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How to get comfortable with being uncomfortable 

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.  


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  1. How do you know you’re not working hard just for the sake of it? Where to draw the line?

    I find myself in this trap of masochism so often, and I find Tim Ferriss’ question helpful: “what would it look like if this were easy”.

    Just to break that self limiting belief or self fulfilling prophecy of: “it will take a lot of effort to reach my goals”.

    It incentivised me to look for shortcuts and “smarter” ways. But are these inherently bad?

    1. Hey Tre!

      Nothing wrong with looking for smarter ways to make things happen. What I’m pointing out here is that in a competitive market place, value creation is most likely to happen when you do things other people aren’t willing to do. I do agree though that it is a trap to equate “hard work” with being deserving of success.

      This article is mainly addressing the people who take shortcuts and try to work as little as possible – doesn’t sound like you are one of them.

  2. Hi Peter,

    Nice read as usual. Thanks for sharing your wisdom!

    Good to know my discomfort is actually normal for entrepreneurs and value creators! One can only say at the point of most discomfort, “#$%*&, hope this all comes off!”

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