Nobody Tells You Freedom Has a Billing Rate
This year in 2026, I turn 40. I’ve been self-employed since I was 25.
That’s fifteen years of answering to no one, setting my own hours, and being my own boss, which, as it turns out, means answering to everyone, working all the hours, and reporting to the most unreasonable boss I’ve ever had.
I mostly love what I do. I want to be clear about that before I say what I’m about to say.
I am not writing this from a place of regret. I’m writing it from a place of hard-won clarity, the kind you get after watching the entrepreneurship narrative play out in your own life long enough to see where the brochure diverges from the building.
Here’s what I’ve learned: we need to stop telling people that starting a business is the ultimate unlock to freedom and wealth. Because for most people, it isn’t. And the continued perpetuation of this myth is doing real damage to real people making real decisions about their one finite life.
Entrepreneurship Is a Job You Can’t Quit
There’s a particular irony that only the self-employed will truly understand.
You leave a job because you want more control over your time, more autonomy, more upside. And then, slowly, through a series of completely logical decisions, you build yourself into a new job. One with worse benefits, no paid vacation, and a manager who sends emails at 2 AM because he doesn’t understand boundaries.
That manager is you, of course. And they’re kind of a nightmare.
Most entrepreneurs don’t build businesses. They build jobs. Jobs where they are simultaneously the janitor and the CEO, the sales team and the fulfillment department, the visionary and the person updating the WordPress plugins at midnight because the site went down again.
And that freedom everyone talks about?
Sure, it exists, theoretically. You can take Tuesday off. You can work from anywhere. You can structure your day however you want. But freedom without financial margin is just anxiety with flexible hours. And for most self-employed people, the margin is thin and a Tuesday off means Wednesday is going to suck.
I’ve been on vacations where I spent four hours a day on my laptop in the hotel room looking at ad dashboards. I’ve missed family events for client emergencies. I’ve had months where the “freedom” of self-employment meant the freedom to not go out on the weekend or pay myself so I could make it through the month. That’s not even a complaint, it’s just the math.
Survivors Are Loud; Statistics Are Quiet
Here’s the thing no one acknowledges about the entrepreneurship narrative: it’s written by survivors.
The people who write the books, give the TED talks, and post the LinkedIn manifestos about “betting on yourself” are, by definition, the ones for whom the bet paid off. You don’t hear much from the ones who went back to traditional employment after three years of grinding, a depleted savings account, and a marriage that got stress-tested past its limits.
This creates a sampling bias so severe it borders on disinformation. We hear about the wins because the wins are worth talking about. We don’t hear about the quiet returns to cubicles, the businesses that “pivoted” into shutting down, the entrepreneurs who discovered that their appetite for risk exceeded their tolerance.
The outcomes you see and read about are uncommon.
They’re not impossible, and I’m not trying to suggest they are. But they are exceptional by definition.
The median outcome of starting a business is not a lifestyle brand and a beach house. The median outcome is a lot of work for uncertain returns, followed by a return to employment with a few good stories and a complicated relationship with the phrase “passive income.”
Meanwhile, the boring path; the one where you join an organization, develop expertise, grow with the company, get promoted, and make solid investments over time produces successful outcomes so routinely that nobody writes articles about it. There’s no memoir in becoming a senior director over twelve years and maxing out your 401(k). But there might be a lake house.
The Rocket Ship Theory of Career Success
Here’s a framework I wish someone had given me at 25: instead of asking “How do I start something?”, ask “What’s already moving that I can get aboard?”
The most reliable path to wealth and stability isn’t building a rocket ship from scratch. It’s finding one that’s already achieved escape velocity and getting yourself a seat.
This means identifying organizations with genuine momentum, companies that are growing, industries that are expanding, teams that are winning, and positioning yourself to ride that trajectory upward.
This has nothing to do with being unambitious. Quite the opposite.
It’s about being strategic with the one career you have. When you join a rocket ship, several things happen that are nearly impossible to replicate as a solo operator:
Your growth is subsidized. Someone else is paying for your education, your mistakes, your professional development. You get to learn on their dime while they pay you for the privilege.
Your network compounds automatically. Every colleague, every client relationship, every cross-functional project adds nodes to a professional network that will pay dividends for decades. This happens almost passively when you’re embedded in an organization. As a self-employed person, networking is a deliberate, time-consuming activity that competes with billable work.
Guess which one usually wins?
Your upside may be capped but your downside is also floored.
Yes, you probably won’t become a billionaire working for someone else. But you also probably won’t have a month where you make negative money. The stability isn’t exciting, but excitement gets old quick when you’re trying to build a life.
Add In The Isolation
Nobody talks about how lonely self-employment can be. Or rather, people talk about it in some romantic, misunderstood-artist kind of way, as if solitude is a feature rather than a bug.
Trust me, it’s a bug.
When you work for yourself, you lose access to the professional development that happens organically in organizations. The hallway conversations, the lunch discussions about industry trends, the osmotic absorption of how things work at scale.
You lose access to mentors who are invested in your growth because your growth benefits them. You lose access to peers who challenge your assumptions because they’re stuck with you every day.
Instead, you get Twitter threads and online communities and masterminds you pay to attend.
These aren’t nothing, but they’re not the same as being embedded in an institution where your professional growth is structurally supported rather than something you have to manufacture in your spare time.
I’ve spent fifteen years building expertise in relative isolation. I’m good at what I do, some would say really good, but I sometimes wonder how much further along I’d be if I’d spent those years inside organizations with resources, training budgets, and senior people who had reasons to invest in my development beyond my ability to pay them.
And The Wealth Building
Here’s where the math gets uncomfortable for the entrepreneurship narrative.
If you take a stable job with a growing organization and invest consistently in low-cost index funds and real estate over a 30-year career, your probability of retiring with significant wealth is remarkably high. Not guaranteed because nothing is guaranteed, but high enough that actuaries build pension models around it.
The S&P 500 has averaged roughly 10% annual returns over the long term. Real estate, held over decades, appreciates while providing tax advantages and forced savings through mortgage paydown. A person who earns a solid salary, lives below their means, and invests the difference, will, with high probability, turn 60 with real wealth.
Now compare that to the entrepreneurship path.
The failure rate of small businesses is well-documented, and depending on how you define failure, genuinely grim. The ones that do actually survive often provide a living but not wealth. The ones that provide wealth are the exception, not the rule.
I’m not saying don’t take the risk. I took the risk, and I’d probably take it again.
But I am saying: understand the probabilities. Understand that the boring path has better odds. Understand that the stories told about entrepreneurship are survivor bias compressed into motivation.
So What’s The Move?
Honestly, I have no idea. If I’m being this clear-eyed about the math, and why have I done this for fifteen years, and Why do I continue to do it, is mostly because some of us just aren’t wired for the alternative.
We don’t do well with authority.
And also because the thing that makes entrepreneurship hard; the responsibility, the uncertainty, the requirement that you figure it out yourself, is also compelling.
But that’s my answer. That’s not advice. It’s a personality trait that I’ve been lucky enough to channel into something sustainable.
What I’m trying to say here, is, as I approach the age where “someday” is getting a lot closer than it used to be, I’ve come to realize that we owe people a more honest conversation about self employment.
We owe them the math alongside the mythology. We owe them the understanding that working for yourself is a path, not the path, and that the other paths deserve more respect than the hustle culture industrial complex has given them.
If you’re reading this and you’ve been feeling guilty about not starting something, not betting on yourself, not taking the leap. I want you to know that the guilt is manufactured. It’s a byproduct of a narrative that benefits the people selling courses about how to escape the 9-to-5, not necessarily the people sitting in the audience.
Finding an organization with momentum, contributing to something larger than yourself, building a career through steady growth and strategic moves, that is not settling. It’s not playing it safe in some pejorative sense. It’s a legitimate strategy with better odds than the one being sold to you on instagram, youtube and tiktok by people who need you to believe that their path is the only respectable option.
You can build wealth. You can have a meaningful career. You can maintain your dignity and your ambition. And you can do it while clocking out at 5:30 and not checking your email until Monday.
That’s not failure. That’s success with better boundaries.
Thoughts at 39
I turn 40 soon. I’ve spent fifteen years building something no one really cares about but me, learning things I couldn’t have learned any other way, and making every mistake available in the self-employment catalog at least twice.
I don’t regret it. But I also don’t pretend it was the only way to build a good life. Or even the best one.
If you’re young and ambitious and trying to figure out what to do with your career, here’s my advice: be honest with yourself about what you actually want, what you’re actually willing to endure, and what outcomes you’re actually optimizing for.
If you want freedom, understand what freedom actually costs. If you want wealth, look at where wealth actually comes from.
If you want meaning, consider that meaning might be found in more places than the entrepreneurship narrative would have you believe.
There are lots of rocket ships are out there filled with good humans. Some of them have seats available. Getting aboard one might be the smartest thing you ever do.
And if you do decide to build your own? Know what you’re signing up for. The brochure lies. The freedom is conditional. The boss is terrible.
But if you’re cut from the right cloth, its totally worth it.
