In 2015, Paul Ford published a 38,000-word essay in Bloomberg called What Is Code? It’s an explainer for non-technical people who may find themselves in technical meetings with software developers and engineers. Recently, on an episode of The Vergecast, Ford says, “I wrote What Is Code? because I really did believe that this was a good way into the middle class, and it had been for me.”

In the same episode, he acknowledges, “There’s somebody out there… who is counting on their tech job. That somebody like me told them 15 years ago was the safest possible bet. And they went and got a certificate in AWS management. And now people are telling them, ‘Why would I ever do that? I’ll just deploy by using Claude.’” These jobs are existentially at risk.

For a generation, the career advice given to displaced workers, uncertain graduates, and anyone looking for a stable path was essentially the same: find a way to get into tech. Learn to code. Become a product manager. Work for the sales or marketing department at a tech company. Join the industry that is the disruption, not the one getting disrupted.

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I’ve worked in the tech industry (and now, tech-adjacent) since 2006. It was well-paying and, until late 2021, felt safe. I left my tech job voluntarily and went into content marketing for tech companies. 18 months later, I lost my job. A lot of factors played into that turn of events, but one was that the tech company was being decimated. Companies no longer had the budgets for marketing, impacting the marketing agency I worked for.

Over the past few years, I’ve watched the ground shift beneath the feet of so many people I know. That assumption that tech is “safe” has crumbled into dust. And the people who believed it most are the ones feeling it hardest.

The decade that didn’t deliver what was promised

There’s a cohort of workers — mostly elder millennials — who arrived at what was supposed to be the “payoff phase” of their careers at the exact moment everything started to change. Mid-to-senior titles. Accumulated equity at startups. Stable (even growing!) compensation. The decade was supposed to deliver on the promise that patience and hard work in tech would lead to security.

But then the pandemic hit. Tech layoffs hit. Generative AI hit. Just as this cohort reached the positions they’d been climbing toward, the industry started dismantling itself.

As of early April 2026, tech layoffs this year alone have impacted over 91,000 workers. In 2025, that number was approximately 246,000 across 783 companies. While some layoffs have been from startups struggling to survive, others are from companies that aren’t strapped for money. Amazon reported record revenue of $716.9 billion in 2025 while cutting 30,000 corporate roles. Block — the fintech company behind Square and Cash App — cut 40% of its workforce, roughly 4,000 people, explicitly because of AI. CEO Jack Dorsey said it wasn’t driven by financial difficulty. After the announcement, the company’s stock went up.

What makes the current wave of layoffs structurally different from what came before is what’s driving it. The first wave of tech layoffs (2022–2024) was a post-pandemic correction. Companies had to dial back the hiring sprees they went on during COVID. Painful, yes, but cyclical. The thing that’s happening now is something else entirely. Companies are explicitly stating that they are replacing human roles with AI systems. In a Resume.org survey, 44% of hiring managers anticipate AI will be a top driver of layoffs in 2026.

And here’s what I keep thinking about: the executives making these workforce decisions are acting on a capability that, by most reports, hasn’t fully materialized. Microsoft’s AI CEO, Mustafa Suleyman, predicted that most white-collar tasks — lawyers, accountants, project managers, marketers — will be “fully automated” within 12 to 18 months. Meanwhile, a randomized controlled trial by METR (published July 2025) found that experienced developers using AI tools took 19% longer on tasks than those working without them, even though they were faster.

The gap between what executives promise (or what they believe will happen) and what workers actually experience is enormous. Employees are bearing the cost of a bet they didn’t place, when we were promised something different.

The decision to pivot

Not everyone who’s leaving tech is being pushed out. Some are choosing to go.

There’s a steadily growing sentiment among the cohort that was supposed to be entering the highlight of their careers. It’s less about the dramatic exits of The Great Resignation and more about a widening gap between what tech promised and what it actually delivers at this stage of life. Kids entering adolescence. Parents aging. Bodies changing. Energy levels changing. Perspectives changing. People already juggling more “life outside of work” are rightfully questioning the constant grinding of their careers.

And the incentive to retool themselves again — this time at the breakneck speed that AI requires inside a corporate structure — just isn’t there. Think of it this way: why apply yourself to learning AI, when all of the benefit goes to the company, not the individual? The company gets more output. The individual gets more work.

Many are choosing something else, such as consulting, starting a business, or even learning trades. They’re turning long-held hobbies or passions into second careers. It’s intentional.

Part of what’s driving this shift is that people want more from work itself. More meaningful work instead of more money. More flexibility and control instead of a prestigious title at a company that might lay them off next quarter. RTO mandates, constant restructuring, AI-related pressures at every performance review… the culture of tech has changed. For some workers, the industry that used to feel generous and exciting doesn’t feel that way anymore.

And then there are the golden handcuffs. The math used to be simple: the paychecks from working for a tech company are often big enough that leaving feels irresponsible. But the equation changes when those paychecks come with layoff anxiety, RTO mandates, and the persistent feeling of dread, thinking that you’re one AI deployment away from being replaced. At some point, the handcuffs aren’t golden anymore… they’re just handcuffs.

I left my work at a tech company years before AI arrived, and before the mass layoffs hit. But the desire for “something else” was my motivator. I felt the thrill of building something — a product I truly believed in — early in my career. As I reached my 40s, with older kids and a post-pandemic lack of tolerance for bullshit, my personal calculus changed.

Was tech ever the destination?

Here’s what’s worth knowing if you’re in that space of “what do I do next?” right now: career pivoters are overwhelmingly happy on the other side. I’ve talked to many, many people over the years. And sure, it’s a small sample, but I feel confident that it’s representative of how people feel overall. They’re relieved, even if the initial “getting through change” phase is hard.

I’ve written before about the portfolio career replacing the career ladder, and about the different types of career pivots people make. What’s happening in tech right now is a collision of several of those pivot types at once: forced pivots from layoffs, anticipatory pivots from people who see the writing on the wall, and boredom pivots from workers who’ve mentally checked out of an industry that no longer resembles the one they signed up for.

Non-linear paths are not consolation prizes. They’re increasingly what sustainable careers actually look like — especially for people who’ve already navigated one or two major industry shifts. They can build on what they’ve learned, instead of clinging to something that’s disappearing.

We don’t fully know how this plays out. But the assumption that tech was a career safe harbor? That’s gone. So if you’re in tech and uneasy, considering leaving, or already have one foot out the door, keep this in mind: your experience is more portable than it feels right now. Systems thinking, project management, data interpretation, navigating ambiguity…. those skills don’t evaporate when you leave the industry that taught them to you.

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

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.

I’ve worked remotely since 2006 (way before it was common). However, my days were filled with calls to colleagues and DMs to chat about everything from work to what we had planned for the weekend.

Now I’m a solopreneur. I have occasional calls with clients, but they’re rare. Most of my days are spent working alone. In many ways, this is great since I have the freedom to work however and whenever I want. But staying motivated when it’s just me requires me to be really thoughtful about how I work.

According to a 2025 report by Leapers, nearly half of self-employed professionals feel lonely occasionally or some of the time. One in five feels lonely or isolated often or always. It can be really hard to stay motivated when you’re working in isolation. You have to create your own structure and find ways to keep going without other people around.

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This week’s Perspectives is an interview with Carrie Olsen, a voice actress, voiceover business coach, and online course creator. Carrie left a corporate career in instructional design to pursue voiceover full-time, and now helps others explore creative careers through her coaching practice and courses.

You can check out Carrie’s 3-step guide to building something that’s yours here:

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This interview has been edited for length and clarity.

Anna Burgess Yang: Tell me about the work that you do.

Carrie Olsen: My primary work is voiceover. Anywhere that you hear a voice but don’t see a face, that’s voiceover. That could be anything from animation to TV and radio commercials, the self-checkout line telling you “Are you ready to pay?”, the voice on the bus saying “Next stop, Broadway Street.” Audiobooks, podcasts, promos. I do a lot of promos for TV shows and live announcing. When you’re listening to the Oscars or the MTV Movie and TV Awards — which I’ve live announced — that’s voiceover work.

Through coaching other people on how to get into voiceover, I found that some people are truly passionate about voiceover. But others are like, “I just want something that’s creative, that’s out of the ordinary. Tell me about this. Is this something that might fit that mold?”

Over the years, I’ve started tailoring my coaching more toward a creative outlet. If you don’t know what your thing is, we’ll figure out what that is. And if you do know what it is, it’s usually psychological barriers that are keeping people from pushing forward. We’ll work through those things.

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ABY: You were at a corporate job and discovered voiceover through a podcast you were listening to. What was it that made you think, “Yes, I could do that”?

CO: I was listening to a podcast, and a voiceover coach was on it. Basically describing a day in the life. I had just had my first daughter, so I was looking for something where I could be at home with her more. And it was checking all the boxes. She would say, “I get up in the morning, do my workout, check my emails, go record a little bit, then go back to the booth.” And I was like, she’s doing that from home, and she’s making a living, and she’s supporting her kids. That sounds like something I could do.

It’s kind of the impetus we all have. When you see someone doing a fun job, you’re like, “Oh, that looks fun and easy. I’m sure I could do that.” That was me being naive going into it. But then, after I had my first coaching session with her and started learning what it takes to build a voiceover business, I got more excited. It was combining my creative side with my entrepreneurial side and building a business from scratch.

ABY: You went from a corporate job with clear structure and a clear title, and now you’re in a field that a lot of people don’t even know exists. How did that change how you thought about yourself professionally?

CO: I’ve always thought about my corporate job as feeling like I was wearing a mask. There are some people who are really good at corporate, and they’re bringing their full selves. But for me, it was being in a stuffy office and having to wear clothes I didn’t choose and sitting in inefficient meetings.

The job I had right before I got into voiceover, as far as corporate jobs go, was fantastic. I liked the work, I liked my coworkers, but it wasn’t ideal. I was still away from my daughter, and it wasn’t what I would have chosen.

When I started my own business, how I thought about myself became less defined. I was creating what I was doing. Everything was my call. When people ask what I do, I always have to explain it. It’s not like saying “teacher.” People are like, “What is that? What do you do?”

I’m a quiet person. I’m introverted. But voiceover became this space where I had to be bigger and louder. I was still getting to explore those other sides of me that you would never get to at a corporate job or in a boardroom. It was really neat to get to explore that creative side.

ABY: Did that exploration change your sense of identity, or did it reveal who you already were?

CO: I think it was the latter. It was always there. But there were parts that I didn’t even know were there, or you’d have to probe really hard for me to admit it. It seems silly for an adult to be like, “I want to be an actor someday.” Responsible people don’t say that. Realistic people don’t say that. So it was this thing that was buried really far underneath, and voiceover opened that up.

ABY: You’ve built a business with multiple income streams: voiceover work, coaching, and an online course. Was that intentional, or did it evolve over time?

CO: That definitely evolved. Getting started in voiceover, I didn’t know what to expect. When I started booking work, it was this leap of faith that my husband and I took. I was booking work on weekends, working after work with a newborn at home. We had this moment where we said, “What would happen if you put full-time hours to this work?” We did that, and it worked out. I matched what I made at my corporate job in my first year of voiceover work.

My corporate job was instructional design. I was a content design specialist for the e-learning department of a construction company. I really love adult learning theory. When people started asking me, “How did you build a voiceover business in a year?”, my natural answer was, “Let me build a course about it.”

It started off as a blog post, and people were reading it. I started building my email list, I thought, “Now I have this asset. What do I do with an email list?” So I started doing webinars to send people to my course. It all just stacked on. I didn’t have a master plan from the very beginning. I just kept seeing what was offered next and saying yes.

ABY: What’s the hardest part about running a creative business?

CO: There’s no steady paycheck. You have to learn how to budget on an irregular income. I’m okay with that. My husband is happier when things are expected and normal. Balancing our two different preferences for how money comes in has been a challenge the whole time I’ve been a solopreneur.

But I think in general, it’s getting over the hump of saying, “I can do this. It’s okay for me to do this. It’s actually good for me to explore something that is fulfilling.” I think that’s a part that responsible people have a hard time with, because we feel like we need to take care of everyone else. And a lot of times that means putting our own desires on the back burner, indefinitely. That barrier is hard to overcome.

ABY: What would you tell somebody in a corporate job who has a creative passion and wants to turn it into a real career? How do they get past that barrier?

CO: You don’t have to quit your job right away. There’s a way to do it responsibly. That’s a barrier for some people, but it’s also kind of the easy barrier that’s hiding other barriers. It’s the easy one to say: “I want to be responsible. I can’t risk losing my job.”

I have a three-step guide that talks about this. The first step is to see the lie: the stories you’ve been telling yourself about the reasons why you can’t write a book or start painting or whatever. Those stories aren’t true. Things like, “I’d be abandoning my family,” or “I’d be doing something irresponsible,” or maybe it’s something your parents instilled in you.

It’s important to recognize that your inner critic is trying to keep you safe. But you’re actually going to be okay. You don’t have to quit your job right away, and you don’t have to jump in with both feet. You can practice putting yourself out there in small ways. That helps you build the muscle so you get more used to what it feels like.

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

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.

A recent Entrepreneur headline proclaimed: “Dell Shrunk Its Workforce By 10% for the Third Year in a Row — Without Layoffs.”

Dell has about 97,000 employees. That’s according to its latest federal filing, published this week. In February 2023, it had 133,000. That’s a reduction of nearly 30% of its workforce in three years.

Except... Dell did lay off 12,500 employees in August 2024. That was less than two years ago. Someone on the editorial team at Entrepreneur failed at the most basic task of “accurate information.” (The article itself notes the layoff, which is a direct contradiction to the headline.)

On top of the layoff, Dell has employed other methods of reducing its workforce, such as hiring freezes, “employee reorganizations,” and a five-day return-to-office mandate. The end result is the same: reducing the size of the workforce. They’re layoffs without negative publicity.

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I wrote about Dell in March 2024, when the company announced that remote employees would be ineligible for promotion. At the time, Dell’s own internal data showed the policy disproportionately impacted women. I said then that it looked like Dell was trying to force employees to quit rather than go through another expensive round of layoffs. When employees quit due to a change in working conditions, the company can shrug and say, “Not our fault that they quit.” Two years later, the numbers confirm exactly what I predicted would happen.

What Dell and other companies are doing is part of a broader shift toward what Glassdoor calls “forever layoffs“: continuous, small-scale workforce reductions that fly under the radar. But they create lasting damage to the people left behind.

The playbook for disappearing workers

In these “forever layoff” scenarios, the work doesn’t disappear. It gets redistributed to the people left behind.

The high-profile layoffs grab attention: Block cut 40% of its workforce in February 2026, with Jack Dorsey explicitly pointing to AI. Meta is reportedly planning to cut 20% of its staff. Atlassian cut 10%. But plenty of companies are taking the same approach as Dell and handling a reduction in force (RIF) much more quietly, to avoid attention.

But the cumulative effect is the same. And the impact on the people who stay is significant. Glassdoor’s research from September 2025 found that after a layoff, employee sentiment among remaining workers takes more than two years to recover. Repeated layoffs have double the impact on sentiment, with the biggest drops among key talent, managers, and new hires. Employee mentions of “layoffs” and “job insecurity” in Glassdoor reviews are now higher than they were in March 2020, at the onset of the pandemic.

The near-constant layoffs-that-aren’t-layoffs are demoralizing in a very specific way. Workers never know when the next “reorg” will eliminate a few people in their department. They absorb more work without more pay. They watch colleagues deactivated in Slack in real-time. Rolling layoffs breed cultures of anxiety, insecurity, and resentment.

“Just use AI” isn’t a workforce strategy

The CEO mantra of “just use AI” as a solution to a smaller workforce doesn’t sit well with the people actually doing the work. AI doesn’t replace a whole human, and certainly makes the remaining workers further wonder if their jobs will be next on the chopping block.

Zuckerberg said in January that he was seeing “projects that used to require big teams now be accomplished by a single very talented person.” That framing — one talented person replacing an entire team — is becoming the justification for cutting headcount across the industry. Though Meta’s plans to cut headcount are in part to offset the $135 billion in infrastructure costs of AI (which is wild, considering how bad Meta is at AI compared to the frontier models). You’d think Meta could spare some of that investment for its human employees.

But how much of Zuckerberg’s claims of employees’ use of AI are actually happening on the ground? Technology reporter Kevin Roose wondered this on the Hard Fork podcast: “The data that we have is largely self-reports. And I think some firms have exaggerated how much they are doing with AI because they want to appear to be cutting edge and futuristic, and look how transformed we are.”

Even if it is the case that humans are now overseeing multiple AI agents, as Zuckerberg suggests, researchers have found that “AI brain fry“ is on the rise. This is defined as a type of cognitive strain and mental fatigue related to the excessive use of, interaction with, or oversight of AI — beyond one’s cognitive abilities. “Doing the work” alongside human colleagues is a far different experience than overseeing a bunch of AI agents.

At the other end of the spectrum, with employees less comfortable with AI experimentation on their own experience a fundamental training gap. Companies are telling workers to “just use AI,” but they’re not investing in teaching them how. If companies aren’t even providing the basics of AI training, expecting workers to use it as a substitute for human colleagues is setting them up for failure. Especially as many employees now report that AI usage is a part of their performance reviews.

It’s no wonder that employees are resentful.

Why the narrative isn’t fooling anyone

Dell, Block, Meta, and others like to claim that AI is so capable that companies genuinely need fewer people. In reality, these companies have decided that workers are the most expendable line item — and are using the current AI hype cycle as cover. When Jack Dorsey announced Block’s layoffs, its stock price jumped more than 20%. When reports of Meta’s potential layoffs surfaced, Meta’s stock climbed too. The market is rewarding companies for cutting people.

So they’re optimizing for short-term gains and framing it as “strategy.” Nobody seems to be asking what happens when the remaining workers burn out, suffer from “AI brain fry,” or when institutional knowledge walks out the door.

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.

One of the things that I love about working for myself is that I don’t need to ask anyone’s permission before making a decision. If I want to make a change, I go for it, on whatever timeline makes sense for me.

But the freedom of solopreneurship can be a double-edged sword. Since you don’t need approval from other people, nothing is stopping you from chasing every shiny tool, course, or strategy that promises to solve your problems.

The ability to say no to distractions is an underrated skill for solopreneurs. There’s a difference between making strategic business decisions and letting yourself be pulled in a million directions. You need to master the former and resist the latter.

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A few weeks ago, I vibe-coded a new website for myself. If you’re not familiar with vibe coding, it’s using natural language (“Hey Claude, we’re going to work on a new homepage for me”) to code something. An article in Microsoft Source describes it this way:

Coding has long been limited to the realm of software engineers who studied it in school. But now there are so-called no-code, low-code and pro-code AI tools. That’s broadening who can build apps, helping everyone from non-technical business professionals to experienced developers solve problems, save time and boost creativity.

It’s addicting… after building my initial website, I spun up several more. I’ve spent hours fiddling with Claude CoWork. It’s exciting and genuinely a big deal for people who like to “tinker.” You can now build the tool you’ve always wanted — either because no company was going to make it (because the use case is too specific to you), or because you don’t want to pay a monthly subscription for something you’ll only partially use.

All of this has a real impact on people’s lives, both at work and personally. But the ability to build doesn’t mean you should build everything. And the line between building something useful and building for building’s sake is thinner than most of us realize.

The new math of building

Companies have always wrestled with the “build vs. buy” decision. If they wanted a tool to do something, they could either build it themselves (which takes time, money, and resources) or buy it (which lacks full control and customization). Now the calculation is murkier, and it can rely on individual decisions instead of a big corporate buy-in. You want something? You can build it yourself. The question is whether you should.

What used to require hiring a designer, a developer, or a consultant can now be done in a few hours with an AI tool. That’s a real shift, and for many people, it’s the first time they’ve been able to bring an idea to life without depending on someone else.

Regular people are building personal websites, scheduling tools, custom dashboards, automations that connect their apps — things that weren’t possible a year ago. The potential is enormous.

But the potential also has a way of expanding to fill all available time, rather than saving time.

Katie Parrott wrote a piece called “AI Was Supposed to Free My Time. It Consumed It.” She describes staying up until 1 a.m., building and rebuilding with her AI assistant. Her piece captures something important: a compulsive quality of AI-assisted building that many people find once they get started. It doesn’t feel like work. It feels like momentum… and that’s what makes it hard to stop. (You can read Katie’s guest essay about productivity for this publication here.)

There’s a version of this playing out on a much larger scale. On a recent episode of The Verge’s Decoder podcast, Hasbro CEO Chris Cocks described how AI-assisted design has transformed the company’s product development. Where Hasbro’s teams used to take one or two toy concepts to the full prototype phase, they can now take 10 or 20. More ideas, faster, at the same cost.

That sounds like pure upside. But it’s also a perfect illustration of Parkinson’s law, a concept based on a satirical essay that contained the line, “Work expands so as to fill the time available for its completion.” When AI makes it possible to generate 20 prototypes instead of two, you don’t stop at two and go home early. You generate all 20. And then you review all 20. And then you iterate on the five most promising ones. The capacity to do more becomes the expectation to do more.

This pattern shows up in survey data, too. The Upwork Research Institute surveyed 2,500 workers in 2024, including executives, employees, and freelancers. 77% of employees said AI tools had actually added to their workload. Workers reported spending more time reviewing AI-generated output, more time learning the tools, and being asked to do more work as a direct result of the technology. More recently, Upwork’s 2025 follow-up study found that of the workers reporting the highest productivity gains from AI, 88% of them experienced burnout.

This cycle of constant building with AI only benefits workers if they were previously overworked, and AI actually reduces the load. If the “newfound time” just gets filled with more stuff (more prototypes, more iterations, more output), then the gains flow to the employer. The worker doesn’t get any time back.

Building with intention

This isn’t an argument against AI tools. I’m a fan, trust me. But it’s an observation that the low friction to get started doesn’t mean you should build everything. It’s no longer a “build vs. buy” question, but instead a “build vs. ‘what do I gain from building?’” question.

The temptation to build everything you can build is real. And the people who benefit most from these tools are the ones who build the right things: the things that actually improve their lives rather than just consuming their attention.

I could stay up allll night (like my friend Katie) and build new things in CoWork or Claude Code. Instead, I’ve got to decide how to meaningfully apply my time and attention. If I were working for an employer, it would be the same.

Before you sit down to build something with AI (whether it’s a custom app, an automation, or a new workflow), a few questions are worth asking:

What specific problem does this solve? If you can’t name a real use case — something that’s actually costing you time, money, or frustration on a regular basis — it might be a distraction posing as a productivity gain.

What’s the real cost? Not in dollars, but in hours. How much time will you spend getting this up and running versus how much time it will actually save you? A tool that takes 10 hours to build and saves you 20 minutes a week will take a while to “pay for itself” (though that certainly compounds if you save 20 minutes a week forever).

When will I stop? Deciding on an end result before you start is fundamentally different from trying to stop once you’re in the flow. (The flow is a trap!)

What will I do with the time I get back? This is the question that keeps the whole building process in check. If AI takes something off your plate, the benefit only exists if you’re intentional about what fills that space. Otherwise, you’ve just replaced one type of busy with another.

Honestly, I’m haven’t reached the point where building gives me more time… yet. I’m too deep into changing processes. Some are things I’ve had in place for years and are forcing me to fundamentally change how I do work. Will it pay off, eventually? That’s the bet I’m making: that this upfront work will be worth something.

Want to build a life-first business? These reflections will help you determine your priorities.

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.

It’s Friday afternoon, and a potential client just emailed asking about your services. You scramble to find your pricing (where did you save that document?) You dig through old emails for a proposal you sent six months ago that you could adapt. You piece something together and curse your past self for not being more organized.

This scenario plays out constantly for solopreneurs. Most chalk it up to the chaos of running a business alone. But constantly scrambling will start to cost you as your business grows — and eventually hold you back.

Most solopreneurs think that “operations” is something only real companies need: businesses with employees, office managers, and HR departments. But the absence of basic systems wastes your time, causes unnecessary stress, and makes you look amateurish to potential clients.

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This week’s Perspectives is an interview with Sarthak Dhawan, co-founder of Turbo AI, a notetaker and study tools app for students. In 2025, Sarthak and his other co-founder, Rudy Arora, dropped out of college to focus on Turbo AI full-time.

I’ve written a lot about AI and its impact on work, so it was interesting to hear Sarthak’s perspective as an “industry insider” working for an AI company.

This interview has been edited for length and clarity.

ABY: Tell me a little bit about your background and how you ended up starting Turbo AI.

Sarthak Dhawan: I started coding in elementary school because my brother got me into it. I got a lot of joy from building things and seeing people use them. It slowly evolved into creating random projects. I met my co-founder, Rudy, in middle school.

When I was going into 9th grade, my school had this portal that students would use to check their grades. But it was really slow and didn’t work half the time. I said to myself, “This seems like an opportunity for me to go ahead and build a nice, pretty mobile app for students to check their grades.” I did that, and it ended up going pretty viral, just by word of mouth. I remember going to my school, seeing people use my app, and they were liking it!

I got into Duke University, and Rudy went to Northwestern. We started Turbo AI with $300 we had saved up from an internship, and used that to create the LLC.

About eight months ago, we chose to drop out of college because the business was doing so well. We have over 8 million signups and are earning more than a million dollars per month.

ABY: What was it like, making the decision to drop out of college and focus on this full-time, rather than finish your degree?

SD: The first time I mentioned dropping out to my parents, they had a terrible reaction. Like, “What are you thinking? Duke is a good school. We’re paying so much in tuition. You worked so hard to get to this point. Why not just finish and do the startup stuff later?” At the time, I thought, “You know what? That makes sense.”

It was only when we were making a sizeable amount of money, growing the team, and needed more employees that I couldn’t justify the amount of time I was spending on school. It wasn’t like I said, “Hey, I think this is going to be big. Let’s drop out.” It was more like, “This is already big.” It was a natural progression. And when it came to that point, my parents realized that their kid was going to be ok.

ABY: What was the transition like from “this is my side hustle” to “this is my full-time job”?

SD: Mentally, there was never really a transition, if I’m being honest. I wake up every day because I find this work enjoyable, and I want to grow the company.

One of the biggest reasons I didn’t want to leave school was actually the social environment. Duke is awesome. When we formed the company, we decided to make the social part a priority.

ABY: When you think about creating a work environment for your team, what’s important to you?

SD: When I think about hiring and building a culture, I think the most important thing is having autonomy in what you do. No one wants to be told, “Do this task,” and be micromanaged the whole time. That makes it painful.

We’re very small for the scale we’re at. When we’re hiring someone, we want them to own that sector of the business, whether it’s an engineer or a marketing person — so they feel like they’re making decisions and having an impact. I think that’s what people derive value from.

With the actual logistics of things, we’re very flexible. If you want to work some days remotely or choose your own hours, it’s fine. I’ve never really understood why that matters. I’m of the perspective that if the work gets done and it’s high quality, I don’t care what you do.

ABY: What do you see in your users’ adoption of AI — mostly students — in how they approach trying new things or how they include AI in their work?

SD: We’ve had a rapid shift in the past few years where people’s attention spans are smaller and smaller, because of social media. That shortened attention span is affecting people in all areas of their lives.

So we’re seeing a problem in the usage of our application where students’ attention spans are so short that even if you take a 100-page PDF and put it into our tool to make four pages, they’re not willing to sit down and read those four pages. Four pages are still too much.

AI is catalyzing this even further because instead of reading a 10-page article, you can ask for a summary and read a few words. It’ll give you exactly what you want.

The awesome part about consuming information before AI was that you were forced to consume a lot of information and synthesize it yourself. And the process of consuming information you don’t necessarily need is really valuable. In this world of AI, you’re not consuming any extraneous information. It’s sort of like tunnel vision that’s been exacerbated by social media being exacerbated even more by AI. What we’re trying to do with Turbo AI is make learning more fun, more enjoyable, and more interactive.

ABY: How do you think about AI’s impact on the workforce as a whole?

SD: When I look at AI from two years ago, when it wasn’t nearly as good, compared to my productivity now, it’s maybe 100 to 1,000X. I think it’s very complementary. We’re not at the stage where AI can autonomously do things. You need a human utilizing these tools.

Historically, when the Industrial Revolution came around, jobs were lost, but many new jobs were created. There was a lot of technology early on replacing jobs that people didn’t necessarily want to do.

The problem we’re seeing now is that AI excels in areas that are highly intellectual. For example, right now we’re seeing that AI is amazing at coding, math, and physics. When jobs at the higher end of desirability start to get taken away, I don’t know what sort of macroeconomic shifts that would cause. It’s a little bit concerning to me, but hard to say.

ABY: What would you say to someone who is uncertain about the job market right now?

SD: Knowledge across the board has never been more democratized. Fifty years ago, if you wanted to understand certain concepts or improve your job prospects, you might have to go to a prestigious college. But now, AI levels the playing field in terms of how fast, how easily, and how cheaply you can upskill yourself.

So the bottleneck is just, are you willing to put in the time to learn something? But that’s a solvable problem, and very realistic.

Want to build a life-first business? These reflections will help you determine your priorities.

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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.

I had to submit my resume for a role. Then I went through three interviews, with nearly identical questions each time.

The biggest problem? The role was for a freelance writing position. Not an employee of the company. I got all the way to the third interview only to learn that the role paid a fraction of my usual rate — even though I’d provided my rates upfront.

I’m experienced enough as a solopreneur to know that going through three interviews was a bad sign. The potential client wasn’t communicating internally (as confirmed by the fact that my rate had been overlooked). Repeated interviews are incredibly uncommon in my line of work, and indicated to me that the company didn’t know how to work with a freelancer.

When you’re a solopreneur, bad clients cost you time and money. They also crowd out better opportunities and put a strain on your bandwidth. Client selection is a core business skill. And if you’re not in a position to turn down work, you at least need to know how to handle sticky situations when they come up.

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Ever feel like the amount of work you have to do is running you into the ground? Most of us — whether working for an employer or working for ourselves — don’t have the luxury of handing off tasks to a team. Everything lands on your plate, and there’s never enough time.

AI won’t run your life for you (despite what some of the big AI companies would have you believe). But it can give you back hours every week. Some tools are AI-first, meaning their primary job is to perform an AI-driven task. You can also look at adding AI features inside tools you’re already using.

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These days, I rely heavily on AI. I can get more done in less time, without sacrificing quality in any of my work.

Here are a few AI tools that can make a huge difference in your work.

Meeting notetakers

An AI notetaker was the first AI-first tool I added to my business. My notetaker auto-joins my calls, records the conversation, transcribes everything, and sends me a recap with action items. Instead of scrambling to remember what a client said three months ago, I have a searchable archive of every meeting.

This solves a real problem: you can be fully present during the conversation rather than taking notes by hand. You also don’t risk missing something important, which can happen with manual note-taking.

Tools: Otter, Fireflies* [affiliate link], Fathom

Knowledge systems

Over time, we accumulate a mountain of valuable material: proposals, client emails, blog drafts, research notes, and random thoughts. Most of it gets buried in folders (or notebooks), which makes it hard to track through your thinking or find related ideas.

A personal knowledge system changes that. It creates a searchable “second brain” – like your own Wikipedia. Add AI into the mix, and you can “chat” with your own content instead of digging through your notes and files. Think of AI as a personal research assistant who has read everything you’ve ever written.

Tools: Google Notebook LM, Tana, Notion AI* [affiliate link], Reflect

Standard operating procedures

Even if you work alone now, you might eventually bring on help (like a virtual assistant, a subcontractor, or a specialist for a specific project). When that happens, you’ll need documented processes. The problem is that writing step-by-step instructions for everything you do is tedious. Most people never get around to it.

AI tools solve this by recording your screen as you complete a task and automatically generating written documentation. You walk through a process once, and the tool creates a standard operating procedure (SOP), complete with screenshots and written instructions — without any extra effort on our part.

SOP tools are uncannily good. I usually only need to make small tweaks to the written version, and sometimes don’t need to make any edits. I store them on my Google Drive so I can easily share them if needed.

Tools: Loom AI, Scribe* [affiliate link], Tango

A business coach

AI chatbots can serve as an on-demand sounding board. They won’t replace your judgment, since they can’t understand the nuance of the real world and human relationships. But they’re useful for thinking through options, drafting difficult emails, or walking you through the different angles of an idea you might have.

In Claude, I’ve created a “Business Coach” project. I’ve uploaded a lot of files so Claude has context, including information about who I am, the work that I do, my brand, and the potential clients I’m targeting. When I’m trying to think through something, Claude asks me questions. By responding, I clarify my own thinking.

You can also do this if you’re working for an employer by providing context about your role, team, or projects. Or your “business coach” might help you think through the next phase of your career, if you’re looking to make a change.

The key is prompting well. The more context you give about your situation, and any constraints (like your time or finances), the more useful the output.

Tools: ChatGPT, Claude, Gemini

AI features embedded in existing tools

Every company has been rushing to add AI features to its products. Some are good. Some are included with your existing subscription, while others treat AI as an add-on.

For example, I rely on Airtable* [affiliate link] to run the “back-end” portion of my business. AI-powered “field agents” have been able to accomplish a lot of tasks I used to do manually.

A few other ideas:

• AI-powered transaction matching in accounting software like QuickBooks or Kick can categorize your expenses and spot anomalies

• AI scheduling assistants in tools like Motion or Reclaim* [affiliate link] can help you plan your day and protect your calendar from too many meetings

• AI email features in apps like Superhuman or Spark can draft replies or prioritize your inbox

The tools you or your employer already pay for are getting better. If AI has been added since you originally signed up, the features are worth exploring.

Start with one new tool

AI fluency is becoming a baseline skill, like knowing how to use a spreadsheet. And it’s becoming ubiquitous: apps will keep adding AI features to make work easier and faster.

But you don’t need to master everything at once. Pick the tool that solves an obvious problem or can complete a task that drains a lot of time from our day. Figure out how to get the most out of it before adding the next thing.

Want to build a life-first business? These reflections will help you determine your priorities.

* Affiliate link: If you sign up, I may earn a small commission, at no additional cost to you.

An executive says out loud what many executives believe privately: “I’m successful because I put work above everything else in my life.” The room — full of C-suite leaders — nods along.

A Wall Street Journal opinion piece by a young entrepreneur took it even further, proclaiming that “Work-life balance will keep you mediocre.” He wrote, “In a winner-takes-all economy, extreme efficiency during your peak physical and mental years becomes a baseline for building wealth that lasts a lifetime.” Sacrificing time with family and personal relationships in college was, by his definition, necessary for success.

These aren’t fringe opinions. They’re the standard playbook of most people in corporate leadership. Ambition should hurt. The hardest worker wins.

This belief system treats sacrifice as proof of commitment — that the only way to earn your success is to give up everything else in pursuit of it. But what if it’s not a requirement for success? What if it’s just a story we’ve been told so many times that it feels like a fact?

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The cost of the sacrifice narrative

I remember nights early in my career, furiously typing away at the keyboard late into the night. I had to be the best. I had to prove how hard I was willing to work. It was effective, because I received promotion after promotion in my corporate life. Work was everything — until I had kids. And thank goodness I did, because kids fundamentally changed my perspective about what was important.

You can’t have it all, as the saying goes. You’ve got to make choices about how you spend your time. But in addition to damaging relationships, the “sacrifice everything” model has measurable health costs. A study co-authored by researchers at Wharton and UC Berkeley examined the long-term effects of stress on CEOs’ health. The findings were stark: CEO lifespans decreased by 1.5 years after an industry-wide downturn. When insulated from intense market pressure, their lifespans increased by two years.

While the study focused on CEOs, the implications extend to other workers. The same pressures — long hours, high-stakes decisions, chronic stress — are present at every level of management. Middle managers, in fact, report the highest rates of burnout of any group, with 71% saying they feel burned out. The people on the path to becoming those corner-office leaders are already paying the price.

There’s a well-known adage that people don’t lie on their deathbeds thinking, “I wish I had worked more.” They wish they’d spent more time with the people they care about and doing the things they love. And, according to the research, intense overwork doesn’t just diminish the quality of life. It actually shortens its length.

Thankfully, the next generation is already opting out. There’s a term for what’s happening: “conscious unbossing.” According to DDI’s Global Leadership Forecast 2025, Gen Z is 1.7 times more likely than other generations to step away from leadership roles to protect their well-being.

This is a rational response to watching their managers burn out and deciding the trade-off isn’t worth it. Younger workers have observed the sacrifice model up close — the missed family dinners, the 10 p.m. emails, the manager who hasn’t taken a real vacation in years — and they’re saying, “I don’t want that life.” They’re refusing to accept that suffering is a prerequisite for achievement.

And research consistently links work-life balance with higher job satisfaction and job performance — not lower. There’s no real evidence for the assumption that balance breeds mediocrity.

Redefining success on your own terms

The appropriate reframe to “success requires sacrifice” is that success requires clarity about what matters to you — and the discipline to protect it.

For employees:

The executives who wear sacrifice as a badge of honor are modeling a particular version of success. It’s not the only one. If your company’s culture treats burnout as a badge of honor, that tells you something about the company — not about what success requires.

If you’re being asked to sacrifice everything and told that’s just “what it takes,” consider whether the system is designed for your success... or for the company’s. After all, companies benefit from your overwork.

For self-employed people:

The sacrifice narrative can follow you out of corporate life. When you’re building something on your own, it’s easy to slip back into corporate habits — working around the clock because that’s what “dedication” looked like for years.

It’s also easy to compare yourself to others. I hear entrepreneurs brag about their revenue or how many hours they put into their business. I have to remind myself that another person’s definition of success is not the same as mine.

The advantage of working for yourself is that you get to define what success looks like, from top to bottom.

Final thoughts:

The people who say “you can’t succeed without sacrifice” may genuinely believe it. But their belief is self-reinforcing. The people who’ve made sacrifices point to their own sacrifice as evidence that it’s necessary. They made it to the top, and the cost was enormous, so the cost must have been required. It’s a circular argument.

What if the question isn’t “how much are you willing to sacrifice?” but “what kind of success are you building — and will you have space in your life to enjoy it?”

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

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You quit the 9-to-5 to have more control over your time. You wanted flexibility, autonomy, and the freedom to structure your days around your life instead of someone else’s schedule.

Yet here you are, apologizing to a client for not responding to a message immediately. Feeling guilty on a Tuesday afternoon when you’ve only worked for four hours that day. Checking Slack at 9:00 PM because that’s been your routine for most of your working career.

Many solopreneurs don’t realize they’ve inadvertently recreated corporate life until they’re already living it. You traded a demanding boss for a dozen demanding clients. You swapped mandatory meetings for back-to-back Zoom calls. That freedom you craved? Doesn’t exist in your solopreneur world.

To find actual freedom as a solopreneur, you have to recognize that you’re following a corporate playbook — and make a conscious decision to change.

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I recently vibe-coded a new website for myself. Even though I worked at a software company for many years, I’m not a developer. But a few hours with Claude Code, and I was able to create a website just by “talking” to Claude with phrases like, “Can you move that to the center?” or “Can you change the color here?”

To pay someone to create a website for me would have likely cost thousands of dollars. Now, it’s a few hours with an AI coding tool — even without any specialized skills.

This is a small, personal example of something much larger happening across the labor market. AI is changing work from two directions at once. It’s changing how people get hired (AI screening, AI interviews, AI deciding whether your resume ever reaches a human). And it’s changing whether companies need to hire at all, as AI agents start replacing headcount entirely.

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Both of these trends are quietly hollowing out the foundation of how careers have traditionally been built. Workers are rightly nervous because they see the seismic shift coming... but don’t yet know how it will impact them.

AI’s role in hiring: gatekeeper or equalizer?

AI is now embedded in the hiring process, but the results are a mixed bag. Sometimes, AI reduces human biases, while other times it reinforces discrimination that has always made hiring problematic.

Derek Mobley, a Black man over 40 with a disability, applied to more than 100 jobs through Workday’s platform. He was rejected every time, often within minutes, sometimes in the middle of the night. He’s now suing Workday, alleging their AI screening tools discriminate based on race, age, and disability.

The numbers are staggering: Workday disclosed that 1.1 billion applications were rejected using its software during the relevant period. The class action lawsuit could potentially include hundreds of millions of members. Even though the case hasn’t settled yet, the message is clear: companies may be liable for the actions of their AI systems if those systems violate existing laws.

But there’s another way to think about how AI can impact the hiring process.

PSG Global Solutions developed an AI interviewer called “Anna” and had researcher Brian Jabarian at the University of Chicago Booth School of Business run an experiment on 70,000 job applicants. Applicants interviewed by Anna were 12% more likely to get a job offer and 18% more likely to stay in the job for at least a month. Reports of gender discrimination were cut nearly in half compared to human-led interviews.

Surprisingly, when given a choice, 78% of candidates chose the AI interviewer over a human. Why? The theory is that people felt the AI was “less judgy.” For example, a human interviewer might penalize a candidate for being nervous (whether consciously or unconsciously). The AI also captured more job-relevant information: an average of nine topics per interview compared to five for human interviewers.

So which is it? AI can reduce human bias, but it can also perpetuate biases at scale. We don’t fully know the answer (yet), but the difference seems to be in how the AI is designed and what data it’s trained on. For the time being, job seekers have no way of knowing whether that’s working for them or against them.

AI replacing humans: the appeal and the problem

In January 2025, I wrote “No, AI isn’t coming for all the jobs.” I truly believed what I wrote at the time. But it seems more and more that AI can replace some of the work of humans, in ways we couldn’t have predicted even a year ago.

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor. After two of his salespeople quit, he made a decision that fundamentally changed how his company: he replaced his entire go-to-market team with AI agents. SaasTr now has 20 AI agents managed by 1.2 humans (one full-time, one part-time) doing the work that used to require 10 sales development representatives and account executives.

The result? Same revenue, 24/7 availability, able to handle greater volume, and instant response times.

His framing is really telling: “The job that would have gone to a new rep now goes to an AI agent. The headcount just never gets added.”

But there’s a problem with this approach. You need seasoned, senior people to train AI agents. It worked for SaaStr right now because the senior people already exist. But what happens five to ten years from now when there are no more junior people becoming senior people?

According to data from Revelio Labs, entry-level tech hiring has declined about 35% since January 2023. While this data is specific to tech workers, the pattern will easily extend to other industries as AI tools become more capable and accessible.

It’s a classic case of short-term thinking with long-term consequences. Companies are solving today’s labor struggles by creating a future talent crisis.

So, as workers, what can we do?

I see people online who are still opposed to AI. I get it: there’s still a lot to figure out. In addition to biases and job displacement fears, many of the ethical and environmental questions are very real and unresolved.

And yet... AI isn’t going anywhere. Continuing to resist will likely be a losing strategy.

Early in my career, I helped banks with digital transformation. Customers had bought enterprise software to replace a lot of manual internal processes. There were always employees who insisted that the “old ways” were better. But, after a period of time, the employees who were most successful were the ones who figured out how the software could help them do their jobs better.

AI is going to become as ubiquitous as a calculator or a spreadsheet. The question isn’t whether it will change your work. It’s whether you’ll be ready when it does.

For employees:

If you work for an employer, you’re probably going to need to learn on your own. Part of this is because companies consistently fail to train employees properly. If you wait for formal training, it may never come.

Lemkin’s advice is practical: “Pick an AI tool today. Train it yourself. Become the person at your company who knows how to make AI agents productive. That skill set is the new job security.”

For self-employed people:

AI can extend your skills without extending your costs or the amount of effort you put in. My vibe coding example is proof of that. But it also means your competitors can do the same. Staying ahead means staying curious and constantly testing new tools and new ways of working with AI.

Final thoughts:

The labor market is being reshaped, and we don’t fully know the outcome. The workers who protect themselves are the ones who see this uncertainty and prepare themselves as best they can.

Want to build a life-first business? These reflections will help you determine your priorities.

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.

This week’s Perspectives is an interview with . Hannah is the founder of Sunlight Tax, and she specializes in friendly, informative tax education for creatives, artists, and people who feel overwhelmed by the business world. Her mission is to empower creative people to set themselves up for long-term success and take control of the financial side of their careers through her program, Money Bootcamp. She also hosts the Sunlight Tax podcast.

As someone who has worked in banking/finance for most of my career, I found Hannah to have a very down-to-earth and refreshing take on taxes. You can connect with Hannah on Instagram, YouTube, TikTok, and LinkedIn.

Anna Burgess Yang: Tell me about your background.

Hannah Cole: I’m a total weirdo. I’m a professional artist. And that was what I knew I wanted to be when I grew up. I got my MFA, and I was actually a professor of painting at Boston University for a while. But at a few different points in my career, I had some really miserable experiences with accountants and with taxes. Terrible.

And like a lot of creative people, because of those awful experiences, I got a bit of an allergy to money. It was as though the world was saying, “Oh, you’re creative, then this isn’t for you.” Which is stupid. And inaccurate. But I passively absorbed that message.

Eventually, I got angry enough that I went back to school for accounting. I decided to specialize in taxes, in part just because I wanted to help my friends who were artists and creative people. Because it’s just so hard to even just be treated with respect when you are in that world.

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ABY: What motivated you to focus on education instead of tax services?

HC: I started out doing tax prep for creative people. But I realized a couple of things. One, tax prep is a commodity business. You will be ground to dust by H&R Block and TurboTax. Anyone doing this work might use tax prep as a loss leader and bring you in for financial advisor services or monthly accounting. So that was a business decision.

The other thing is that there is so much financial illiteracy in the U.S. The Tax Foundation just did a survey and found that tax illiteracy costs the average U.S. taxpayer $1,000 per year just because they don’t understand how tax brackets work.

Also, people don’t even realize the bad smell of random tax advice that’s coming from someone without a license, and not someone you should be listening to.

ABY: What type of education do you focus on?

HC: I went to Yale, and I wanted a grounding in a broad liberal arts education. One of the things I was interested in was linguistics and cross-cultural communication. I’ve come to realize that this is my skill and my gift to the world. I translate the language of culture and accounting to the world of creative, dynamic freelance people who are out there taking risks and doing cool work. But they’re flying by the seat of their pants on the tax and accounting side.

One thing I feel strongly about is treating people I’m talking to with respect. The work they’re doing is amazing. I just don’t assume that they’ve learned any tax information. We should be taught in high school. But nobody has a baseline. I teach the basics to everyone. I do over 50 tax workshops per year for big organizations.

ABY: What do you think are some of the big misconceptions self-employed people have about taxes?

HC: Most people don’t realize that self-employment tax is going to be more than half of their tax bill, and most of their taxes are paying into Medicare and Social Security. When you work for an employer, your boss is paying into those systems on your behalf. So when you’re self-employed, that number gets doubled, and you don’t even know what it is.

People are radically underestimating how big their tax bill will be, and then they don’t know how the quarterly tax system works. Some people are really diligent and try to do a good job. Maybe they’re even setting aside money in a separate bank account. And that person doesn’t realize that they’re going to get penalized because they don’t pay every quarter as the law requires.

ABY: What is a challenging part of this type of education that you’re doing?

HC: Honestly, it’s just my reach and the fact that I’m just one person. I’m pushing against a culture that is anti-tax and anti-tax education. When I teach people, I teach the civics behind why we pay into Medicare and Social Security. It’s essentially insurance and works like life insurance.

I find that after my workshops, people think the system is much fairer. There’s unbelievably bad press out there, and usually when people have the information, they feel better about the system and paying into it and what it provides for them.

ABY: Do you think self-employed people struggle with the “paperwork” part of their finances?

HC: Yes, I think so. And it doesn’t have to be complicated. But when you only have random bits and pieces of info, it’s hard. For example, a lot of people try to do their bookkeeping off of receipts. It’s incredibly common, and it’s a nightmare.

Having a separate business bank account is a better baseline for your bookkeeping. Just that little shift makes the paperwork so simple. But I think people lack information about even getting to that point.

ABY: What types of formats do you think do really well in financial education?

HC: One thing is timing. People only get their eyes opened when they’re experiencing acute pain. And that’s an awful way to learn. That’s nothow I want people to learn, but that’s when people pay attention.

I try to have a mantra in my own business: “Never waste your pain.” If something is awful, take a minute. Do what you need to do to clean up the mess. But also, let’s stop the pain so we don’t continue to have it recur. Because taxes are there every single year. How do you want next year to look?

ABY: And you have a book, Taxes for Humans! What prompted you to write it?

HC: I’ve always loved writing. But what prompted me is that someone reached out after one of my workshops. I had an email in my inbox from a literary agent. I talk about how civics can feel really good and build a community that we want. Putting systems in place empowers people to do the amazing work they’re doing. The agent said, “I think you have a real vision, and this would make a good book.”

ABY: On top of everything you do with Sunlight Tax, you’re also an artist. How do you balance those two things?

HC: I think balance is a bit of a myth. There’s no way I could do tax workshops, talk to clients, and then go into the studio. I’d just be thinking about tax stuff. So I work seasonally. I’m 100% in when I’m teaching taxes. And then after tax season is over, in July and August, that’s my studio time. After April 15th, I can turn things onto a low simmer, and I can just walk away and be in my studio. I love that.

Last year, I lost my studio and all of my life’s work. Twenty years of art in Hurricane Helene. Things happen, and there’s no guarantee. It’s not like a hurricane is supposed to come five hours off the coast up a mountain. No one was prepared for it.

I was applying for FEMA aid and made a little help page – sunlighttax.com. I figured – not wasting my pain — let’s make a little tutorial about this for everyone else.

Want to build a life-first business? These reflections will help you determine your priorities.

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.

Running a solo business can feel like operating without a map at times. Sometimes, you can stumble through the path, figuring things out as you go. Other days, you look around and realize that you’ve wandered pretty far off course.

One of the hardest parts is not having anyone to rely on for guidance. That’s why community matters so much for solopreneurs. Rather than operating in a vacuum, you can bounce ideas off other people. Or, you may find that community reduces your feelings of loneliness and isolation.

The sooner you find (or build!) a community, the easier it becomes to navigate the inevitable ups and downs of being a solopreneur.

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In 2022, I was working at a marketing agency. My manager was... not good at his job. In my prior role at a tech company, I’d been a manager for many years and recognized all the ways the company was spiraling under his indecisiveness and lack of experience.

After a few months of struggling under his leadership, I admitted to him that the job wasn’t working for me. I wanted to come up with some type of exit plan that could allow me to transition out, something I thought he’d be open to as a purported “people-first” company.

His response? He fired me the next day. The role had changed dramatically from what I was hired to do, and we both knew that its current iteration was not the right fit for me. When I said the words out loud, it gave him permission (in his mind) to cut me loose.

As someone who cares deeply about words, I found myself stuck in a strange linguistic limbo. When people asked what happened, I didn’t know what to say. “Fired” implies wrongdoing — like I violated company policy or didn’t perform. But I hadn’t done anything like that. But “laid off“ wasn’t the right phrase either, since it implies business decisions, like restructuring or budget-driven factors.

What actually happened was different: I lost my job because the environment was dysfunctional. The management was bad. The fit was off, not because of some failing on my part, but because the company didn’t know what it wanted from the role and then failed to set me up for success.

I found myself struggling to describe how the job ended, because we don’t have words for that scenario. In the end, I usually say simply, “I lost my job.” Sometimes I’ll say, “I was laid off.” But I refuse to say, “I was fired” because I didn’t do anything wrong.

Without the right language, employees absorb shame that doesn’t belong to them. And employers face no accountability for their role in the situation.

We don’t have employment protections

In many countries, employers can’t just fire someone because the situation isn’t working out. They have to prove cause.

In Japan, “at-will” employment doesn’t exist, and arbitrary dismissals can lead to serious legal consequences. Japan’s Labor Contract Act explicitly states that if a termination lacks “objectively reasonable grounds and is not found to be appropriate by general societal terms,” the termination is considered void. The Philippines takes a similar approach. Employees have a legal “right to security of tenure” and can only be dismissed for “just” or “authorized” causes as defined in the Labor Code. The burden of proof falls on the employer to justify why the termination was necessary.

The United States, by contrast, offers almost zero protection outside of organized labor unions. According to the OECD’s indicators of employment protection legislation, the U.S. is the least regulated country when it comes to dismissing individual workers. At-will employment — which is the default in 49 states — means you can be fired for almost any reason, or no reason at all, as long as it’s not explicitly discriminatory.

Americans have internalized a uniquely individualistic narrative around job loss. We assume that if someone lost their job, they must have done something wrong. The absence of structural protection becomes an invisible weight we carry. Institutional failures become personal shame.

How to reframe your story

Bad management is one of the leading causes of employee departure. According to data from BambooHR, 58% of people leave their jobs because of bad managers. Yet somehow, if the employer makes the decision to part ways instead of the employee, it’s the employee’s fault.

Employers often lean on vague language like “not a good fit.” It sounds neutral, but carries an implicit accusation: that the employee was somehow wrong for the role, rather than the role (or the management, or the culture) being wrong for the employee. The vagueness leaves you holding the bag (and on the financial hook) for a situation you didn’t create.

If you’ve been in this situation — or you’re in it now — here’s how to think about moving forward.

Document what actually happened. You may not need to use it, but having a clear-eyed record of the dysfunction helps you own your story. Write down the specific incidents, the patterns of bad management, and the moments when you tried to make it work. When you write it down, you have clarity. You’re less likely to rewrite history with yourself as the villain.

Don’t use their language. If “fired” doesn’t capture the truth, don’t use it. You can say “the role ended,” or “we parted ways,” or “the job wasn’t sustainable.” You don’t owe **anyone **an explanation that makes you the bad guy in a story where you weren’t.

Recognize the shame isn’t yours to carry. When a job wasn’t a “good fit,” that’s a problem with hiring. You were brought into a situation where you couldn’t possibly succeed. It’s not your fault that you got mixed up in it.

The standard career advice world tells us to never badmouth a former employer. There’s some truth to that. Bitterness isn’t a good look, and interviewers don’t want to hear you trash-talk.

But maybe the real problem is that we’ve made it taboo to call out dysfunction when we see it. We’ve created a system where employers can create toxic environments, make poor hiring decisions, and provide inadequate management — and then frame voluntary or involuntary departures as the employee’s fault.

Until we have language for “I lost my job because the company sucked,” employers will keep escaping accountability. And employees will keep bearing the brunt of those decisions.

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The stat that will surprise no one: more than 60% of meetings have no agenda at all. No stated purpose, no direction, no clear reason for existing beyond the fact that they’re already there. Research from Atlassian paints an even grimmer picture: meetings are ineffective 72% of the time, while 78% of people say it’s hard to get their work done because of meetings.

And yet, we keep showing up.

We know meetings suck. But yet, most companies/managers haven’t put in the effort to figure out better ways to collaborate (which might be asynchronously, at a coffee shop, cameras off, etc).

The issue isn’t that meetings are inherently bad, per se. I worked for a company that was very meeting-averse, because the whole team worked asynchronously. We’d only hop on a meeting when the back-and-forth via our project management tool started to get out of control. In that case, it was faster to hop in a meeting and hash things out (and document the decision after the fact).

But on the whole, many people don’t question whether a meeting is the right tool for collaboration. Instead of evaluating the options, we accept the calendar invite (and then wonder why we have Zoom fatigue by 3 p.m.).

Meetings as a default way of collaborating were born during a completely different era of work. Everyone showed up to the same building at 9 a.m., sat in the same conference room, and didn’t have technology to collaborate. Those constraints no longer exist, but the habits remain. They persist not because they’re effective, but because they serve a different purpose entirely: management’s need for visibility and control.

Stuck in a meeting rut

When remote work skyrocketed during the pandemic, it was an opportunity to rethink meetings. We didn’t. We just took the structure of a physical meeting and moved it online.

Not only that, but meetings increased. According to Microsoft’s own data from that year, weekly meeting time jumped 10% almost immediately after offices closed. For the average employee, this was an additional three meetings per week.

To a large extent, I get it. That was a very difficult time since many people abruptly changed their work environments (moving from in-office to a home workspace). People were overwhelmed, and it wasn’t the time to imagine new ways of working. But we’ve had plenty of time since then, and meetings are still terrible.

There’s also a disconnect between workplace flexibility and how meetings are structured. You can work from home, from a co-working space, from a different time zone. And yet, that flexibility rarely extends to how people collaborate. The contradiction is glaring. We acknowledge that people work best at different times and in different environments, but force everyone into the same synchronous meeting format regardless.

Part of this is about optics. Meetings create the appearance of productivity. People in meetings look like people who are working. For remote employees in particular, visibility becomes a proxy for engagement. If you’re not on camera, what are you doing? Meetings scheduled “in the name of transparency” are often just performative — a way for managers and leadership to skirt the harder work of trusting their teams to get the job done.

Asynchronous communication could handle many of these “updates” more efficiently. A written summary takes five minutes to read. I actually think this is a good use case for AI, scouring an email inbox (for example) and writing a succinct recap that keeps the team informed.

A 30-minute meeting takes 30 minutes, plus the context-switching on either side. But async only works if managers are willing to let go of the comfort that comes from seeing faces on a screen and hearing voices in real time. And have to come up with an asynchronous format that’s actually meaningful and not furthering performative work.

Rethinking how we collaborate

Too many people have made “meeting” synonymous with “collaboration.” Companies are stuck in the belief that if people aren’t on a scheduled call, they’re not really working together. But some of the best collaboration happens in writing, over days, with time to think. It happens while out on a walk, when the creative juices are flowing. It happens in environments that look nothing like a conference room or a grid of faces on a video call.

The solution isn’t “better meetings.” It’s questioning whether a meeting is the right tool in the first place.

Before scheduling one, ask yourself what you’re actually trying to accomplish.

• Quick question? How about a Slack message or a short Loom video.

• Brainstorming? Start as a collaborative doc that everyone contributes to before a short meeting.

• A decision that requires input from people? Maybe a 30-minute call, not 60 minutes, with the agenda shared in advance.

• Status updates? That’s a written recap. No meeting required.

If you’re on the receiving end of meeting invites, push back. Ask, “Can we do this async?” or “Do we need the full hour?” If you can, block off meeting-free time on your calendar. Protect this time so you can actually get work done.

True collaboration flexibility means having no default at all. If there’s no automatic assumption that a meeting is the answer, people are forced to actually think about the goal. “Easy for the system” (i.e., maintaining the structure of meetings) rarely means “effective for the people.” And the people — not the system — should be the driving factor.

Want to build a life-first business? These reflections will help you determine your priorities.

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Most people think of solopreneurs as a one-person machine. The solopreneur (according to social media…) sends invoices, juggles client calls, manages marketing campaigns, and troubleshoots their own website — all before lunch. It’s a compelling narrative because it celebrates endless hustle and grit.

But it’s also a myth. Solopreneurship simply means you make the business decisions. You don’t have to consult anyone else or wait for approval. It doesn’t mean you’re the only person doing the work.

Most solopreneurs eventually bring in support (including me, in my solo business). Hiring help doesn’t mean you’re “no longer a real solopreneur.” It’s a sign that your business is growing. You recognize the value of your time or the limitations of your skillset.

Smart solopreneurs hire help as an investment. Outsourcing work or projects can expand your bandwidth while still allowing you to maintain full control over the direction of your business.

When to bring in professional support

One of the hardest parts of running a solo business is deciding when to get help. Many solopreneurs wait too long because they assume they should be able to do everything themselves. But if you feel like you’re working endless hours or you’re spending too much time on tasks, it’s probably time to hire.

Think of hiring as a strategic business decision, not a financial “splurge.”

Accounting or legal help

The first category many solopreneurs consider is financial and legal support. They recognize that they don’t have the expertise needed — and financial or legal mistakes can be costly.

An accountant or bookkeeper can manage tax compliance, keep your books clean, and help you understand your cash flow. Their jobs are to be familiar with accounting and tax laws, so you don’t have to stress. Typically, accountants or bookkeepers provide ongoing (monthly) support.

Legal help becomes important as your business grows in complexity. A lawyer might review your client contracts or help you navigate trademarks if you’re developing a brand. Depending on your legal structure, you may also need a lawyer to help with documentation like Articles of Organization (for an LLC). You don’t need a lawyer on retainer. Even a few hours of legal support per year can prevent legal problems later.

A virtual assistant

A virtual assistant (VA) is often the first hire for solopreneurs who are stretched thin. A VA can manage your inbox, follow up with clients, organize your files, or complete other organizational tasks that eat up hours of your time each week.

I rely on a lot of automation in my business. Tasks are completed automatically in the background between apps (using Zapier). But eventually, I reached a point where I couldn’t automate anymore. Some work needs a human touch. It was either me, or a virtual assistant. I chose to hire a VA so I could focus on the more strategic/creative parts of my business.

Most VAs work on an hourly, project-based, or monthly retainer model. With the right VA, you can start small and expand later if needed. Even a few hours per week can give you breathing room and help you stay focused on the work that generates revenue.

Project-based work

Not every type of help needs to be ongoing. You might hire a specialist when you’ve hit the limits of what you can do yourself.

For example, for a long time, I created my own brand assets. Eventually, I hit the limits of what I could do in Canva and wanted a more professional look for my business. I hired a brand designer to create my logo, choose fonts, and clarify my brand messaging. He gave me hundreds of Canva templates for various purposes.

If you need a website, a brand refresh, or automation support, a temporary engagement with an expert might make sense. That way, you don’t have to spend your time acquiring skills you don’t otherwise need and can start using the “finished product” quickly.

Building a team that supports your business

Before I started my own business, I was a manager in the corporate world. Being responsible for other people’s career success was hard for me, and I don’t think I was particularly good at it.

Bringing on help as a solopreneur doesn’t mean you have to become a “manager” in the traditional sense. Often, you’re hiring other independent professionals, like you. With the exception of a virtual assistant (who has to learn your systems/processes), the people you hire may not need a ton of oversight or hand-holding.

Bringing in help doesn’t have to mean building a team in the traditional sense. But before you hire, you should consider these three things:

• Revenue stability: Can your income support this additional expense?

• ROI: Will freeing up your time allow you to earn more or reduce stress in a meaningful way?

• Alignment: Does delegating this work directly support your business and create value?

If the answer to any of these questions is “no,” you may not be ready to hire yet.

Solopreneurship doesn’t mean doing everything alone

Your business works best when you’re working in your strengths. The rest can be delegated or outsourced.

I’m not a designer, so I hired someone to help me with design. I’m not an accountant, so I hired someone to help with my bookkeeping.

You’ve got to know which parts of your business you should hand off so your business can thrive. The goal isn’t to grow headcount, like a traditional business would grow. It’s about protecting your time and energy — the greatest assets your solo business has.

Thank you for your support of Work. Better. If you want me to answer a question about careers or career pivots that you’d like me to answer in a future issue, send an email to annabyang@substack.com.

Not all career pivots have the same impact on your life.

I’ve made several career pivots in my life — some by choice, some not. I made a clear decision to leave a 15-year career in fintech to try something new. After eight months at a marketing agency, I left and joined another agency (not really a pivot, just a job change). I was laid off a year later and started my own business. Each of those transitions felt completely different.

When people talk about pivoting, they often lump everything together. But understanding what kind of pivot you’re making (or considering!) can help you approach it with the right mindset. A pivot born from boredom requires different energy than a pivot forced by a layoff. A pivot driven by curiosity looks nothing like one driven by fear.

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Not every pivot will fit neatly into one of these categories, but identifying your primary driver can help you figure out what you actually need.

1. The forced pivot

This is the pivot nobody wants, but many of us experience. You get laid off. Your company folds. You face industry upheaval. Suddenly, the path you were on doesn’t exist anymore.

Forced pivots are really disorienting because they can strip people of part of their identity. One day, you have a job and an identity attached to it. The next day you’re updating your resume and wondering what just happened.

The silver lining (if there is one) is that forced pivots often push people toward things they wouldn’t have chosen on their own. I had been considering a new path as a freelance writer, but the timing never seemed right. At what point would I have made the leap on my own? Who knows. But losing my job forced the situation.

Let me be clear: I do not think “everything happens for a reason” or any of that nonsense. You are not meant to lose your job so that you’re forced into a stressful situation. I only mean that stressful situations might force you to consider options you otherwise might not have considered.

If you’re in a forced pivot, give yourself permission to grieve the old path before rushing into the next one. But if your financial stability is at stake, speed also matters. You’ll need to adapt quickly, even if you don’t feel ready.

2. The anticipatory pivot

This is the pivot you make before you’re forced to. You see the writing on the wall that your current work won’t be viable for much longer. Maybe it’s AI reshaping your industry. Maybe it’s a shift in market demand. Maybe it’s your company slowly sinking. You decide to move before the decision is made for you.

Reactive pivots require foresight and a willingness to act on information that isn’t yet urgent. Most people wait until the disruption hits them directly. If you can anticipate the change and reposition yourself early, you’ll have more options than those scrambling after the fact.

The risk here is acting on a prediction that doesn’t materialize. Let’s say your company announces a merger with another company, and you think, “I don’t want to stick around for that, I’m out.” So you spend a lot of time and energy finding a new job. Then after you leave, the merger falls apart.

But the bigger risk — for most people — is waiting too long and having the forced pivot happen anyway.

3. The growth pivot

This type of pivot comes from a different place: you’ve outgrown your current role and want something new. Maybe you’ve mastered the skills required, or maybe you’ve hit a ceiling at your current organization.

Growth pivots are driven by a desire for challenge. You’re not running away from something; you’re running toward something. You want to learn new skills, take on bigger problems, or finally make the jump to a different type of role (like managing a team or a decision-making role).

The tricky part? Depending on how much you’re itching to try something new, you might jump into something too quickly and end up in a role or at a company that isn’t the right fit. You don’t want to spend a lot of time and energy looking for a new job only to find yourself at a job you hate.

It also can be difficult to find a new job that requires the skills you want, but don’t have yet. You know you can do the role, but the hiring manager has to be convinced of the same. And, from an employer’s perspective, hiring someone who has “done the job before” is a safer bet than taking a chance on someone.

Growth pivots require you to be honest about what “growth” actually means to you. Is it a title? More money? More autonomy? More impact? The answer will shape what kind of move makes sense.

4. The boredom pivot

This is similar to the growth pivot, but with a crucial difference: you’re not just looking to go up in your career. You’re looking for different.

Boredom pivots happen when the work itself no longer holds your interest. You could keep doing it, and you’re probably really good at it. But you’ve mentally checked out and you’re not sure you can fake enthusiasm in a similar role at another company. This type of pivot often leads people to change industries or start their own business.

This is a harder pivot to justify to others (and sometimes to yourself). “I was bored” doesn’t sound as legitimate as “I wanted to grow” or “I got laid off.” When I told people that I’d quit my executive job at a tech company, I said, “I’m pursuing work I love” (writing).

Boredom is real, and staying in work that doesn’t excite you has costs: your energy, your creativity, and (eventually) your performance. You can’t do your best work if you’re just churning out the same output over and over.

Start paying attention to what does interest you, even if it seems unrelated to your current career. That’s often where your next chapter is waiting.

5. The exploration pivot

This is the pivot fueled by curiosity. You’re not unhappy where you are. You’re not bored. You dind’t lose your job. You just... want to try something else.

Exploration pivots are common among self-employed people and solopreneurs. Your first exploration might be making the leap from corporate to solopreneur. As you build something of your own, you might decide to add a new income stream or test a new product or service.

Think of this type of pivot as experimentation. You’re willing to try something totally different, even if you’re not sure what the final destination will be.

With an exploration pivot, you have to embrace discomfort. You have to be comfortable being a beginner again, and you need enough natural curiosity to put in the time to learn something new. You’re constantly making changes based on what you’ve learned.

What kind of pivot are you considering?

If you’re feeling like you need to make a change, it’s worth asking yourself which of these types of career pivots is driving you.

Most pivots aren’t purely one type. My pivots were a combination of several factors. But understanding the primary driver can help you set the right expectations, identify the right timeline, and find the right support.

Want to build a life-first business? These reflections will help you determine your priorities.

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What happens to your work when you truly can’t keep all the plates spinning?

I’m not talking about a head cold. I’m not talking about a mental health day. (Though I think it’s important to take days as needed and don’t feel like you have to power through).

I’m talking about when your body or mind makes a demand in a way that overrides everything else. When work falls to the absolute bottom of your priority list because you have to put yourself first.

Last year, I found out that I had a brain tumor. It was benign, thankfully, but it still required surgery and a long recovery. It wasn’t the type of absence where I could check in occasionally while lying in bed. I had to completely step away from work for almost two months.

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For anyone who has faced a serious illness — cancer, autoimmune conditions, surgery, mental health crises, etc. — you know how quickly the ground can shift beneath you. One day, you’re worrying about deadlines, deliverables, and the next meeting with your client/boss. The next, you’re trying to process what your doctor just told you while your mind swirls around the question, “What will happen to me?” The dissonance is staggering.

Once you have your bearings, you realize that you have to deal with more than just the personal impact. You have to figure out what will happen at work.

The illusion of indispensability

We’re conditioned to believe we are indispensable. That if we step away, everything will fall apart. Our value is tied directly to our presence and output.

I’ve taken maternity leave three times throughout my career (plus two extended leaves after pregnancy loss). Set aside the fact that paid maternity leave doesn’t exist in the U.S., but I felt pressure to continue interacting with my employer while on leave. I answered emails and handled a few projects behind the scenes. I worked for a small company and definitely had a “What will they do without me?” mentality.

Stepping away to recover from brain surgery was different because the recovery was non-negotiable. I had to stop, no matter how I felt mentally. Every instinct screamed at me to keep going. To not become a burden or inconvenience to my clients and people around me. Internal pressure is baked into our workplace systems, whether we’re working for an employer or working for ourselves.

On top of that, when you’re facing something serious, colleagues often don’t know how to step in (or don’t realize they should). The work piles up. No one picks up the slack, because there’s no road map for “what comes next” with major medical issues. That feeds into the perception that we’re indispensable.

A study from the University of South Florida identified an implicit or explicit expectation that you show up, no matter what. The study refers to this as “presenteeism pressure.” But pushing through comes at a cost: recovery may take longer. And it also takes a toll on mental health, since you’re putting work ahead of health.

A major medical issue can feel like you’re falling off the edge of the world, with no clear path back. Outside of the need to step away from work, suddenly you’re in a different place from everyone around you. They’re exchanging their time and skills for a paycheck. You’re doing the same, while also trying to survive an intensely difficult time in your life.

Helping others

I wish I could tell you that the solution is systemic change. Countries outside of the U.S. have figured out that paid sick leave should be a mandatory benefit. Step away from work, take care of yourself.

But here, there’s no such security. People drag themselves to work when they’re sick because they’re afraid of losing income (or, worse, their job and health insurance). Or they’re afraid of “letting the team down” or “being a burden to others” because it is so ingrained in our culture of Every Person For Themselves.

I have no illusion that companies will suddenly start treating illness like the human reality it is. Instead, change will come at the person-to-person level in how we take care of each other.

If you work for an employer

Take your sick time. I know that sounds obvious, but so many people don’t. Use whatever you’re allowed to take, without guilt. Paid time off is part of your total compensation package, so not taking sick leave is effectively donating your time to the company, when the company should be paying you not to work.

You may not be able to overhaul a company’s lack of a backup plan, especially for an extended medical leave. But you can request better documentation, cross-training, and coverage plans. These can be the difference between feeling supported and lying awake at night panicking about what’s happening in your absence.

Be the person who steps up when someone else steps away. It doesn’t have to be a grand gesture — that’s for the company to figure out. But you can take something off that person’s plate, or send a message that says, “I’ve got this. Focus on yourself.”

If you’re self-employed

This is admittedly harder, especially if you’re running a solo business. You don’t have a team you can turn to. At best, you can have systems in place so things continue to run smoothly, even when you’re away.

Designate someone who can triage things like incoming inquiries or anything critical that might potentially come up (think of it as a solopreneur buddy system). Automate what you can: invoices, recurring communications, project updates. Document your workflows so that if someone else ever needs to step in, they’re not guessing.

Stepping fully away from my business to recover from surgery was incredibly hard. I wondered if everything would collapse without me there. But I prepared as much as I could and had to hope for the best, because working after brain surgery was simply not an option.

Asking for help

People in our lives often don’t know how to support us. They’ll say, “Let me know how I can help.” I hate this, because it puts the burden on the person who needs help to think of something. But the reality is, in a situation like work, they don’t know what would be helpful to you.

If you’re facing a health crisis, prepare your responses to this question. As soon as you can think clearly, make a list. When someone offers to help, reply, “Actually, if you could do XYZ thing for me, that would be great.” As much as you can, match the ask to the person’s interests or skillset.

We treat health crises like a very individual problem, even though most health crises are completely outside of our control. Bodies break down. Work culture that doesn’t account for this is unsustainable at best and inhumane at worst.

If you go through something in your life, take care of yourself first. It’s ok to lean on other people, even at work (especially at work).

And if you know someone going through a major medical issue, be the person who shows up and offers real support.

If you need to step away from work, this free guide walks you through everything you need to do to prepare.

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