Sabina Zetkova started her career as a lawyer in Slovakia. After deciding that a career in law wasn’t for her, she joined the support team at MailerLite, a remote-first company that makes an email newsletter platform. Today, Sabina leads customer experience operations there while also living as a digital nomad. When I talked with her, she was living in Indonesia. You can find Sabina on LinkedIn.

This interview has been edited for length and clarity.

Anna Burgess Yang: Tell me a little bit about your career and where you started.

Sabina Zetkova: I graduated from law school in Slovakia, and that was also my first professional path. I worked for two years as a lawyer for a regulatory body overseeing radio and television in Slovakia. Later, I worked as a lawyer for an NGO focused on human rights, where the main area of focus was refugee law.

Currently, I’m leading customer experience operations at MailerLite. I work mostly with our processes, all with the final goal of helping our customers in the best possible way.

ABY: What originally drew you to law?

SZ: That’s a good question. I think figuring out what drew me into it also helped me move away from it eventually. I was one of the smart kids at school, and where I’m from, when you were a smart kid, you were supposed to aim for a career that had prestige. It was either becoming a lawyer or a doctor. I didn’t like blood, so for me, the path was law.

Even my parents would say they were very surprised I chose to pursue this degree. But I loved learning, and I loved challenging myself. It seemed like the right choice for me at the time.

ABY: What prompted you to move away from law after a couple of years of working in the field?

SZ: Law was never a dream of mine, even though I was naturally inclined toward justice, seeking fairness, and protecting others. When I chose law as my degree, I had never talked to a real lawyer in my life and never really understood what that life would look like. Law school was amazing. It was super challenging, super interesting studies. I was very busy with it, and I didn’t really think about whether this was what I was going to do. I just liked studying it.

Two years into my legal career, I figured that I would like to learn what the world looks like. I applied for a scholarship and was granted one to go study in Indonesia for a year. After that, I traveled more and went down to Australia. Then COVID hit, and I felt like it was time to figure out my life.

I felt like I needed to give law one more chance, but I wanted to do something where I felt needed and where I could make a real impact on people’s lives. I secured a job back in Slovakia and started working as a refugee lawyer. This was supposed to give purpose to my life and be very meaningful for me. It definitely was, but I didn’t feel content. It was quite an unhappy period of my life, trying to be in a place where maybe I didn’t belong.

I think the post-travel depression was also catching up with me. Europe was going through the second wave of COVID, so we were in lockdown, and I worked very long hours on very sad stories. While I was making a lot of impact on other people’s lives, at times I felt like I was pouring from an empty cup.

Around that time, I got an offer from MailerLite. It was a dream offer, and one that allowed me to create the life I’d wanted for myself.

ABY: What led you to look at a company like MailerLite? What appealed to you about that type of job versus what you’d been doing?

SZ: I think it was mostly the lifestyle. I first traveled to Indonesia in 2018, when the concept of digital nomads and remote work wasn’t that widespread. That’s where I saw for the first time that people were able to work from these amazing tropical places. For them, traveling didn’t mean letting go of a job, which was always the case for me.

I started observing that it was usually IT or software companies allowing people to work location-free. That’s also how I learned about MailerLite and them being a remote-first company. It wasn’t a company that adjusted to a remote setup, but a company that built its culture around being remote. That was something that really caught my attention.

I’ve been traveling full-time for the past six years.

ABY: Were you nervous at all about moving from law to a software company?

SZ: 100%. It’s a change of identity. You build up this perspective of yourself playing the role of a lawyer in a society that outlines a path for you, professionally and maybe personally. With each stage of my pivot, I was more sure about the final change.

I was definitely nervous when I said yes to the offer from MailerLite. But what helped me was that I left both of my legal jobs on very amicable terms, and I knew the doors were open if I ever changed my mind. That helped me venture out. But the move to MailerLite was definitely a risk.

ABY: What skills from your legal career fit with your new role at MailerLite?

SZ: I definitely believe in the transferability of skills. When you look at what you’re actually doing on a day-to-day basis, many jobs can have a lot of similarities, despite their titles and despite being in a different field.

What definitely helped me was analytical thinking: considering multiple points of view on the same situation and the ability to think a step ahead. And at MailerLite, I like to say that I’m advocating for our customers’ rights within the boundaries of the company. At the end of the day, there’s always a human at the end of the chain, and I’m looking for ways to optimize their experience and deliver the best possible outcome to them.

ABY: And what did you have to unlearn? What was part of working in the legal world that just doesn’t apply to working at a company?

SZ: Working for a software company like MailerLite is very dynamic, and that’s quite the opposite of what working in law can feel like. When I was a lawyer, there were a lot of boundaries. Even though it’s very creative work, the guardrails are very strong. Achieving change takes a lot of time and a lot of effort, and at the end of the day, you might still be limited by what the authorities allow you to do.

When I joined MailerLite, I needed to unlearn that limited thinking. In a product like ours, where new features are being shipped on a daily basis, questioning the processes and the system is very welcome. So I needed to feel brave enough to point out things that I believed could be changed.

ABY: What was a day like working as a lawyer, and what’s a day like now? What’s different about the structure of your day or the work you’re doing?

SZ: First of all, I would have to commute to the office. In the wintertime in Slovakia, it’s dark until 8 a.m., and it gets dark again at 4 p.m. So commuting to the office meant spending your day in the dark. My days would be spent in uncomfortable clothes, sitting on a specific chair in a specific office in a specific city.

In law, a lot of the time, you were analyzing. I needed to read through a lot of documentation and spend hours investigating, then write my argument. Back then, that was very tiring for me. I think that’s why I thrive in a software working environment, where things are shifting really quickly, and you work on multiple tasks. In my legal career, I could spend three days working on one particular task. On some days, I would go to court and need to defend my plea in front of judges, as a young girl in my twenties in a post-communist country. That was another challenge and another stress factor. It all felt so heavy.

I couldn’t relax into it, but I think I was playing my part well. I enjoyed the process, but maybe I was only enjoying it because I believed that this is what was expected of me, and that the path to satisfaction in any form should be challenging and very difficult.

My days now, especially when I’m here in Indonesia, start with a sunrise surf, then coffee with friends. Then I get work done, and then I wait for my colleagues to wake up so we can overlap working hours. I shift tasks quite often and need to readjust priorities based on what’s happening, so it’s much more relaxed.

That’s not to say the job can’t get stressful as well. There are critical moments when I need to work hard and use all my brain cells. But being able to choose where I do the work from, and whether I want to sit on a couch or at a table, adds so much value.

ABY: You’re currently leading customer experience operations. How has your idea of career progression changed?

SZ: When I was younger, I saw the world more narrowly. I felt that to have a place or an impact in society, I needed to define what I wanted to do in my life and what I wanted my profession to be. That would determine how I could grow.

I needed to shake that kind of thinking up, and maybe tame my ego along the way. Along my personal journey, as I tried different jobs and perspectives, I made peace with maybe not knowing what I want to be when I grow up. I prefer to see my life as an opportunity to collect experiences from different areas.

That’s how I see career growth: more as personal growth and as growing into the version of yourself that you’re proud of being, no matter what your job title is.

ABY: What would you say to someone who’s looking at making a big shift like the one you made?

SZ: For me, the most liberating moment was when I realized that I was trying to win a race that wasn’t mine in the first place. I was trying to follow social norms that didn’t make me happy. I was making a high impact, yet I felt very unsatisfied in the evening after my day at work. Realizing that broadened my horizons and allowed me to take responsibility for my own happiness. I don’t want this to sound like a cliché, but based on many beliefs, we have just one life, and it’s our own responsibility to make our 80-year-old self proud when looking back.

I know it takes a lot of courage, and I’ve always been very supported by my family. My parents only dreamed about the freedom that the current regime allows my generation to have. I was also making these changes in my twenties, without any big obligations, so that changes the perspective too. But I think that deep down, if we tune in, we all know whether we’re trying to win a race we want to be in. And it’s never too late to shift and make a difference.

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A few years ago, portfolio careers were framed as a deliberate choice: a forward-thinking decision to build experiences across industries and skill sets. The advice that came with it sounded empowering, because you gained an advantage from a career with more breadth than climbing a single ladder.

That framing assumed people had options. Right now, a lot of people don’t because the job market is absolutely brutal. Jobseekers fill out hundreds of applications, many of which disappear into AI-filtered queues, never to see the light of day. As a result, more people are building portfolio careers because they have run out of alternatives. The choice comes down to working or not working. For people pushed into new career paths by layoffs and a shrinking market, the standard advice to “own your non-linear path” feels hollow.

A portfolio career only becomes an asset when a hiring manager sees the throughline. And right now, that translation work — the work of making a non-linear path understandable to the people evaluating it — falls entirely on the jobseeker.

Traditional resumes don’t work for a portfolio career

Bonnie Silva wrote for Business Insider about shifting from bartending to becoming a doula to going back to school for a career in design. She sent 83 applications in a single month. Zero interviews. She had the experience and the skills. But they couldn’ land her a job. She wrote, “Making a career change shouldn’t feel this impossible.”

At the absolute baseline level, resumes are chronological. So are LinkedIn profiles. So are job applications, which ask for experience listed in reverse order, one role after another. The assumption is that your timeline should tell a story. When the story is clean — like a decade at one company with steady promotions — the format works fine.

When a person’s career spans three industries with a freelance period and a mental health break in the middle, the story requires “explanation.” A portfolio career, dropped into the typical chronological format, reads as instability. A busy hiring manager might simply pass over the candidate, rather than ask for the story.

Even though companies may claim to value skills over credentials, they haven’t followed through. Either it was an on-paper-only claim, or the hiring manager is too overwhelmed to give a resume more than a few seconds of time. And most jobseeking advice never teaches people how to frame a portfolio career in today’s saturated job market.

In 2021, when I changed careers, my shift from working at a tech company to content marketing (with no marketing background) opened doors. It was a unique combination of experiences. Today, I’d be shocked if the same resume would land me any job interviews. And the interview was critical to persuading a hiring manager that I could do the job, despite having no formal marketing background. Without the interview, my portfolio career wouldn’t have made sense.

A career that’s more than a chronological list on a resume

Translation — showing a hiring manager how the disparate parts of your career make sense for a new role — is a necessary skill for anyone with a portfolio career. Everything else in the portfolio is stuck without it.

The experiences don’t necessarily speak for themselves, and you may never get the opportunity to do the speaking if you can’t get an interview.

Today, it shows up in:

• The “Overview” section at the top of your resume

• A cover letter (or video, since some companies want videos now)

• A powerful description in the “About Me” section of your LinkedIn profile that makes the pitch

• The homepage and “About Me” sections of your website

• The “About Me” section of a proposal you send to clients

You get a quick glance — a few sentences at most — in each asset to explain yourself. Make them count. Practice writing them in different ways to see how much you can say in the fewest words. Because it’s not only an explanation of what you’ve done; it’s also how your portfolio career benefits the person trying to hire you.

The work of explaining your career is easiest when it’s not urgent (i.e., you’re not looking for a new role), but that’s also when it’s easiest to put off. If you’re in a stable role right now, or between projects with some breathing room, work on the translation part of any assets you have. If you’re in the middle of a job hunt, take the time to review everything a potential hiring manager sees.

Your career already has the material. The work left is making sure other people understand it.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

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In October 2022, I became self-employed. This month marks four years of working for myself.

I could write about the different things I’ve done to make it work, running my own business, but I’ll save that for LinkedIn…

Instead, I want to reflect on how much my perception of work has changed in that time. And not just because I now work for myself: because work has changed. I lost my job at the start of a downturn in the job market, and it has only gotten worse. Many people, like me, choose a path of self-employment because it seems preferable to finding a new job. A choice born from necessity isn’t really a choice (though it forced me down a path I was likely headed anyway).

Fear drives a lot of what we do with our careers. Fear of the unknown. Fear of discomfort. Fear of giving up job security.

So whether you’re considering a voluntary career change or are pushed into one, here are four things to keep in mind.

1. The beginner phase is shorter than you think

When people consider a career change, they tend to assume that everything about the new career will be unfamiliar. That was certainly my assumption when I left a tech job I’d been at for 15 years and pivoted to a new career in content marketing.

And some parts of a new job will make a newcomer feel inadequate. Every industry has its own jargon, for example, and not knowing it is a fast way to feel like the least experienced person in the room. (Imagine my adjustment when “SQL” went from meaning “structured query language” to “sales qualified lead.”) But jargon can be learned. It usually just takes a few months of listening and asking questions.

And you’re never truly a beginner again, even if you start over in a completely new industry. That assumption ignores everything a career pivoter already brings. Someone a decade into their career has made hard decisions and kept complicated projects on track. Those skills take years to develop, and someone at the start of their career hasn’t had as much exposure to a wide range of experiences.

The beginner phase is real, but it tends to be short-lived.

2. What you take with you are your boundaries

People always have a specific reason for leaving a job, and a lot of the time that reason is a boundary that got pushed or crossed. Maybe it was a boss who expected answers late at night. Maybe it was an ever-increasing workload without an increase in pay. Maybe it was an intolerable co-worker.

These days, finding a new job takes months of effort. Nobody wants to go through all of that only to end up with the same problems at a different company.

So people hold on to the boundary. What you didn’t tolerate at one job becomes something they actively try to avoid at the next one. Plenty of people leave a job with a very clear list of what they won’t tolerate.

That list — whether it’s actually written down or exists only in your mind — is the most portable thing anyone takes from an old job. Titles and skills may vary between roles and industries. But a firm grasp of what you want and what you’re willing to give (and give up) won’t change.

Boundaries also make it easier to see the employment relationship for what it is. Companies hire people because they need the work done, and nobody employs anyone as a favor. You’re trading your time and talent for money. Holding firm to a boundary ensures the exchange stays fair on both sides.

3. Security doesn’t come from structure

For a long time, a full-time job with a salary and benefits was the safe choice. Working hard inside that structure was supposed to add another layer of protection, via promotions or, at least, respect.

Layoffs have shown us that the social contract is broken. Companies have zero loyalty to their employees (yet still expect loyalty). Staying late or picking up extra projects often doesn’t change the outcome of who is impacted by a layoff.

For years, tech, in particular, was the industry that was supposed to be safe. At this point, outside of unionized jobs, nothing seems to qualify.

Some will argue that a steady paycheck is still safer than self-employment income. But a paycheck can disappear without warning, and then a person has lost 100% of their income.

A lot of people have been mistaking survival mode for stability. They hold on to a job because leaving feels riskier than staying.

Self-employment carries its own risks. Clients leave, and projects end. Both paths of working carry risk; it’s just a matter of choosing your risk — and building your own forms of a safety net if needed.

4. Ambition changes shape

Back in 2021, I wrote about redefining ambition.

The title-and-promotion version of ambition is what society has historically decided to value. A title gives people clout when they introduce themselves, telling everyone in the room how important someone is.

But titles are often meaningless. I held an executive role at a tech company and had a title of Director. After I left, my replacement — who was given less responsibility than what I had — was offered a title of Vice President. At first, I was miffed. Then I realized that he was probably lured with a title in lieu of compensation. The company didn’t want to pay him as much, so the title was a consolation prize.

Four years out, my ambition looks different. I don’t call myself a “founder” or “CEO” of my one-person operation. My goals have shifted to being recognized for the value of the work itself. That kind of ambition is certainly harder to show off at a networking event. But success for me comes from doing good work without sacrificing everything else for it.

If you’re thinking about a pivot, you’ll still have your ambition. It may just start taking on a different shape.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

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Note: October is Pregnancy and Infant Loss Awareness Month.

In 2015, I had a stillborn baby girl. I found out during a prenatal appointment that my daughter had no heartbeat.

Because I was in my second trimester, I was admitted to the hospital’s Labor and Delivery ward. The same ward where women deliver living babies. Except I did not get to bring my baby home.

I’ve talked openly about pregnancy loss for many years. I’ve advocated for more openness in the workplace. It’s a way to honor my daughter: to use my voice to make things better for other grieving parents.

Bereavement policies should cover pregnancy loss

My employer at the time had a very flexible leave policy. I ended up taking nearly three weeks off from work after my daughter’s stillbirth. My entire world felt like it didn’t make sense anymore. My body needed to heal.

Unfortunately, pregnancy loss often falls into a gap in companies’ bereavement policies. They don’t allow any time off for a miscarriage or stillbirth. I met a woman through a support group who delivered her stillborn baby via c-section and had to go back to work mere days later. When there’s no living baby, maternity leave does not apply. And the standard 3-day bereavement leave that many companies have is wholly inadequate.

Only a few states in the U.S. provide any guaranteed bereavement leave, and even fewer specifically include pregnancy loss as a qualifying event. It’s mostly up to individual employers to craft their own policies.

Many years later, I was working for a young company that was working to solidify its leave policies for the first time. I asked the HR person to include pregnancy loss leave specifically. I said, “You don’t want to wait until a situation comes up and then be scrambling to define the leave.”

I fear that happens too often. Companies don’t include pregnancy loss in their bereavement leave until an employee asks about it. At that point, the employee is in the throes of grief, which is the worst time to wait for HR to figure out a leave policy.

In 2022, TheSkimm launched a Show Us Your Leave campaign. Pregnancy loss leave was included in the data collected. If you can influence HR policies and are unsure what type of bereavement support to offer, TheSkimm’s database is a place to start.

How to support a coworker who has experienced pregnancy loss

Pregnancy loss is incredibly common: 20% of pregnancies end in miscarriage, according to WebMD. Some researchers believe that the number is much higher.

Yet, pregnancy loss is still a taboo topic, especially in the workplace. As a result, parents feel isolated in their grief.

Recently, a friend came to me because one of her employees had a miscarriage. She asked me, “What can I do to support her?”

I believe that caring, compassionate co-workers often don’t know what to do, especially if they’ve never experienced pregnancy loss themselves.

Here are my suggestions:

• Review this list from the Miscarriage Association of what to say (and what not to say)

• Listen to this podcast episode: How to Support Someone Experiencing Pregnancy and Infant Loss

• Set a reminder on your calendar to check in on a regular basis — even weeks or months later. Offer to listen if the person wants to talk.

If you’ve experienced pregnancy loss yourself, I’m so sorry. I know how devastating and isolating it is. I highly recommend resources from Share Pregnancy and Infant Loss Support.

I want to see the narrative around pregnancy loss change, especially in the workplace. I didn’t simply “lose a pregnancy.” My much-loved child died, as did all the dreams I had for her. There’s a hole in every family photo, because she isn’t there.

Workplaces can – and should – do better. Pregnancy loss isn’t rare. The workplace shouldn’t be a source of awkwardness or additional pain. Companies and coworkers need to figure out how to support someone, because it will inevitably come up.

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When I was in college, I was working at a community bank in Wisconsin. In the summer of 2003, I was given the task of converting the bank’s paper loan files to digital files. I sat at a desk with one other person, and we ran thousands of pages through a desktop scanner, organizing them into different folders.

At first, the work was awful. Not unbearable — we had a radio and listened to music while we worked — but monotonous. But eventually, I saw the end result. Loan officers were able to pull up documents without leaving their desks. Paper files were messy; scanned versions weren’t. And a few months after we started, the entire project was done.

Of course, not everyone liked the change. Once scanned, the paper files were stored where the officers could no longer access them, to force the change to digital files. One loan officer started hiding files under her desk because she didn’t want to give up the paper versions. During her lunch break, I would retrieve the files and scan them.

After graduating from college, I went to work for a software company (the same company that made the loan imaging platform I’d been using for years). My first role was implementation specialist. I traveled around the country, helping community banks learn to use the product they just purchased. Not just for scanning loan files, but a whole suite of loan management features.

Without fail, I’d encounter bank employees resistant to change. Some thought their current process was better. Some didn’t like the disruption to their routine. A few were uncomfortable with computers in general and struggled to navigate a new piece of software.

After getting through the presentation part of training — showing employees how the software worked — I often sat next to them. I’d gently guide them: click here, now click here, see how that works?

Throughout my career at the software company, which ended up lasting 15 years, I was the person who pushed for internal change. Much as the company wanted its customers to abandon manual processes, its own internal systems were lacking. I always wanted things to be better: to eliminate anything tedious or manual, so everyone could focus on the more interesting parts of their job.

I don’t get to do much of that now. Hardly any, in fact. Working for myself, I can make any changes I want, any time I want. But it’s not the same as listening to and solving for other people’s problems. Banks would often present me with complex workflows that I’d have to “translate” and reshape into the software I’d shown them. I occasionally consult with other solopreneurs and help them figure out their tools and systems, but those projects are very short-lived.

Nilay Patel, editor-in-chief of The Verge, talks about people who have “software brain.” He wrote an entire essay, The people do not yearn for automation. He writes,

“So what is software brain? The simplest definition I’ve come up with is that it’s when you see the whole world as a series of databases that can be controlled with the structured language of software code.”

It’s true that I spend more time tinkering with tools and automation than I’d care to admit. I have a ring that connects to my to-do list. I’ve vibe coded a menu planning app for my family.

But, as Patel points out, software eventually collides with human reality. In the business world, you can tweak the database or the software code to match the business use case. Human life outside of work is much different.

And in the work I do with fellow solopreneurs, it’s more like a personal life than a business use case, because work and the human are deeply intertwined. It’s not solving for a large team moving a loan file through departments. It’s solving for one person, who has fewer dependencies and limited bandwidth. All the automation capabilities in the world have to be accompanied by a force function for change.

Earlier this week, a repair person came to my house to fix my garage door. At the end, I asked if he’d prefer a check or a credit card. He told me a credit card, because otherwise he’d have to call the main office with my card number to run the transaction.

Of course, there are plenty of apps and tools that would allow him to process the credit card with his cell phone. He was halfway there: I signed for the work on an app and was emailed a receipt, which was more than the dishwasher repair person a few weeks ago who handed me a paper copy. The garage door company is quite large, but must not be feeling enough pain from the current way of doing things. So the technician has to call the main office a few times per day to run a credit card… not a big deal (to them).

Always and forever, I want to make processes and the way things work better. But I recognize that not everyone has the same desires or motivations.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

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Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.

Is burnout an inevitable part of success? A survey found that 40% of workers believe this is the case. That’s far more than a fringe belief: it’s a working assumption that almost half of the workforce ascribes to. We’ve absorbed the idea that achievement requires running ourselves into the ground.

Over the past several years, I’ve watched the anti-hustle culture movement push back hard against the “rise and grind” mentality. Fewer social media posts celebrating 80-hour weeks as proof of dedication and sacrifice. People sharing their experiences of stepping away from work to recharge.

The criticism is warranted (and overdue). Chronic overwork does lead to burnout. The culture of pushing through when our bodies and minds are telling us to stop has long been a structural problem, even though the hustle bros would have you believe it’s a personal failing.

But somewhere in the backlash, the conversation fell into two camps. Either grinding is the path to success, or intensity itself is the enemy. You can’t have both. Both sides treat work intensity as a permanent setting — you’re either “on” or “off.”

That framing misses how we move through different seasons of life. Including dialing up and dialing back as needed.

In my career, I worked intensely at a tech job for 15 years. In many ways that I won’t enumerate here, that was bad. The pandemic hit, and I was tired of it all. But I had to keep hustling and pushing myself in order to find a new landing place in my second career.

That season of intensity was necessary. Not because the hustle-culture crowd was right, but because building toward something new or different requires it.

The question should be: Is this hustle temporary? Or a permanent fixture in your work life?

Hustle has its place when it’s temporary

Hustle mentality is usually seen as a character trait. And, of course, some people will still pursue relentless hustle in pursuit of their goals.

But for many people, hustle might be tied to circumstances. Two situations come up again and again that look nothing like “hustle culture as a way of life.”

Trying to leave a job

When I knew that I wanted to leave my tech job, I put in long hours. I had my regular 9-5 job, and then was freelancing in the evening, often for several additional hours per day. This was necessary to build the writing portfolio I needed to change careers. Then I added applying for new jobs into the mix.

It was utterly exhausting. But I knew it wouldn’t last forever, and I was right. Three months after I started freelancing, I landed a full-time job at a content marketing agency and a retainer agreement at a magazine.

That kind of intensity has a clear purpose (build the skills necessary to get out) and a clear end point (the new job). If I’d only said, “I’m working 60-hour weeks,” it would have looked like hustle from the outside. But it didn’t feel like hustle because it was temporary, and saying otherwise would have been performative. I wasn’t trying to prove anything to an employer. I was doing it because the alternative was staying “stuck.”

Unfortunately, the current job market demands even more of this kind of effort. Job searches may stretch into months of interviews and take-home assignments. Or a job-seeker may spend a ton of time networking. Anyone in the middle of a career transition knows this. The work of finding a job is a much longer season of intensity and can be hard to sustain.

Trying to build something of your own

The same principle applies when someone is building a solo business or pivoting to self-employment. The early days are intense by nature. You’re taking on the work of finding clients and building systems, often without support. There are months when the hours are long, and the to-do list feels absolutely endless.

This was my second season of hustle in recent years. I lost my job and decided the next day that I was going to freelance full-time. Even though I had some pieces in place from freelancing alongside my 9-5, it was a mad scramble to build up a full roster of clients and pull in the income to support my family.

But the early hustle of building a business on your own terms is completely different than corporate overwork. Every client relationship and everything you create is an asset that belongs to you. Corporate hustle often comes without a reward proportional to the effort an employee puts in. Employees trade their nights and weekends for what? A modest raise or a new title? In far too many cases, they get nothing at all.

When the intensity is in service of your own thing, there’s a direct relationship between what goes in and what you get in return. I’m not a fan of never-ending hustle, but the connection between effort and outcome makes a temporary hustle season tolerable… maybe even energizing. And unlike a corporate environment where the expectation of intensity never slows down, the self-employed person’s hustle phase can dial back when they reach the point of a sustainable business.

Building so you don’t have to hustle (as much)

The anti-hustle crowd gets one thing right: permanent intensity is destructive. Without an end date or a target in mind, it becomes a state of being that leads to burnout. We’re simply not designed to operate that way.

Ask yourself: Am I choosing this intensity, or is it choosing me?

Corporate hustle is often unchosen or a baseline expectation. Seasonal hustle is deliberate and has a particular outcome.

Jay Clouse, founder of Creator Science, put it this way on his podcast:

“I want to be world-class at something, but I want to be world-class on my terms. I don’t want to be world-class in a way that requires me to build a business that I don’t want to build in a way I don’t want to build it. … And in this season, I just don’t want to [do more].”

My days now look so different than the way they did in 2020 (at a corporate job) and in 2022 (when I first started my freelance business).

That’s the whole point. Hustle seasons should have boundaries. You push hard and work toward what you need, and then your hustle season ends. It’s not because your ambition disappears, but because the season did its job. Your goal is to create a season that means the next phase of your career can look different than the last.

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The word “freedom” shows up constantly in conversations about work — everything from debates about return-to-office mandates to freelancer lifestyle content.

A 2025 Randstad report found that more than half of workers would give up higher pay for more control over their working hours. But what most people describe when they say they want “freedom” what they actually mean is flexibility. They want the ability to take an afternoon off for their kid’s soccer game or maybe skip the daily commute when the weather is bad.

Flexibility is what an employer offers you, most often with constraints. You might have a hybrid schedule that requires an in-office presence three days per week or working core hours. Workers have to operate within those constraints.

Freedom is something else. Freedom is the ability to make the choice yourself — not just when and where the work happens, but what the work is and who it’s for.

Most conversations about work don’t make that distinction. Flexibility is certainly one component of freedom, but freedom goes further. And once you start thinking about what you’re choosing between, you realize that every work arrangement trades one kind of freedom for another.

Every work arrangement is a trade

For more than a decade, I worked in a very unique setup, called a Results-Only Work Environment (ROWE). Even though I had an employer, I had complete autonomy over when and how work got done. Only the results — a designated end point — mattered. If I wasn’t feeling well, I could simply take the day off and wouldn’t need to ask for permission. Working around my kids’ school calendar was easy.

I had the ultimate flexibility, and for a long time I mistook that for freedom. It was hard to imagine working for another employer where my working hours might be constrained in some way. But the tradeoff was working toward an employer’s goals, which eventually became misaligned with my own.

Subsequent employers (two of them) imposed the exact constraints I feared. My last employer before going solo had a four-day workweek. At first, that seemed amazing, but eventually I realized that the other four days were a grind. Butts in chairs at 8:00 am, working nonstop until the end of the day, to cram five days’ worth of effort into four days. The tradeoff was less schedule control for other things I valued. Eventually, that was no longer enough, and the best option, for me, was to work for myself.

But no work arrangement gives you everything. An employee trades full autonomy for stability: someone else sets the direction, but the paycheck is predictable. A self-employed person trades stability for control: the income fluctuates, but the work is self-directed. There’s no safety net, but also no ceiling.

We talk about these arrangements as if they exist on a spectrum from “less free” to “more free,” with self-employment sitting at the top for people who want to maximize their freedom. But that framing is wrong, because there are still trade-offs. The question is which trade-offs you’re willing to make.

I have to look at money differently than someone who has an employer. For some people, that’s unfathomable because they like the “freedom” that a reliable income brings.

Instead, I think it’s wrong to pit self-employment and working for an employer as more or less freedom. Instead, the actual freedom comes from the ability to choose.

The difference between choosing and settling

The real dividing line in all of this is whether you chose your trade-offs from a position of genuine options… or if you’ve accepted your current work situation because you felt like you had no good options.

There are two versions of being trapped. The first is staying at a job you’d leave in a heartbeat if you could, because you rely on an employer’s health insurance (a structural constraint). The other is being self-employed, not because you chose it, but because the labor market sucks and you weren’t able to find a full-time job. In both cases, the arrangement chose you.

The freedom conversation often assumes that self-employment is the destination. That if you just had enough savings or enough clients or enough grit, you’d obviously prefer to work for yourself. But that’s not true for everyone. The trade-off of instability — unpredictable income and no employer-sponsored benefits — may not be worth it. The constant mental weight of running everything yourself is its own kind of cost.

On the podcast The Vergecast, senior reporter Elizabeth Lopato said:

“I don’t want to make a business. I have a job because I don’t want to think about accounting, and I don’t want to hire my own libel lawyer. I want to write things that are meaningful, and the more time I can spend doing that, the better. And one easy way for me to do that is to have a job where all I do is write. And somebody else takes care of the business stuff.”

Choosing to stay with an employer because you want stability is a valid choice. Freedom at work is what you choose to build your career around. The trade-offs don’t disappear — whether you’re employed or working for yourself, something is always being exchanged for something else. But when you’re making decisions about trade-offs, when you pick them from real options and decide you can live with whatever you’re giving up, that’s real freedom.

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I’ve written many times about how I started my own business in 2022 after I was laid off from my marketing job. But in reality, that’s not struck out on my own. The first time was when I was 23 years old.

I was working for a financial technology company. I liked the company and the product, but I got a new boss, and she was awful. I was so stressed all the time. As much as I liked the job, I didn’t think I could keep working there.

The company was located in Kansas, but let me work remotely from Wisconsin. I loved the arrangement. Remote work was uncommon at the time. I knew that if I left, finding a similar job might be tricky. There were no tech companies in my small hometown in Wisconsin, and my husband was still finishing college. I felt like I was stuck, at least until my husband was done with school and we could move elsewhere.

At the time, I was leading software implementation for community banks. Projects were often up to 6 months long, complex, and involved many people. The culmination of the project was traveling to a bank location and spending 3 days on-site, training employees.

One bank mentioned in passing that they would love to hire me as a consultant to get more dedicated help. It seemed like a way out of my current job situation. I spoke to the bank’s vice president and said, “Were you serious about that offer?” and he told me, “Yes.”

I decided to quit my job to work as a consultant. Once I was done with that project, I would move on to the next one.

When I told my boss that I was quitting, the company’s COO reached out to me. She told me that she thought we could work together. I could stay on payroll and keep my health insurance. The company would process the payments from my consulting contracts, take a cut, and pay me the difference as a bonus. There was a benefit to the company also: they could offer their clients my services as a consultant. I agreed.

I spent six weeks at the first bank location. Another bank ended up hiring me for almost three months. They put me up at a corporate apartment near their headquarters in Jefferson City, Missouri.

It always worked out, and I was able to get the “next project.” I did everything myself, from scoping the agreement to negotiating with the bank. I rarely interacted with my employer-on-paper. I even read a book about consulting. When one bank wanted to extend my contract, but for less money, I replied, “Sure, that’s fine. Then let’s figure out how to reduce the scope.” They re-signed at the original amount proposed.

But being on the road 100% of the time was really hard. Corporate apartments were boring. Since each stint was temporary, I never got to know the town or found anything interesting to do. And I frequently went back to Wisconsin on the weekends.

Then my direct boss quit. The COO reached out and asked if I’d like to return to my prior role. I negotiated a salary that was equivalent to what I was earning as a consultant and agreed.

Once I became a regular employee again, I stepped into more contract negotiations and defined the scope for custom projects. That work excited me because I was good at it. I stayed at that company for 15 years in part because they gave me opportunities over and over to define my own path. I became the company’s first product manager. Later, I managed the entire customer service department and carved out what that role would look like for me. I left, in part, because I ran out of ways to grow.

So while I wasn’t technically self-employed as a consultant, I was functionally on my own. I had mentally prepared for self-employment at the time I quit. Even though it ended up being a brief stint, it was an indication early in my career that I wanted to chart my own path.

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Ask executives how much interest their CEO takes in improving the work environment, and 69% say it’s high or very high.

Executives think they’re building workplace culture, but “wanting to develop culture” and developing and sustaining a particular environment is more than simply a mandate from the top.

When companies notice a workplace culture problem, the response is usually a project. New values get announced, or an executive committee is formed to brainstorm ways to improve company culture. Sometimes there’s an all-hands meeting about who we are and what we stand for (with slides!)

One review of workplace culture found that executives who rolled out new values reverted to old habits and a focus on tasks the moment they were under pressure. The supposed values or emphasis on company culture were nothing more than a communication exercise.

I’ve experienced this disconnect many times in my career: the company that proclaims to be people-first, and then lays off employees with no notice and no severance. It’s left me feeling like company culture is a farce, because when push comes to shove, the company will always put itself first.

Yet, I’ve seen companies that — at least from the outside — have amazing company culture. Employees seem to love working there, as evidenced by how much they talk about their employer online and the average employee tenure.

We assume that company culture flows downward from the top. And true, leadership sets the tone. But does everyone else simply absorb it? Or is workplace culture created by everyone?

How organizational culture is created

Sociologists settled on what culture means a long time ago: the shared values, beliefs, behavioral expectations, symbols, and artifacts that make up a group’s way of life. Organizational culture — aka workplace culture — is a bit different. It can run independently of the wider societal culture or alongside it. A company doesn’t invent a culture from nothing. It develops one through the way it interacts with the people who work there.

Company culture lives in the ordinary stuff. Hallway conversations and Slack channels. Emphasis on quality versus taking shortcuts. Whether people collaborate or throw each other under the bus.

Dr. Marcus Collins, a clinical associate professor who studies the influence and impact of culture on human behavior, told me:

Most organizations describe their culture by way of celebratory rituals (happy hours), objects (foosball tables), or perks (summer Fridays). Their articulation hardly ever constitutes the underlying cognitions that inform these kinetics, the shared thinking that drives our shared doing.

This omission, unfortunately, often prevents corporate leaders from rolling out a desired cultural state for the organization.

A company’s leadership sets the conditions, without question. There are absolutely situations where the problem starts at the top — operating in a culture of fear is a real thing, and one executive’s behavior can set the tone for everyone reporting to them.

But setting the conditions isn’t getting at the root of what leads to a positive workplace culture, as Dr. Collins notes. It’s missing the “shared thinking” and “shared doing.”

Starbucks has long set the narrative that it’s a great place to work. Once upon a time, that may have been true. But more recently, one journalist argued that “many employees went from feeling like they had ‘the coolest job on the planet’ to something closer to a third-shift factory worker.” The company shifted drastically over time — whether intentionally or not.

Culture sometimes shifts because of external forces. Technology changes. So do regulations, or the market. Any of those can reshape what the work feels like day to day. Explosive growth can also impact culture, if you look at companies like Meta or Google, once heralded as great places to work. Few would say that now.

What this means for employees

Most workplace commentary, including a good deal of mine, focuses on what companies and leadership get wrong. That criticism is warranted: leadership failures are real and expensive, and the people most impacted are those with the least power.

But even if leadership determines a company’s direction, that doesn’t mean change will actually happen. Dr. Collins points out:

When a company says it’s “changing its culture,” the change is predicated on how the organization ultimately responds to said forces. This response is not determined by leadership mandates pushed from the top down but by a collective negotiation that happens from both ends. Just like the marketplace when new ideas are introduced through media or industry, the population decides if the idea sticks.

That negotiation plays out all the time. A company’s “About Us” page may describe the company culture and values one way, and the employees describe something completely different. That disconnect is what people are pointing out when they say a company “lost” its culture. The company keeps broadcasting one version of itself, but that ideal did not permeate through the ranks through collective negotiation. The employees either rejected it or recognized that it was nothing more than lip service.

I’ve written about what happens when employees stop caring and about how management needs to stay connected to the team. Both are relevant to workplace culture: it gets made at the level where the work happens.

None of this means employees should be handed the job of fixing a broken workplace. Some companies like to say that “culture is everyone’s responsibility.” Employees may have some agency, but ultimately, the people responsible are those whose paychecks support that level of responsibility.

I asked Dr. Collins what happens when people feel like a company’s culture and values are no longer aligned with their own. He replied,

When people feel like their values no longer line up with their place of work, what they really need to evaluate is (1) whether they believe what the organization believes and (2) if the organization is living up to it.

If the answer to the first prompt is “no,” then it’s definitely a mismatch, and that person should go find a better fit. If the answer to the second prompt is “no” but the person aligns with the organization’s beliefs, then it’s worth trying to make a change. In fact, this is a potential opportunity to lead.

One of the interesting things about leaving a job — for another job, or to work for yourself — is finding out how much of the culture came with you. You have assumptions about how work is supposed to feel. I remember leaving a toxic job, and when I went to my next employer, I said, “Wait… people are actually nice to each other? On purpose?”

You can walk out of the building and still be running the “how to survive” playbook you learned while there. Which is worth knowing, because that’s the part of the culture that will change, no matter where you land.

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From 1870 to 1930, the U.S. census counted “gainful workers.” The definition was purely a data point: a gainful worker was anyone who reported an occupation in which they earned money or a money equivalent, or in which they assisted in the production of marketable goods.

The government wanted a number for how many people were attached to paid work, and “gainful” was the word that separated earners from non-earners. (I’m not a census historian by any means. But the language we inherit comes from somewhere, and this one came from a form.) In the 1940 census, the Bureau replaced the whole approach with the “labor force” concept, which asked about employment status instead of occupation.

But yet the words “gainful employment” never dropped out of our vocabulary. In fact, it’s taken on a different shape. Look up “gainful employment” in Wikipedia today, and the definition goes like this: an employment situation where the employee receives steady work, payment from the employer, and enough income to be self-sufficient.

Look at who is the giver and who is the receiver in that sentence. The census was describing a person who earned money. The current definition describes a person an employer pays.

I ran into the difference in a conversation a few years ago. I was talking about burnout and leaving a job I’d been at for 15 years, and the response was, “Sure, but your prior employer kept you gainfully employed for a long time.” On the spot, I didn’t know how to reply — but knew that the phrase made me feel uncomfortable.

Reflecting on the exchange, the word that’s off-putting in that sentence is kept. Somewhere between the original census and that conversation, “gainfully employed” implies that because the employer provides, the employee should be grateful.

The transition from earnings to a provider

The original census data point looked at the worker’s side of the equation. The gain in “gainful” was money the person earned or goods the person helped produce. The employer doesn’t appear in the definition at all, because the employer wasn’t the thing being counted.

In ordinary use now, the phrase describes what a company did for a person. Companies provide gainful employment. Workers have it — they’re on the receiving end. (And self-employed people are… somewhere else?) It’s not about the worker’s accomplishments at all.

Perhaps I’m reading too deeply into an old phrase. But U.S. employment law supports why the phrase feels icky. At-will employment means an employer can end the arrangement at almost any time for almost any reason. Outside of mass layoffs covered by the WARN Act, there’s no federal requirement to give notice or pay severance. The employer holds all the power to provide employment.

In today’s labor market, workers feel increasingly like they have little control. Whether the job continues really does sit wholly with the employer. Employer mismanages the company? Layoff. Employer wants to hand roles over to a bunch of AI agents? Layoff. The employee is screwed. When one side holds that much power in the arrangement, calling that side the provider is pretty accurate.

In the conversation I had many years ago, I’d been talking about burnout and about watching people get treated badly for years. “Gainfully employed” was the rebuttal. My steady paycheck was supposed to offset the question of whether all those years had been good ones.

A two-way transaction, not a favor

A paycheck is what a company owes you in exchange for your time and expertise. Mine was money I could have gotten somewhere else, and my employer was never the only option. Saying an employer “keeps you gainfully employed” — under today’s definition — erases the worker’s side of the equation, and what the employer gains in return.

There’s plenty to say about what money does to our sense of a job’s worth (I’ve written about that before.) But the transaction itself is simple. I gave 15 years of work and was paid for 15 years of work.

Nobody was doing anyone a favor.

The things I gained from those years don’t appear anywhere in the phrase. I learned what I won’t tolerate in a workplace anymore, which turned into boundaries I still maintain to this day. I can also recognize a good colleague immediately now, because I spent many years around the other kind.

Under the original definition, “gainfully employed” describes the worker’s position in the labor market. You work, you sustain yourself. But today’s framing of the employer at the center of the universe reinforces the structural imbalance. It’s time to retire the phrase.

As a self-employed person, nobody says I’m “gainfully employed.” Since the employer — a company — is now the primary driver in the definition, self-employment falls outside of that (apparently). I talk a lot about how self-employment isn’t as risky as people think, especially when you consider the employer’s power in an employer-employee relationship.

The relationship works when both sides can clearly state what they’re getting out of it (gaining). Trouble starts as soon as one half of it gets called “generous” and the other side is “lucky” to be on the receiving end. So when someone tells you that a company kept you gainfully employed, think only of the math. If you got paid, you came out fine.

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For more than seven years, I was a product manager at a software company. Product managers guide the direction of the product based on feedback from customers, sales, and leadership teams. They keep the company updated on the progress of projects and initiatives. And they constantly juggle tasks and deadlines when projects go off track or something unexpected comes up.

It often felt like herding confused cats out of a building that’s always on fire.

A significant amount of my time was spent buried in documentation. Preparing reports for the leadership team, reviewing spec documents for new features (or writing them myself), and preparing release documentation for customers that explained new features and bug fixes.

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I look back at the amount of time I spent on much of this work and how it limited what I could get done during the day. Today, that role would be incredibly different, thanks to AI.

David Pierce, Editor-at-Large at The Verge, said in an interview:

The thing that I am hopeful for, and frankly already grateful for in the technology, is that it can do a lot of the busywork I don’t want to do. It’s not creative. It’s not even thoughtful. It’s just administrative.

We can all find better things to do than turning an Excel file into bar graphs in a PowerPoint. So if we can automate that out of existence, I’m actually extremely hopeful for what we can all go find to do instead.

Product management is a critically important role in many companies, but also one that is drowning in tasks. The sources of data are scattered, like customer data, the upcoming project plans, a calendar of due dates, analytics, and more. It’s a chore to pull everything together.

What I would hand over to AI

The same job, today, would be almost unrecognizable. I’d have more time for the things that make a product manager role interesting (thinking about the direction of the product) and spend less time on “paperwork.”

For example:

• AI could spot patterns. I used to pore through hundreds of customer support tickets, looking for things that customers were complaining about or asking for. Those with the most requests often received higher priority, but identifying them was an intensely manual process.

• AI could create a design prototype. For new product features, developers would work from a mock-up that was painful to create. AI could create this in seconds.

• AI could write reports. I produced a monthly report on each project’s status for the leadership team, but the data lived in multiple systems. On top of that, the CEO liked to see the report in a very specific format. All of that could be handed over to AI. I could have even produced more frequent reports with the time saved.

• AI could write release notes. AI could determine from the project management and coding tools which features and bug fixes actually made it into a release and draft the release notes into a format suitable for customers. This process used to take hours (if not days) to compile.

What I could have done with the extra time

At a guess, I think the current version of AI tools could have saved me at least 10 hours per week. Maybe more, during the weeks when I was creating design prototypes or writing release notes.

And none of these required human creativity.

• Spotting patterns is simply compiling data. The judgment for “What should we build?” is still human.

• Design prototypes were based on well-established product specifications, just applied to a new feature (like “This button always goes in the upper-right corner, and when you click it, it does XYZ thing”). Developers simply needed a visual reference so they could code the new feature.

• Reporting was also mainly compiling data, with the addition of formatting. Explaining the project’s progress to the leadership team would still come from a human.

• Release notes were taking a description of a bug fix written in “developer speak” and translating it into something a customer could understand.

Without the hours spent on these tedious (but necessary) tasks, I could have:

• Talked to customers. Product managers at bigger companies with larger teams often talk to customers to understand their pain points. As the sole product manager, I rarely had time for this and had to rely on support tickets written by the customer service team.

• Made better product decisions. Since my process of looking through support tickets was so manual, customer needs and pain points were often missed.

• Fixed things myself. The company had hundreds of outstanding bugs to fix at any given time. Some were incredibly minor, so they were never prioritized. But with vibe coding, it’s likely that I could have learned to apply a fix myself and let a developer review it. Fewer outstanding bugs, happier customers.

I’ve always tried to automate repetitive tasks throughout my career. I did as much as I could back then, but there were simply limits to what I could do — especially with some of the most time-consuming tasks. Generative AI has changed that.

Of course, I recognize that this also blurs the lines for different roles. Should a product manager be expected to code bug fixes? Maybe not (though I would have enjoyed just fixing something rather than letting it linger).

My point is that I would have found the job much more fulfilling if I had been able to spend more time on the work that required human judgment. Talking to customers would have been incredibly valuable, but it wasn’t a requirement to move forward. So it got pushed to the bottom of the list. Creating a report for the CEO — while tedious — was an expectation of the job.

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In June 2026, two major publications ran stories with a similar message: remote work might be hurting you. NPR published “People Love Working From Home. But Does It Love Them Back?“ The New York Times followed with “We Liked Remote Work. Then We Looked at the Data.“ Both cited the same study — Emanuel, Harrington, and Pallais, published in Science — which surveyed 588,000 Americans and found that workers in remote jobs experienced a 58% rise in hours spent alone and a 72% rise in spending their entire day with no human contact. This led to more anxiety, more depression, and more medication to treat these things.

The data is real. And the findings around isolation absolutely deserve attention.

But these articles treat isolation as though it’s baked into remote work itself, rather than examining what companies and workers can do about it. The headlines imply remote work is the villain — not the way companies have implemented it (or, more accurately, failed to implement it). Nor do they look at the broader question of whether the office was ever providing the social connection it’s now being credited with. And certainly not in the context of the “loneliness epidemic” that many experts agree is prevalent in American society as a whole.

The arguments against remote work are so predictable at this point: find a downside and frame it as “proof” that the whole model is broken. Meanwhile, there’s no discussion around whether the tradeoffs are worth any downsides. And all of these arguments pretend to put the employees’ interests first in RTO mandates, rather than looking at the company’s motives. (Spoiler: they’re not thinking about employee well-being at all.)

It was never about your loneliness

Every argument about remote work isolation rests on the assumption that in-person work provides positive social connection. The office is where meaningful human interaction happens!

But what about the interactions people are relieved to avoid? Microaggressions. Hostile managers. Office politics. The energy required to context-switch all day. The NPR piece quotes a researcher lamenting that remote workers miss out on casual interactions: “not even a wave to a barista.”

That’s the bar we’re supposed to use to measure wellbeing?

These articles pretend to care about people. We’re looking out for your loneliness. Or perhaps the reporters and researchers truly care about people and the impact of loneliness. But that’s not at all aligned with what CEOs have in mind when they order people back to the office.

The business case for bringing everyone back also doesn’t hold up. Studies consistently show that return-to-office mandates don’t have any impact on productivity or financial returns.

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Maybe these companies believe that they will benefit. Maybe they’re truly concerned about employee isolation (though doubtful). But research published in 2026 found that the only personality trait that consistently predicted objections to remote work was narcissism. The more self-important and entitled the company leaders, and the more they coveted power and status, and the more they favored return-to-office mandates.

Psychologists have long suggested that narcissism operates like a drug. Narcissists crave a regular supply of attention and validation. Remote work deprives leaders of that supply. These leaders see any kind of remote work as a threat to their authority and attention, and ordering people back to the office full time is a power and status move.

Loneliness is a convenient argument for something much simpler: leaders perceive remote work as a loss of control.

What remote work actually supports

“But people need human connection — the data is clear!” Yes. But conflating “human connection” with “office presence” is a faulty argument. People who study the loneliness epidemic in the United States find that the leading causes are technology, insufficient time with family, people being overworked, and living in a society that’s too individualistic. Remote work is not one of them.

In fact, if “being overworked” is a cause of isolation, that’s an argument in favor of remote work. Removing a lengthy commute from the day leaves more time to interact with other people. People can also get more rest if they’re working from home.

The loneliness framing fails to ask a basic question: what is gained? Remote work provides structural support for the people who need it most. Women choose remote work because remote work makes it possible to manage caregiving responsibilities (that still disproportionately fall on women). People with disabilities may find commuting draining or offices inaccessible. People face discrimination at the office (racism, misogyny, microaggressions) that drains energy and erodes mental health over time. The disparate impact of return-to-office mandates falls hardest on these groups.

Even if companies are well-meaning (and the narcissism research suggests many are not), the argument assumes that “loneliness” outweighs accessibility, safety, caregiving, and basic equity. When my kids were little, I had to drop them off and pick them up at day care. I had to take them to doctors’ appointments during the day. Even if I’d felt lonely, I wouldn’t have traded the flexibility that remote work gave me. The logistics of my life would have been exponentially harder if I were working in an office.

Some in-person connection with coworkers is valuable. But full-time office attendance is unnecessary. Atlassian found that a quarterly gathering does more for connection and belonging than daily commutes to the office.

So instead of asking “Is remote work bad for workers?” companies should be asking what they’re doing to support remote workers. The answer, for most, is: very little. Culture requires intentionality from leadership — whether the team is in one office or spread across ten cities.

If remote work is what allows you to be present for your family, manage your health, or do your best work without the overstimulation of an office — that’s reason enough. It’s worth being aware of the risks of isolation (as a whole, not just tied to remote work). But no one should pretend that isolation is the only — or most important — factor in someone’s work life.

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Early in my career, I had to travel a lot. I was working for a financial technology company. A bank or credit union would buy the software, and I would travel to the customer’s location. These were mostly really small banks, with maybe only a few branches, in small towns.

Getting to them was an entire production, often involving a flight to a major airport, then renting a car and driving for a few hours. I started working for the company in 2006, before the iPhone. Heck, I wouldn’t even own a smartphone for another four years.

As such, I had to carefully prepare how to get around. I’d print stacks of Mapquest directions. Airport to hotel. Hotel to bank. Exploring the city was too risky (what if I got lost)? But there usually wasn’t much to see anyway. Food was limited to whatever was in my line of sight between the hotel and the bank.

I traveled heavily for about three years. Once I had my first baby in 2009, the company changed its overall method of delivering training to a web-based approach. My boss realized that she wouldn’t be able to retain a lot of the company’s talent with roles that required 50% travel. After the change, I only traveled a few times per year.

The towns I visited were sometimes so small that there were only a few main roads. Even so, I simply wasn’t brave enough to explore. I’d get done working for the day, grab a sandwich from Subway, and collapse in my hotel room with CNN and my laptop.

I thought about this while I was in San Francisco this past week. I bounced all over the city, relying on a combination of Google Maps, Waymo, and public transit. I looked at Yelp reviews of local restaurants, eager to try a little dive dinner in Haight-Ashbury or a walk-up dim sum place in Chinatown.

I wonder about everything interesting I probably missed in these small towns. Navigating the roads, restaurants, and landmarks was just so different back then.

On one of my first trips, as a new employee, I was headed to western Kansas from the company’s headquarters in Topeka. Another employee was with me to show me the ropes of working on-site at a customer’s location. He drove, and we sat in silence for most of the trip. We barely knew each other and had little to talk about (though we later became friends). He would often call his girlfriend on his cell phone and talk to her for hours at a time while I sat, listening to his half of the conversation.

We were driving along the roads of Nowhere, Kansas, when he announced that we were taking a detour to visit the world’s largest ball of twine. There was nothing I could do but agree. We got out of the car and walked around the “landmark.” In today’s world, I would have been snapping photos. But back then, I didn’t have a smartphone, and it never occurred to me to bring a digital camera on my trips.

Part of me is sad that I have no documentation of my travel. I never wrote anything down, even though I experienced a lot. The only time I took photos was when I was sent to Kalispell, Montana, and planned ahead to visit Glacier National Park.

I don’t even remember what the world’s largest ball of twine looks like... only that we made the stop.

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In February 2013, Yahoo CEO Marissa Mayer banned all remote work. The move surprised everyone: Mayer was a new, young CEO, and Yahoo had a well-established remote work policy. The stated reason was collaboration and innovation, which Mayer thought was lacking.

The real context was much simpler: Yahoo was losing the competition with Google and Facebook, and Mayer needed to look like she was doing something. The RTO mandate was the “something.”

Fast-forward thirteen years. The mandate didn’t save Yahoo. Verizon acquired it for $4.5 billion in 2017, merged it with AOL, then wrote down the value by more than it paid. At the time of acquisition, Forbes reported, “The biggest story is how Yahoo squandered its massive head start and let each wave of new technology in search, social, and mobile pass it by. Yahoo remains largely the same company it was a decade ago.” Yahoo was sold again in 2021, and the Forbes sentiment remains true.

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When companies are struggling, they change the rules workers operate under and call it “strategy.” But these moves are almost always a cover for a business problem leadership can’t figure out or won’t name. And, over and over, we’ve seen that the companies that abandon their core principles under pressure don’t save themselves. They just lose what made people want to work there in the first place.

When the company you joined stops existing

The company formerly known as Facebook (now Meta) debuted at number one on Glassdoor’s Best Places to Work in 2011 and held the top spot three times. By 2023, it had fallen off the top 100 list entirely.

In April 2026, Meta deployed what it calls the “Model Capability Initiative”: software that captures employee keystrokes, mouse movements, clicks, and periodic screenshots. CTO Andrew Bosworth confirmed there is no opt-out. (European employees are exempt, because GDPR won’t allow it.) Employees have said that the initiative makes them really uncomfortable.

In June 2026, Meta laid off 8,000 employees, and several thousand more were reassigned to the Applied AI Engineering unit — and had no option to transfer elsewhere. Some have reportedly taken to calling themselves “draftees.”

The company that once topped every “best workplace” list is now tracking every keystroke in some type of nightmare dystopian workplace and telling thousands of employees they can either accept a role they didn’t sign up for or leave. The company still exists. But the company people joined? That’s long gone.

Starbucks has drifted from its own identity, too. For years, Starbucks built its brand on being the “third place” — a community space between home and work. But Starbucks has had an identity crisis over the years, amidst sagging performance. Should it optimize for mobile orders? But then that detracted from the “third place” vibe. Should it add more seating inside the stores? But then that made the stores more crowded. Employees have been dragged along for every iteration, and meanwhile, the company has taken a strong anti-union stance, trying to prevent workers from organizing to protect themselves.

The Starbucks experience changed, and so did the working conditions. What was once a company built around the idea of community became, for many of its workers, a volume operation that happened to sell coffee.

Nothing tells you more about how a company’s values than how it treats its employees when it is struggling. Webflow, once a company known as a great place to work, laid off employees in May 2026 by locking them out of their laptops at 7 am with no advance notice. Employees discovered they’d been impacted when their Slack and email access vanished — before any email from HR arrived.

And I’ve personally experienced this. I worked for a company that proclaimed to be “people-first.” The company began to struggle during my year there, leading to me losing my job unceremoniously. I was shocked by how it unfolded, since I had believed that this company cared about its employees — that’s what it had proclaimed, every step of the way.

Your values are the only constant in your career

Roger Lynch, CEO of Condé Nast, was recently on the podcast “Channels” with Peter Kafka. In 2020, the employees indicated that they wanted the company to focus more on diversity initiatives and sustainability. The global media conglomerate put together internal teams to address both. In the interview, Lynch said:

“It’s discouraging to see all these other companies dropping these initiatives, but it only says one thing: that it never was a core value, it was a convenience.”

“Companies have to adapt to survive — you can’t expect them to stay the same forever.” That might be the claim of Meta, Starbucks, or even my former employer. True. But there’s a difference between adapting your strategy and abandoning the principles that attracted your workforce. Yahoo opted for command and control of the office. Meta turned to surveillance.

You can’t get attached to a company’s stated principles. Unfortunately, there’s no way to predict which companies will abandon everything when the market gets rough or the industry changes. Companies may last decades and go through several iterations, and new leadership may usher in entirely new values (just look at Twitter, now X).

Every company will put itself first. The question is whether you’re building a career that depends on a company continuing to be the company you joined. Because if there’s one pattern that holds, it’s this: you can’t trust the company not to change in ways that you fundamentally disagree with.

The only thing you can truly depend on is what you build for yourself. That’s not saying you should quit when there’s company upheaval (that’s not realistic in the current job market). But it’s worth asking whether the stability you think you have is real, or whether it’s contingent on a company continuing to honor the values it used to recruit you. And it’s worth thinking about what you’re willing to tolerate to stay, even if the company has changed.

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Every promotion moves you one step further from the work itself. First, you’re doing the work. Then you manage the people who do the work. Then you manage the people who manage the people who do the work.

At each step, the daily reality of the job gets a little further from your line of sight. You may no longer be aware of the tool that no longer meets the team’s needs, or the client requests that have started absorbing entire afternoons.

I went through a few iterations of this throughout my career. I moved from a role in enterprise software implementation to the company’s product manager. Though I was no longer talking directly to customers, I was still “touching” the product constantly as I tried to figure out how to make it better.

Then I moved to an executive role. Though I was still the product manager (dual role), I no longer had time to tinker with the product. I was meeting with my team of seven people, preparing reports, and organizing vast swaths of data for the development team. The longer I was in the role, the more I realized that I no longer understood what the new features of the product did. I was also removed from the pain points that customers were experiencing — the kind that the customer service team had to deal with every day (and made their work harder).

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The further you move up in an organization, the easier it is to lose sight of what the people below you do all day. It’s even true of self-employed people who may start to outsource some work. It’s imperative to stay in touch with the work in some shape or form. Being too removed from the work is what causes bad decision-making.

The disconnect happens because of distance

Each rung up the ladder adds a layer of abstraction between you and the work.

When I was an individual contributor, I lived inside the daily friction of customers. As a manager, I was only hearing about it. My boss (COO) and the CEO only heard the summaries I provided. At larger companies, these are reduced to quarterly metrics.

By the time the information reaches the top, it’s been compressed so many times. The context is gone, and the context is how people actually understand the problems. (This is part of why so many people feel trapped in the middle as a middle manager.)

When I moved into a product manager role, I was responsible for reviewing issues reported by customers. I wasn’t receiving them directly, but I looked at the tickets. The tickets would contain notes from the customer support rep (if a phone call) or the direct emails from the customers. I could get a sense of the urgency or level of pain that the issue was causing. But the other members of the executive team (the COO and CEO) only saw numbers: how many customers reported the issue? It was my job to convey urgency, but this was often stacked against other priorities.

In Glassdoor’s Worklife Trends 2026 report, mentions of “disconnect” in reviews that reference leadership rose 24% year over year. “Miscommunication” rose 25%, and “misaligned” jumped a whopping 149%. Employees are well-aware of the structural distance — and when they feel like they’re not heard, they may check out entirely.

Part of the problem for managers is the endless barrage of meetings and reports. Your calendar is filled with strategy reviews, daily standups, and quarterly planning, and you stop having time to understand the work itself. You spend your days staring at dashboards and tracking outputs instead of staying tuned in to how work actually gets done.

A manager who only sees the metric can’t tell the difference between “the team is behind schedule” and “the team is behind schedule because something in the process is completely broken and the workaround takes three times as long.”

Freeing up time to stay involved in the work

I remember the intensely uncomfortable feeling that I no longer understood the product that I was supposed to manage. My days no longer had any time built in to get my hands on the product and play around.

But the fix isn’t to swing to the other extreme and do everyone’s job for them, which is what some managers do. That’s a failure mode all on its own: the leader who refuses to let go and hovers over every decision. (And founder mode is the worst version of this.)

Stepping back so people can do the work they’re good at is the entire point of building a team — you hire smart people precisely so you can let go.

The ideal is informed distance: close enough to understand how the work actually gets done, far enough to let people do it without you breathing down their necks. You step aside on every single detail, but stay connected to the how.

I’m an advocate for AI when it’s actually useful (i.e., not slop), and it has a place here: buying back in a manager’s day. I think back to the hours spent prepping for meetings, compiling information scattered across five different systems, and turning raw numbers into a summary for the CEO — a lot of that is now work that can be done with AI.

And the point isn’t more output. If done correctly, that reclaimed time flows back into understanding the work itself. In an episode of the podcast How I AI, host Clare Vo says:

I know so many people who feel like they’re in meeting after meeting after meeting. And when they’re not in meetings, they’re preparing for meetings… You would much rather your managers be hands-on doing the work, filling a creative impulse, than prepping for meetings.

Management roles can often suck the fun out of work. There’s creativity in being an individual contributor that disappears with a promotion to a manager role. Imagine if managers actually had the time for creativity. They’re more connected to the team and get to keep work interesting.

Most of the conversation about AI at work is about cutting headcount or increasing output. But for managers specifically, the most valuable thing added is giving them more time for attention — the time to actually watch (or put their hands on) the work again.

For managers

The structure of most managerial roles causes a disconnection that most managers feel. The system moved you away, then handed you responsibilities that make it impossible to stay connected.

The best leaders stay curious about what the work feels like, not just what it produces. They know the difference between a number on a report and the context behind it. They get that story by talking to the people living it. That only happens when you have time in your day for curiosity. The management team above you won’t give you that time, so you’ve got to find ways to claim it for yourself.

For self-employed people

The same management scenario applies the moment you stop being a team of one. When you hand off work — to a contractor, a VA, or a subcontractor — you need to understand more than just the end result.

You should absolutely hire people more capable or more specialized than you, but it’s too easy to forget about the work altogether. Distance creates the same blind spot for a solopreneur, the same way it does for a VP. You stop thinking about the “why” or “how,” and the work loses meaning.

So as you hire help, resist two urges: the pull to micromanage (let the person do their thing!) and stepping so far back that you lose sight of the work. Stay close to the process even when you’re no longer the one doing it.

The goal is always to keep your eyes on the work without constantly putting your hands all over it. And to build time into your day that lets you do just that.

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A few days ago, Webflow laid off a significant portion of its workforce with no warning. Employees found out when they couldn’t log in to their work laptops or Slack for the day.

It was so bad that one employee posted this on LinkedIn, tagging the company CEO Linda Tong:

Webflow, a tool for designing websites, was once considered a great place to work. Now, it finds itself in the spewing the same BS that we hear from startups every few days: “Today, we’ve made the difficult decision to reduce the size of our workforce.”

It happens over and over. Abrupt layoffs repackaged as “restructuring” or “adapting to the world of AI.” Every time, the response follows the same script. We share the LinkedIn posts, we express outrage, we say, “This is horrifying.” Then we move on until the next company finds itself in the temporary spotlight when it makes a similar announcement.

And yet we keep not asking the obvious question: why does this keep happening?

The answer is brutally simple. The only reason this keeps happening in the U.S. is because nothing prevents it. Outside of unionized workers — which account for just 10% of the U.S. workforce — American employees are largely at-will. They can be fired at any time, for any non-discriminatory reason, with no notice and no severance required. We’ve built an entire employment system around the assumption that workers are disposable. All the power is held by the employer.

I’ve written before about how we underestimate the risks of traditional employment. The never-ending barrage of tech layoffs has proven to be one of the starkest examples of how this can play out.

What worker protections actually look like

I’ll frequently share screenshots like the LinkedIn post above. Without fail, someone will comment, “If you don’t like the way these companies function, start your own business.” (I did, as a matter of fact, but that’s not the point here.)

The power employers hold is a uniquely American experience, as is the idea that employees are entitled to nothing when their employer decides to cast them aside.

As part of my client work, I’ve spent a lot of time researching employment laws in other countries — particularly around how termination works. The contrast with the U.S. is striking.

Here are a few examples from my research.

Japan

Japan takes worker protections very seriously. Employees can only be dismissed for “objectively reasonable grounds.” Employers have to demonstrate they’ve done everything possible to avoid termination — document issues, offer performance improvement opportunities, consult with labor unions, consider reassignment — before resorting to it.

The standard notice period is 30 days (or 30 days’ pay in lieu). Japan even offers Employment Adjustment Subsidies to help companies retain workers rather than lay them off. (Imagine if that existed here.)

Netherlands

The Netherlands doesn’t allow at-will employment. Employers typically need permission from a government agency or a court to dismiss someone, and they need a valid reason. Notice periods range from one to four months depending on tenure, and employers are required to pay mandatory “transition compensation.”

Philippines

The Philippines has enshrined “security of tenure” in its labor laws. Employees can only be dismissed for legally recognized causes. For business-related reasons like redundancy, the employer must give 30 days’ written notice to both the employee and the Department of Labor. The employee is paid severance based on the length of their tenure.

South Africa

South African labor law requires dismissals to be both “substantively fair” (valid reason) and “procedurally fair” (proper process). For redundancy, employers must go through a formal consultation process — notifying affected employees, applying fair selection criteria, and considering alternatives to termination.

Turkey

Turkey requires valid reasons for all terminations, with notice periods ranging from two to eight weeks based on tenure. Employees with at least one year of service receive one month’s gross salary per year of service in severance. Pregnant employees, those on parental leave, and union representatives are protected from dismissal except in cases of gross misconduct or company closure.

This wouldn’t fly anywhere else

Every one of these countries requires a valid reason for termination. Most mandate weeks to months of notice. Most require severance. Several give employees the right to challenge their dismissal and be reinstated with back pay.

This is the polar opposite of U.S. at-will employment, where most workers can be let go at any time with no notice, no reason, and no recourse.

Japan’s framework is particularly striking when held up against what happened at Webflow. Japanese courts allow redundancy as a valid reason for dismissal, but with strict restrictions. Employers have to demonstrate a genuine business necessity. And they have to prove they did everything in their power to avoid a layoff first.

Now think about Webflow. Webflow said it was restructuring “because AI.” This is a company that has raised hundreds of millions of dollars in venture capital funding and had a $4B valuation in 2022. If AI truly was the reason (and that’s a generous reading), they could have chosen to do more with the same people. Instead, they chose to do the same with fewer people.

Under Japan’s labor laws, that argument would fall apart. Under the Netherlands’ system, they’d need government permission first. Under Philippine law, the dismissals could be invalidated for procedural failures alone (no notice period).

But in the U.S.? Nothing. No mandatory notice, no required severance, no mechanism for employees to fight the layoff. Hundreds (if not thousands) of employees have their lives upended. And once the company gets past the bad PR, they get to operate as they were before.

Power is 100% in the hands of the company. And when fear of a layoff becomes the driving force in how people think about their jobs, that’s not an individual problem. It’s a structural one.

These companies deserve to be publicly dragged. Because right now, nothing else is holding them accountable.

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The other day, someone asked me if my clients would start demanding that I lower my prices “because of AI.”

The primary way I earn money is by working as a freelance content marketer for B2B SaaS companies. It’s a question that a lot of people are facing right now — freelancers, employees, anyone whose work has gotten faster or more efficient thanks to AI tools. The assumption baked into that question is that if something can be produced faster, it must be worth less. Or that workers should be producing significantly more of it for the same price.

The pressure to lower prices or produce exponentially more “because AI” rests on a specific assumption: that the value of work is measured by how long it takes to produce it. If something gets done faster, it should “cost” less in some shape or form.

That assumption was always wrong.

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The “do more with less” trap

The demand that AI should make workers cheaper or exponentially more productive is the latest version of a pattern that has been squeezing workers for years. Automation did it before AI. “Lean” management did it before automation. CEOs have long demanded “more with less” — AI is just the latest mechanism.

The basic way economists measure productivity is in output per hour. If you produce more output in the same number of hours, that makes you more productive. No wonder CEOs are salivating.

I had written almost this entire draft and was ready to publish when the CEO of ClickUp (a project management software) decided to further illustrate my point. He wrote on X/Twitter:

Today we reduced headcount by 22%. The business is the strongest it’s ever been. So I think it’s important to be direct about what I’m seeing and why.

This wasn’t about cutting costs. Most savings from this change will flow directly back into the people who stay. We’ll be introducing million-dollar salary bands. If you create outsized impact using AI, you’ll be paid outside of traditional bands.

The primary change is that we’re reconstructing around what I call 100x org. The goal is 100x output. The roles required to build at the highest level are fundamentally different than they were a year ago.

The 100x org is actually heavily dependent on people — infinitely more than today. This is only possible with 10x people that have embraced and adopted new ways of working.

(There was a lot more after this about the 100x org… it was a long post.)

Translation: “This isn’t about cutting costs. I just don’t give AF about the people who work for me.”

He doesn’t care about the former employees and families of nearly 25% of people who are now unemployed at the whim of the CEO.

He doesn’t care about the employees left behind, because 100x output is insanity. And even though he says that they will be increasing the salaries to match the impact… is it 100x? No. The difference between the impact, what flows to the company, and what flows back to the employee is what’s outsized.

He said the quiet part out loud (at least, according to a CEO’s way of thinking): AI isn’t about freeing up anyone’s time, as it promises. It’s about creating and requiring more work.

The infuriating part of his word salad of a statement was saying that the 100x org is “heavily dependent on people.” Just… not the people that the company had already hired, apparently.

How to think about your value at work

100x org aside, productivity gains that flow entirely to the employer or client have absolutely no benefit for the worker. What is the point of a 100x org? It’s a means of extracting more output for the same money (or the same output with fewer people, or for less money).

The conversation about AI and compensation — whether that’s salary negotiations, freelance rates, or even workload expectations — needs reframing now, before this intense and unrealistic focus on increased output becomes the new baseline.

For employees: When a manager suggests that AI should allow the team to take on twice the workload, that’s a change in the requirements of the role — and workers need to treat it as such before it becomes the default expectation. 100x is ridiculous. He’s probably blowing smoke, but it’s smoke he chose to blow in public. I know for many people, quitting is not an option, but I hope the CEO’s post scares away any new talent.

If you take AI out of the picture and were asked to take on more responsibilities, you are being asked to do more for the same pay (which isn’t right). Even ClickUp’s promise of higher salary bands isn’t aligned with the 100x output the CEO is expecting.

I’ve long advocated that people research a company before applying for a job, and public statements like this are self-filtering. Don’t apply unless you plan to create value only for the company, and not for yourself.

For the self-employed: Thinking about client expectations in a world of AI, the frame is simpler (though the stakes may feel high because your livelihood depends on clients). The deliverable is the deliverable. If the quality hasn’t changed, the price hasn’t changed. No “extra output” for the same cost, and certainly not a lower cost. How you produce the work is your business — literally.

I’ve used AI in many parts of my business. I used to have a manual process (copying/pasting) from client briefs to my own project management tool. Automation and AI now do that formatting for me, saving time with every deliverable. I have one client who requires heavily researched articles. Claude now does the bulk of the research, and I check the results to make sure it’s correct and relevant to what I’m writing. These are process improvements, not a devaluation of my work.

If you’re navigating these conversations right now, don’t concede the premise that “faster” means “cheaper.”

This latest wave of “do more with less” doesn’t have to be the one that pushes people over the edge.

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In 1944, the CIA published the Simple Sabotage Field Manual — a guide for ordinary citizens in occupied countries to disrupt their workplaces from within. The tactics are delightfully mundane: refer all decisions to committees, bring up irrelevant issues in every meeting, and haggle over the precise wording of every communication. The genius was that it all looked like normal organizational dysfunction. Sabotage was indistinguishable from business as usual.

Eighty years later, the tactics are different, even if they have the same end result.

In mid-2022, 70% of workers said it was a good time to find a quality job. By 2026, a Gallup survey found that number had flipped: only 28% agree, with 72% saying it’s a bad time. “Don’t quit” has become the default career advice.

Labor economists call this era “The Great Stay.” But that framing makes it sound like a choice, when really, it’s more like being stuck. The next company will be the same or worse. Or the fear is that the job market is so frozen there’s nowhere to go at all. People are living with career discomfort, and wondering if it’s the new baseline, rather than a temporary rough patch.

So what do people do when they can’t leave?

They resist from the inside.

The new performance theater

Think back a few years, and remember quiet quitting? Resistance showed up by doing the job as described, nothing more, and definitely nothing extra. But the resistance has evolved into something more active and more creative. The driving factor is forced AI adoption, and workers are pushing back in ways that would make the CIA’s sabotage manual proud.

Companies are mandating AI use, tying it to performance reviews, and treating skepticism as an undesirable trait in its workers rather than a legitimate response. Meta created internal AI leaderboards, and CNBC reported that almost every Fortune 500 company is now tracking overall AI usage. The message to employees is unequivocal: use the tools, or else.

But token usage is a terrible proxy for productivity — and workers know this. A term has emerged for gaming the system: tokenmaxxing. Running up token spend with bad prompts and producing volume without value. Workers see through the metric and are playing the game while knowing it’s absurd. On top of that, AI usage can cost companies thousands — if not millions — of dollars.

And it goes beyond gaming metrics. A Fortune report from April 2026 found that 29% of workers were intentionally sabotaging their company’s AI rollout — out of genuine fear that their roles will become obsolete. Sabotage ranges from putting a company’s proprietary data into an AI tool to intentionally generating low-quality work to make AI appear less effective.

One of my friends saw a job posting recently for a role to come in and train a company’s AI systems. She said, “So I’m training the thing that will replace me?” She wondered if she should go in and intentionally sabotage it.

The response from leadership is always the same: workers should just adapt. But adaptation requires trust — trust that the tool helps the employees, not just the company. When AI fluency is tied to performance reviews while layoffs are happening simultaneously, workers are interpreting the message in front of them: they’re being asked to build the thing that replaces them.

Nilay Patel put it well on a recent Decoder episode: the lack of worker empowerment is “causing a specific kind of nihilism” — and the people pushing these mandates have “all greatly contributed to” it. It’s a rational response to a culture of fear.

An alternative that used to seem riskier

Some workers reach a different conclusion: if no company will listen, leave the corporate system altogether.

At a minimum, the math has changed. The current job market is terrible for finding another corporate role. But that same instability makes the solopreneur path look less risky by comparison. If both options come with uncertainty, at least one of them comes with some control.

Sabotage and disengagement might provide a temporary outlet, but they’re unfulfilling. Most people want to feel like they’re contributing something that matters — not just running out the clock until the next round of layoffs.

And companies are (inadvertently) making this transition easier. The same organizations cutting full-time roles? They’re increasing contractor budgets. They want flexibility without commitment, a workforce they can scale up and down on a whim. It’s a model that self-employed people can use to their advantage. You want to treat labor as interchangeable? Fine. But the arrangement works both ways. Contractors can bounce from client to client, and losing one contract isn’t the same as losing an entire salary overnight.

As a solopreneur, I purposefully don’t require retainers or minimum commitments from my clients. While logistically a bit trickier to juggle, it makes my work an easy “yes” because clients know they can come to me when they need me.

The labor market is genuinely bad, and most people can’t just walk away. But for workers who’ve already mentally checked out — who’ve already stopped caring — the question becomes: if the anxiety about job security is going to be there either way, would they rather be anxious while building something of their own?

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The general public’s discomfort with AI is well-documented and growing. The tech industry thinks we should all be clamoring for what it’s offering, and most people… aren’t. A Gallup poll found 31% of Gen Z is angry about AI, and 51% are anxious about it.

I use AI every day. It’s found its product-market fit as a business tool. That’s how I interact with it: in a work context. I’m sure it would be the same, even if I were working for a company and not self-employed.

I’m not naive about the risks. The environmental concerns are real. Data centers are wildly unpopular, expensive, and may have unknown health risks. The over-hype is real, and a bubble may still be looming. But the tool itself is useful as a business tool. The genie isn’t going back in the bottle, and my stance is that we have to figure out how to live with it — like every other technology revolution.

This relationship between me and technology goes back more than 20 years. I’m also not new to people’s pushback. It was literally my job to convince people to try something new for a large portion of my career.

Yet I feel significant tension in writing and talking about something that is genuinely useful and also poses enormous threats to people, both their jobs and potentially all of humanity. I’m angry beyond belief at how companies are rolling it out and how it’s impacting employees.

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And so I wanted to explore my longstanding career that’s been built on finding ways to use technology and how AI is both “just another chapter” and “fundamentally different.

Then and now: what’s changed

My first job was working as a bank teller at a community bank in my hometown. I stayed at the job through college, eventually working as a mortgage underwriter in the 2003/2004 era. Interest rates had dropped, people were refinancing like crazy, and the loan officers were overwhelmed. I offered to help, which involved learning a bunch of new software.

The following year, the bank decided to digitize all of its paper loan files. At the time, this wasn’t common. Most banks still relied on enormous file cabinets of paper files. But I, along with a few other college students, was assigned the task of sending paper documents through a desktop scanner.

It was unbelievably tedious work. And at first, it seemed like brainless work. But I quickly realized a problem: inconsistency. Each college student organized the digital files in different folders, with different names. Loan officers couldn’t find anything in the digital version. As a result, the loan officers wouldn’t use the digital copy, and would pull out the paper file.

And I set out to fix the problem. I came up with an organization system and naming convention. Once the already-scanned files were fixed, I advocated that the paper files be moved so that the officers couldn’t rely on paper: they’d be forced to use the digital version. Eventually, everyone accepted the change.

After college, I went to work for the company that made the bank software I’d been using. I helped other banks implement digital loan files, along with other loan management tools. One of the final products I worked on (later as a product manager) was a tool that could automatically recognize the data from a bank customer’s tax return and analyze it, saving bank staff from repetitive data entry.

I saw software as a way to solve a problem: large banks have nearly unlimited resources for all types of tasks. Small banks don’t. Automation lets smaller organizations compete with larger ones. They don’t have to spend time on the boring, repetitive work and can instead focus on relationships with customers.

That core principle came with me when I started my own business. I knew I could do more if things simply hummed along in the background. I could focus on client work instead of things like “organizing files” or “manually creating checklists of fifteen items.” One of my friends joked, “I didn’t know how you could do the work of ten tireless humans. Then I realized all the systems that you have running in the background.”

And then along came AI.

AI: Different and yet the same

The current framing of AI is dominated by either hype (”AI will replace everything!”) and backlash (”AI is terrible, and I refuse to use it, ever”). There’s a third position that doesn’t get a lot of attention: people, like myself, who have found ways to make work easier.

Here’s a specific example: One of my clients gave me a spreadsheet of 27 rows. Each row contained some changes that they wanted to make to blog posts, with the changes embedded as bullet points within a cell. The final deliverable back to the client wouldn’t be a spreadsheet: it needed to be a Google Doc of the changes. So I had Claude extract the data from the spreadsheet and put it in a Google Doc for me. That took about one minute. If I had to do it manually, it would have taken at least an hour, maybe more, to do all of the formatting.

That’s the “genuinely useful” category. There’s no glory or anything to be gained in me manually formatting a giant Google Doc. The client is paying me for the writing and editing, not my ability to copy/paste from a spreadsheet.

That’s where I see similarities between the anti-AI position and what I heard throughout my career implementing software. Refusal to use AI is giving up legitimate ways to make work easier. I compare it to the example of extracting data from tax returns when I worked on bank software. The process of keying in numbers was just repetitive, manual work. Interpreting the numbers was part that required a human.

Where I feel the tension most, as I write about AI, is that my experience is not the same as most of corporate America. I have the freedom to explore and find what works for me (and what doesn’t work). Many companies are taking an iron-fist approach and insist that employees “use AI”… without providing any guidance.

And that is the disconnect. I know from experience that a free-for-all doesn’t work. Not everyone has a “software brain” and can immediately see how to use software to do work differently. They need to be given step-by-step instructions.

This is further compounded because AI has a much less obvious path than automation tools. Automation typically follows a specific process: if one thing happens, then this other thing happens. AI is much more open, like my spreadsheet example. That’s a thing I needed one time, and will probably never need again. It’s not a repeatable process. Yet I reached for AI as a tool in my toolbox, knowing that it could do what I needed.

What companies should be doing is providing specific training. That’s always the key to successful software implementation. I used to train a small group of “cheerleaders” within a bank. They would, in turn, figure out how to apply the software to their specific processes. And then they would train everyone else on the specifics.

Instead, CEOs are yelling, “Figure it out!” while simultaneously saying, “You will be evaluated on your use of AI on your upcoming performance review!”

On an episode of Decoder, Dr. Adam Dubé said the following about AI in education:

There’s some research that looks at school climates and teachers who get demotivated for their use of generative AI in education and what causes demotivation. And for them, it was being forced to use these systems when there was a top-down rule that you had to use generative AI…That is demotivating for educators. They don’t like being told which tools to use because it feels like it’s removing their autonomy. And so whenever we remove workers’ autonomy or their own sense, basically their control over their own work environment, people get demotivated.

Automation very clearly removes boring and tedious work. But AI is often a push (from the top) to replace creative work. Or to simply “create more!” without answering the question, “But why are we creating more…?”

That’s where companies are getting it wrong. They’re applying AI to the wrong use cases, and why people working with these scenarios are resisting (and demotivated). It shouldn’t be used to replace the parts of work that people find fulfilling. Yet that’s the push in the attempt to squeeze every last drop from worker capabilities.

This is why my feelings around AI are complicated. I’ve seen exactly how it saves time and effort. And I think most companies are doing it wrong, and workers have a right to feel frustrated by the threats to their jobs because their employers are trying to apply AI to everything, instead of the right things.

I think a “never AI” stance is going to leave some people — especially small or solo businesses — struggling to keep up. They simply won’t be able to keep up with people who do things like “use AI to save a few hours formatting a spreadsheet.”

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In 2021, I left my career at a tech company after 15 years and decided to pursue content marketing and journalism. The first marketing agency that hired me assigned writers to levels — 1 through 9 — based on experience. I came in at a level 2, the second-lowest. Fifteen years of product management, executive leadership, and deep domain expertise in financial technology didn’t “count” for anything. In this new world, I was a beginner.

That part of career pivots is often uncomfortable. We hear about the bold decision to quit. We hear about the eventual success story. But there’s a space in between where everything you knew in your prior career doesn’t quite translate yet.

It’s humbling in a way that catches people off guard, especially at mid-career, when you’ve spent years not having to prove yourself. I went from being the most knowledgeable person in the room to the least. And for a while, that felt like starting over from zero.

But it wasn’t zero. Not even close.

Nearly 70% of U.S. workers considered changing careers in early 2025. That number is a reflection of the current economy more than anything else — people can’t find new jobs in their current industries, or the industries themselves are shifting underneath them. More than 38% of new freelancers in 2025 were previously laid off.

Those numbers suggest something that the fear of starting over tends to obscure: the gap between “I left” and “I landed” closes faster than most people expect. The expertise from a previous career doesn’t evaporate. It’s waiting for the right context.

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What actually transfers

The narrative around career pivots tends to focus on what gets lost: title, salary, status, and the expertise that took years to build. But the more interesting story — and the one I’ve lived — is what transfers to a new career path.

After I quit my fintech job, I worked at two different content marketing agencies. Eighteen months later, I was laid off. The job market had tanked. I decided to go out on my own as a freelance writer, something I’d been considering. The layoff forced me to make a decision: try to find a job in a crappy job market, or make the leap.

What I didn’t expect was how much my fintech background would become a competitive advantage. I assumed that most clients would see me the way the first content agency did: a level 2 writer, with very little experience.

But most writers can’t speak the language of banking technology. Most fintech experts can’t write. The combination turned out to be rare and valuable.

The same pattern showed up in other ways. The systems thinking I’d developed as a product manager — implementing automation, streamlining processes, evaluating software — transferred directly to running a solo business. I’d spent years at a small company finding ways to make processes faster and better for my team. As a solopreneur, those same instincts kicked in. Except now the team was just me, and I reaped all the benefits.

The broken promise and the new path

Over the past few years, something has shifted in how people think about career risk. It used to be common sense: a corporate salary equals security. Self-employment is the risky path.

Like many people, I grew up believing that if you stick with your employer, stay loyal, and put in the time, you’re going to be rewarded. I think people just don’t believe that anymore. The social contract between employer and employee has broken. If the loyalty won’t be reciprocated, the job becomes unfulfilling. On top of that, people are constantly nervous about layoffs. Or restructuring. Or the next round of cuts.

Here’s how I think about it now: both paths carry risk.

With a traditional employer, one day you have a salary, and the next day you might have nothing. When I was laid off from the marketing agency, that’s exactly what happened. No warning, no safety net beyond a piddly amount of unemployment. The U.S. has almost no protections for employees (whereas other countries have things like mandatory notice periods and mandatory severance).

Working for myself, if I lose a client, that’s a fraction of my income — not my entire income. I purposely work with a couple of core clients and then take on additional projects as they come. My income is more variable, sure. But it’s never 100% to zero. I feel more secure now than I would if I were working in a corporate job (And I realize how counterintuitive that sounds to someone who grew up thinking self-employment was the riskier path.)

Self-employment isn’t a consolation prize for people who couldn’t make the traditional path work. It’s increasingly what sustainable careers look like — especially for people who’ve already navigated one or two major shifts. And the assumption that any particular industry is safe? That’s gone.

If you’re sitting in a job that no longer serves you, wondering if you have what it takes to try something else: you probably do. The expertise you’ve built isn’t wasted. It’s more portable than you think. It’s only a question of how long before your old career catches up with your new one.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

If you want to support my work as a writer, you can subscribe to receive additional issues I publish.

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Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.