Want to succeed as an entrepreneur? Nothing is more critical than becoming resilient to discomfort. 

I have to thank Thomas Oppong for saying it better than I could:

“Nearly everything that generates enduring value requires effort, focus and discomfort” 

Aspiring entrepreneurs quake in fear when they hear this. Or, they secretly hope that they’re smart enough that these rules apply to everyone else, not them. 

This fear of discomfort drives the wannabe’s endless search for shortcuts. They’re desperate for hacks to achieve easy success without the hard work. A massive industry of phony entrepreneurial self-help capitalizes on their fervent hope that such hacks truly exist.

It’s all a distraction. 

The wannabes become real entrepreneurs when they realize the only “secret” they’re missing is the courage to act. They realize that execution is everything. That entrepreneurial discomfort itself can serve as a compass, pointing to the true north of genuine value creation. 

And there lies real, concrete success. 

To get comfortable with being uncomfortable is as simple as realizing: Discomfort is where the value lies. Follow it and you’re headed in the right direction. 

The entrepreneur wins when they work overtime to personally phone the first thousand customers for their software startup. The easy route would be automating support or hiring some VA to do it. And it’d rob the founder of all the learning, market-fit insight and customer empathy that transforms an version 1.0 idea into a huge 2.0 success.   

The entrepreneur wins – exactly as AirBNB’s founders did – when they pull out a camera and schlep around town themselves, to help early users get their vacation rental listings looking as attractive as possible. This really happened. 

The modern world is terrified of pain

Our mainstream culture will do anything to avoid pain and suffering. We have pills to make all manner of discomfort go away. 

Our culture is confused about the point of life. We’re obsessed with hedonic pleasure, with freedom and escape from the suffering of work: Lifestyle design. Living for the weekends. We optimize for indolence and set goals of passive consumption. 

This all means – to use two crude metaphors – that there’s money laying on the table. But it is not “low hanging fruit”. 

Terrific opportunity lies on an uncomfortably high table top, waiting only for someone willing to stretch up (ouch!) and grab it.

Most people won’t even try. 

Becoming comfortable with being uncomfortable is easy when you realize that the people obsessed with avoiding all pain are actually miserable. They missed the point. 

For entrepreneurs especially, becoming comfortable with being uncomfortable gets easier when you realize that the competition vanishes when things get tough. That there’s no traffic on the extra mile.

Playing it safe, optimizing for hedonism, avoiding work, doing the minimum required to have freedom to binge-watch Netflix… these are all the games of people who are chronically asleep-at-the-wheel.

You’ll get comfortable with being uncomfortable when you realize that pushing hard – leaning into the discomfort for the purposes of creative entrepreneurship and genuine value creation – is where you feel the most genuinely alive.  

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. 

Every wildly successful entrepreneur with an ounce of genuine self awareness and intelligence knows that luck is a big part of their success. 

Finding product market fit. Timing. Chance meetings that change everything. Bad decisions that ultimately led to good places… 

All these things are present in the biographies of super successful founders. They are all integral to their success. 

This isn’t to minimize entrepreneurial smarts, hustle, determination or discipline. Those things matter enormously too. There are countless books and gurus offering strategies for optimizing these. 

But what about manufacturing luck? 

Luck only appears impossible to create at the surface level. Go a little deeper and you find the simple idiomatic truth: The harder you work, the luckier you get. 

(Lady fate helps those who help themselves.)


Entrepreneurs can do even better though. Let’s go deeper: 

Luck is as much a game of endurance as it is a game of chance 

Entrepreneurs who optimize for longevity – being able to iteratively play the game of business for as long possible – increase their chances of luck finding them. 

This is why we see young people hit home runs with technology startups. Getting involved in “The Startup World” in your early twenties makes a ton of sense, so long as you can find a way to pay your (relatively few) bills while you play with your ideas. Keep at it and – chances are – you’ll eventually win in some way. 

Conversely, the people who start companies with short runways and enormous expectations driven by hard financial necessities in their lives… seldom get lucky. 

Think of the financially vulnerable forty something who’s always wanted to start their own company. The kind of person who only does so after attending a seminar teaching some scammy strategy to make millions online (or in real estate, or whatever) with “zero money down”. 

People jump into such courses – often going into debt to pay for them – needing to make five figures a month. They’ve got kids, a mortgage to pay for. They get sold on the idea that having their “back to the wall” is a good thing. It isn’t. It’s just a tool fake gurus use to sell courses to desperate people

The problem is these people don’t have the time.

When would-be entrepreneurs only have a couple of months to manufacture a win, they don’t give Lady Luck the time she needs. It doesn’t even matter if they’re hardworking and disciplined.  

Luck is notoriously late to every party. The stress of a super short cash runway doesn’t help either. You have to play the long game for her to help you out. 

There is a second way to optimize the odds of Lady Luck showing up:

Optimize for meeting people

Luck manifests most often through other human beings. It shows up in the game-changing conversation with a super qualified mentor who just feels like helping you out. Or in meeting the  person who’ll become your ideal biz partner. 

Or, just finding that would-be customer who becomes your first major fan and advocate. The person who singlehandedly jump-starts your word-of-mouth marketing. 

At my Accountability Coaching company Commit Action we talk a lot about the double-edged sword of technology: Thanks to the internet, it’s never been easier to start a business (all you need is a laptop) but working from home with just a laptop is actually not an environment that lends itself to business success. 

At CA, we mainly focus on the isolation and lack of accountability problem that prevents people operating as the highest leverage versions of themselves possible. But another side-effect of working from your home office – or even from seductively “location independent” poolside places – is that you’re unlikely to run into the people who can change everything for you. 

Getting out to events, visiting the cities that serve as hubs for your industry, taking a leadership role in connecting others… all these things serve to construct weighted dice in the craps game of early stage company building. You need to be doing them. 

I suspect that this step is the key to overcoming a lack of privilege. As a white male, I can’t say I genuinely know first hand, but it seems to me that the best way to find “unfair advantages” in business is through community/network… and if you’re a member of a minority community you should be leveraging any and all opportunities available to you. 

My personal analogue for this is when quite recently (and to my shock) I connected with several people involved in New Zealand’s government whose jobs are dedicated to “supporting kiwi entrepreneurs overseas”. 

I’d been happily going it alone for the best part of a decade. Turns out that all manner of grants, incubators, subsidies and mentorship had been available to me all along. All because I’m a card carrying member of a faux-minority called “Kiwi’s doing business overseas”. 

I’m very fortunate to have such connections, but the point is that it took me a decade of muddling away before I stumbled upon them. Because I just didn’t think to proactively seek this stuff out! Now, it’s actually too late and I’m not even qualified – I’m much too far along/experienced – for most of the juiciest opportunities. 

Don’t make the same mistake. Seek out opportunity and support.  If it’s not local government, then perhaps it family. Or friends. Or applying to an incubator. You don’t have to do this alone.

One last thing: 

Speed of execution invites luck in

The math is simple. When you sit down to play roulette, the faster you play the more chances you have. 

The metaphor is imperfect because with actual gambling, the house always wins. There’s nothing to learn from each spin of the wheel, so the next game has exactly the same odds as the last one. 

Entrepreneurship is fundamentally different though: Speedy execution is amazing because it accelerates your education. 

There are certain street-smart wisdoms that mega successful entrepreneurs talk to each other about. They’re difficult to describe to people who haven’t “been there, done that”. They can’t be easily written down, which means they cannot be learned by reading. They have to do with testing ideas, learning, pivoting, gaining true empathy for your customer and more. 

These are things about entrepreneurship you can only learn by doing. And they must be learned.

This is why perfectionism is the natural enemy of luck in business. 

Anything that slows down the process of iteration, of shipping to the market, of getting feedback from the real world… and then of integrating that learning into the next iteration… anything that retards any of these essential processes is counter-effective to getting lucky.

Executing relentlessly and quickly, seeking out and investing in relationships and simply staying in the game as long as possible are practical tactics to play the game of business with a tremendous lucky advantage. 

The last decade I’ve spent working with entrepreneurs around the world was also a decade spent studying entrepreneurs around the world. 

(Best free MBA ever. In fact, I got paid to do it!)

And if I had to pick one thing that unites the upper echelons of extraordinary overachieving founders – if something definitively sets them apart from everyone else – it is this one thing: 

Entrepreneurs take an unreasonable amount of responsibility. 

For everything. 

It’s almost pathological, the level of responsibility that ultra-successful business owners take. 

Prospective investors said no in the pitch meeting? I could have done better. 

Critical, depended-upon employee ups and leaves for personal reasons? I should have seen it coming. 

External economic forces put a financial squeeze on the industry? I should have pre-empted all this. 

The examples are countless. In every aspect of business and life itself, entrepreneurs have an outsized belief in their own ability to predict and manage external events. 

This comes with a tremendous burden: Many business owners I’ve worked with describe – in their darkest moments – feeling as though everything is their fault. 

This mental schema for seeing yourself at the causal center of the universe is a classic double-edged sword: When you’re winning, everything is your fault. Unfortunately… it’s also your fault when you’re losing. 

What these entrepreneurs have realized is that in both good times and bad, to assume responsibility is the most powerful posture you can take. 

Whichever way events in your life and business unfold, owning them and acting “as if” you’re the driving force behind them – even if that’s a bit of a hallucination – increases choice, flexibility and agency. In a chaotic world, those feelings are powerful medicinal.

Responsibility is a helluva drug. 

The non-entrepreneur “civilian” world is largely made up of people who’re uncomfortable with any responsibility they have. They seek to defer it or escape from it, handing it over to bosses, corporations, market forces or politics. 

This makes newly minted entrepreneurs feel like they’re having some wake-up-from-The-Matrix moment… when they realize that the people around them are desperate for someone to come along and take outsized responsibility. 

It’s a weird hypothesis – especially since I also believe in (and am grateful for) the incredible luck and privileges that my life is built on – but I’ve seen the effects first hand: 

If you want to accomplish extraordinary things as a business owner, adopting a presupposition of outsized personal responsibility for everything in your life is the singularly most significant mental step you can make… to stack the odds winning big in your favor. 

For entrepreneurs in particular, the internet has become the new late night television. Got a problem? Hurting? Struggling? Click here. There is a guru waiting to give you the answer to all your problems.

Instead of miracle cleaning products or exercise equipment it’s the course, the revolutionary training or seminar that promises “secrets”.

This happens despite the fact that there are no real secrets anymore. The internet has revolutionized our access to information in a way we’re only just beginning to comprehend. The chance that some formula for success is still actually hidden from you is zero.

Yet we keep getting sucked in.

Maybe it’s our enduring sense of imposter syndrome. Entrepreneurs just can’t seem to shake the feeling they don’t know what the hell they’re doing. And they can’t help but suspect that the other guy doesContinue reading “How gurus exploit imposter syndrome for profit “

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