For entrepreneurs, “freedom” too often means having a choice in what kind of cage you’ll find yourself in once you double down on your business.
I ran into a meme on Twitter last week where people were joking about quitting their nine-to-five to work 24/7 instead. It often feels that we have to endure a lot of restrictions on our path to freedom. Or at least that’s what I told myself for the last decade.
My friend Dagobert Renouf commented on that meme, too. He pointed out that there is a difference between freedom and autonomy, and I want to dive into this very important distinction today.
Freedom and autonomy are often mixed up, especially by entrepreneurs. Just because you start a business doesn’t mean you’re free. You might not have a boss who can order you around, but if you want to make money and grow the business into something meaningful, new constraints arise.
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To many of us (who want to escape employment), freedom means doing what we want. We long to build something for ourselves, not just create value for others and be compensated for our time. But starting a business brings its own rules. To sustain your quest for freedom, you have to keep things running smoothly, like making sure your software company’s servers are up, and customer support is responsive.
If you can’t guarantee that, your business will fail eventually.
And that guarantee is the opposite of freedom. It’s an all-encompassing threat to your freedom, and many founders deplete their mental health reserve quite significantly when dealing with downtime and enraged customers.
The only freedom I have seen in the entrepreneurial world is the post-multi-million exit mindset of post-economic decision-making: when you stop thinking about paying the mortgage and start thinking about how to invest your wealth while it can sustain you indefinitely already, you have removed a major constraint.
But that happy moment is in the future for most of us. Right now, we’re chasing freedom.
And I think we should get rid of both the word and the idea of it being a reasonable thing to strive for.
Instead, let’s embrace autonomy. It’s a better concept for a more pragmatic approach.
Being an entrepreneur does let you build the business you want, but once it’s up and running, your freedom is pretty much gone. Instead, you have gained autonomy.
You set your own rules and decide what your business will do—and won’t do. No more decrees and memos from the boss. That is now you. On my podcast, Channing Allen and I discussed this and how it impacted the IndieHackers.com business. We talked about choosing the constraints that shape your business — for the IH founders, that meant pausing their wildly popular podcast because it’s a resource drain. It was a tough choice, but it was a choice they made intentionally and willingly.
True autonomy means being able to say no—to work, customers, features, products, and events. Maybe even to running a podcast.
But when you’re starting out, you don’t have the luxury of employing your autonomy like that. On your path to product-market fit, you often have to say yes just to see what works. Building a new business is unique every time; it’s an experiment with many choices. No two businesses are alike, and you have to try things to see if they might work for you and your unique combination of circumstances.
Here’s another limitation, particularly for us notoriously undercapitalized bootstrappers: we must make tough decisions about who our product serves and who it doesn’t. You can’t please everyone. And you shouldn’t try. A well-defined niche or a clear vertical is a must for a business built around a specialized product. And again, your freedom to do whatever you want is limited here. Niche product, niche people, niche strategies. Committing to this is picking a set of constraints you can and want to live with.
And when you get started, you have no one to tell you what to do. For most of us, this means we have and ultimately want to do everything. Hence, the meme about entrepreneurship eating 24 hours a day.
It’s not wrong.
Running your own business might take more time than a full-time job. And while it takes away some freedoms, like free time, it gives you control over important choices that affect your wealth and legacy. That’s the trade we make. And by “we,” I mean a particular kind of people.
Autonomy attracts problem solvers who want to create something lasting—not just make money for someone else or even themselves. The lure of entrepreneurship is more than that million-dollar exit. Don’t get me wrong, we all want to get there, but the journey matters just as much as the destination. You get to set your own goals and work towards them at your own pace, using your own methods.
Some people are scared by this. They would rather have clear structures to operate in. They prefer executing processes over establishing them. It’s a perfectly fine choice, if you ask me, just not one with much autonomy.
It’s not impossible to have both, though.
Full-time entrepreneurship can be demanding and, frankly, too much for some people (at least where they are in their lives right now.) It might be better to find autonomy in a career while exploring side projects without the pressure of needing immediate income. The constraint of having to get to revenue in a few months is massively impactful on your mental health. Take the slower but less explosive side project path if you want to pace yourself.
Look for autonomy in the right places before diving into entrepreneurship full-time.
And this, as my final point, particularly applies to advice.
Choosing who to listen to as an entrepreneur is tricky. There’s tons of advice out there, and it’s important to pick the right voices to guide you. This is a big part of your power as a founder, your decision-making autonomy, along with setting your own goals and path.
Here’s what I do: I personally tune in to those who are where I hope to be one day. I focus on people living the life I dream of, which means I often skip advice from others, even if they’re hugely successful.
I talked about bootstrapping earlier. Well, there are many other ways of funding your founder journey. I admire venture capital-funded founders who run big companies, but that’s not the life for me. So, I don’t follow their advice, and I don’t read the blogs they read or listen to the podcasts they enjoy. Instead, I look up to those who have limits and constraints similar to the ones I want for myself over the next five to ten years. People like Jay Clouse or Amanda Goetz. My people. By listening to them, I learned about an indie-founder-compatible kind of freedom and just how powerful autonomy is for creators. Yet, still, I get to see people who take breaks, prioritize their families, and tune out work when they don’t feel it.
Now, that is the kind of freedom I want to see in my own life. The empty calendar. The “sure, let’s talk a walk right now, why not” lifestyle.
I’ve seen people work just a few days a week on projects that grow massively over time, and that’s what I want. So, I’ve been taking advice from people who live that. And if I’d listened to others, who knows, I might not be where I am today.
