to start coaching businesses that might never break even. I've seen highly skilled mid-level professionals take their feet off the gas in order to spend more time building a content channel for five followers (at the time, we all gotta start somewhere).

From a purely economic standpoint, it makes no sense.

But from an identity standpoint, it's the most rational thing in the world.

When your day job pays well but doesn't pay attention to the parts of you that matter most, you'll find ways to pay yourself in recognition, creativity, and control, even if the math doesn't add up.

The Question We're All Avoiding

If side hustles aren't really about money, why do we keep talking about them like they are?

Maybe because "I started a side business" sounds more legitimate than "I needed a place where I felt like myself."

Maybe because "building multiple income streams" feels more strategic than "my day job is slowly killing my soul, and goddammit I just needed to be creative again."

Or maybe because admitting that we're willing to work twice as hard for half the money just to feel human at work reveals something uncomfortable about the work we're already doing.

What We're Actually Building

69.6% of Americans now have a side hustle, and I don't think it's because we've collectively decided we love working more hours.

I think we're collectively redesigning what work means because, to many of us, work stopped meaning anything.

Perhaps on some level we are pursuing side gigs for the extra income, but I strongly believe that there’s more to it than that.

I believe American side hustles have become the new conduits for full selves to exist in a professionally-palatable way.

What I’m still untangling (in order to be able to write about it here) is the firm belief that not every part of our identities need to (or should) be monetized! That’s for Part 2, I guess!

I'm curious: if your side hustle disappeared tomorrow but your day job salary doubled, would you take that trade? What does your answer tell you about what you're really building on the side?

Instagram post

This week, I’m highlighting an excellent question I received during my Glassdoor Hot Seat Q&A last week!

Ah-ha. I've navigated this as a job seeker, myself, and I found that the real culture shows in how people answer specific Qs like: “What happens if someone makes a mistake?” or “When’s the last time someone got promoted?”

Think about real desires or deal-breakers in your job search, then craft a few specific interview questions around them. Some more examples that my clients have used successfully: "How often do fire drills come up? How does the team respond to them?" and "What does recognition look like besides promotions/raises?"

BTW: There’s a whole vault of smart questions to ask to help you clarify your career goals in Pivot With Purpose, below!

It’s about damn time you found a career that fits!

What 30+ Women Had to Unlearn to Finally Thrive

Janel Abrahami — Fri, 05 Sep 2025 09:55:00 +0000

This week, I posed a question to my social audiences and group chats:

“If you’re a woman over 30 who is genuinely thriving and at peace, what is something you had to unlearn to get to where you are today?”

The responses really moved me, so I wanted to share some of the top ones with you in this week’s newsletter:

“If you’re a woman over 30 who is genuinely thriving and at peace, what is something you had to learn (or unlearn) to get to where you are today?”

That being willing to navigate difficult conversations with people is a sign of love and respect, and doesn’t have to be a sign of conflict. –Jillian
How to stop being “cool girl” and start actually being how I wanted to be. —Elizabeth
[The false belief that] my life would really begin once I was in a committed relationship/had my own children. –Dana
Unlearning the urge to be helpful, and asking for what I need first –Linda
Everything is not supposed to be hard all the time! If a part of life feels like you are just trudging through every day (for me, this was work, which bled into the rest of life), something else is probably a better fit for you! –Sarah
Letting others feel their issues without getting the empath side of me involved –Elysia
Asking questions isn't a weakness or showing you're not smart, but a way to build a relationship –Sarah
It’s ok to admit you don’t know something. Not knowing everything doesn’t mean you’re dumb, it just means you don’t know that specific thing. –Kim
People aren’t always going to understand or get you. That’s not your problem to deal with, as long as you feel confident in yourself and your own decisions. –Harper
Just because I’m disappointed doesn’t mean I did something wrong, and therefore, I don’t need to beat myself up about it and fixate on how to make sure I’m never disappointed again. –Judy
Don't wait until you feel the need for self care. By then it's likely too late. Build it into your everyday life. –Tammy
Emotional tears are healthy. They literally help flush cortisol out of your body. Let them flow. –Theresa
Believe people when they show or tell you who they are the first time. –Kelly
You don't get what you deserve; you get what you negotiate for. –Alice
I learned to stop apologizing when I don't have anything to apologize for, but instead mean something like "I'm uncomfortable / concerned / feeling too vulnerable and I don't know how to give that voice.” –Becca
I had to unlearn my whole plan. Having a rigid plan was keeping me from discovering what I was actually good at and what I actually loved. –Mallory

Respond to this email and tell me– what is something you had to learn (or unlearn) to get to where you are today?”

This week’s question comes from Cole, a lawyer in Austin, via TikTok:

Brand partnerships!

When I first started creating content, I assumed any real income would come from live coaching or Pivot With Purpose course sales —things I had “built” myself. But the momentum of brand partnerships surprised me. Once a few videos hit and I had a consistent point of view, companies started reaching out to collaborate. Some of those deals ended up being more lucrative per project than the things I had poured months into building.

On the flip side, coaching— while incredibly fulfilling— has ebbs and flows I didn’t anticipate. Demand isn’t always steady, and I realized it required a lot of my direct energy to scale. That’s what pushed me to find retainer consulting clients that feel more sustainable long-term.

So, don’t underestimate the “unexpected” revenue streams that come when you’re visible and consistent. Sometimes the thing you thought would be a side dish ends up being the entrée!

It’s about damn time you found a career that fits!

How the Job Market Actually Works (vs. What You Were Told)

Janel Abrahami — Fri, 29 Aug 2025 09:55:00 +0000

You've been staring at job boards for months.

Your LinkedIn profile is "optimized."

Your resume has been through seventeen iterations. You've applied to 147 positions that feel like varying degrees of soul-crushing compromise.

And you have exactly three interviews to show for it—two of which ended with "we've decided to go with someone who's more of a cultural fit" and one that resulted in a lowball offer for a role that somehow required both entry-level enthusiasm and senior-level experience.

If this sounds familiar, let me save you some time:

It’s not you. Your college career counselors (myself included!) prepped with you career advice more outdated than Aztec-print leggings.

Here’s how the job market actually works today vs. what we were told:

The Shot Before the Chaser

Some data that might make you feel less insane about your job search experience:

The application “black hole” is real:

The average corporate job posting receives 250+ applications (Harvard Business Review, 2024)
Only 2% of applicants get interviews from online applications
85% of jobs are filled through networking, not job boards (Federal Reserve Bank of St. Louis) → but you knew this one already, right?

The experience trap has gotten worse:

61% of "entry-level" positions now require 3+ years of experience, up from 35% in 2019 (Burning Glass Institute)
Mid-level roles increasingly demand experience with tools, platforms, or strategies that didn't exist five years ago

The hiring process has become performatively complex:

Average time-to-hire is 44 days, up from 23 days in 2010
Companies are conducting an average of 6-8 interview rounds for roles that used to require 2-3 (!!)
42% of job postings are "ghost jobs"—positions companies post but never intend to fill, either to gauge market interest or meet internal posting requirements

Confessions of a College Career Counselor:

This one hurts my soul, but I need to own it. I was a peer career counselor for three years in college, prepping my classmates for the “real world” with resume critiques, mock interview prep, and on-campus recruitment opportunities.

Eleven years ago, I was one of the (very well-meaning) people who taught you to:

"Tailor your resume for each application" (spend hours customizing keywords for jobs you'll never hear back from)
"Follow up professionally" (send thank-you emails into the void)
"Research the company culture" (insert mission statement buzzwords into your cover letter)
"Show your passion" (send an Edible Arrangement to the recruiter’s office)

What we prepared you for: A world where merit was transparent, where "the best candidate" got the job, where “going the extra mile” to stand out actually worked, where following the rules and working hard guaranteed upward mobility.

What you got instead: A hiring landscape dominated by applicant tracking systems that filter out qualified candidates, referral networks that prioritize connections over qualifications, and companies that have turned recruitment into elaborate theater while making actual hiring decisions through completely different channels.

And while this advice wasn’t “wrong” for the time, no honest career coach should still be supplying it today without any caveats or more strategic approaches is not long for this market…

How to Land a New Job in 2025

Alas, here’s the advice I’m giving today.

The 70-20-10 Rule of Modern Job Searching:

70% of your energy should go toward building relationships and visibility within your industry
20% should focus on direct outreach to specific people at target companies
10% should be spent on traditional applications (and only for roles where you have an internal connection)

What this looks like in practice:

Instead of applying to 50 jobs this month, identify 10 companies where you want to work and find 2-3 people at each company who are doing work you admire or are in positions adjacent to what you want. Comment thoughtfully on their LinkedIn content. Share their posts with your own insights. Send a brief, genuine LinkedIn message about something specific they've worked on or posted and why it matters to you.

Yes, this feels like "networking," which might make your skin crawl.

But it's not the same as the transactional schmoozing you were taught to fear. It’s relationship building at its core, and it's how the job market really functions.

Why it’s important (and what we couldn’t admit back then):

Most hiring managers would rather hire someone they know (or someone vouched for by someone they trust) than wade through hundreds of applications from strangers. This isn't corruption (most of the time), but human nature combined with company resource constraints.

And, the people getting hired in 2025 aren't necessarily the most qualified– they're the most memorable. In a market flooded with talent, being memorable matters more than being perfect.

The job market rewards people who understand that hiring is fundamentally about risk reduction, relationship building, and pattern recognition. It's a complex social system disguised as a professional process (not the meritocracy we thought it was back in college).

This doesn't mean the system is fair, and it doesn't mean you should stop pushing for change. But it does mean that succeeding within it requires understanding how it actually operates, not how we wish it operated.

So, your next move isn't to apply to more jobs; it's to get better at the game that's actually being played.

What's your take? Are you seeing these patterns in your own job search, or have you found strategies that actually work? The comments are open—I'm curious how this matches (or doesn't match) your experience.

This week’s question comes from Maxime over on Instagram. She writes:

I’ve always been an advocate for a few strategically-placed personal details that will make you more than just a list of bullets on a resume!

In your “Skills” or “Additional Experience” sections, I’d choose 1-3 personal hobbies, skills, strengths, accomplishments, or affiliations that are meaningful to you (and that you’d be excited to talk about in an interview, because someone is likely to use them as an icebreaker!).

Good examples of ones I’ve seen from clients or people I’ve hired:

5-time NYC Marathon finisher
WSET 3 Sommelier
10-year Dungeons & Dragons Game Master
Planned Parenthood Phone Bank Organizer
Trained concert violinist
Won a car on The Price is Right (!!!!)

It’s about damn time you found a career that fits!

Why Your Parents Don't Understand Your Career Struggles

Janel Abrahami — Fri, 22 Aug 2025 09:55:00 +0000

When I was on the job hunt two years ago and frantically refreshing my email to see if I’d been invited to the next interview round, I swear my mom’s favorite thing to say was, “You just have to call HR!”

I’m sure you’ve had the same kind of conversation with your own Boomer loved ones. Maybe it happens at holiday dinners, during phone calls, or in those moments when you're venting about work frustrations. Your parents listen, then offer advice that feels completely disconnected from your reality:

"Just stick it out—every job has its challenges."
"When I was your age, I was grateful to have any job."
"You've been there two years already. Why would you want to start over?"

And you sit there feeling misunderstood, maybe even a little crazy for wanting something different. Like you're being dramatic about struggles that seem perfectly reasonable to you but sound like first-world problems to them.

But as annoying as this is for me to admit, we’re both right.

Our struggles are real, and their confusion is understandable. But we’re living in two different economic universes, and that gap is wider than most people realize.

That was Then, This is Now

The generational career divide is more measurable than most folks realize:

⌛ Job Tenure Reality:

Baby Boomers averaged 10+ years at each job during their peak career years
Millennials average 2.8 years per job, with 91% expecting to change jobs every three years
60% of millennials are open to new job opportunities at any given time (compared to 45% of Gen X and 37% of Boomers)

🫠 Economic Foundation Shift:

In 1980, the median home price was 3.2 times the median household income
Today, it's 7.7 times the median household income
Wages for college graduates have been essentially flat since 2000, while housing, healthcare, and education costs have skyrocketed

💼 Career Advancement Reality:

70% of Baby Boomers experienced steady salary growth throughout their careers
Only 23% of millennials report the same trajectory, with many seeing income stagnation despite job changes and skill development

Our parents built careers in an economy where loyalty was rewarded with security.
We’re building careers in an economy where loyalty is often punished with stagnation.

Total System Shift

When our parents entered the workforce, there was an implicit contract: show up, work hard, stay loyal, and the company will take care of you. Pensions existed(!). Healthcare was largely employer-funded. The social safety net was stronger.

That contract has been systematically dismantled by a few key changes:

1️⃣ The Loyalty Trap: Many companies have elimintated pensions, reduced employee benefits, and normalized layoffs as profit-optimization strategies. But they kept expecting employee loyalty while offering none in return.

2️⃣ The Skill Treadmill: The lifecycle of job skills has shortened from years to months in many industries. Our parents could master a skill set and ride it for decades. We’re expected to constantly upskill just to stay relevant. (I’ve seen this push from the other side, too, during my 8 years in corporate HR.)

3️⃣ The Gig-ification of Everything: Even "stable" jobs now come with gig economy uncertainty—contract work, freelance elements, project-based roles that offer no long-term security.

Our parents didn't job-hop because, frankly, they didn't need to.
The system rewarded staying put.
We job-hop because the system seems to punish staying put.

“Ugh, You Don’t Get It!”

Here's where it gets emotionally complex: our parents genuinely cannot understand our career struggles because their frame of reference is fundamentally different.

Their Mental Model:

Career = job security
Success = climbing one ladder
Fulfillment = a nice-to-have that comes after security
Risk = leaving a "good job"

(Have immigrant or first-gen parents, like me? Yeah, multiply that 👆 by 100.)

Our Mental Model:

Career = portfolio of experiences
Success = autonomy and impact
Fulfillment = essential for sustainability
Risk = staying somewhere that's not growing you

Neither is wrong, but they're incompatible worldviews shaped by completely different economic realities.

When they hear us say, "I'm not fulfilled," they hear "I'm ungrateful."
When we hear them say "just stick it out," we hear "your happiness doesn't matter."

And when the people closest to you don't understand your career struggles, it amplifies the feeling that maybe you are being dramatic, ungrateful, or unrealistic.

The isolation of being misunderstood by your own family about something as central as your career creates a specific kind of loneliness. You start to wonder if you're broken for wanting more than just a paycheck.

The Permission You Don't Need (But Deserve)

You don't need your parents' understanding to make career decisions that align with your reality. But you deserve to know that your struggles make sense within the context you're actually living in.

The career path that feels "right" to you might look chaotic to them. The risks that feel necessary to you might seem reckless to them. The fulfillment you're seeking might seem indulgent to them.

All of that can be true and your choices can still be rational, strategic, and brave.

You're not job-hopping because you can't commit.
You're job-hopping because staying committed to employers who won't commit to you is economic self-sabotage.

You're not seeking fulfillment because you're spoiled.
You're seeking fulfillment because you've realized that unfulfilling work in an unstable economy is a recipe for burnout without the payoff.

You're not starting over because you can't figure out what you want.
You're starting over because the career path you chose at 22 was designed for an economic future that no longer exists.

You're not broken for wanting a career that works within the economy you actually live in.
You're realistic and adaptive.

Text This to Your Parents:

The generational career divide isn't going anywhere. Hell, the economic structures that created it are likely to deepen, not resolve.

But understanding why your parents don't get it can free you from needing them to get it. Their career advice comes from love , but it also comes from a world that no longer exists (they genuinely think HR departments still have phone numbers).

Your career struggles are valid. Your desire for fulfillment isn't selfish. Your willingness to change course demonstrates intelligence.

The economy changed the rules, and you’re just playing by the new ones.

What's your experience with this generational divide? Do your parents understand your career choices, or do you find yourself explaining a reality they can't quite grasp? I'd love to hear your take in the comments.

This week’s question comes from Thomas over on LinkedIn:

First of all, good on you for building a strong personal brand! What you’re experiencing is the push and pull between the identity you’ve built publicly and the career path you’ve been following privately. Here’s how I’d think about it:

Monetizing the brand works best if you’re energized by creating, sharing, and experimenting online/publicly. If your online presence feels like an authentic extension of who you are, monetization can open up new possibilities, like consulting, partnerships, courses, creative collaborations. But the tradeoff is that it’s less linear, less predictable, and requires you to be comfortable with seasons of trial and error.
Aligning with a traditional move is a great path if you’re craving structure and a clear(er) trajectory. Your personal brand doesn’t go to waste here; it actually makes you stand out as someone who can build influence, communicate, and lead. The key is choosing roles and organizations that value that visibility rather than seeing it as “extra.”

It’s about damn time you found a career that fits!

Going Places

Millennials don't want to retire, we want out.

First, The Story in the Data

The Retirement Dream Means Something Different Now

The People Who Rejected the Question Entirely

What We Actually Want (And Why It's Harder to Name)

So What Are We Actually Working Toward?

What This Means For How We Build Now

A Final Thought

It's not corporate vs. entrepreneurship. It's way more interesting than that.

⏳ 🔁 Time for Money × More Predictable Income

⏳ 🎲 Time for Money × Less Predictable Income

🧠 🔁 Insights for Money × More Predictable Income

🧠 🎲 Insights for Money × Less Predictable Income

How to Use This Matrix

100 Ways to Land a New Job

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A subscription gets you

The Art of Corporate Espionage (the legal kind)

1️⃣ Determine your minimum + maximum time split

2️⃣ Cash, Clients, Content

3️⃣ For cash, pick 3 RGA’s + focus there

4️⃣ Context-switch at your own risk

5️⃣ And finally: have an emergency brake ready in case shit hits the fan.

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A subscription gets you

Part-Time, Contract, or Freelance Jobs to Apply to This Week

Jobs for week of Feb 9, 2026

Senior Social Media Community Strategist @ Ruggable →

Event Sponsorship Sales Lead @ Running Remote →

Community Manager @ The What →

Marketing Lead @ ProMom AI →

UX Researcher @ Prose

Portfolio Careers Come in 5 C's- Which is Yours?

👉 Choosing your first “C” without overthinking it

The First Annual 'Going Places' Reader Survey

Ooh, fun! Let’s start the survey →

Contribute to the dashboard→

Let’s jump in →

How to Productize Your Career

But there’s another way to look at this:

If a career is treated as a product, different questions emerge:

How to Actually Start Productizing Your Career (The Practical Part)

1: Extract Your Core Product Stack

2: Identify Your "Customers"

3: Explore Your Packaging Options

4: Test One New Package

5: Notice What Feels True vs. What Feels Assigned

💌 SPECIAL INVITATION for January 23rd

🎥 The Great Millennial Career Crisis: Now What?

The "Ambition Dial"- Why we're choosing selective ambition

Ah, the good ol’ days.

But there’s one thing I definitely do not miss about that era, and that’s my very rigid understanding of ambition + drive.

Think of ambition not as something you either have or you don’t, but as a VOLUME DIAL, one that you get to adjust, based on your priorities in this chapter of your life.

A simple way to use the Ambition Dial today

Big Career Changes are Happening This Year

Observation #1: Women are forming "consulting collectives" (a new term I'm coining right now)

Observation #2: Women are using AI to complement their EQ

Observation #3: Women are scaling creator businesses

Observation #4: Women are demanding more from corporate

Observation #5: Women are angel-investing in their own self-interests

There’s More Than Just Corporate OR Entrepreneurship:

The Career Model Matrix ©

⏳ 🔁 Time for Money × More Predictable Income

⏳ 🎲 Time for Money × Less Predictable Income

🧠 🔁 Insights for Money × More Predictable Income

🧠 🎲 Insights for Money × Less Predictable Income

How to Use This Matrix

Consulting Collectives are the Future of Independent Work

Consulting Collective (noun): when 3-6 independent consultants or freelancers band together to operate as a unified business entity, without actually forming a traditional company.

Why they’re popping off everywhere right now:

The Upsides:

The Downsides:

How to Start One:

The Bottom Line:

Is the Great Millennial Career Crisis Solvable?

We solve the Millennial Career Crisis by replacing the old promise of "arrival" with a new guarantee of mobility.

1) You + Me: Shift from “find your one calling” to “build your career operating system”

2) Organizational: Stop managing humans like disposable line items

3) Policy and economics: Make stability possible again