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The self sabotaging paradox of being obsessed with freedom

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. 


+ Add Comment
  1. I almost ignored your email because I was busy. I am glad I took the five minutes to read this. Thanks!

  2. geez Peter! You are tapped in for sure. I am so glad that you have sacraficed freedom to shine your light nd take guide us ambitious entrepreneurs

    1. Ha true that. I trap myself into writing 500 words a day, and it never feels like “freedom” – but this material comes out of that constraint. So you’re right!

  3. Peter, I hear you. I get where you’re coming from in one sense. But in another, I have to challenge the definition of freedom you use here because I would don’t want to toss out the “baby with the bathwater.”

    Freedom is a “life word” for me. It is a value I hold dear and espouse as a very real possibility for those I get to teach.

    I can’t help but think of the bible verse that that says “Christ set us free to live a free life”. No matter what you believe about Christ or the bible- is the point- so just notice the type of freedom being espoused here.

    I do believe freedom as you speak of it, can be it’s own prison if you think of it as self serving. A freedom “from” something- a soul sucking job; to never have to work again; to have enough money to be able to say F*** this.

    But the freedom I love and espouse, that is deeper than freedom “from” kind. It is the freedom “TO” kind of freedom. Dan Sullivan speaks of these 2 different kinds of freedom very well.

    To me, freedom to purse fulfillment, pursue connection with others, pursue a bigger and better life is a north star kind of freedom entrepreneurs would do well to pursue.

    Inherent in the pursuit of this kind of freedom is the ability to change my circumstances, and along with that, serving others by showing them they have the freedom to change theirs too. It can be what makes our lives have impact.

    Freedom from keeps you imprisoned. Freedom to sets you free. One keeps me afraid, the other keeps me hoping.

    My 2 cents…

    1. Hey Dean! Great seeing you comment here 🙂

      I think I agree with you, but it is a semantic difference. I wrote this article because most people don’t make this distinction and just mentally roll all freedom into one mental bucket. But yah, I agree with your definition of “Freedom to…”. I might call that “Agency”. And I think it’s totally worth valuing.

  4. Many thanks.

    Having considered myself free for 18 years, it’s amazing I’ve got so far.

    I will spend the weekend resetting the brain and who knows what the future will bring : )


  5. Have only recently started tapping into your emails and I already love how your mind works Peter!

    Look forward to more!

    PS. Freedom for me is liberation from mental and emotion constraints that don’t serve my purpose.

  6. Thank you Peter. This student was ready.
    I’ve had a sense for quite some time that something’s been wrong with my way of approaching life. I’ve been self-employed for over 20 years now, because I wanted to be “free” from other people running/managing my life. Freed myself of marriage for the same reason.
    But now I’m working ALL. THE. TIME. And that’s not freedom by any stretch of the imagination.
    And I’m alone, too busy to establish and maintain relationships.
    My latest obsession has been seeking financial freedom.
    More of the same, I see now, thanks to you.
    Time to re-think this life.
    Thank you so much for sharing your wisdom this freely.

    1. Wow Laurel, thanks for this comment.

      It’s interesting isn’t it? It sounds to me like you elevated “Freedom” as your primary value and actually HAVE accomplished it. You’re free from many constraints you used to have. But it’s come at a price: You’ve given up connection, relationship, your time.

      This is precisely the kind of “be-careful-when-you-rub-the-genies-lamp” point I was trying to make. Thanks for sharing.

  7. You’ve made such an important point. Complete freedom is an illusion, We just need to define what we want to be responsible for, what we stand for, what we allow to tie us down. Without having some anchor, we are the Flying Dutchman, sailing aimlessly.

  8. Damn – I am not an entrepreneur but this is absolutely a description of me. Absolutely obsessed with optimization and minimalism to the point of pathology. It makes me unhappy and this idea of freedom is deeply connected with it. Good points here.

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