The Trap of Success (& How to Escape It)
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The Trap of Success (& How to Escape It)
I have a close friend—we'll call him Ben.
Ben is very successful. He's in his 30s, sold a company for $100 million, and earns over $10 million per year in his current role.
I was recently out on a walk with Ben when he admitted something interesting:
He hates his current job. He finds no fulfillment in the work and dreams of leaving to start something new. Something that would bring him alive again.
So, naturally, I told him to quit. I mean, he has enough money for many, many lifetimes, and that affords him the freedom to do so.
My logic was basically this classic from Bobby Axelrod on Billions:
"What's the point of having f*ck you money if you never say f*ck you?"
Well, as it turns out, he can't quit. He's trapped. Perhaps not in a literal sense, but in an even more damning psychological one.
Today, I want to talk about this fascinating trap, how success and freedom can find themselves at odds, and how to design your life to avoid that fate.
The Truth About Success & Freedom
This is the most significant lie you've been told:
Success leads to freedom.
From a young age, you're indoctrinated into a belief that achieving success in a domain will result in freedom, fulfillment, and happiness.
But here's a harsh truth:
If you're not careful, success can create its own unique form of servitude.
The success you thought would free you begins to own you.
I call it the Trap of Success—it's exactly what my friend Ben and so many others fall victim to.
There are two core types that I've observed:
The Financial Trap
The Identity Trap
Let's talk about what each one looks like...
The Financial Trap
This one's easy to spot (but difficult to break once you're caught in it).
You start earning more year after year, but your lifestyle scales right alongside that growth.
You upgrade your houses, your cars, your travel, your things. You hire more, build a bigger team, outsource every inefficiency in your life. Your life becomes a business in and of itself, with a full payroll of people meeting your every need.
You and your family become accustomed to this life—which is built around peak earnings.
You may still enjoy your work today, but by the time you realize the work is no longer meaningful or fulfilling, it's too late.
The trap is already set.
Change is no longer easy. Change means walking away from an entire life. Change means telling your partner and kids that those things they expect are no longer available. Change means pain. And pain is bad.
So, you stay on the path, wondering how the hell you got here in the first place...
The Identity Trap
This one's harder to spot (and even more difficult to crack).
As you achieve your success, you become known for it. You become your success. Your identity is tied up in your achievements. You are the type of person who has that success.
The money. The admiration. The respect. The likes. The follows. The views. The fame. All of it.
Your entire identity is the success you've achieved. You are the entrepreneur. The investor. The writer. The performer. The executive. Whatever.
But what happens when that identity is no longer aligned with who you are (or want to be)?
To become the new you have to unbecome the old—but the idea of tearing down what you've created is intolerable. Like erasing everything about who you are. You worry that you will become irrelevant. That the respect and admiration you commanded will disappear. That you will become invisible.
So, you stay on the path, wondering how the hell you got here in the first place...
The Solution: Margin of Freedom
The fundamental problem here is the belief that your growth in life will follow a constant upward trajectory.
If you believe that's true, then there's no issue with your expectations—whether financial or identity-based—growing on a parallel (or identical) path.
Unfortunately, growth doesn't work that way.
It's more like a series of rolling peaks—you reach a new level, but need to endure a temporary regression before you can experience the next leap forward.
If you've allowed your expectations to scale in line with your reality, you will do everything to avoid that temporary regression, as it would mean your reality dipping below your expectations for a period.
That is the Trap of Success.
But therein lies a solution: The Margin of Freedom.
The Margin of Freedom is the buffer you intentionally create between your reality and your expectations.
By deliberately creating that buffer, you have the space to explore, experiment, and evolve without fear.
I visualize it like this:
You can manage your expectations across the two areas with simple actions:
Financial Expectations: Keep your lifestyle well-below your means. Create slack in the system. Never match an economic leap forward with a lifestyle one.
Identity Expectations: Avoid the perils of thinking you are as impressive as people say you are. Never get high on your own supply. Practice identity diversification in how you think about yourself. Tinker with new ideas and micro-reinventions regularly.
Well-managed expectations create your Margin of Freedom.
And your Margin of Freedom—not your money—is what allows you to (very politely) say "f*ck you" every once in a while.
Build Your Margin of Freedom
You thought success would set you free.
But freedom doesn't come from the number in your bank account. Or the awards on your shelf. Or the fame, admiration, and respect.
Freedom is a byproduct of design. Intentionality.
Build your Margin of Freedom...
Keep your lifestyle below your means. Never inflate to match peak earnings.
Maintain relationships that keep you grounded. Never forget who you really are.
Detach your identity from your output. You are never as good (or as bad) as people say you are.
Design space for regular play. Experiment, tinker, reinvent.
...and then protect it.
It's the only way to keep yourself from becoming a prisoner of your own success.
Identity trap victim here. I built a whole life around who I thought I should be.
But I got out. Left the corporate world. Started slow traveling. Reclaimed my time, my energy, and my voice.
I wrote a bit about how I escaped in the piece below.
There’s a way through. You just have to stop asking for permission.
Very important to detach ourselves from our outputs, more likely most of the times this is a consequence of external factors rather than our own self. Very important to develop a strong sense of self stripped from what we get or not get to do~