Being Comfortable Being Uncomfortable

I’ve come to realise that anything that’s worth doing is located at least one foot outside your comfort zone. The things that matter are there, like starting relationships or ending them, diving into your next startup, learning a new skill. All these things come to people who put in the work and spend time time doing things that are uncomfortable. The tough part is that most of these things aren’t essential. You can live a life inside your comfort zone and do just fine. Just, fine and probably not much else. The way to stop doing ‘just fine’ and start doing well is to become a person who enjoys discomfort. Someone who revels in it. When that happens, it becomes a drip feed of the reward you’re chasing and fuels you to the finish line. The biggest change I made on a personal level was realising the value of discomfort and putting in the work to be a person who likes working there.

Five years ago, discomfort was the fence around my decisions. My limit for doing hard things was about as long as it took to finish an essay the night before it was due. I was anxious, introverted and lacking self confidence. Looking back, there were numerous opportunities I passed up because they were outside my comfort zone. Often I would have dozens of reasons to justify why something was a bad idea but deep down, they were excuses biased by an aversion to discomfort. Worse than passing things up was indecision.

A common sign of the comfort zone dweller is having lots of ‘projects’. Projects aren’t bad but having lots of them means that when one gets tough there are escape routes everywhere. The ‘task management done properly’ project I started in 2011 languishing without a single contribution is an ironic portrayal of my mindset at the time. I would start things, lots of things. Things I’d never finish. The reason they sat unfinished was because when a choice had to be made about which project to focus on, comfort got an extra vote. Why battle through that problem I had last week when I could work on any of these other projects. This happened more than I’d care to admit and extended beyond work and pet projects into my social life as well. I was blind to the problem but a rude awakening was just around the bend.

That rude awakening came in the form of a PhD. I’d finished my undergraduate studies and was offered the opportunity to keep studying. Looking back part of that decision was probably made because it was what I knew. Around 3 months into my PhD I came to the realisation that I’d stepped into something bigger than I could handle at the time. As hard as it is to admit before then I had little need to take initiative and self direct. The anxiety of not knowing how to continue or what to work on built up and I knew I needed to make a change. I turned to the internet for motivation. Life hacks, mind hacks, study hacks and other get productive quick schemes. Almost everyone will see a productivity boost tying some new ‘hack’ for about a week. Almost everybody will see that boost taper away when the shine wears away.

The thing I found consistently was that the true test of almost any method is a shitty day. When things are working out and it’s business as usual it’s easy enough to rack up pomodoros and crosses on the calendar. When things fall apart, the little ticking tomato on your desk becomes a painful reminder that everything is still broken. It’s that moment when the system falls apart. When the stress crosses that threshold of comfort and becomes anger. Eventually I got tired of the hacks and decided I needed something more fundamental. I noticed others around me. There was a subset of people who worked as hard, hit as many problems but didn’t let it slow them down. These people were the high performers, publishing like crazy while keeping their sanity.

I spent time trying to distill the differences between them and me. After a long process of illumination and a dispelling of imposter syndrome, I found the magic bullet. The people I looked up to faced discomfort head on and moved through it. They knew that the hard thing was a barrier to the valuable thing and they wanted that valuable thing bad enough to push through it. Heading back to the books and blogs I found that others knew this secret too. I soaked it in and took the plunge, no more Mr. Easy Street. I was going to embrace discomfort if it was the last thing I did.

All journeys look shorter from the finish line. If I’m being honest becoming someone who enjoyed discomfort was a gradual process. I figured small steps were the way forward seeing how quickly my ‘hacks’ had burned out in the past. I kept a log of my work, knowing that’s what I wanted to improve, and set myself a goal of doing more things just outside my comfort zone. I started with taking cold showers in the morning as I read somewhere online it was a good place to start.

Cold showers suck. Nobody is likely to argue with that, ice cold water is not something many people bound towards. It teaches a valuable lesson though. Cold showers suck, for the first 5 or so seconds. After that the discomfort subsides pretty quickly and it’s just a shower. Most other uncomfortable situations are fairly similar. There is an initial hurdle of resistance and then it’s typically not as bad as it looked from the outside.

Cold showers led to other little challenges. Talking to strangers in lines. Calling for pizza (I hated answering the phone more than just about anything). Forcing myself to work for 5 more minutes before getting angry at a problem. One by one the small steps added up and I noticed myself changing. At the end of the day I had achieved more and didn’t feel quite as overburdened. Tough problems became a challenge I enjoyed facing and I felt the reward of heading to the goal not just reaching it. When there was work to do, I would do the work, comfort be damned.

Taking the easy path is easy, as the term suggests. There are hundreds of options along the easy path, temptations are plentiful. Just like chocolate milk and ice cream are easy to eat, taking the easy road will come back to haunt you. Comfort zone bias is a formidable force. As humans, we are experts in post-rationalisation, but don’t let it fool you. Being uncomfortable is the practice of going against your gut; doing the things that’s hard because something exponential might happen.

In a business context, the ability to be uncomfortable, often referred to as ‘grit’, is a large contributing factor to big success. The Facebooks and Teslas of the world all started doing something outside the norm. Socialising online and driving an electric car were once the habits of a reclusive subculture but have since become (or are becoming) the default. For Mark or Elon to have gotten where they are now as business leaders, there were no doubt moments of discomfort; ones they had to push through despite having a voice in their head telling them they are making a mistake.

These founders have an air about them. You can feel the passion the have for their business and the war stories they tell give the feeling they’re in it for the long haul. When things get tough they don’t move onto a new business, they soldier on and move them selves one space forward on the business board game. This kind of attitude should be seen as a competitive advantage. In an ideal world everyone would work hard and embrace discomfort to build the unicorns of tomorrow. In the world we live in this is far from the case.

So take the plunge. Or rather, take a thousand small plunges. Challenge yourself to do uncomfortable things. Showers, phone calls or just working on hard problems. Do the small things to build the strength to be uncomfortable when it matters. Train for the day that all the voices in your head are shouting stop and you push on anyway. Embrace the discomfort, step outside your comfort zone and find the things worth doing.