"Fuck You Money” is Useless Without the “Fuck You”
How to escape the psychological prison [The Other Side of Enough]
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The Way of Work explores stories of where we fit in the world of work. This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again.
What is the point of financial freedom if we never feel free?
Do you remember Brooks from The Shawshank Redemption? He’s the old timer that became so “institutionalized” by the prison system that when he was finally paroled, he couldn’t handle the independence.
Here’s Red, Morgan Freeman’s character, describing Brooks:
“He’s just institutionalized… the man’s been in here 50 years… this is all he knows. In here, he’s an important man, an educated man. Outside he’s nothing.
I’m telling you these walls are funny. First you hate them. And then you get used to them. Enough time passes, you get so you depend on them.”
We, of course, are not like Brooks. No, no, no. We’re not institutionalized, comfortable inside the warm embrace of our conventional structure, our routines, our place in the social hierarchy. When we become free, we’ll be just fine. Right?
Instead, we see ourselves as Andy Dufresne (Tim Robbins). We’re the protagonist — wronged by this life and freedom will complete our redemption. And the beach hotel in Mexico (or your version of the fantasy) is waiting for us.
But more people are like Brooks than they think.1
They’ve spent so long adapting to a system — whether it’s work, status, or achievement — that when they finally break free, they don’t know what to do with themselves. Rather than independence, what they’re really after is a kind of psychological comfort. A nice hug that comes from the validation they get working the system. They don’t really want the independence – it’s too much freedom and too much responsibility over their life.
Money, then, doesn’t help them escape the prison. It just transfers them to a better cell.
Psychological > material independence
We chase financial freedom, believing it’s the key to independence. But the real prison isn’t material, it’s psychological. It’s the internal constraints that traps us, often long after the external ones are gone. The “fuck you money” transforms into something more like: “oh, fuck me!”
From my interview with Khe Hy:
“Material independence is what most people chase. It’s ‘hitting your number’ – having enough to never work again. Many believe that reaching this milestone will bring peace.
Psychological independence is… when you are no longer a slave to money in your head. You stop obsessing over financial worries or chasing more wealth as a proxy for self-worth. You don’t let money dictate your every decision.”
The material prison is easy to understand. It’s the hard walls we can see and touch and feel around us: the bills, obligations, and responsibilities that dictate our lives. And the way out is obvious: money.
But while money may help us step out of the material prison, we then step right into another prison on the other side. And instead of the hard walls, it’s the squishy stuff that comes in the form of things like: self-doubt, fear, and loneliness.
“I realized it was never my job that was holding me back. It was self-doubt.” - Brandon (aka The Mad Fientist), from Should you put off life for the future?
We think we’re breaking free, but the real fear sets in when we are faced with the responsibility of living life on our own terms.
Escape the prison
To me, this is one of the most important questions from the series: what’s the point of financial freedom if we’re still prisoners in our own minds?
This is not the therapy chair — overcoming mental barriers that may be embedded deep within you is well beyond my expertise. But from the interviews, several perspectives emerged on how to break free from the prison of psychological dependence:
First, embrace the 2nd hero’s journey. If you think that independence is the finish line, where your life simply rides off into the sunset filled with warm feelings of contentment and peace inside, you’re in for trouble.
“Because the dragon's already dead. So now it’s different. Your sword does you no good at all.” - Jeff, from After ‘Happily Ever After’
Independence isn’t the end. It’s a milestone. And while it’s a great achievement, beyond it lies a mess of existential uncertainty that most people aren’t prepared for. You won’t feel wonderful. You’ll feel lost and will flail for years. It’s gonna take some time to unlearn that institutionalization.
Better to see this, not as the end, but as the start of another journey, one you’ll have to navigate without a map.
Second, find a purpose-project. No, I’m not talking about something big-and-ambitious in a change-the-world type of way. We’ve covered that before. I’m talking about something simple – a creative or service-based project.
Andy had his hotel. Sara had her art. Brandon pursued music. Jordan had his writing. Cathy found service. The interviewees who picked up projects like these, reported a 40% increase in meaning after reaching independence. They weren’t about checking external boxes, but about reconnecting with something deeper inside themselves.
“Unlike the hollow expertise I developed during my corporate career, the mastery I pursue now feels very rich and rewarding. It helps me explore why I exist at all and allows me to connect to others in ways that feel very natural.” - Sara, from Waiting Decades to Finally Follow Your Dreams
Build an identity outside of work. Like Brooks, if your whole sense of self is tied to the system you’re trying to escape, you’re in trouble. It’s no surprise that mortality rates often increase after retirement. Without a strong identity outside of work, many struggle to adapt to the freedom they’ve earned.
Most of my guests gained meaning after independence. Except for two: the founders, who seemed to have the strongest identities tied to their prior work. They fell hard, experiencing a 50% drop in meaning, despite experiencing the biggest drop in stress (80%).2
Apparently, money buys meaning… unless you’re a founder.
“You feel like you have this sense of direction and purpose. And then that just disappears. You're just left with a void because you haven’t really thought about any other path.” - Omar, from Will you get what you want, after reaching financial independence?
The same singular drive that creates early retirement is often what makes it impossible to enjoy when you get there. Instead, consider adopting a diversified portfolio of identities, so if one identity is disrupted, you’re not left adrift.
Finally, be willing to say “fuck you.” Of course, no one put it like this. But every single one of my guests did this in some way. To their old careers. To external expectations. To the prestige and status of their former lives. To the “shoulds.” To the endless chase for more.
What’s the point of financial freedom if you can’t use it to live meaningfully? What’s the point of independence if you don’t exercise it?
The most important question may not be whether you can break out. It’s whether you can live on the other side.
Next up, will be the final essay in The Other Side of Enough, where we’ll answer the question for readers who say: “Yeah, but I still want that money!”
Before you consider Brooks an anomaly, consider two recent examples of the founders of Loom and MVMT sharing their life after exit:
Of course, none of this is statistically significant.
Nature abhors a vacuum. The man, woman, or child that escapes a system that they thought was a tool, but was actually a crutch is sure to stumble.
You had me at Shawshank references