What nobody tells you about starting over mid-career
Your skills are more portable than you think.
In 2021, I left my career at a tech company after 15 years and decided to pursue content marketing and journalism. The first marketing agency that hired me assigned writers to levels — 1 through 9 — based on experience. I came in at a level 2, the second-lowest. Fifteen years of product management, executive leadership, and deep domain expertise in financial technology didn’t “count” for anything. In this new world, I was a beginner.
That part of career pivots is often uncomfortable. We hear about the bold decision to quit. We hear about the eventual success story. But there’s a space in between where everything you knew in your prior career doesn’t quite translate yet.
It’s humbling in a way that catches people off guard, especially at mid-career, when you’ve spent years not having to prove yourself. I went from being the most knowledgeable person in the room to the least. And for a while, that felt like starting over from zero.
But it wasn’t zero. Not even close.
Nearly 70% of U.S. workers considered changing careers in early 2025. That number is a reflection of the current economy more than anything else — people can’t find new jobs in their current industries, or the industries themselves are shifting underneath them. More than 38% of new freelancers in 2025 were previously laid off.
Those numbers suggest something that the fear of starting over tends to obscure: the gap between “I left” and “I landed” closes faster than most people expect. The expertise from a previous career doesn’t evaporate. It’s waiting for the right context.
What actually transfers
The narrative around career pivots tends to focus on what gets lost: title, salary, status, and the expertise that took years to build. But the more interesting story — and the one I’ve lived — is what transfers to a new career path.
After I quit my fintech job, I worked at two different content marketing agencies. Eighteen months later, I was laid off. The job market had tanked. I decided to go out on my own as a freelance writer, something I’d been considering. The layoff forced me to make a decision: try to find a job in a crappy job market, or make the leap.
What I didn’t expect was how much my fintech background would become a competitive advantage. I assumed that most clients would see me the way the first content agency did: a level 2 writer, with very little experience.
But most writers can’t speak the language of banking technology. Most fintech experts can’t write. The combination turned out to be rare and valuable.
The same pattern showed up in other ways. The systems thinking I’d developed as a product manager — implementing automation, streamlining processes, evaluating software — transferred directly to running a solo business. I’d spent years at a small company finding ways to make processes faster and better for my team. As a solopreneur, those same instincts kicked in. Except now the team was just me, and I reaped all the benefits.
The broken promise and the new path
Over the past few years, something has shifted in how people think about career risk. It used to be common sense: a corporate salary equals security. Self-employment is the risky path.
Like many people, I grew up believing that if you stick with your employer, stay loyal, and put in the time, you’re going to be rewarded. I think people just don’t believe that anymore. The social contract between employer and employee has broken. If the loyalty won’t be reciprocated, the job becomes unfulfilling. On top of that, people are constantly nervous about layoffs. Or restructuring. Or the next round of cuts.
Here’s how I think about it now: both paths carry risk.
With a traditional employer, one day you have a salary, and the next day you might have nothing. When I was laid off from the marketing agency, that’s exactly what happened. No warning, no safety net beyond a piddly amount of unemployment. The U.S. has almost no protections for employees (whereas other countries have things like mandatory notice periods and mandatory severance).
Working for myself, if I lose a client, that’s a fraction of my income — not my entire income. I purposely work with a couple of core clients and then take on additional projects as they come. My income is more variable, sure. But it’s never 100% to zero. I feel more secure now than I would if I were working in a corporate job (And I realize how counterintuitive that sounds to someone who grew up thinking self-employment was the riskier path.)
Self-employment isn’t a consolation prize for people who couldn’t make the traditional path work. It’s increasingly what sustainable careers look like — especially for people who’ve already navigated one or two major shifts. And the assumption that any particular industry is safe? That’s gone.
If you’re sitting in a job that no longer serves you, wondering if you have what it takes to try something else: you probably do. The expertise you’ve built isn’t wasted. It’s more portable than you think. It’s only a question of how long before your old career catches up with your new one.
Thinking about a career change? Download my guide: 5 Types of Career Pivots.
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