Choosing To Do Something Hard

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Before the start of every athletic season at my high school, the varsity teams would have a meeting for all athletes who were interested in trying out to be on the team. I remember every year my high school wrestling coach hosted this meeting, he would say the same thing to the group:


“Everyone who is in this room has made a decision to do something that is very hard.”


He would go on to talk about how the decision we had made was harder than the decision that the hockey and basketball players had made.


Wrestling is a very difficult sport. It is demanding mentally in the repetition and deliberate training that is required to become proficient. It is demanding in its physicality, the toll it takes on the body and the mental toughness required to endure through fatigue. And it is mostly demanding in that it requires its participants to be round-the-clock vigilantes of their weight and the mental battle of being alone on the mat against an opponent for everyone to see. It is often not fun, but the reward can be found in enduring the challenge.


I appreciated what my coach had to say for a few reasons. First, it validated how I was feeling. I was not a wimp for thinking wrestling was hard because it was hard and he was the first person to acknowledge it. Second, it made me proud. There is pride in choosing to do the difficult thing. If life were easy and the easy thing to do was always the right thing to do, everyone would always take the easy route. People need to do the hard thing and often make difficult decisions to see long-term success. And third, it helped me build camaraderie with my peers who had made the same decision. We were like-minded in our decision to do something hard. That alone was enough to pull for one another.


When I think back about various decisions in my life, I often regret not doing the difficult thing, and I hardly ever regret making the difficult choice even when I fail.


For example, between my sophomore and junior year of college, I had an opportunity to go study abroad in London for a semester. But I was nervous about going away since I had a girlfriend, especially so because this one semester in particular, I would be the only Princeton student going abroad to this specific university in London. I was scared of being alone and I decided not to go. Shortly thereafter, my relationship with my girlfriend ended, I was relatively unhappy on campus with the stimulation of my studies, and as the years passed and I learned how unforgettable it was for all my friends to have studied abroad, I realized I had made a massive mistake because I was unwilling to make myself uncomfortable.


Conversely, I walked on to a Division 1 wrestling team in an effort to challenge myself and eventually quit the team. I’ve never regretted the decision to give that a shot. If anything, I regret not getting to the finish line. It taught me an invaluable lesson about how personally I take it to fail at anything I have set out to do. Because I had that uncomfortable experience, I have been a little extra resilient in other matters in my life where I would have otherwise been eager to just throw my hands in the air. I needed to feel that discomfort and understand how much giving up pains me in order to become stronger.


I talk about the idea of choosing to do something hard any time I talk to people who are thinking about working at a startup. Making a decision to work at a startup is almost always a conscious decision to do something hard. I have spent most of my career working at startups and I often wonder what it is like to have the wind at my back in everything that I do – a big brand name everyone knows, unlimited resources, having your logo everywhere at the tradeshow. Sometimes I speak to salespeople at bigger organizations whose job it is to keep one customer happy or maybe a handful of customers. I wonder what it must be like to have so much free time.


Things have not always been easy, and sometimes I have wondered if I would fail. At my first job, the company pivoted into something entirely different within 6 months of my joining the company right out of college. My role and everything we were focused on changed overnight. I did not even understand that companies could do such a thing. Candidly, I did not handle it very well at first. But I decided to stick it out. And I am glad that I did.


The people I admire the most are people who go out of their way to do something hard. I have a coworker who jokes about “callousing his mind” with new challenges – running a marathon on a treadmill or eating the spiciest Indian food he can find in Manhattan. And while I like to give him a hard time since we have that kind of relationship, deep down I am filled with admiration for his ability to seek new challenges and strengthen his mind through the endurance of struggle.


We all have moments where we feel down. Sometimes we feel like we have failed in some way. The bigger question is “Did I fail, or did I fail myself?” Failing and being a failure are two different things. Failing is as simple as not meeting a goal. But being a failure is someone who gave up or who avoided the difficult path en route to failure. That is a key distinction. The hard thing is not always the right thing, but the hard thing never fails to teach us a lesson.

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