But to simply apply a cheeky “maxxing” filter on the rise in self-employment curiosity (and necessity) implies that there’s a version of this you can optimize your way into winning. And that’s where I want to slow us down.

I built three different maps of the self-employment landscape (below) based on my own experience + the experiences of my network. None of them show one winning plan, but they do illuminate important tradeoffs you’ll have to make when you choose the path of self-employment, and I think seeing the tradeoffs is much more helpful than pretending working for oneself is a one-size-fits-all experience.

• Model #1: Does it require an audience, or does it require a network?

• Model #2: How long can you actually go without a paycheck?

• Model #3: Are you buying leverage with money, or building it yourself?

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We need more self-employment transparency more than ever

More than 70 million Americans are now part of the gig economy (that’s something like 36% of the total U.S. workforce), and freelance job postings climbed 22% in the last six months alone.

Some projections put the U.S. freelance workforce at 86.5 million by 2027, which would put more than half the country working independently in some capacity within two years.

Some of that growth is coming from the demand side, not just from people jumping. Following the corporate layoffs of 2024–2025, a majority of employers say they turned to freelancers specifically to fill the specialized roles they used to keep in-house full-time. TL;DR: Companies want the skill without the headcount.

Choose your model based on your trade-offs

I mapped fifteen self-employment models (everything from Independent Consultant to Influencer to Fractional Leader to Platform Gig Worker) across three different matrices. Each one answers a different question, and each one will change which model looks “smart” to you.

Model #1: Does this require an audience, or does it require a network?

Some self-employment models (Influencer, Knowledge Creator, Online Coach, both flavors of B2C Founder) don’t pay you a cent until you’ve built a public following first, and even then, the income stays unpredictable. Others (Independent Consultant, Fractional Leader, Agency Owner) run almost entirely on warm outreach and reputation, no follower count required, and tend to land closer to predictable. If you don’t already have– or want to build– a public audience, stop benchmarking yourself against the creators. You’re not playing their game, and their playbook won’t work for you long-term.

Model #2: How long can you actually go without a paycheck?

This is the question almost nobody asks themselves honestly before quitting. Platform work, freelancing, coaching, and consulting can put money in your account within weeks, but nearly all of them come with an income cap because you’re still the one doing the hours. The models with more open earning potential, like licensing your IP or building a following that sells for you, are almost always the slowest to pay off. If your runway is under six months, the “uncapped” models are not your move right now, no matter how enticing the framework looks on paper. Speed to first dollar should be your priority until your runway gets longer.

Model #3: Are you buying leverage with money, or building it yourself?

Most of the models on this list don’t require much capital to get started, but they also have hard limits on what you personally can do in a week. The way out of that isn’t always more money. Sometimes it’s a team (an agency model), and sometimes it’s an asset that keeps selling after you publish it (a course, a book, or a framework you license). Physical product businesses are the one path here where scale really does require capital first. Before you assume you need funding to “get big,” consider whether you actually need a system instead of a check.

What this actually means for you

Every self-employment model on my list is a bet about which kind of uncertainty you’re willing to put up with: income timing, audience-building, capital risk, or a cap on your hours.

So before you draft your resignation letter: which trade-off are you actually signing up for? Are you optimizing for speed, for scale, for control, or just for the exit?

Tell me in a comment below!

References:

• MBO Partners (gig economy / independent workforce data), via Carry.com — 2026 Gig Economy Trends for Freelancers and Self-Employed Workers

• selfemployed.com — Freelance Economy Growth 2026: U.S. Tops 72 Million Independent Workers

• DemandSage — 19 Freelance Statistics 2026 – Facts & Global Trends

• NeatPenny (cites Federal Reserve, BLS, Upwork, Census Bureau data) — 27 Freelance Statistics and Self-Employment Trends for 2026

Back in school, you’d submit your essay, hold your breath, and wait for that plagiarism percentage to load. And, something most folks seem to forget: your result was never a black-or-white “yes” or “no” in terms of “did you copy this word-for-word?”

A paper could be 75% original wording and still get flagged, because plagiarism has never been about lifting someone’s exact words, it’s always been about the thinking behind them. If the argument, the structure, the “aha” wasn’t yours (if you took someone else’s idea and just rewrote it in your own sentences so the teacher wouldn’t clock it) that was still cheating. You and I knew this when we were 14 years old.

So, when did we all decide that rule stopped applying the second we left high school and started posting content online?

Because right now, in the creator economy, if you change the b-roll, swap the font, say it in your own cadence instead of theirs, it’s just considered something “inspired by” someone else. When, last time I checked, it was actually theft.

The common excuses I see in comments sections are:

• “We’re all thinking about the same stuff.”

• “We’re all saying the same things around here.”

• “This wasn’t an original thought anyway,” / “Nothing is original anymore.”

• “You’re not the first person to think or say this, so she didn’t steal your content.”

and I have had this conversation more times than either of us can count. Maybe we’re precious about our original ideas, but we’ve also watched it happen to friends and to people neither of us have ever met but whose timelines we both track because we can see the pattern.

I’ve been transparent about my most jarring experience with seeing my original words recycled by someone else to the tune of 6M+ views, and Roxy’s recent experience is what inspired this article.

TL;DR: Roxy posted this video, and a few days later, a video from a burgeoning content creator popped up on my feed and immediately set off my Spidey senses. Turns out, the script was copied word-for-word in some places, “just changed a little bit so the teacher wouldn’t notice” in others, and the other creator used one of the top comments on Roxy’s post as the caption of the plagiarized post. There was, quite simply, no way that was a coincidence.

But the guilty creator doubled down when we called her out, saying, “I’m inspired by many, including you Roxy, so thanks for the inspo!”

Um, no. The real problem with her flippant response is this:

Content isn’t just content anymore. As long as the guilty creator kept this particular video live on her page, she’d continue to get more views/engagement on it (it was her highest-performing video by a long shot– not a coincidence). The more engagement she got, the more she’d earn through platform monetization and the more she could charge for brand monetization, and the more money she would make as a creator off the back of someone else’s work.

It actually is that serious.

So what actually counts as stealing someone’s work?

Let’s try to build a real framework together, because “I know it when I see it” isn’t good enough anymore. Not when there’s real money, real audience growth, and real career capital on the line.

This a working guide, but from the most defensible to least defensible act of recycled content, we have:

🚨 Level 1: The same idea was crafted independently. Two people notice the same cultural moment and make content about it in the same week. This happens constantly and is not theft– trends exist because multiple people are looking for patterns in the same space.

🚨 Level 2: The same idea was posted after seeing theirs, just reworded. You saw their video, were inspired by it, recorded yourself saying something very similar, and didn’t credit them. You said the same argument in your own words, posted while theirs was still trending. This feels like the Turnitin zone, where it’s technically “original” wording, but still unoriginal/stolen thinking.

🚨 Level 3: Same shit, different title. Someone spends months building an original concept– a term, a matrix, a five-step model– and you take the meat of it and put your own title on top. Reheating someone else’s nachos.

🚨 Level 4: The same words. The script, caption, jokes, hooks, etc. are all recycled close to verbatim. Everyone already knows what this is.

The internet wants you to believe only #4 counts as plagiarism on social media, which is convenient, since #4 is the easiest for someone avoid while still doing #2 and #3 constantly.

The case for more plagiarism guidelines in the “content era” gets stronger by the day, because it doesn’t start and end with “content creators.” , author of the bestselling Substack “Link in Bio,” recently called out AI-native media company 360i and media agency Denstu for “blatantly plagiarizing” a guest essay she published by Matthew Stasoff (receipts below).

Why is this happening now, and not, say, ten years ago?

Here are a few structural reasons that may explain why this has gotten worse lately:

• There’s no social media editor. Traditional publications like newspapers and magazines (even the digital editions) have a plagiarism-check step baked into the process before anything goes live. But creators have phones and a “publish” button. The entire system that used to catch this simply doesn’t exist here.

• The algorithm rewards speed over originality. If people see your take first, you often get credit for it , regardless of who actually presented it first. Being loudest beats being original online, because the platform can’t (and won’t) verify provenance. It just rewards whoever converts attention best.

• “Inspired by” has become an acceptable alibi. Nobody wants to say “I copied this,” but most are OK saying “this was so inspired by [vague gesture],” which sounds enough like credit but is still just a loophole in most cases.

• Ideas on social media don’t seem like intellectual property. A framework, a phrase, a way of titling a feeling or a phenomenon don’t feel ownable the way a photo or a full paragraph of text does. So people who would never dream of stealing a blog post in full will absolutely take your framework, round the edges off, and call it their own thinking.

Importantly, plagiarizing something on social media is not the same as “remixing,” and that’s where the most gray area lies. Memes, text trends (hi, butter yellow block text), duets, and stitched responses are, one could argue, the internet working as intended.

But there’s a difference between building on top of something and co-opting the specific thing that made it work– the framework, the phrase, the structural insight– and presenting it as your own original thought. The first is culture, the second is copying.

And social media content plagiarism stings in its own way, because it’s rarely dramatic enough to “prove.” You can’t screenshot a stolen thought process the way you can screenshot stolen text. So the person who had the idea first is left in this strange position: certain of what happened, and with almost no language the culture agrees is legitimate to call it out (see common excuses/explainations above).

What we actually think ownership means here

We’re really not trying to be the Content Police, and we’re not saying every creator needs a copyright lawyer on retainer. We’re saying the bar can’t be “as long as it’s not a word-for-word copy-paste, it’s fair game,” because that didn’t cut it in 9th grade English class. It should not be the standard for people’s actual livelihoods.

Original thinking is the entire asset in the creator economy.

So, maybe the question isn’t “was it word for word?”

Maybe it’s the same question your high school teacher would’ve asked: “Would this piece of content exist, in this form, if the other creator’s version didn’t exist first?”

If the honest answer is no, you know what that is.

What’s your line? Where does “inspired by” end and “you copied their homework” begin, and has this happened to you? Tell us in the comments.

– Janel + Roxy

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I want to talk to the high-performers specifically, because I don’t think you’ve been warned about this one. You did the college thing right, the promotions right, the “always exceeds expectations” review right. And I think a Performance Improvement Plan is becoming unavoiable for a good chunk of you, anyway.

Almost every exasperated client I coach through this says some version of the same sentence: “I don’t understand, I’ve always gotten amazing feedback, and now I’m ‘not meeting expectations?!’”.

One quarter they’re the person leadership points to in the all-hands. The next, they’re in a meeting being told their work has “concerns” nobody flagged before, with a 30-to-90-day clock attached and language vague enough that you can’t actually tell what “success” would even look like.

The word “gaslighting” gets thrown around too liberally these days, but I personally believe that putting a high-performer on a PIP and pointing to arbitrary new goals is a form of corporate gaslighting.

Why is this happening to so many of us now?

As someone who has worked on HR teams at covetable companies, here what I believe is happening most of the time: a straightforward layoff is expensive. A real reduction in force means severance (which adds up quickly when it’s tied to tenure), sometimes continued benefits, sometimes a legally required notice period, and a public number that shows up in press coverage and slows the stock the next morning. Reputational cost of mass layoffs has only gone up since 2020.

So managers under pressure to cut headcount, without the budget or appetite to do it the expensive way, have two sneakier levers:

1. One is what’s now being called “quiet cutting”: reassigning someone to a smaller, less visible, less desirable role and waiting for them to leave on their own. A recent industry survey found close to a quarter of companies admit to doing this outright, and roughly a third of employees say they’ve been on the receiving end of it.

2. The other lever is the PIP: a document engineered less to help you improve and more to build a defensible paper trail for termination “for performance,” not “a layoff”. AKA, the version of termination that usually comes with no severance owed.

More data backs up the high-performer-on-a-PIP theory:

• Formal performance write-ups have climbed nearly 30% since 2020.

• And by most industry estimates, somewhere between 70% and 90% of employees placed on a PIP don’t survive it– they’re terminated.

• Amazon‘s own internal numbers make the pattern almost too on-the-nose: in the months before its 2022–2023 layoffs, the company bumped the number of employees entering the first stage of its internal PIP process by almost 70%, and doubled the number moving into the second.

Why it goes straight for the jugular (your identity)

I don’t think it’s a coincidence that this is landing hardest on the most loyal people in the building.

If you’ve spent your whole career being the reliable, hardworking rule-follower, the one who stayed through the reorg, covered for the open headcount, said yes to the stretch project, a PIP throws off your entire center of gravity. That’s the gaslighting mechanism at work, whether or not anyone above you would ever use that word for it: you’re handed “evidence” that contradicts years of lived experience, and all that lived experience has no impact on the outcome of your PIP.

And it works, precisely because you’re the kind of person who takes feedback seriously. The same conscientiousness that made you a high performer is the exact trait a bad-faith PIP is designed to exploit. You’ll re-read the plan four times looking for what you missed, try in earnest to fulfill the parameters of your improvement plan, and, if you’re terminated anyway, you’ll likely spend years licking the wound from being betrayed by an entity that you went above and beyond for.

As I was combing through client coaching notes to draft this essay, I kept coming back to the same comparison: getting high-performer-PIP’d is starting to feel like the professional version of dating someone in your twenties who you were sure you could fix, if you just tried a little harder.

In both experiences, you assume the relationship is a meritocracy of effort, so you respond to bad treatment by increasing your effort. And both experiences end the same way: it’s not that you weren’t good enough, but that the partner or company was never negotiating from good faith to begin with.

You can’t fix them, no really, you can’t.

High performers, please rise

If this has happened to you, or is happening right now, “just work harder on the PIP” is not useful advice, and I’m not going to pretend it is.

The more useful move is usually recognizing early which situation you’re actually in (is it a real developmental conversation, or is it a paper trail with your name on it?) and making decisions from there, not from the PIP’s timeline.

But mostly I want the high-performers reading this to know: if it happens to you, it was never proof that you weren’t good. It might be proof that you were good enough to be worth documenting your way out of instead of just laying off.

Has this happened to you or someone you know? What did the plan actually feel like it was really about? Reply to this email or tell us in the comments. 🫶

Instead, I believe they’re rejecting the traditional job search process before the job search can reject them.

At first I thought I was watching a handful of outliers cope in their own weird way.

Then I started asking around.

Then I started doing the math from my own two job searches in six years.

And now I don’t think this is a coping mechanism at all. I think it’s a rational response to a broken system with abysmal return on investment.

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Job market math backs this up

Start with the basic math of applying for a job right now: the average response rate across a job application sits around 2 to 3%, meaning something like 97 or 98 out of every 100 applications end in ghosting or auto-rejection. And that’s the good scenario, before you account for the listings that were never real to begin with.

Because a real chunk of what you’re applying to isn’t real. Depending on whose count you trust, somewhere between roughly one in seven and one in five job postings right now is a ghost job (a listing kept alive to build a talent pipeline, satisfy an HR policy, or make a company look like it’s growing, with zero real intent to hire). TL;DR: the gap between “jobs listed” and “jobs actually filled” has never been wider.

Meanwhile, the mass layoffs feeding people into this broken funnel aren’t slowing down. 2025 saw over 1.2 million layoffs in the U.S. alone, 58% more than2024 and the highest total since the 2020 shutdowns.

And most telling: the percentage of workers who said they planned to job search dropped from 93% last year to just 43% this year.

Where are all these job seekers supposed to go?

Yes, applying online was always a numbers game. But the numbers used to make sense: you applied, a person read it, you got a callback some percentage of the time. What’s happened instead is that application volume exploded (anyone can apply to anything in two clicks now) while hiring intent fizzled out (a growing share of what you’re applying to was never going anywhere).

Importantly, a referral can still improve your odds by 10 to 20x, which tells you everything about where the real hiring is actually happening: in someone’s DMs, not in the “apply now” button.

Anecdotally, I was laid off from a “dream” tech job in 2024 after less than a year in the role. I was still shaking off the trauma of the first job search process just 8 months prior when I dove right back in, head first, applying to an average of 10 jobs per day online.

I expanded the types of roles I was looking for, casting a very wide net into HR, comms, coaching, higher ed, and even ghostwriting. And I was ghosted or rejected from even the roles where I actually had a real shot– where a mentor’s brother-in-law was the hiring manager, or someone texted my resume directly to a decision-maker. I’d had the inside track and I still got nowhere.

Which told me something I didn’t want to hear yet: this might be a losing game.

Should you quit a game you can still technically play?

I know personally that opting out of the traditional job search feels like admitting that you’re a failure, not like a smart strategy.

We are handed exactly one script for what to do after a layoff, and it’s “look for another job, the same way you looked for the last one, just faster.”

So when that script stops producing results, the instinct isn’t to question the script, it’s to assume you’re doing it wrong. You hire a resume writer, you stalk another job board, you talk yourself into applying for roles that you don’t even want to do.

But as long as you cling to the sunk-cost fallacy of traditional job searching (“I’ve already invested all this time, money, and energy into this process, changing course now would be a waste,”), months, if not years, of your income, identity, and sense of forward motion sit in someone else’s inbox, unanswered.

Nobody taught us what to do when the rules themselves are the problem. We’re fluent in “work harder within the system” and functionally illiterate in “the system doesn’t want what you’re selling, so sell something else.”

What else can we do?

For me, “selling something else” meant:

• Pivoting to applying for part-time and fractional roles through Generalist World, Fractional Jobs, and Moxie (all of which moved faster than a single traditional application ever did)

• Pitching executive coaching and workshops directly to companies instead of applying to their open reqs

• Doubling down on brand partnerships and 1:1 coaching, where I could control the terms

Almost two years later, I’m still in the part-time role I landed through that process, with zero interest in going back to full-time, because the stack of income streams I built compounds in a way one salary never did.

And I’m not alone in this. I’m hearing the same story from a growing number of friends and connections: “They took me on part-time,” “the project proposal got more traction than my resume ever did,” “I stopped applying and started pitching.”

Freelancers now make up close to half the U.S. workforce, and more than half of Gen Z job seekers globally say they’ve shifted their focus away from full-time roles entirely. I see that as a real redistribution of where people are putting their effort, because the traditional funnel stopped being where the effort paid off.

Where this leaves us

Maybe the opt-out isn’t permanent for everyone. Maybe it’s a seasonal strategy. But I think it’s worth calling out: choosing not to keep feeding a system with a 2-3% return rate is a rational decision.

If you’ve considered pausing your job application efforts and building something else instead — pitching, freelancing, going part-time, stacking a few smaller income streams — I don’t think you owe anyone an explanation for that.

Are you opting out too? Or are you still in it, playing the traditional game by traditional rules? I want to know where you land– tell me in the comments.

-Janel

Here’s my stab at steering you in the right direction, based on the different career design models I’ve written about recently:

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1. Which trade-off sounds the worst to you?
A) Doing the same kind of work for the next ten years
B) Never having a single “home base” you can point to
C) Staying somewhere just because leaving feels scary
D) Working hard to build something that might not succeed
E) Getting full credit for an idea that isn’t fully yours
F) Being tied to one paycheck, one boss, indefinitely
G) Never being fully known for your own individual work

2. When you imagine “security,” it looks more like:
A) One steady paycheck, cleared direct-deposit
B) Several smaller income sources, so no single one can sink you
C) Enough $$ runway to make your next real move without panicking
D) An empire you built yourself, so no one can take it away
E) A steady base with room to experiment inside it
F) Skills so in-demand you’re never without options
G) Working with a group of people you trust who’d catch you

4. What kind of risk actually excites you (vs. just stresses you out)?
A) None, TBH, you’d rather optimize what already works
B) Juggling multiple things at once, as long as you control the mix
C) None, you want to conserve energy for the “big” decision down the line
D) Betting entirely on yourself
E) Pitching a new idea inside a system that already trusts you
F) Constantly proving yourself to someone new
G) Sharing the risk (and the win) with other people

5. What does “being known for your work” mean to you?
A) Putting in the reps over time to be known as excellent at your craft
B) Being known for range, the person who can do many things well
C) Being known isn’t the priority right now, you’re focused on getting somewhere solid
D) Being known as the person who built the thing
E) Being known as the innovative “secret weapon” behind the scenes
F) Being known for deep expertise that transfers anywhere
G) Being known as part of a trusted group, not just as an individual

7. If money and ego were a non-issue, you’d genuinely rather:
A) Master one craft over decades
B) Run three or four different things at once
C) Take real time to pause and figure out what you actually want
D) Build one big thing from nothing
E) Build something new and nimble, but inside a place with existing resources
F) Rotate through different challenges and collaborators constantly
G) Build something great alongside a small group of equally-skilled people

MOSTLY A’s — The Linear Path.
You want depth, mastery, and a track to professional development that you can actually see. To you, the career ladder doesn’t feel like a trap. In fact, that’s the whole appeal, as long as it’s the right ladder you’re climbing.

What your peer said about choosing linear career paths that feel aligned →

MOSTLY B’s — The Portfolio Career.
You’re not built for one job speaking for all of you. Diversifying your projects, clients, and income streams is how you actually feel most secure and most yourself.

Here’s how to find + setup the portfolio career structure that’s right for you →

MOSTLY C’s — The Bridge Job.
You’re open to taking some creative moves (side steps, unconventional moves, or even an intentional pause) because know the real move is coming, and you’d rather have income and stability while you figure it out than force a decision before you’re ready.

Examples of smart bridge jobs →

MOSTLY D’s — The Founder Path.
You’re wired to own the whole she-bang, risk included. Working inside someone else’s structure (even a good one) will always feel like an itchy, too-tight sweater.

How an ex-Nike Creative Director made the jump to solo work →

MOSTLY E’s — The Intrapreneur.
You want the thrill of building something innovative without giving up the safety net. You’re risk-selective (not totally risk-averse), so you look for established workplaces with pockets that need your creativity internally.

Why breaking the “career rules” is the only option now →

MOSTLY F’s — The Fractional Career.
You want range over deep roots. You’re ready to package up your depth of expertise and get more breadth of exposure working for a few select clients in the same leadership role, with zero interest in being anyone’s full-time anything.

How to start your Fractional career →

MOSTLY G’s — The Consulting Collective.
You don’t want to build alone, but you also don’t want to answer to a hierarchy. The ideal setup for you is working with a select group of peers who share the risk, the credit, and the client base.

How to set up your Consulting Collective →

Share in the comments– where did you land? And what questions can I answer for you about your ideal career design?

x Janel

Hello to the 50 new subscribers who have joined our corner of the internet this week 🙋‍♀️. I am so glad you’re here. I’m Janel Abrahami, a former HR gal whose mission it is to help solve the Great Millennial Career Crisis with tools, stories, and musings on the new world of work and ambition. Reply to this issue and introduce yourself— I read every single response!

Today, I’m ripping off the bandaid and sharing a private journal entry I penned a few months ago after a particularly challenging day as a solo-entrepreneur. On this day, I swear I saw at least a dozen TikToks doing that “My husband helping me run my business/doing the dishes/holding it down because I didn’t marry a loser” trend.

Honestly, I love that trend. I can concede that it’s also not a trend that’s made for me in this season of life, as an unmarried 30-something woman living and working on her own, nor does every trend/message on the internet *have* to be for me! But in that particular moment, I kinda wished there was a version of that trend that was like,

“Me, running a profitable business, creating high-performing content, pitching myself for another dream opportunity, paying my whole mortgage, playing phone tag with the plumber, fixing the broken window crank, and walking the groceries home on one salary because I didn’t marry anyone yet.”

I’m nervous to publish this one, for fear that partnered entrepreneurs will read it as bitter or jealous. Really, I hope it can land as curious, hungry for more transparency and connection, because I know in my bones that one’s marital status does not automatically solve any of the challenges of this thing we’re all doing— building something of our own. ❤️

And so, here’s what I feel like I can only admit to my single friends about building a business on my own:

Dear married entrepreneur friends,

I’m often envious of the built-in sounding board you have in your partner. And endlessly grateful to my mom for being that for me right now. I call her with “meeting minutes” after every big/promising/intriguing/frustrating meeting.

I wish I had that someone who could wrap me in a huge hug at the end of a stressful day of rejection, roadblocks, and responses-less pitches.

Sometimes, I’m jealous that you can rely on your partner’s senior-level corporate job to float you through the tougher times in entrepreneurship. I wish more married women founders and entrepreneurs were more transparent about how they’re able to keep their ventures going, pay their mortgage, keep their unlimited boutique fitness membership, and buy Harry Styles tour tickets.

If you’re able to do all of that but you’re actually in debt, I kinda wish I knew that (even though I know it’s none of my business).

And if you’re able to do all of that because you received outside funding– can you share your pitch deck?

I turn to you for cheerleading and pep talks on the exciting days and the hard days, not to brag or for really for validation, but because you’re still that go-to person for me. I know your partner is that for you, but you’re still that for me. And that makes me self-conscious sometimes.

I feel a confusing tension between pride for doing this all on my own, and a deep desire that I didn’t have to do it all on my own.

Sometimes, I wonder if I’m still so career-oriented in my 30s because a partner hasn’t made it necessary that I be relationship-oriented. (Kind of like this iconic line from Fleabag Season 2). I can’t control when the right relationship happens, but I can control how aggressively I build my career. So I do what’s in my control.

Sometimes, I worry that you pity me for being single.

Sometimes, I unkindly pity you for not having the total freedom to prioritize your goals over anyone else’s.

But I know that’s not fair.

I feel this weird self-imposed pressure to push as hard as I can in my business and career before I “settle down” with a partner, for fear that it will mean my business growth will stall when that happens. I want you to tell me if this is true or not.

Thank you for sharing the messy moments that come with balancing a partner and children with your own ambition.

Thank you for inviting me to your beach house/lake house/the home you share with your partner in another city to get me out of my navel-gazing bubble. I need that nudge. Thank you for seeing that and always extending the invitation.

Thank you for reminding me not to settle. “You’ve waited this long for the right thing,” you tell me, “so why would you shift priorities for anything less than The One?”

I will always remember when I called you in tears, wanting to burn it all to the ground, and you cleared your schedule, asked your husband to entertain the kids for the day, and let me feel my feelings for the entire day without judgment. And then you ordered me dinner and paid for my 40-minute Uber home later that night. Even thinking about that now makes me emotional.

But mostly, I know we can both assume that the grass is greener on each other’s side of social media and quick catch up texts, but I think our relationship would grow even stronger if we shared more bits of reality.

I’ll go first.

Love,

Janel

In the month of June, I gave keynote talks on overcoming the modern career crisis for three different audiences (NYU, Indeed, and adidas— this flex makes sense here, I promise).

During each Q&A, someone asked me a version of the same question: “I’m making a career pivot, so how do I convince them I can do the job?”

“Them” could mean recruiters, hiring managers, someone they follow online and admire, investors in a business they want to start, anyone.

In the first speaking gig, I gave a useful answer about speaking the language of the person hiring, only mentioning relevant skills and experience, getting clear on how your past and your future make sense, etc.

But the word “convinced” kept bugging me after the session, so when I heard it again a week later, I tried to articulate something else:

As long as you keep asking, “How can I convince them that [I can do the job/ I have the skills/ I have the passion/ I’m worth betting on]?” you’ll always be on the back foot. And you’ll always be exhausted.

You want to shift from convincing (outbound effort) to turning up the volume on your own visibility (when inbound opportunities come to you.)

Here’s how:

1. Stop pitching your future self & start documenting her

Convincing puts you in the position of asking someone to imagine you differently than your resume or LinkedIn headline suggest. That’s a heavy lift for a stranger with fifteen minutes and a stack of other candidates to get through.

When you have visibility, that does the imagining for them, before you ever ask for anything. You write about the thing you want to be known for, post the half-formed thought, the project you did for free, the smart commentary bouncing around in your head. Sharing it with the world will do most of the “convincing” for you, and by the time you’re in the room, they’re already half way to hiring you.

2. Talk about your pivot like it’s already happened

Every time you frame your career change as something you’re hoping to be allowed to do, you hand the other person veto power. “I’m trying to break into X” = “I’m auditioning for the role of…”.

On teh flip side, “Here’s what I’ve been building/working on” tells them you’re already there, a worthwhile bet.

This isn’t about lying, but being intentional with what tense you’re speaking in: convincing lives in the future conditional tense— if you let me, I would. Visibility is in the present tense— I am, and here’s the proof.

3. Let proximity do the talking

You don’t need every hiring manager or potential boss to see your work. You need to be in the rooms (physical or virtual) where the right five people already are, consistently, without an ask attached. Comment on their posts, show up to the event, be the person whose name they’ve seen three times before you ever email them.

My friend Sharon is the best example of this: she has a visible track record of doing the jobs she wants before she’s actually hired for them, and it pays off brilliantly for her.

“Convince” is the word we reach for when we don’t yet believe the pivot is legitimate. We think we’re asking how do I get them on board, but we’re really asking how do I get myself to stop feeling like an impostor long enough to say this out loud with a straight face.

Turning up the volume on your own visibility only works once you’ve stopped treating your own ambition like something that requires outside approval before it counts.

Leave a comment: What’s something you’ve been trying to convince someone of, that you probably just needed to believe first?

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JURY spent years as a Nike director leading entertainment collaborations and Basketball apparel — one of the most coveted creative roles in the industry. Then he quit the dream job to rap.

But this isn’t a story about following your passion. It’s about what happens when the job that was supposed to be everything starts costing you everything else — your creativity, your identity, and the version of yourself you actually want to become.

In this episode of Going Up, JURY breaks down:

• Why he suppressed his music for years to “crush it” in corporate

• The moment he realized a dream job and a dream life are not the same thing

• How he turned his taste level into a business model — and what that actually looks like financially

• Navigating a major career leap with a spouse and a mortgage

• What ambition really costs (and why he thinks it’s worth it anyway)

• The LinkedIn take that will probably make someone’s feelings hurt

If you’ve ever hit a milestone that was supposed to feel like arrival — and it didn’t — this one is for you.

🎙️ Guest: JURY — Artist, Creative Director, Former Nike Director of Entertainment Collaborations

But more on that in a future newsletter.

For now, I want to share a back-of-the-napkin method I’ve been using in these moments of overwhelm to get a big-picture view of what I really want for my career.

I use an X-Y graph to make sense of all of the different careers I want to try on, where one axis is a measure of Stability and the other axis is a measure of Fulfillment.

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This is just a half-baked idea from trying to figure out my own multi-hyphenate, multi-passionate career and the question I kept butting up against, which was:

“Is there any career out there for me that bridges the Stability-Fulfillment gap? Or will I inherently have to sacrifice some measure of fulfillment in order to achieve a sense of stability?”

Why stability and fulfillment, specifically? Well, those are the two variables that have always seemed at odds in my brain, especially as someone who’s felt this for years.

Here’s what the graph ended up looking like when I tried this for myself:

As you can see, nothing landed in the top right corner, which would be the most stable + most fulfilling option, but some options were pretty close!

And maybe it’s just me who always needs a visual aid to make any kind of decision, but seeing all of the careers I’m drawn to plotted according to metrics that I care about is really helping me grapple with that swirly stage of career confusion.

You can do this with whatever metrics you care about.

Some other values and variables I think would yield interesting graphs are:

• Earning potential x Adventure potential

• Autonomy x Income ceiling (the freelancer’s eternal dilemma!)

• Extraversion x Deep Thinking

• Energy output x Energy replenishment (especially useful for people with burnout history — are you giving more than you’re getting?)

• Social visibility x Private life preservation (relevant for anyone considering the creator path)

• Learning curve steepness x Speed to income (useful in a career pivot — do you have the runway for this?)

Let me know if you would try this and what criteria you’d use!

If this energized you, here’s a related read you might like, too:

In the 1950s, British psychiatrist John Bowlby developed attachment theory, the idea that the bonds we form early in life shape how we relate to other people as adults. Mary Ainsworth later gave us the three attachment styles: secure, anxious, and avoidant.

If you’re a millennial-adject woman, you’ve probably read her ultra-popular book Attached and self-diagnosed all of your excess’ attachment styles.

Anxious attachment: you over-perform to keep people close, constantly scan for signs you’re about to be left, and your sense of safety lives inside someone else’s behavior.

Avoidant attachment: closeness feels threatening to you, and commitment feels like a trap. This style may look like self-sufficiency, but it’s really self-isolation.

Secure attachment: you’re both fully invested, but not fused together, you can be close to someone else without disappearing from your own self, and you choose to stay— which is different from needing to.

I’ve been thinking about this framework a lot lately, except not in the context of dating. In the context of work.

What I keep seeing is a generation of high performers in an anxiously attached relationship with employers who are, structurally, avoidant.

Look, your company isn’t “avoidant attached” because it’s cruel, it’s avoidant because it’s literally just a company. It was designed to be profitable, not loyal. When the numbers require cutting, it cuts, with the same bureaucratic neutrality it used to hire you. It’s cold and detached and impersonal, because to the company it isn’t personal at all.

But we were trained by our college career centers and 2010s girlboss culture to show up to work anxiously. We stayed late to show our commitment to the company, we didn’t negotiate our salaries or benefits because we didn’t want to seem ungrateful, we wound our identities so tightly around our titles that a reorg threatened our entire sense of self. We checked email at 11pm not because we had to, but because the anxiety of potentially missing something felt worse than the cost of never fully logging off.

While we called it dedication or “being a team player” (vom), Bowlby and Ainsworth would have called it unhealthy anxious attachment.

It also didn’t help that the language of the workplace has always been relational: loyalty, family, culture, belonging, with an implicit promise that if you kept improving your performance, you’d be safe.

And then: three years of mass layoffs at companies posting record profits. High performers, gone, in a “quick chat” meeting invite that lasted 15 minutes.

Secure career attachment doesn’t mean you stop caring about your job, or that you up and quit one morning to go freelance or build a Substack empire. (Though, I mean, hi.)

It means your job is one source of income, identity, and meaning, not the only one.

It means you have a financial runway and core skills that you can “sell” in multiple different ways, skills that you own and are not products of your employer’s org chart. It means you have a network that exists outside this one building, this one Slack channel, this one role.

It means the difference between staying because you’re choosing to and staying because you’re scared to leave. And while those two things can look identical to a stranger on the outside, internally, they produce completely different versions of you.

The version of you who stays out of fear is always waiting to be abandoned.

The version of you who stays by choice already knows they’ll be fine regardless.

That’s the whole thing, really. Not blowing up your life in the name of independence, just doing enough— updating the portfolio before you need it, posting content on LinkedIn, taking the freelance project, building the savings number that represents your personal runway— so that you’re not gripping.

Bowlby argued that the solution to anxious attachment was earned security. That’s a feeling of security that comes from trusting yourself enough that you don’t need to hold on so hard.

Corporate loyalty is a choice, but corporate dependency is a fear response.

Your job can still be a good job, you can still like the people you work with, believe in the work you do, and genuinely want to be there. But shifting the nature of your attachment to it all is, in my opinion, the key to “future-proofing” your career in any age.

In 2026, the most secure career is the one you could walk away from if you had to— and have chosen, consciously, not to.

Secure, anxious, or avoidant — how would you describe your relationship to your job right now? I’m curious if this framing lands differently when it’s about work.

What you have back was a very revealing set of responses and a vulnerable snapshot of the modern millennial career in 2020.

So, here’s what we know now:

You are mid-career + in-motion, and most of you do not feel okay about where you are.

The majority of respondents were 28–42, college-educated, urban, and solidly mid-career– most with 8–17 years of professional experience. By any reasonable external measure, this is a group that has put in the work, mastered the ropes.

And yet: nearly 65% felt behind.

Based solely on the sincere “trust your timing” posts that flood our social feeds, you’d be forgiven for thinking our generation had successfully rejected the traditional post-graduation milestone timeline.

But most of us still feel behind, and the “timeline” still feels very real. We feel behind in ways that show up differently at different income levels, but show up nonetheless.

One of the more striking findings in this data: the “behind” feeling does not resolve with more money. Respondents earning $100K–$150K were more likely to reject timeline pressure than those earning less– but a meaningful percentage still felt it. Even at $150–200K, more than half said they felt a little behind.

Your biggest tension is alignment > ambition.

“Alignment” in this context = the state of harmony between your inner self (values, beliefs, and soul’s purpose) and your daily actions.

When asked to describe their career right now, only 6.8% of respondents said they were “thriving.”

The majority (over 70%) were looking for clarity, exploring new career options, actively searching, building something new, or simply stable but questioning it all. Our cohort is not sitting idly by while the world of work changes at the speed of light, but we’re not rushing into complete reinvention, either.

Ambition is actually everywhere in this data, but it’s aimed at different targets than it used to be. When I asked you what “end of career success” meant to you, impact and purpose outranked titles and promotions, financial freedom showed up more than status, and legacy showed up more than recognition.

The tension I see is between what people have built and what they actually want, and the mounting suspicion that those two things may not be the same.

The data made this unignorable: your employment structure predicts alignment more than almost anything else.

• Self-employed respondents averaged a 6.9/10 on alignment

• Full-time employees averaged 5.1

• People between jobs: 4.6

The more autonomous your employment structure, the more aligned you felt. I think this tells us a lot about what our generation is actually optimizing for in their careers, now that the old incentives like long-term stability have dried up.

AI is top of mind, but not for the reasons you’d think.

80% of respondents use AI tools weekly or more. Daily usage was at 47.5%. So yes, we have embraced the rapid changes in the AI landscape, thankyouverymuchMelRobbins.

What’s interesting, though, is why people aren’t using AI more. Soapy headlines will have you believing we’re rejecting AI because of job security fear (but that came in at less than 1%). The biggest reason you gave for not using AI more was ethics. Accuracy and inauthenticity came in second and third.

Going Places readers are asking harder questions than “Is AI coming for my job?” that point to a much more sophisticated relationship with the tech than is being talked about. Questions like: “Is this good work? Is this actually me? Can I trust this output?”

So what does all of this mean?

“I should be further along.”
“I should have more figured out.”
“I should want different things than I want.”

All of these feelings are so deeply personal, yet universal.

The timeline we were told to follow was designed for a different economy, a different set of options, and a different definition of success, and most of you are already writing a new one.

The full 2026 State of Millennial Careers report is below. Browse the slides, sit with the numbers, and tell me in the comments: which finding surprised you most, or which ones make you feel the most seen?

Keep going,

Janel

Kelly Bennett graduated college in 2009 into one of the worst job markets in history — and never worked corporate a day in her life. In this episode of Going Up, the CPG brand strategist breaks down 16 years of freelance, why she ignored a mentor's advice to "drink her way" to the top, and the underrated career move she swears by that nobody talks about.

Keep up with Kelly on Instagram

Tune into Kelly’s podcast

Check out Kelly’s website

 I'm Kelly Bennett, brand strategist for emerging CPG food and beverage brands.

What does that job even mean?

So basically, people come to me with their ideas for a new product for food or beverage, and I help them roadmap what that looks like to take that idea and put it onto retail shelves.

Is this the job you thought you would be doing when you were a kid?

I had no idea this was a job when I was a kid, so it's really been a journey to figure out that this was a real job that I could do. I knew I wanted to build brands, and I knew I loved better-for-you brands and businesses, but I had no idea how that would actually come to be.

So how'd you get started?

I graduated college in 2009, where it was a really challenging career market, and so the only job I could get was an internship in an ad agency. I learned about social media. That's when brands were just getting online. And honestly, I've been working for myself ever since. I left that gig at the agency. I realized that was not for me, and I've been freelance for 16 years, and it's really been trial and error to find the business I have now.

How do you make freelance successful?

A lot of side hustles. I did a lot of side hustles over the years, but really it was all about having the curiosity of testing, experimenting, documenting as much as I could. Again, I was just on the cusp of when social was becoming a thing. I had a blog. I was always networking. I was always looking to be engaged with community and building brands that way, and it was really just experimenting to find my lane.

What's a career dream that you've completely outgrown now?

When I was younger, I thought you build brands by working for a brand, and I never worked corporate. I never worked for a company that that's how I learned. There was one year in my whole career in 2019 where I worked for a startup full-time, but it lasted one year, and I again quickly realized that just working for myself was always going to be my lane. But I thought when I was younger that working for a company would be the way I worked up.

When you realized that working for yourself was the right answer for you, was there anyone's reactions that you were particularly nervous to hear or scared of?

I think my parents were really banking on me finding a good cushy job, working up the ladder, you know, like that career path that parents would always think for you to have. So when I told them that I graduated college with four degrees and that I wanted to move back into their house because I was starting a blog- Mm-hmm ... they were like, "What the hell happened?" Yeah. "What are you talking about?" I was like, "No, I'm gonna build my own business and I'm gonna use social media." But again, this was 2009, 2010, where this was not really a thing, and so they were like, "This kid lost the plot." Like, "What the hell is she talking about?" And so it took a while for them to figure out what I was doing, and honestly what I was doing too, I was trying to figure it out. But I knew the pieces that I kept getting drawn to, and that I could see where it was going, but I didn't know necessarily the verbiage yetof how that was gonna work as a business model.

What is some career advice you were actually smart to ignore?

I remember I did a call with an entrepreneur that I really admired. I saw that she was building brands and businesses, and she told me that I had to go out and drink and network, and that was gonna be the way I move forward. And I remember feeling so crushed at that time of like, well, that's not necessarily my personality. I would rather meet someone for a morning coffee or like go to a yoga event and network, and she was like, "No, that's not how you're going to make it." And it was very specific too for the industry we were in and the culture we were in, and she was like, "That's not how you're gonna move forward." And so I was really taken aback that that was her advice and how she said that she was moving forward of just like becoming drinking buddies with investors, and I was like, "That's not gonna be my path." And it, it really made me upset at the time thinking that that was the only way. And so I totally did the opposite and I started collaborating on a morning project that was the first Sunday of every month, and that's how one of the brands that I helped build really kicked off and what launched my career, was literally doing the opposite.

What's an underrated career move that no one really talks about?

Testing, experimenting, and getting the B roll. What I mean is that even if you're not documenting and sh- or I should say sharing everything in the moment, take B roll. Literally what I mean is saving clips of what you're doing, because you're not quite sure what the story is yet, but there will be a really good story to tell, and you're gonna want those random, at the time, clips of you doing something or testing something or working on a project or on those calls and meetings. But that will really help you give a visual storytelling piece to where you land, and it's a really impactful way to build your career.

We're going up, but where are you going next?

So as I said, I'm a brand strategist for CPG food and beverage brands. I also have a podcast where I interview brands who are hitting shelves next. And for me, what I wanna do is invest and back the brands hitting shelves next, so that's the next chapter I'm building out.

Is job hopping a red flag or a smart strategy?

I didn't necessarily job hop, but I worked on projects and then would go to the next, so I always had this sense that if I knew everyone in the room, I needed to move on.

Would you rather be overworked but overpaid or underworked and underpaid?

Over. Always overpaid.

Would you take a pay cut for work that actually means something to you?

I've done it, yes. But also know the time when you have to move on, know what you're leveraging that for.

For twelve months between 2020 and 2021, I had a secret morning ritual. I’d open my laptop, log into my HR Business Partner job at a buzzy tech company, and remind myself that I hadn’t given up.

I’d landed the role after 5 months of peak-pandemic job searching from my studio apartment in San Francisco, and the job felt like a life raft and an albatross all at once. Although I was so grateful to have landed the job, for me, it was just a pit stop on the way to a further destination.

I’d taken the role because the leap I actually wanted to make into full-time independent career coaching was further than I could jump in one move. I needed more financial runway, a bit more recruiting experience under my belt, and the consistent income to maintain my life. So I built a bridge.

I want to talk about bridge jobs, because I think they’re the most undiscussed move in the modern career playbook… and the one most likely to subtly betray you.

My definition of a bridge job is a stepping-stone role that gives you experience, income, and/or stability on the way to a longer-term goal. You take it because the direct path doesn’t exist yet. Maybe you need savings before you can go independent, a credential or a specific type of experience, or you want to test whether the industry you think you want actually fits.

It’s like taking a local train instead of the express.

And while I was in the thick of my bridge job, it helped to remember that it was just a means to an end, a temporary container before my dream destination. Except… somewhere around the nine-month mark, I noticed I was getting really, really comfortable on the bridge.

I’ve watched millennials mid-career crisis take bridge jobs for every reasonable reason, like:

• A strategist who took a Recruiter role at a non-tech company because she wanted to break into tech recruiting once the market warmed back up

• A corporate woman who stayed in financial services while she completed the prerequisites for her Master’s in Social Work

• An HR generalist who took a hybrid case coordinator role because it let her build a skillset she couldn’t access in her current org

At first, these people and many others felt like taking a bridge job was “settling” for something shy of what they really wanted. But the way I see it, taking a bridge job is strategic.In an economy where the direct path to almost anything has been quietly dismantled, bridge jobs are realistic, pragmatic workarounds.

But, dear reader, all is not rainbows and butterflies in bridge-job-land. A bridge is only a bridge if you can still see the other side.

The risk isn’t that you take a stepping-stone role, but that the stepping stone gets too comfortable. When the paycheck at your bridge job is nice and steady, you start kiki-ing with your teammates, and the work is predictable enough that you can do it on autopilot, you can finally exhale for the first time in years.

And then one day you look up and realize you’ve stopped working on the thing the bridge was supposed to lead to.

This is the part I didn’t see coming in 2021. I thought the danger of a bridge job would be the bridge itself, but the actual danger was the fading of my destination from my vision. The longer I stayed, the harder it got to remember why I’d started building the bridge in the first place: the independent career coaching version of my life started to feel less urgent and less real.

By no means am I saying that you should be miserable on the bridge. The whole point of a bridge job is that it’s supposed to be more sustainable than what you’re leaving and less than what you’re going toward! If you’re miserable, the bridge job isn’t working.

But there’s a difference between sustainable and seductive. A sustainable bridge job gives you energy to keep building the other side, whereas a seductive bridge job slowly convinces you that the ultimate destination was never that important anyway.

Signs your bridge job is becoming the destination:

• You stop talking about the long-term goal out loud, because you’ve stopped thinking about it enough to bring it up.

• Your timeline keeps extending, little by little. Six months becomes a year becomes “let me just get through this next promotion cycle.”

• You start defending the role to yourself in ways that sound suspiciously like the rationalizations you used to have in your last misaligned job. “It’s not that bad.” “The benefits are good.” “At least I’m not [previous worse situation].”

• The skills you said you’d build “on the side” aren’t getting built, the portfolio you’d assemble in the off-hours hasn’t grown, or the runway savings you were going to stockpile got absorbed into your regular lifestyle

If any of the above sound too familiar, don’t panic–you haven’t “failed” at the bridge job (that’s not a thing), you’re just a normal human being who relaxes into stability, which is exactly what stability is for.

But if the bridge job was supposed to be temporary, that relaxation is the thing you have to watch.

The bridge job needs maintenance. Schedule quarterly check-ins with yourself about whether the other side still looks like what you wanted, and whether you’re still moving toward it in any visible way.

It also means accepting that sometimes the destination does change while you’re on the bridge. That’s OK! Outgrowing your original goal is not the same as abandoning it under pressure. The question is whether the new direction is something you’re actively choosing, or something the comfort of the bridge has chosen for you.

I left my HR bridge job after exactly 13 months when I got to the point where my 9-5 job and the business I was building on the side were both starting to suffer from my divided attention. I took that as the sign that the bridge was complete enough for me to step onto the other side with more confidence, and I kept building the path one brick at a time.

So I want to ask you: if you’re in a bridge job right now (or you’ve been in one for a while) can you still see the other side? And when’s the last time you actually looked?

Leave your questions for Alexis in the comments!

Leave a comment

If you loved this interview, you’d also love:

• “Being recognized for your work is actually pretty simple” →

• “The rise and shift of the personal brand economy” →

• “Rule followers, we’re cooked” →

Connect with Alexis here:

• Substack

• LinkedIn

• Read her book, “Too Smart for This: A Journal to Build Self-Trust and Stop Settling for Less Than You Deserve”

Interview transcript:

ALEXIS: I do 10 million things. So I’m a creator, writer, speaker, and consultant, coach, business woman, all of it, you know.

JANEL: And how old are you?

ALEXIS: 27.

JANEL: And how did this happen?

ALEXIS: Honestly, I was stupid. And when I was working at Google when I first got out of college, I started posting lifestyle content on the internet and built a following, and since then I’ve tried to monetize it in every single different way while also maintaining my full-time jobs.

I got my MBA from Wharton after I left YouTube, and so I’ve just sort of been, you know, working in the creator economy ever since.

JANEL: What’s a misconception about getting your MBA these days?

ALEXIS: People think that getting an MBA is stupid, um, and that it’s like you can learn all of that on ChatGPT, which is like, okay sure, you can t- technically you could learn the information that you get taught in business school, 100%, but the network and the connections and the personal challenge that it takes is really what the actual benefit is, and I actually think that my experience and my MBA is going to increase in value over time even though the information may be more readily available now.

JANEL: So would you say that your MBA was right-priced, too expensive, or too cheap?

ALEXIS: Listen. You know what? It doesn’t matter because I had to pay for it. You know what I’m saying? I mean, I don’t look at prices. I look at, value, and I think that however you measure the value is however you measure it.

JANEL: One year out of your MBA, what’s been the ROI so far?

ALEXIS: Oh my God, the instant credibility marker is something I did not expect at all because I was always gonna go to Wharton. It’s sort of a checkbox on my career path. But to... And I’m feel very privileged to say that, but I also worked very hard for that.

For a lot of people, they’re like shocked by it, and I did not realize how much it would get me in the door. One of my mentors went to Wharton 30 years before me, and I think me going there is what allowed her to step into my world and like create an opportunity with her,

JANEL: How did that happen?

ALEXIS: My mentor, Pauline Brown, she was the former chairwoman of LVMH and she’s the author of a book called Aesthetic Intelligence and the podcast of the same name. She’s a [00:02:00] star, incredible, and I think she was really interested in what an MBA meant today and why building your personal brand is so important. And so she reached out to me, and since we’ve had like a really great relationship

JANEL: If a personal brand is so important, why don’t more women start them?

ALEXIS: Women are pretty mean to other women, and men are pretty mean to women, too, particularly women who stand out and want to get attention for whatever they’re doing, and we are criticized way more than other people. And oftentimes it’s us doing that to each other, and so honestly, I think that people are scared of the cringe.

I don’t think that there’s any lack of education or clarity or creativity from women, um, nor is there any lack of knowledge and intelligence. It’s really a matter of being afraid of speaking up because people can be so, like, scary online. And I think that once you get over that, and you get over the cringe, you get over the fact that, like, you are going to upset people if you want to skyrocket, then I think it’s a lot more fun, and also we get a lot further as a society.

JANEL: If you were standing in front of another accomplished, bright, incredible woman who just refused to start her personal brand because of all the things you just said, what would you wanna say to her?

ALEXIS: Don’t be stupid, first of all. Look at the data, all right? Like, if you look at w- the, one of the highest growing industries in the world right now is the creator economy, growing 22% year over year. By not participating you’re literally leaving possibly millions of dollars on the table. So just start there and look at the numbers, and hopefully that’ll make you feel better about it because, like, that’s a defensible reason to get started, right?

All my Wharton classmates are still very afraid of getting started online, so I completely understand and empathize ‘cause it is a real fear, but the longer you wait, the less money you’ll make, and the less skills you’ll have, um, for the future of work.

JANEL: And do you think creating content is necessary to get ahead in the future of work?

ALEXIS: For 90% of people, absolutely. I think for a small 10%, you know, there’s those people who are like, “I wanna be private one day,” whatever. Sure, okay, do whatever, like, if you wanna be private, but, like, honestly, when else have we had the democratized ability to show our work, to speak for ourselves, to create our own actual businesses like we haven’t before? And so take advantage of it.

JANEL: Is this what you thought you’d be doing as a kid?

ALEXIS: Listen, I always knew I wanted to look good and talk for a living, okay? Like, that was always the goal. But, um, I think when I was little I wanted to be an author, and that’s what I’ve become now, and I think that, like, I was always meant to be talking to people and inspiring people, but I definitely thought it would be m- in more of a corporate environment, for sure.

JANEL: What did you use to want from your career that you don’t want anymore?

ALEXIS: Validation from gatekeepers when I was in college, I would always be made fun of by my guy friends because I decided not to go, like, the big three consulting route, and I was gonna go marketing at Google, and boys were looking down on that or whatever.

And I always was like, “I’m gonna prove, like, to every finance dude that, like, I’m the smartest person in the room.” And then I realized quickly that, like, that proving energy was rooted in external validation, not in my zone of genius and what I can actually contribute to the world. And so now, like, I do not look at money or, like, the Forbes list or, like, somebody’s resume to determine whether or not that work is impactful.

I actually, like, just think to myself, like, “How many people can I help?” And that’s what matters. And I do think that’s a little privilege from, you know, having a really stacked resume really early on, which, like, I, again, worked very hard for. But at the same time, it made me realize that, like, these people are no different than, than me. There’s no one to put on a pedestal. Take everyone off of a pedestal and focus on the work.

JANEL: What career advice were you actually smart to ignore?

ALEXIS: Following the rules. I became a creator at the same time I started at Google, and I was in a program that was supposed to be 18 months, and you could not leave before 18 months was up.

And, , I realized I didn’t really like it, started looking for other roles, and ultimately got poached by the YouTube Shorts team to help launch YouTube Shorts, where I got visibility into C-suite level executives, got to work with brands like Vogue and Sephora, MrBeast, all of these people. And they said, like, “You can’t leave after 18 months.”

I left after 10 and I just... Nobody batted an eye. Like, if I would’ve kept myself in that box, then I never would’ve had my dream job.

JANEL: job hopping, red flag or smart strategy?

ALEXIS: Depends, but stay everywhere for at least 10 months to a year. I just said, I I just said that. Be smart about it.

JANEL: Would you rather be overworked but overpaid or underworked and underpaid?

ALEXIS: Oh my God, overworked and overpaid, what are you talking about?

JANEL: So would you take a pay cut for work that really meant something to you?

ALEXIS: I don’t believe in that. You can always create more money and create more opportunity for yourself. I definitely think I, I am very strategic. There are things I lose money on that are really important to me, but that doesn’t mean that, the rest of my financial world has to also be in straits.

JANEL: Posting on LinkedIn.

ALEXIS: Up.

JANEL: Corporate loyalty.

ALEXIS: Down.

JANEL: Making friends with your coworkers.

ALEXIS: Up, always. You never know where somebody’s gonna go. Some of my best friends from YouTube are now, like, execs at other companies, and I never would’ve met them if I didn’t go to the office, by the way. But absolutely, make friends with your coworkers, but don’t tell them all your business.

JANEL: Adding your boss on social media.

ALEXIS: No, absolutely not. Do not do that. Do not do that, okay?

JANEL: Work-life balance.

ALEXIS: Not a real thing. Not a real thing at all.

JANEL: Well, we’re going up, but where are you going next?

ALEXIS: I’m just at the beginning of building my empire, okay? I’m just getting started, so more books, more shows, more brands are on the horizon. Prepare to be sick of me !

A few months ago, a video went viral like a creator’s wet dream: hundreds of thousands of views within hours, the whole comments section on fire, skyrocketing from 10k followers to 100k followers in a matter of days.

The creator was making a point about modern careers that I have, on the record, made many, many times — in newsletters, on podcasts, in talks I’ve been paid to give, you get it. Well, she wasn’t really “making a point” so much as regurgitating my exact words and original phrasing to describe the Great Millennial Career Crisis…

Same exact words, slightly different delivery, and a ~6M difference in views between our videos. Fuck.

Uncomfortable admission #1: Once her video started taking off, countless friends and peers of mine tried to console or commiserate with me using a similar refrain: “She doesn’t even talk about careers, so she can’t really go any further from here! You’re the one who’s studied career development for a decade!”

Up to the point of posting her Great Millennial Career Crisis video, she was a nutrition coach turned furniture flipper, that was her whole thing. She’s openly career confused, she doesn’t (to my knowledge) have a degree in organizational psychology or a thesis on career development. I do. And nobody cared.

Uncomfortable admission #2: My first reaction was the obvious one: “But I’m more qualified to say this!”

My second reaction, a few days later, was the more painful one: “So what?” The “right” qualifications were never what made her message hit for millions of people. It was her delivery and her timing.

The fact that she said what I’d been saying, but in a way that made people feel something and respond so passionately, without the academic foundation I keep instinctively leaning on, is what’s made her content creation journey so successful in such a short time.

And the most uncomfortable admission of all: She isn’t disqualified from being a compelling voice in this space just because she didn’t study it the way I did. In fact, for 300,000 people, that’s exactly what makes her compelling.

I have two degrees in work psychology. She has a furniture-flipping studio in her garage. The market chose her.

What most millennials still aren’t accepting is this: the competitive advantages we banked on aren’t competitive advantages anymore. Here’s what I mean:

We were raised on a very specific deal: do well in school, get into a good college, get into an even better grad school, build a resume of recognizable names, accumulate the right credentials, and the gate would open for us. Because the world we were preparing for was a gatekept one. The alumni network mattered because you needed a warm intro to get a real interview. The degree mattered because it was the filter that recruiters used to weed through a stack of resumes.

Every single one of those advantages was real up until 2020.

Today? If you can write a compelling cold email, you don’t need the alumni network.

If you can spin up a website and sales funnel in an afternoon, you don’t need the venture-friendly Stanford MBA pipeline to start a company that makes real money.

If you can build an engaged audience on the internet, you don’t need the gatekeepers at all. In fact, you can become the gatekeeper.

The “success infrastructure” that used to require credentials, capital, and connections now requires a Wi-Fi connection and a willingness to feel stupid online for 18 months.

Millennials trained for survival of the most-decorated. The new reality is survival of the scrappiest, but a lot of millennials still aren’t willing to take that ego hit.

What Gen Z is getting right

Here’s the part that should genuinely rattle the millennial “credentialed class,” as I’m calling it.

A new Gusto report dropped this week revealing that, for the first time in history, Gen Z has surpassed Boomers in new business starts. Seventy-one percent of Gen Z founders used AI to launch their businesses.

The Guardian recently profiled a wave of Gen Z grads who saw at the disappearing entry-level opportunities and AI obliterating the bottom of the corporate ladder and just went around the whole system.

ZipRecruiter found that nearly 38% of recent grads are considering starting their own business instead of looking for a traditional job (not “in addition to”).

I keep seeing older generations’ commentary frame this as “Gen Z is getting eaten alive by AI.” But that’s our all-or-nothing, meritocracy-trained read on it.

I think the more honest read is: Gen Z isn’t fighting our fight. Whereas millennials and the generations above us feel like we’re the savvy ones trying to outsmart the system, Gen Z just aren’t entering the system in the first place.

This is what made the copied-content moment so destabilizing for someone like me. I was still banking on the “rule” that credentials should matter in who gets attention and recognition for something, and that earning “legitimacy” through the “proper channels” is the precondition for being heard. (I’m done with the air quotes now, sorry).

The reason I felt that flash of resentment watching her videos go viral and her audience growth skyrocket wasn’t really about her, it was about me. It was the sobering realization that the old competitive advantages that I’d felt so proud of (pedigree, depth, logos on my resume, the years of work I’d put in to be qualified to say things) aren’t necessarily competitive advantages anymore, at least not in the space we’re both playing in, content.

What I’m not willing to discard

The easy version of this essay would be to declare credentials dead and tell you to start an Amazon drop-shipping operation for whatever products currently have the highest margins. I’m not doing that.

There are things I genuinely still believe in, like intellectual integrity, business integrity, the discipline of saying “I don’t actually know that yet” instead of confidently selling a framework you made up on the toilet.

Just because you can spin up a sales funnel for a coaching program you have no business running doesn’t mean you should. The democratization of tools means the democratization of grift, too.

Uncomfortable admission #3: I don’t think integrity is a competitive advantage in the short term. I want to be honest about that. The supplement bros are winning right now, from an income standpoint at least. The “vibey” business coaches are swindling people looking for a liferaft in unemployment out of disgusting amounts of money lille MLMs. The people repackaging other people’s ideas with better delivery are doing growing across all platforms. I believe, in most cases, that if you’re making the bet on doing things with care and credibility, you have to be open to the possibility of losing the short cycle to win a longer one.

Integrity is a longer-term bet that trust will eventually compound, that the grifters will eventually get found out, and that the people who built slowly with their name attached will still be standing when the cycle turns. That bet might be wrong, but I’m making my moves in accordance anyway.

Here’s what I can’t quite resolve, and I want to put it to you instead of pretending I have it figured out.

If the old advantages — credentials, networks, pedigree — have been commoditized, the new advantages are commoditizing just as fast… if anyone can spin up a website or write a cold email with ChatGPT or launch a Substack, the skills I would’ve called “future-proof” two years ago are table stakes now. So what actually compounds from here?

My current best guess is the things that can’t be commoditized easily:

• Trust built over years rather than reach built over weeks.

• Discernment, knowing what to actually do with all this available information.

• Resourcefulness, that old “try three before me” energy our teachers drilled into us, which now means being the person who can figure things out without immediately outsourcing your brain to AI.

• Live, unrehearsed human intelligence, being able to hold a real conversation, read a room, send an email without being coached by Chat in real-time.

• Real relationships

Also, this experience has taught me that I’m not willing to hold myself back out of pride, so I’m now following @jessiejeanhome and actually learning A LOT from her advice on becoming someone who is more interesting and engaging to follow on the internet. Growth, a concept.

What do you think? What competitive advantage are you still defending? Do you fall in the Millennial Credentialed Class, and are you willing to evolve?

Sunday, 5PM. You’re staring at your calendar for the week ahead, and something is wrong. Not catastrophically wrong — you’re not crying in the bathroom, you haven’t drafted a rage-quit email in your notes app (this week). But there’s a low nagging off feeling that you can’t quite pinpoint.

If you’re a 30-something professional who used to be the kind of person who got energized by Monday morning, this feeling ins’t new.

What’s harder is figuring out what to do about it. Because before you can fix it, you have to name it. And “I don’t love my job anymore” is currently doing way too much work as a diagnosis.

I’ve been thinking about this lately, because I keep getting some version of the same DM: “I don’t know if I’m burnt out or if I just hate my job.” And my honest answer is this: those are really different problems. They feel similar from the inside (heavy, foggy, vaguely doomed), but they have completely different root causes and different antidotes.

So, I want to try to pull them apart. Here are three states of carer dis-ease that get lumped together but shouldn’t:

🥱 Boredom is when the work is too small for you.

Boredom is something us high-performers tend not to consider, because it sounds like an ego problem. It’s actually a job-fit problem.

Boredom is what happens when you’ve fully metabolized a role: you can do it on autopilot, you can predict the outcome of every meeting before it starts, the “stretch” projects feel like filling time rather than enriching you. You still have plenty of energy, you just have nowhere to put it that feels worthwhile.

The boredom tell: you’re restless. You’re rooting around for side projects, signing up for things, googling grad school at 11pm. You don’t feel heavy, you feel itchy, under-stimulated.

If this is you, more rest will not fix it. More rest is the opposite of what you need.

🪫 Burnout is when the work has taken too much from you.

Way past “I’m tired,” burnout is the specific exhaustion that comes from extending past your capacity for so long that your nervous system is crying out at you. The work itself might still be meaningful, your team might still be decent… hell, the company’s mission might still match, but you have nothing left to give it.

The burnout tell: it’s in your body before it’s in your head. The crashouts that start on Tuesday, not Sunday. Crying at things that are not, by any rational measure, cry-worthy. Whereas boredom is a dull malaise, burnout is sharper because you’ve been operating at 110% for so long that to give 80% now feels impossible.

Burnout is the diagnosis where the cultural script is most likely to fail you, because we’ve turned “burnout” into a personality type and an aesthetic instead of what it actually is: an injury. You don’t positive-think your way out of an injury.

If this is you, what you need is recovery — more than a long weekend. You need a sustained period of reduced output., which I know is a privilege that most of us cannot just take. Which is part of why we stay stuck.

🌱 Outgrowing is when the work no longer matches who you’ve become.

Outgrowing your current work situation is the sneakiest predicament, because, technically, nothing is wrong. The role isn’t bad, the company isn’t bad. In fact, maybe just a year ago you would have killed for this exact setup. But something has shifted in you, and now the same job that fit perfectly is suddenly the wrong shape.

Outgrowing isn’t about capacity (you have it) or stimulation (you have that too, sort of). It’s about meaning. The mission you signed up for at 26 was the right mission for the person you were at 26. You are no longer that person., so the metrics that used to feel like wins now feel kind of hollow or uninspiring.

The outgrowing tell: you feel flatness when good things happen. The promotion lands and you feel… nothing. The project ships and you don’t care. The anxiety or exhaustion isn’t really there, but you’re just strangely uninterested in your own great performance here. That’s usually a sign of your values shifting, and your job hasn’t caught up.

This one is hardest to admit to yourself because it’s the hardest to justify changing for. You’d have to leave a job that, on paper, you should love, and explaining that to your parents is going to be a whole thing.

So: how do you tell which one you’re in?

A few questions, less as a quiz and more as a mirror:

1. When you imagine taking three months off, what does the fantasy look like? If it’s learning something new, building something, going somewhere harder — that’s boredom. If it’s sleeping, lying down, and not being asked anything by anyone — that’s burnout. If it’s figuring out who you actually are now — that’s outgrowing.

2. When you imagine your job being objectively easier — fewer hours, less pressure, same money — does the wrongness go away? If yes: burnout. If no: probably not burnout.

3. When you read about someone in your field doing something completely different, do you feel envious or relieved? Envy is information, and relief is even bigger information.

Suggested Antidotes

Here’s the part I want to be careful about, because I don’t want to hand you a diagnosis and then a five-step plan. The truth is that these three states are not clean categories — they overlap, they cause each other, and you are probably in some custom blend of all three. Burnout makes you bored because you can’t bring your full self to work. Boredom can curdle into the kind of low-grade resentment that looks like burnout. Outgrowing, left long enough, becomes both.

But I do think the first move looks different depending on where you are.

▶️ If you suspect boredom, the experiment is to introduce difficulty on purpose — you don’t need to quit, just start to deliberately put yourself in a room where you’re the dumbest person there. A new skill, a new professional relationship like a mentor, a rotational role, a conversation with someone two levels above your pay grade. See if the itch goes away when you’re actually being challenged (good way).

▶️ If you suspect burnout, the experiment is subtraction. What is the smallest thing you can take off your plate this week without anyone noticing? Do that. Then do it again next week. You are not going to positive-mindset your way out of the injury that is burnout. You’re going to have to actually reduce the load, even if it feels irresponsible (it’s not, promise).

▶️ If you suspect outgrowing, the experiment is curiosity without commitment. No resignation letter or pivot required just yet. Just start paying attention to what you’re drawn to when you look away from your work laptop — what you read, who you envy, what you’d do on a Wednesday evening with no obligations, whose content you’re proactively searching for, and why. Outgrowing reveals itself slowly, and the worst thing you can do is panic-pivot before you actually know what you’re growing toward.

You’re not bad at your job, or weak, or ungrateful. You’re a person who has been working long enough to have actually changed, in an economy that doesn’t really build in any room for that. The fact that the same role doesn’t fit you forever is a feature of being alive, not a bug.

So: which one do you think you’re experiecing right now? And have you been refusing to consider it because the answer is inconvenient?

Somewhere between “I quit to go freelance” and “I went back to corporate,” there’s a third option that most people don’t know exists — and the folks who’ve found it are still gatekeeping it.

It’s called fractional work. And I think it might be the most underrated career move available to experienced professionals right now.

So what is it, exactly?

Fractional work is when a company hires you to fill a senior-level role — Chief Marketing Officer, Head of People, VP of Finance, Director of Strategy — but only part of the time. Maybe one or two days a week, maybe ~10 focused hours a month. You are embedded in the organization, in the meetings, in the Slack channels, making real decisions with real authority. You are the person in that seat.

Just not every day.

The name comes from the arrangement: you’re giving a fraction of your time, and the company is getting a fraction of the cost of a full-time executive hire. For smaller companies — your Series A startups, your growing agencies, your bootstrapped businesses that need senior thinking but can’t yet justify a $200,000 salary — fractional hiring is often the only way they access that level of expertise at all.

For the person in the role, it means something different. It means you can hold two, three, maybe four of these engagements simultaneously; your income is no longer dependent on a single employer’s goodwill; and the expertise you spent a decade building is finally being compensated at the level it was always worth.

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Fractional =/= Freelance

This is important: people collapse fractional work into freelancing all the time, and they are genuinely not the same thing.

A freelancer is typically project-based. You come in, you deliver something specific (a campaign, a deck, a piece of code), and then you leave. The relationship is transactional and finite. You are a vendor.

A fractional executive is ongoing and embedded. You’re not delivering a project, but occupying a function. You’re setting strategy, managing teams, sitting in leadership meetings, owning outcomes over months, sometimes over a year or more. The company is buying your judgment, not your output — on a recurring basis.

Read more about the time- vs insight-for-money trade here:

Knowing that fractional is not freelance impacts how you price your fractional work, how you show up with your client companies, and what the relationships look and feel like. Whereas freelancers quote project fees, fractional leaders charge monthly retainers — typically anywhere from $3,000 to $15,000 per client depending on the role, the scope, and the seniority level.

Why it’s popping off now

The fractional model isn’t entirely new — fractional CMOs and CFOs have existed for decades, particularly in startup ecosystems where financial expertise is critical but a full-time marketing or finance chief is premature. What’s new is the expansion: fractional CHROs, fractional COOs, fractional “heads of” everything are more visible than ever. The model has gone from a finance-specific workaround to a legitimate career architecture across virtually every function.

A few things converged to make this happen:

1. Remote work normalized the idea that presence and productivity are not the same thing. If a full-time executive can do their job from home across three time zones, the logic that they need to be physically present five days a week starts to break down, and with it, the logic that full-time is the only way to get senior-level work done.

2. The startup ecosystem also played a role. As venture funding became more accessible and the number of early-stage companies grew, so did the demand for experienced operators who could help founders navigate growth without the overhead of a full executive team. Fractional became the elegant solution.

3. The supply exploded: a generation of highly experienced professionals who burned out inside large organizations, left, and discovered they had no interest in going back, but still wanted intellectually challenging, well-compensated work that used everything they’d built. Fractional gives them a structure that fits.

What the math can actually look like

I want to get concrete here because this is where the model gets very interesting.

Let’s say you’re a seasoned marketing leader (15+ years of experience. You left your last role — VP of Marketing at a mid-size company — and you start taking on fractional CMO work. You bring on three clients. Each one pays you a $5,000 monthly retainer. That’s $15,000 a month, $180,000 a year — likely more than your previous salary, working significantly fewer hours, with no single employer holding leverage over your livelihood.

Obviously the math varies enormously based on your function, your seniority, your industry, and how quickly you can build a client base. And it typically takes six to twelve months to get to that kind of stability. But the ceiling is real, and for experienced professionals it often sits higher than they expected.

Read more on how to find your first clients here:

What makes the model work financially is the retainer structure. Unlike project-based freelancing, where your income is lumpy and unpredictable, fractional engagements are ongoing. You know what’s coming in each month, so you can make longer-term financial plans, and because you’re embedded within the company, clients don’t churn the way they do on project/freelance work — a good fractional engagement often extends well beyond the initial term.

How to start exploring fractional work

If fractional work sounds like it might fit where you are, here’s how I’d think about approaching it.

• Start with specificity. The professionals who build fractional practices fastest are the ones who can articulate exactly what function they serve, for exactly what type of company, at exactly what stage. Not “I help companies with marketing.” But “I’m a fractional CMO for B2B SaaS companies between seed and Series B who need to build their demand generation function from scratch.” The narrower you go, the faster word of mouth works.

• Build your proof before you need it. One or two case studies that show the specific outcomes you’ve driven — with numbers where possible — do more for your fractional practice than any wordy LinkedIn headline. If you don’t have them yet, your next project at your current job is an opportunity to create them.

• If you can, start while you still have income coming in. One fractional client on the side of a full-time role tells you more about whether this model works for you than six months of research ever will. It’s the best possible pilot.

Read more on how to build your side income while you have a 9-5 here:

The question I keep asking myself — and I’m curious where you land on this — is whether “fractional” is a career stage we move through on our way to something else, or a career model we move into permanently. Because the people I know who’ve been doing it for a few years aren’t looking back.

Are you already doing fractional work, thinking about it, or is this the first time someone’s given it a name that made it feel real? If you’re making fractional work work for you, tell us how in the comments!

-Janel

I almost didn’t send a pitch that got me $6,000.

My idea was solid, and I was totally qualified to be the one to create the campaign, but my speaker kit deck wasn’t finished.

I only had the outline of a few slides, and I still hadn’t researched “speaker pitch template best practices,” download a few other people’s kits to learn from their positioning and style, and then send the deck draft to a trusted friend for feedback. And all of those small steps felt so daunting.

So I waited and I planned. And while I was waiting and planning (being responsible! being thorough!) I learned that someone else DMed the brand on Instagram and secured the campaign for themselves.

Excuse me?! You just “DM’ed the brand”? You just “told them you were interested” instead of sending a formalized ask? You just, like, effed around and found out?

That’s when something clicked for me: the good girl, rule-follower conditioning I was praised for my entire life is costing me in my career.

The Making of a Rule Follower

If you grew up being the responsible one (looking at you, eldest daughters, overachievers, kids who read the instructions before starting the assignment) you were rewarded constantly, by teachers, by parents, by a school system that was explicitly designed to sort and reward compliance.

Does anyone else have a core memory of that one pop quiz in middle school with two pages worth of instructions, only to have the very last one be: “Ignore all of the previous instructions and just sit silently at your desk?” That “gotcha moment” was my rule-follower villain origin story. Like, I truly still think about it.

And being the good girl rule follower worked out for us, for a while! In a world with clear rules, rule followers thrive. Corporate ladders were basically built for us: show up, do excellent work, wait to be recognized, get promoted. The traditional career path rewarded patience and preparation, and we were very, very good at both.

That world is all but gone now, but a lot of us are still playing the antiquated rules and losing for it.

The New Rules (There Aren’t Any)

Here’s the truth about how careers actually work in 2026 (and from now on):

There are no rules, so opportunities go to the people who make their own.

While you’re waiting for your hard-earned promotion to come after two dutiful years in your current role (because that’s the conventional order of things), Brad just started doing the job he wanted and got a new position made up for him after 6 months.

While you’re waiting for someone to nominate you to be a paid speaker at that conference, Jessica (who knows less about your industry than you, btw) just whipped up her own in-person event, sold tickets to her IG followers, and made more money than you would have from the conference speaker fee.

While actors who have spent years studying at the best drama schools were taking even more acting classes after work, self-taping, making connections, and waiting for their big break, content creators with nerve and no connections just started their own shows on TikTok that turned into bonafide production deals from Amazon, Netflix, Hulu. (Yes, I just watched Overcompensating for the fifth time while Ride is on hiatus, sue me.)

You’ve been trying to get a book deal with a traditional Big 5 publisher by taking a course on book proposal writing, researching literary agents into the wee hours of the night, perfecting your query emails to the very last letter. Meanwhile, someone else decided to self-publish their book on the same topic, got creative with TikTok marketing, and became an instant Amazon Best-Seller.

“But that’s not how you do it!!”

It is now, babe.

The people winning right now are operating with a fundamentally different internal rulebook. I used to see them as reckless, but now I know they just have a much higher tolerance for imperfection-in-motion. They’ve internalized “ask for forgiveness, not permission” as a career strategy, and it’s paying off.

I’m starting to call this the Good Girl Tax: the invisible cost paid by anyone who was socialized to be a responsible, self-sufficient, low-maintenance planner.

But the people who were never conditioned to follow the rules in the first place never pay the tax.

My brilliant friend Anna is going viral for her weekly “scaredy cat exposure-therapy” ritual, Shoot Your Shot Wednesday, and I’m starting to do it, too!

This Isn’t a Permission Slip to Be Chaotic

I want to be careful here, because the answer isn’t to abandon integrity, leave havoc in your wake, or manufacture confidence you don’t have.

The rules that still matter:

• Be a good person

• Move with integrity

• Don’t take shortcuts that harm others

The rules that were always made up:

• Hard work = first place

• Loyalty gets rewarded

• Wait to be discovered by someone

• You need a final draft before you can talk about it

• You need to wait x amount of time before you can ask for something

What I’m Still Unlearning

I’m not going to pretend I’ve cracked this nut myself. I still feel the pull to prepare more, do more, wait until I’m more sure, or that I have something fully baked before I can present it to someone (you should see my Reels draft graveyard). That conditioning is in my bones, and operating in this “fuck it, just do it” world of work feels unnatural most of the time.

But I’m learning to distinguish between preparation that genuinely makes something better and preparation that’s really just procrastination.

One question I’ve started asking myself: Is this making the work better, or is it making me feel more professional?

Those are two very different things. One is a legitimate reason to give something the time it needs to make its full impact, and the other is Good Girl conditioning making you think you’re doing the right thing, when actually, you’re the only one who cares.

Tell me: What rule are you going to break this week?

Are you a rule follower who’s felt the cost of it in your career? Or have you found a way to shake off the conditioning? I want to hear how it shows up for you!

Let me say something that's going to sting a little — and then hopefully set you free.

Somewhere out there, a Brad or a Chad just got a role, a project, a speaking slot, a board seat, a promotion — that was, objectively, yours.

He's less experienced than you. Probably less thoughtful. Definitely less prepared. But he was visible. He was on their radar. His name came up in the room when you weren't in it, and that was enough.

This is one of the most demoralizing, under-discussed realities of corporate life for women who are doing everything "right."

You're excellent at your job. You're producing. You're showing up. And you keep watching opportunities land in the laps of people who seem to have done a fraction of the work — because they've mastered something you haven't: the art of being known.

So let's talk about what visibility actually looks like + why it doesn't require you to become an influencer to use it.

The Visibility Gap

We've been sold a lie that great work speaks for itself.

That if you keep your head down, deliver results, and wait your turn, the right people will notice.

But here’s what's actually happening: decisions about who gets promoted, tapped, or referred rarely happen in real-time performance reviews. They happen in casual conversations, Slack threads, on panels, and over coffee.

They happen in the mental Rolodex someone pulls out when they're thinking, who do I know who would be great for this?

If you haven't given people anything to remember you by outside of your immediate team, you're not in anyone's Rolodex. And the person who is (even if they're less qualified) will always have the edge.

The solution: make your thinking more visible.

You Don't Have to Be a Content Creator. But You Do Have to Be Visible.

This is where I want to push back on an assumption a lot of high-achieving corporate women hold: that visibility requires self-promotion, and self-promotion is performative, and performative content is for people who need the attention.

You don't need a personal brand in the influencer sense. You don't need to post about your morning routine or document your career pivots. You don't need 50k followers or a newsletter like this one to make this work for you.

You just need to share what you already know — consistently, intelligently, and in public.

Back when I was working in corporate full-time, I built a scrappy "thought leadership” framework for myself so certain coworkers couldn’t keep getting credit for my good ideas. 

The Going Places Thought Leadership Model: “Know, Think, See, and Do”

Most people assume thought leadership content means having hot takes or radical ideas. But for corporate professionals, the bar is actually much lower — and the opportunity is much bigger — because so few people do it at all.

Here's what it actually looks like:

1️⃣ What You KNOW — Your expertise, made accessible. The how-to's, the dos and don'ts, the things that seem obvious to you because you've been doing them for a decade but would be genuinely useful to someone else. A quick breakdown of how you approached a tricky stakeholder situation. A post about what most people get wrong about performance reviews. The industry knowledge that lives in your head, finally exiting your head.

✍️ Here’s a recent example.

2️⃣ What You THINK — Your perspective and your stances. Where do you agree or disagree with the conventional wisdom in your field? What's your take on a trend, a news story, a shift happening in your industry? You don't need to be controversial — you just need to have a point of view. An opinion, clearly expressed, is incredibly rare on LinkedIn. Which means it gets remembered.

✍️ Here’s a recent example.

3️⃣ What You SEE — Trends, changes, patterns, cycles. What are you noticing in your work, your industry, your organization? What's shifting that other people haven't named yet? This is observation-as-content. It doesn't require expertise so much as attention — and attention is something you already have.

✍️ Here’s a recent example (and it’s getting spicy!!).

4️⃣ What You DO — Behind-the-scenes. Recaps. Live footage of your work in the world. Attended a conference? Share one thing you took away. Led a project? Reflect on what you learned. This is the least performative of all four — it's simply documentation of a professional life you're already living.

✍️ Here’s a recent example.

Note: You don't need to be in all four categories every week. But rotating through them  even once or twice a month  gives people a rounded, memorable sense of who you are and how you think.

What it Looks Like in Practice

I want to talk about Carmen Vincente for a second, because she's a perfect example of what this looks like in action.

Carmen, a social media strategist, just landed an incredible new full-time role at Slate and was recognized as a “LinkedIn Top Voice” all because she posted work-related content on LinkedIn.

She wasn't building an audience just for the sake of it — she was consistently demonstrating her thinking, her expertise, and her perspective in public. When the right people were in those conversations, they already knew her. She'd done the work of being on the radar before she ever needed to be.

That's the compounding effect of visibility: it feels like nothing in the moment, and then suddenly it's everything.

Notice: Carmen “only” has ~11k followers on LinkedIn, but what matters more is that the right people saw her posts.

What Consistent Visibility Actually Builds

When you show up consistently with what you know, think, see, and do, something starts to happen that's hard to manufacture any other way.

People begin to associate your name with a type of thinking. They forward your posts to colleagues. They mention you in conversations you're not in. They think of you when something comes up that sounds like you.

You stop being someone who does a job, and start being someone who has a perspective — and perspectives travel further than performance reviews ever will. (Not to mention, people with actual unique perspectives are painfully rare these days.)

This doesn't happen overnight, but it certainly compounds. And the alternative — staying invisible while waiting for great work to be enough — has a track record we've all seen play out in real time.

The next time a room full of decision-makers needs to fill an opportunity, you want to already be in their mental Rolodex. The content you share this week, this month, this quarter is how you get there.

Brad got there through golf and proximity. 😉 

You can get there through what you actually have to say. 💁‍♀️ 

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.

Sign up here to stop dreaming and start doing.

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

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.

Sign up here to stop dreaming and start doing.