After spending many years working for myself, I’m regularly approached by people thinking about making the leap from a traditional job to freelancing or self-employment. Two themes always come up in these conversations: risk and difficulty on one hand, freedom on the other. I might tackle the first topic in a future post, but today I want to share some thoughts on the second.

The surprising truth about freelance freedom#

When people ask me if it’s nice to be free, I always give the same answer: when you’re self-employed, you’re absolutely not free. In fact, you’re probably even less free than when you had a regular job. But here’s the thing—the illusion and feeling of freedom? That’s genuinely wonderful.

This usually surprises people because it doesn’t match the image we have of entrepreneurship. We picture flexible schedules, working from anywhere, being our own boss. The reality is quite different.

The constraints nobody talks about#

If you start from the principle that you want to serve your clients as well as—if not better than—you’d like to be served yourself (which, in my view, is the absolute foundation of this work, whether some people have figured that out or not), you quickly realize something uncomfortable.

You need to be available for your clients in the evening. In the morning. On weekends. You constantly rearrange your schedule to satisfy one client or another. You have to be highly responsive, sometimes immediately so. These are real constraints, and they don’t go away just because you’re your own boss.

Why employees actually have it easier#

In a traditional job, you can manage these pressures much more effectively. You can delegate. You can ask for help. You can take more time. You have colleagues to share the load. And let’s be honest—less scrupulous employees have no shortage of ways to manage expectations that simply aren’t available to the self-employed.

Where employees have room to maneuver, freelancers have only one option: lower the quality of service to their clients. And I don’t know about you, but for me, that’s simply not an option.

The science of believing you’re free#

I recently read a scientific article explaining that simply thinking about exercising has a measurable impact on muscles, even when they don’t actually contract. I’m no psychologist, but maybe the feeling of being free actually gives you a little bit of real freedom. That wouldn’t surprise me at all.

There’s something powerful about perception. When you believe you have choices—even if those choices are constrained—you approach your work differently. You take ownership. You feel responsible in a way that energizes rather than burdens.

The magic is in the illusion#

What’s truly magical about being self-employed isn’t the freedom that comes with it, because that freedom doesn’t really exist. It’s the illusion of being free. And that, I’ve come to believe, is priceless.

The feeling that you chose this path. The sense that every constraint you face is one you accepted willingly. The knowledge that if things change, the decision to adapt is yours to make. None of this makes you objectively freer—but it makes the constraints feel completely different.

So if you’re considering the leap to freelancing, don’t do it for the freedom. Do it for the feeling of freedom. That distinction might sound small, but it makes all the difference.