The word “freedom” shows up constantly in conversations about work — everything from debates about return-to-office mandates to freelancer lifestyle content.
A 2025 Randstad report found that more than half of workers would give up higher pay for more control over their working hours. But what most people describe when they say they want “freedom” what they actually mean is flexibility. They want the ability to take an afternoon off for their kid’s soccer game or maybe skip the daily commute when the weather is bad.
Flexibility is what an employer offers you, most often with constraints. You might have a hybrid schedule that requires an in-office presence three days per week or working core hours. Workers have to operate within those constraints.
Freedom is something else. Freedom is the ability to make the choice yourself — not just when and where the work happens, but what the work is and who it’s for.
Most conversations about work don’t make that distinction. Flexibility is certainly one component of freedom, but freedom goes further. And once you start thinking about what you’re choosing between, you realize that every work arrangement trades one kind of freedom for another.
Every work arrangement is a trade
For more than a decade, I worked in a very unique setup, called a Results-Only Work Environment (ROWE). Even though I had an employer, I had complete autonomy over when and how work got done. Only the results — a designated end point — mattered. If I wasn’t feeling well, I could simply take the day off and wouldn’t need to ask for permission. Working around my kids’ school calendar was easy.
I had the ultimate flexibility, and for a long time I mistook that for freedom. It was hard to imagine working for another employer where my working hours might be constrained in some way. But the tradeoff was working toward an employer’s goals, which eventually became misaligned with my own.
Subsequent employers (two of them) imposed the exact constraints I feared. My last employer before going solo had a four-day workweek. At first, that seemed amazing, but eventually I realized that the other four days were a grind. Butts in chairs at 8:00 am, working nonstop until the end of the day, to cram five days’ worth of effort into four days. The tradeoff was less schedule control for other things I valued. Eventually, that was no longer enough, and the best option, for me, was to work for myself.
But no work arrangement gives you everything. An employee trades full autonomy for stability: someone else sets the direction, but the paycheck is predictable. A self-employed person trades stability for control: the income fluctuates, but the work is self-directed. There’s no safety net, but also no ceiling.
We talk about these arrangements as if they exist on a spectrum from “less free” to “more free,” with self-employment sitting at the top for people who want to maximize their freedom. But that framing is wrong, because there are still trade-offs. The question is which trade-offs you’re willing to make.
I have to look at money differently than someone who has an employer. For some people, that’s unfathomable because they like the “freedom” that a reliable income brings.
Instead, I think it’s wrong to pit self-employment and working for an employer as more or less freedom. Instead, the actual freedom comes from the ability to choose.
The difference between choosing and settling
The real dividing line in all of this is whether you chose your trade-offs from a position of genuine options… or if you’ve accepted your current work situation because you felt like you had no good options.
There are two versions of being trapped. The first is staying at a job you’d leave in a heartbeat if you could, because you rely on an employer’s health insurance (a structural constraint). The other is being self-employed, not because you chose it, but because the labor market sucks and you weren’t able to find a full-time job. In both cases, the arrangement chose you.
The freedom conversation often assumes that self-employment is the destination. That if you just had enough savings or enough clients or enough grit, you’d obviously prefer to work for yourself. But that’s not true for everyone. The trade-off of instability — unpredictable income and no employer-sponsored benefits — may not be worth it. The constant mental weight of running everything yourself is its own kind of cost.
On the podcast The Vergecast, senior reporter Elizabeth Lopato said:
“I don’t want to make a business. I have a job because I don’t want to think about accounting, and I don’t want to hire my own libel lawyer. I want to write things that are meaningful, and the more time I can spend doing that, the better. And one easy way for me to do that is to have a job where all I do is write. And somebody else takes care of the business stuff.”
Choosing to stay with an employer because you want stability is a valid choice. Freedom at work is what you choose to build your career around. The trade-offs don’t disappear — whether you’re employed or working for yourself, something is always being exchanged for something else. But when you’re making decisions about trade-offs, when you pick them from real options and decide you can live with whatever you’re giving up, that’s real freedom.
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This nails the distinction most 'be your own boss' content skips over, flexibility and freedom get treated as the same thing and they're not. The Results-Only Work Environment example is the clearest illustration I've seen of how much autonomy can still come with strings attached. Every arrangement has a cost, the real question is just who gets to choose it.