How to Not Regret Your Career

Hello friends and welcome to curious jay! If you want to join 6,500 other readers learning about life and business, subscribe below:

Feel free to check out my other articles and follow me on Twitter, and if you want to chat about writing, newsletters, social media, or well, anything else in general, book a call here!

If there’s one thing you should know about me, it’s this:

I’m a competitive person. Put simply, I like to win games.

But after an enlightening walk with my family along the river… I realized that there are some games that I can never win.

For example, how do you win a walk with your family?

If you walk faster than them and get to the end first… do you win?

No, that’s ridiculous.

How do you win listening to music?

If you play the song at 2x speed and finish faster… do you win?

No, of course not.

And that’s when I realized:

There are games you play to win, and games you play to keep playing.

Career as an infinite game

James Carse has this idea of finite and infinite games.

The problem?

Most people think of their career as a finite game.

They try to “win” their career as if getting to the end the fastest would bring them the most meaning.

This was a trap I recently fell into.

“I’ll just grind really hard in my 20s so I can chill in my 30s.”

“It’s okay if I don’t like what I do now because then I can do what I want later.”

But if the primary goal of your career is to “win” the game, then you’ve already lost before you even started. If you win the rat race, you’re still a rat.

Instead of thinking, “How do I win the game?”, the correct question to ask is “How do I find a game worth playing?”

Setting anti-goals

Knowing what you want to do with the rest of your life is nearly impossible to answer. So instead of trying to answer it directly, a helpful mental model is to start with what you don’t want.

• What would a horrible, unfulfilling, soul-sucking career look like?

• What would the worst-case scenario look like?

• What do you not want to do with your life?

Work your way backward to gain a clearer understanding of what you DO want to do.

Title work vs. Actual work

Many people (myself included) like the idea of a career more than the actual career. Let me explain.

One of my friends wants to be a surgeon, yet she can’t stand cutting people open and staring at blood.

She likes the idea of being called a doctor but doesn’t like the day-to-day tasks of being a doctor.

So the question then becomes…

Do you like the title or the actual work?

When most people answer this question, they find that they like the title more than the actual work. Yet the day-to-day work is what makes up your career… not your title.

Climb the ladder

I came across this exercise from Sahil Bloom. At the time he was an Analyst at a PE firm. He quit to run his own business because he looked up at the people who were winning the game (the partners, the executives, the board) and realized he didn’t want their life.

They were overweight, divorced, bald, and perpetually stressed.

Climb the ladder of your current career path. Are the people at the top happy? If you could switch places with them… would you?

While there is no one definite answer to finding a career you find fulfilling. These three mental exercises may help:

What do I not want to do?

Do I like the title or the actual work?

Do the people who are winning the game have what I want?

If you stumble upon a career you find meaningful, go all in.

Because most don’t experience the joy of creating a career they genuinely love.

Jay “Retirement is when you stop sacrificing today for tomorrow” Yang