The Power of Discomfort

It is a strange thing, but things that are good to have and days that are good to spend are soon told about, and not much to listen to; while things that are uncomfortable, palpitating, and even gruesome, may make a good tale, and take a deal of telling anyways."

- The Hobbit

 

A few months ago, I was having lunch with a friend when he casually mentioned to me that he had started to train for a marathon. I hadn’t known him to be a runner, but plenty of people I know have “run a marathon” somewhere on their bucket list.

I asked if that was the case, to which he responded,

“No. In fact, I’ve never wanted to run a marathon.”

 
 

My friend had held senior roles in both startups and big tech companies, with increasing challenges at every step. After leaving his most recent role, he decided to take a well-deserved sabbatical.

During his time off, he reflected on experiences at Facebook, Salesforce and others, and realized that he had become comfortable. Complacent.

As my friend replayed in his mind the past decade of his career, he recognized that a key ingredient during his times of greatest success and personal satisfaction was that he was doing something to make himself uncomfortable. And that something wasn’t necessarily work-related.

Which brings us back to the marathon. When I asked him why he was running a marathon, his response was simply,

“Because it’s hard.”

In the few short weeks since he had started training, my friend was already perceiving an increased level of focus and clarity. Increased curiosity and motivation. Increased velocity and an increased sense of urgency in all aspects of his life.


There’s no shortage of research into and posts about the power of discomfort. My friend, Marvin Liao often writes about it in his newsletter, The Hard Fork:

I’ve gone through most of my life subconsciously avoiding pain and suffering. Basically trying to avoid being inconvenienced and chasing comfort. Because that was what I thought I was supposed to do. But all my biggest leaps of knowledge, understanding and wealth came when I tackled and embraced challenges directly. Or usually indirectly as my curiosity and naivety took me in that direction.

This is why I always encourage and push for everyone to push themselves, physically and mentally. Chase the hard stuff that makes you feel pain. If you feel pain, it means you are growing. Develop a huge capacity for hard work. Be prepared to grind for a long period of time. It’s all about self-development. Becoming a higher level of yourself.

The concept is nothing new. Most people understand that athletes build muscle because their workouts cause microtears, which become stronger when they heal.

Yet many founders let themselves off the hook with the built-in excuse of “I’m working at a startup, so my life is by definition uncomfortable.” While that can certainly be true (especially early on), even startup founders quickly reach a level of comfort within the natural unpredictability of a startup.

The daily unpredictability itself becomes predictable.

 

Wise words from Pete the Cat’s Groovy Guide to Life

 

When I was a founder, I played a lot of sports. That was how I pushed myself outside of work. In the mornings, I would run along the Embarcadero. At night, I played on a mens soccer team in the winter and paddled outrigger in the summer. All of these things provided different challenges — both physical and mental — than those I faced in startupland.

Today, I have two young kids. It’s difficult to fit in both workouts and family time. I’ve learned enough about myself to know that I need physical challenges to operate at my best, so for the past few years, I’ve exercised early in the morning or late at night:

 
 

This seems like a pretty intense start to the day, right? It seems like it would be pretty uncomfortable. But as I reflected on my lunch conversation, I had to admit that this was no longer my regular morning routine.

It was my “sometimes” morning routine.

Rather than pushing myself, I was avoiding pain and discomfort. If I was tired in the morning, I would sleep in and skip my workout. I was probably doing that 1-2 times each week. And it wasn’t like I was making up for it at night (either by exercising or trying to go to bed earlier). All too often, I was staying up late wasting time doom scrolling.

I was becoming comfortable. Complacent.

 

Pushing myself to the limit

 

That night, after the kids went to bed, I got on our exercise bike (which I hadn’t touched in…I don’t know how many months) and did my first two-a-day in years.

It wasn’t anything mind-blowing, but it sure was uncomfortable. And it felt great.

The next morning, even though I was tired, I got up and did my workout. And that night, I got back on the Peloton.

It’s been three months since that lunch.

The only morning workouts I’ve missed were due to meetings or family time (there was zero chance I could convince the kids to wait until I got in a workout to open Christmas presents). And I consistently ride the Peloton 3-4 nights each week.

Like my friend, I feel an increased focus and clarity at work. Increased curiosity and motivation. Increased velocity and an increased sense of urgency in all aspects of my life.

Oh, and I lost 15 lbs. Not bad, eh?

So as you start thinking about what you want to accomplish 2024, ask yourself this: what am I doing right now that makes me uncomfortable?

 

See you on the bike!