Why I Stopped Trying to Be Rich and Started Trying to Be Free
The moment I stopped optimizing for the biggest number and started optimizing for optionality, everything clicked.
For the first several years of my career, my financial goal was simple and unexamined: make as much money as possible and grow the number as fast as possible.
I never questioned what the number was for. It was just supposed to be big. Bigger was better, and that assumption sat underneath everything I did, from the long hours to the career moves to the savings rate to the investment strategy. More money, more security, more success. The number was the scoreboard, and I’d internalized the rules of the game without ever asking who wrote them.
Then I read two books within a few months of each other that broke this open in a way I wasn’t expecting.
The first was How to Get Rich by Felix Dennis. Dennis was a self-made multimillionaire, someone who actually did the thing most people fantasize about. And his honest assessment of what it cost him, the relationships and the health and the years consumed by obsession, was genuinely unsettling. He got rich and he’s telling you, with no agenda and nothing to sell, that it might not have been worth it.
The second was Die With Zero by Bill Perkins. His argument was the inverse. Most people save too much for too long and under-invest in the experiences and freedom that money is supposed to buy. What’s the point of dying with the biggest number if you never used it to live the life you wanted?
These two books, taken together, forced a question I’d been avoiding: what is the money actually for?
The Accumulation Trap
The default mode in personal finance is accumulation. Save, invest, watch the number grow, celebrate milestones at $100K, $500K, $1M. The entire culture is oriented around the number going up.
Look, I’m not against accumulation. I’ve spent years building a system that grows my net worth consistently, and that system is working. But accumulation without purpose is just hoarding with a spreadsheet.
At some point, you have to ask what this money needs to do for you. Not in retirement, not in some abstract future, but in the next five to ten years to make your life meaningfully better. When I finally sat down and answered that question honestly, the answer wasn’t “be as big as possible.” The answer was much simpler: give me the freedom to make choices based on what I want, not what I can afford.
That’s optionality. It’s a fundamentally different goal than wealth maximization, and it leads to different decisions.
Rich and Free Are Not the Same Thing
I’ve met people with significant wealth who are completely trapped. Golden handcuffs, lifestyle commitments they can’t unwind, a standard of living that requires them to keep earning at a pace they can’t sustain. They have money and no freedom, and on a long enough timeline that’s a very expensive prison.
I’ve also met people who aren’t traditionally “rich” but are profoundly free. Low fixed costs, meaningful accessible savings, work they chose instead of work they endure. The difference between these two groups has almost nothing to do with income and almost everything to do with what they optimized for.
If you optimize for maximum wealth, you make decisions that increase income and returns at the expense of flexibility. The higher-paying job with the longer hours. The bigger house that locks you into a higher mortgage. Each decision grows the number but quietly shrinks your room to maneuver. I wrote about this dynamic in The Raise Trap, where the bigger income usually comes bundled with obligations that consume it on arrival.
Optimizing for freedom looks different. You keep fixed costs low, build savings you can actually touch before 59½, and choose work that aligns with how you want to live even when it pays less than the theoretical maximum. Each of these decisions might slow the number’s growth, but they all widen your ability to change course.
I spent years in the first camp before realizing I wanted to be in the second.
What Freedom Actually Looks Like
Freedom isn’t a number. It’s a set of capabilities, and the capabilities are what make the number matter.
The first is the ability to say no. To a job that’s making you miserable, a project that doesn’t align with your values, a lifestyle expectation that’s costing more than it’s worth. When you’ve saved enough that you can afford to say no without financial panic, the entire power dynamic in your professional life shifts. Nobody who has seen this shift from both sides would go back.
The second is the ability to take risks. Starting something new, trying a different career, pursuing an idea that might not work. Every meaningful professional risk is easier and smarter when it’s backed by a financial foundation that gives you runway. Without that foundation, every risk is actually a bet-the-house decision, even when it doesn’t look like one.
The third is the ability to wait. Not taking the first offer. Holding out for something better. Letting a situation develop instead of reacting from scarcity. Patience is a luxury that money buys, and it’s one of the most undervalued assets in career and investing. I’d argue half of what looks like “good judgment” from the outside is actually just the ability to wait that the person’s financial situation affords them.
The fourth, and the one I think about most, is the ability to walk away. Not retirement, just the ability to walk away from anything that isn’t working, knowing you’ll be fine. A job that turned toxic, a city you’ve outgrown, a business arrangement that’s tilted against you. Walking away is only possible when you’ve built a foundation that doesn’t depend on any single source of income or any specific arrangement holding together.
None of these capabilities require being rich. They require having enough that your decisions aren’t dictated by financial necessity, and the gap between those two things is much wider than most people realize.
How This Changed My Strategy
When I shifted from optimizing for wealth to optimizing for freedom, three things changed in how I actually manage money.
I stopped prioritizing accounts I can’t touch. For years I maxed my 401(k) above everything else because the tax advantage was obvious on a spreadsheet. Now I contribute enough to get the employer match and then redirect the rest of my investing to accounts I can access before 59½. My freedom timeline is sooner than traditional retirement, and my money needs to be available on that timeline. The optimal tax decision and the optimal life decision are not always the same decision, which is something most personal finance content refuses to say out loud.
I started valuing flexibility over marginal returns. I keep a larger emergency fund than most finance people would recommend, not because I’m afraid of the next crisis but because cash is optionality in its purest form. When an opportunity appears, I want to be able to act on it. The “opportunity cost” of holding extra cash is the price I pay for freedom of movement, and I’ve concluded that’s a price worth paying.
I defined my “enough” number. Not a vague aspiration, a specific calculation. Fixed costs, investment income that would cover them, and the gap between where I am and where I’d need to be for complete optionality. Having a concrete target changed saving from an abstract virtue into a measurable project with a finish line. JL Collins lays out exactly how to think about this math in The Simple Path to Wealth, and it’s the clearest framework I’ve found for calculating when “enough” actually arrives.
The Question
The question that redirected my entire financial life wasn’t “how do I get rich?” It was “what would I do differently if money weren’t a constraint?”
Not what would I buy. That’s a different question and a much less interesting one, and I think the fact that most of us default to it says something unflattering about the stories we’ve absorbed. What would I actually do? How would I spend my time? What work would I choose, and what would I stop tolerating?
The answers to those questions became my financial plan. Everything I save and invest now is in service of closing the gap between the life I have and the life I described when I answered that question honestly.
What to Read Next
📖 How to Get Rich by Felix Dennis. The most honest reckoning with the true cost of wealth I’ve ever read. Dennis made his fortune and tells you plainly what it cost him. Half the personal finance industry would have to shut down if this book were required reading.
📖 Die With Zero by Bill Perkins. The book that forced me to ask what the money is actually for. Read this alongside Dennis and you get the full philosophical picture: one book on the cost of accumulating, one on the cost of never spending it.
📖 The Simple Path to Wealth by JL Collins. The tactical playbook for actually building the financial independence that makes freedom possible. If you read one investing book, make it this one.
📖 The Psychology of Money by Morgan Housel. Housel’s core argument, that “enough” is a concept most people never stop to define, is the quiet thesis running underneath everything in this article.
🎧 All four are excellent on Audible. The free trial gives you one credit to start, and I’d spend it on Die With Zero. Perkins reads it himself and his urgency comes through in a way the page doesn’t quite capture.
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