A Gift for Sisyphus


When do you choose to do very hard things?

Some people take on all-comers — at least when they have the bandwidth. Some are reactive — they have something to prove. Others, still, are more strategic.

What is your strategy? Can you sum it up in a sentence or two? What is your signal to go? To wait? To stop?

For the record, I would define a Very Hard Thing as something that:

  • Requires significant personal change
  • Requires you to say no to things that you normally say yes to — maybe forever
  • Tests the highest levels of your skills and determination

We tend to assume that Very Hard Things will have a commensurate payoff. Yet, that’s not guaranteed. Sometimes, that’s because we are practicing resilience in a deliberate way. We might jump into ice baths or sign up for gruelling obstacle course races. We do it for the experience.

But what if that’s not why you’re doing it? What if you’re doing a Very Hard Thing with a specific outcome in mind — but you never get there?

Few things are more frustrating.

Toiling without a clear payoff can make you feel like Sisyphus; cursed to roll a boulder up the hill over and over again — only to have it slide down every time it nears the top.

How not to be like Sisyphus: One-time behaviours
We tackle the one-time behaviours first because it’s like tipping a domino over. Or maybe a miniature boulder. There is a cascade of effects. Performance becomes easier. Movement becomes more fluid.

  • If you’re wearing rollerblades, take them off before you start working on that boulder. Get some good pushin’ shoes. You deserve them.
  • If you’re struggling with willpower around certain foods, get them out of the house — and off the shopping list. High quality olive oil only.
  • If you’re dealing with pain, injury, or apprehension, sign on with a therapist or trainer who gets it. Stay limber. Take care of your knees. Don’t anger Zeus.

With one-time behaviours, we don’t have to exercise extreme discipline every time we pass the bowl of cookies. Or deal with the friction that comes with unknown risk. Choosing the right one-time behaviour(s) sets you up for success.

Next, find a cruising speed
Here, we get a sense of what regular practice feels like. What is the sensation of your palms on hot stone? How often do you need to train your legs? How much of a difference does an extra 30 minutes of sleep make?

Here, we ask questions about process instead of outcomes.

Pressure is low on this part of the hill. We’re allowed to make mistakes. Run experiments. Find out what rules can be bent, stretched, or broken.

Sisyphus pushing a boulder over the crest of a hill


When it’s high time for high effort
I would argue that there is one key time to use all you’ve got. It is when the boulder is already near the top. That’s when effort, discipline, and gut-wrenching hard work pay off. That’s when you push with everything you’ve got — and enjoy the unique privilege of watching that sucker roll downhill all on its own.

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