After a decade playing therapist to entrepreneurs in almost every industry you can name, I’m convinced that The Search for Freedom is one of the most dangerous, destructive ideologies an entrepreneur can pursue. 

It will twist your brain.

It will make you miserable.

You’ll make bad decisions.

You’ll likely screw up.

And lose. 

How could freedom – something so wholesome and valuable on the surface – be so paradoxically toxic? 

When freedom becomes an entrepreneur’s ultimate objective, it kicks off a very specific flavor of self sabotage. To understand why, we have to go deep into the psychology, linguistics and underlying philosophy of Freedom itself. 

If that sounds uninteresting, ask yourself why you’re living your life with a singular objective you haven’t even taken the time to properly research.

It is mind-boggling how many people live their lives with Freedom as their north star, without having ever explored what their ethos actually means. 

So let’s unpack Freedom to learn the truth: 

First up, know this: Freedom is not a thing. 

It doesn’t exist. Get the best electron microscope in the world. Switch on the Hubble telescope. Look anywhere. Between the stitches of the red-white-and-blue. In the deepest, darkest quasars of distant galaxies. 

You won’t find a single ounce of freedom. Not one iota. 

Freedom is a mental construct – a collective hallucination – we humans have invented. It is a story we tell ourselves about the meaning of things. 

“So what?” you might say. 

… “Fulfillment” and “Happiness” are also abstract. And there’s nothing wrong with turning abstract ideas into goals. 

The problem with Freedom lies in it’s inability to be defined as anything but an escape. 

Freedom isn’t just an abstract idea like “joy”. It iss the word we use to represent the breaking of bonds.

Freedom is escape. Freedom is moving from a place of constraints to a place without constraints. 

In other words, you cannot have freedom without also having a cage. 

You cannot experience freedom without having recently experienced being trapped. 

To know what freedom is – to really FEEL it – you need to know what it is to be caged. 

The goal of freedom sabotages entrepreneurs because they already have it. Once you set yourself free, you can’t have more freedom… unless you convince yourself you’re still trapped. It is only when you are trapped that the pursuit of freedom take on real meaning. 

When you quit your job to strike out on your own, that’s freedom. You win it. You feel the shackles break. It’s AMAZING.

When you hire that project manager, or 2IC operations person, and delegate your day-to-day business owner grind… you’ve escaped. And you feel free! 

When you sell your company in an all-cash, no golden-handcuff transaction… you’ve done it! You’re free. 

1. Escape velocity. 
2. F*** You Money. 
3. Totally passive income. 

These are all metaphors for entrepreneurs breaking bonds. They’re the milestones of freedom. 

The problem with achieving “escape velocity” – just to pick on one freedom metaphor – is that it’s a goal that is entirely defined by what you’re running away from, rather than what you’re moving yourself toward. 

In my experience, the entrepreneurs who obsess over freedom – the ones who crave it, who worry they don’t have enough of it, who lay up at night sweating over it – tend to fall into painful existential crises of meaninglessness. With predictable regularity. 

A special kind of depression develops, when you elevate freedom as your primary goal and life value. 

Once an entrepreneur actually creates an experience of freedom for themselves, they celebrate and then – almost immediately – feel deeply unhappy.  

This happens because what REALLY fulfills humans… is the pursuit and fulfillment of our deepest values.

When we hold Freedom as that deepest value, the moment of fulfillment is vanishingly small. 

In the moments you feel your bonds breaks – as you set yourself free – you are ecstatic. 

For a jubilant, exhilarating moment. 

As soon as you grow familiar with your new found freedom, when it starts to feel normal, your satisfaction and gratitude for what you’ve accomplished… fades away. 

This feels like a sort of unhappy uncertainty. 

Freedom obsessed entrepreneurs – on the depressing other side of achieving a “freeing experience” – start wondering what is missing. They look around for something that’ll make them have that liberating, free feeling again. 

And there’s only one way to do it: Discover other ways in which you’re trapped, then liberate yourself from those too. 

What this amounts to is an insane mental scrutiny of one’s life: The proactive search for trapped-ness. 

Depressed, freedom-obsessed entrepreneurs will hunt around in their lives for sources of that shackled, trapped feeling. That old liberation – of quitting your nine-to-five job for example – is no longer gonna cut it. 

I’ve seen entrepreneurs – in searching around for the source of their trapped feeling – start to view the expectations and responsibilities they feel for their actual customers… as a trap. Customers have needs and wants after all. So they’re a total drag on the old freedom project, as a consequence. 

I’ve witnessed entrepreneurs resent the “trap” of their staff – the team they built – who now demand leadership, structure and routinely showing up. 

In some cases, the entrepreneur will start to resent the “trap” of their spousal relationship or their kids. All of whom represent a sort of shackle of responsibility. 

The absolute obsession with freedom will push an entrepreneur to purge their entire life of responsibility, expectations and ultimately connection of any kind. 

The thing they never tell you about “escape velocity” is that it’s a rocketry metaphor… and once you’re in outer space, you’re totally alone. 

(The thing they never tell you about “F*** you money” is that you’re using it to tell the world to go F*** itself… and that leaves you kinda lonely.)

The worst cases of pathological freedom obsession will cause entrepreneurs to fantasize about living life as a kind of lone-wolf investor, perhaps deploying capital passively to make insane income, with zero accountability or obligations to anyone, ever. 

(This archetype is so deeply appealing that it’s baked into countless fantastical stories pop culture tells us about success: Think films like Iron Man, Limitless or Wolf of Wall Street.)

Finding something that matters more 

The thing about freedom is that it’s a juvenile value. It’s valuable as a stepping stone to something else: A deeper, richer life purpose. 

It is great to have freedom be your north star when it pushes you to quit your job and bet on yourself. Once you step into that first level of living free as an entrepreneur though, it’s time to find something else. 

You need to figure out a value that matters to you more than freedom. 

The truth about life – and humans – is that we’re interdependent, social primates. We’re embedded in relationships with others. We’re not meant to be utterly liberated from others. It’s not good for us – it does not feel good. 

(When you totally grok the psychological truth of this, you’ll understand why – for example – researchers are beginning to understand that solitary confinement is one of the most psychological damaging things to do to a person.) 

So if you want to really be happy and fulfilled – if you want to really achieve incredible entrepreneurial success – you need to figure out what it’d be worth accepting some “bonds” for. 

A vision to make an impact. Wanting to scale something massively. Taking care of people that matter to you. 

There are many different versions of it, but the thing they all have in common is finding a goal that is worth accepting some amount of constraints in order to accomplish. 

When you figure out what is so valuable to you that you’ll actually sacrifice freedom to make it happen, you will truly arrive at the highest echelon of entrepreneurial success. And you’ll be happier than ever too.