“Don’t get comfortable.”

Said my brother, late one evening as I picked him up from the station. He had asked how my work was going, and I, having freelanced for a little over a year by then, naively explained that it was going well, and that I was finally getting comfortable with things.

“Don’t get comfortable.” He looked at me with the same serious conviction that makes him such a good lawyer. “You have the rest of your life after you retire to be comfortable.”

I didn’t think much of it at the time, but this simple philosophy has guided me through some of the biggest decisions in my life.

When I eventually decided to leave the comfort of my own freelance practice and join a small struggling startup, I was uncomfortable.

When Satish and I had the bright idea to start our own agency in the middle of a recession with next-to-zero prior experience, we were both very uncomfortable.

When Shopify told us that they wanted to take Jet Cooper, the studio that we were certain we were going to build for the rest of our lives, and fold it into a rocketship of a company, we were collectively a team of 25 really uncomfortable people.

And on Thursday, when I board a one way flight to start a new journey with Kit, away from the city, people, and literally everything that has made me who I am today, you can bet that I’ll be feeling the weight of discomfort in each and every one of my steps.

My greatest successes have always come from the pursuit of forced discomfort. This has become a personal truth for how to grow.

So as you start the yearly process of making plans and resolutions for the year ahead, treat this as a simple reminder to ensure they include the things that scare you, push you, and require you to grow.

Whatever you do, just don’t get comfortable.


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