The Theory of Difficulty

One of your most powerful tools in life design.

Life is hard. It’s better when you decide which parts.

Once you decide which things in life you want to be difficult, life gets a lot easier. If you fail to choose, your challenges will be chosen for you.

Here’s how the theory works. When you faced a difficult test in school, you studied harder. Regardless of the test results, your increased efforts led to you knowing more. It was your choice to accept the test as difficult. People ignore obvious difficulties all the time. I’ll prove it. Learning an instrument, for example. It’s hard, but millions pick up a guitar thinking it will be easy. That’s why so many people turn their guitars from an instrument to a piece of decor.

But don’t be hasty. The solution is not telling yourself everything will be hard. A brilliant person once said:

You shouldn’t take [everything in] life too seriously, or you’ll never get out alive — Van Wilder.

The Theory of Difficulty will help you figure out what you want out of life. It’s a question you will have to answer many times. You didn’t have a choice when taking the tough test in school, but as you become more autonomous, you get to decide what struggles you face. And from struggle comes growth.

I have been a member of many gyms in my years on the planet. My favourite is Fulton’s Fitness in St. Catherines, Ontario. It has 3 rooms filled with steel weights and few pieces of cardio equipment. I have never sweated more than at Fulton’s. They didn’t have air conditioning. Only a few fans in-between the squat racks.

Another gym I was a member of, Anytime Fitness, was kept cool. I stopped sweating while working out there. The cold air felt nice walking in on a hot day, but it set me up to expect an easy workout. And that’s what I got.

I didn’t know it at the time, but switching from Anytime to Fulton’s was a powerful lesson in life design. One that wouldn’t hit me until many years later.

The problem is our brain. It encourages us to avoid challenges. Thinking it will make life easier. But if you remove all difficulty you remove growth, become less efficient, perhaps a little unsettled, unmotivated, unhappy, and those become your new challenges.

Let me clear one thing up.

I’m not talking about grinding it out, hustle culture, working 14 hours a day, running 3 businesses, bla bla bla. Forget those people bragging about how busy they are. I am talking about finding something worth struggling for. Not all the time. But sometimes.

If you don’t choose the hard thing it will choose you.

Let’s use dating as an example. A friend of mine, let’s call him Jeremy, hadn’t dated much growing up because he got a girlfriend young who would later dump him as an adult. He unconsciously decided that finding a new partner would be easy like it was the first time. He created a Tinder and Bumble profile. After a few matches but no dates he was frustrated and complained about how impossible it was to stand out — even with the classic man with dog picture. There was a mismatch between what he expected, something easy, and what he got, a very complicated process of finding another person to connect with digitally only to follow that up by figuring out if you match in person.

When you decide something is going to be easy, typically you will get mediocre results. Sometimes you get lucky and strike gold with little effort. But life is too important to wait for luck.

When you decide something should be easy, you are deciding not to worry about the result. That is okay for some things. Maybe you are learning to bake. If you put too much salt in the cookies (my sister once used an entire cup!) you won’t be too upset. Hopefully, you will laugh at yourself for many years (I still laugh at her). Then you make another batch. No pressure. It’s light. It was fun.

With dating, you care about the result. Who you end up with will be the one to support you through dark days. Someone you fight with but swallow your pride and say sorry. Maybe you believe in fate, but fate doesn’t come to those who expect everything to be easy.

Deciding what will be hard is deciding what you will work hard at.

I loved playing basketball growing up. Still do. Subconsciously, I decided it was going to be an easy thing. I peaked in grade 10 when I hit a game-winning jumper while playing for the senior varsity team (the only game we won that season). I was never the best because I never took it that seriously. I missed practice because it wasn’t really playing to me. Too many suicides. I had fun playing and that was enough. There was another challenge in my life that I was tackling.

I was a shy kid, and nervous to talk to girls and decided that was something I should change. I read Men Are From Mars Women are From Venus and The Game: Penetrating the Secret Society of Pick Up Artists and just about any articles that gave me an edge in talking to girls. I forced myself out of my comfort zone. And as evil as it sounds, I went out with some girls I saw as practice. Hopefully, I was good practice for them too. I made dating hard so that later it would be easy.

I could have just sat back and waited for the right girl to come along. But to me, that was too risky. What if she didn’t? The right girl did eventually appear as my next-door neighbour. But without all those years of practice, we would have never switched from neighbours to life partners.

Jeremy ended up going on some dates, but they led to further disappointment. He settled on a partner he wasn’t thrilled about and dated her for about a year. After a frustrating year they broke up and he felt further away from finding a mate.

Jeremy and I had a heart to heart and I told him about my theory of difficulty. I explained that to achieve his desired outcome, he was going to have to do the hard stuff so that later it would be easy. He needed to grow to attract his match. He was struggling already because he was unhappy but wasn’t choosing his struggle.

Some people ‘have things easy’ he said to me. People who are biologically less attractive think beautiful people have it easy when it comes to dating. People predisposed to having a heavier build think skinny people have it easy. Genetics play a role in our lives, for sure. But beautiful people can end up divorced many times over, and thin people may wish they had bigger muscles. The sexy divorced person may never choose their challenge, and the scrawny guy may never pick up a heavy enough weight.

Instead of having unhappiness as his struggle, I told Jeremy to choose his challenge. He didn’t choose unhappiness, it chose him. But once he decided to go on bad dates, experience more awkward situations, ask himself tough questions about who he really is, things got a lot better for him. He was choosing his challenge.

Hard things don’t have to stay hard. If you move to a new city, you might decide that finding new friends is going to be hard and push through the challenges of going out, meeting people you don’t connect with, finding yourself in awkward situations, being rejected, and feeling lonely. Then one day you will have built a friend group you feel connected to and it moves off the hard list.

The reason we make things hard is to grow from them. Everything doesn’t have to be hard all the time. Just like something easy may become hard. One day you may hit a rough patch in your relationship. You can decide to keep things easy. Or you can decide to do the hard thing and have an uncomfortable conversation that will help you grow. Then you are back on easy street.

Choosing what will be hard helps you be more like a stoic.

When we decide something is going to be hard, we quickly find out whether we actually wanted to do that thing. If the difficulty of a thing scares us from doing it that is a sign that maybe we should reconsider.

Making something you enjoy harder could lead to your greatest self. But ask yourself why would you do such a thing before driving yourself mad.

Ancient wisdom says we shouldn’t expect certain outcomes. It’s a philosophical tool to find happiness and peace. When I think about cleaning the house, I want all the dirt gone. From the fridge, behind the toilet, the shower, floors, the carpet, under the sink. But cleaning all those areas is hard. And I don’t care about the process. I just want it done. So I pay someone to do it. When choosing your hard thing(s), you need to have as much invested in the process as the outcome.

There is a famous interview with Kobe Bryant after game 2 of the 2009 NBA finals. They were playing against the inferior Orlando Magic. They just went up 2–0. When asked why he isn’t smiling, the quote that will be long remembered is ‘jobs not finished’. He loved the process so much he was willing to put off pleasure until the outcome was resolved.

Kobe is a rare breed. From the rare breeds, we learn. Winning an NBA championship is the hardest thing a basketball player will do (except if you’re Robert Horry). Kobe saw it as such and would go on to win the series 4–1. I don’t think we should all turn into Kobe or MJ. We can’t. They were freaks. But deciding what will be hard can help you be happy. It will help you chose to struggle with things that matter. Even if you don’t win your championship, by doing something you know will be hard, and not shying away from its difficulty, you will achieve an outcome you can enjoy.