The common advice you receive from motivational speakers is to do what you love, find something you’re passionate about, and chase it. They say that if you’re passionate, you’ll love what you’re doing, and that will drive you to win. I still feel strongly that that’s BS advice, that making emotional and selfish decisions is not the way to win at all, and that doing what you love is selfish and not how to go about your career.
Think of your career as a series of games, and each phase or move is one game. The key to winning is taking a step back early on in your career and figuring out what game to play. Too many people play the wrong game with too many people, the competition is tough, and the prizes are bad.
What’s your goal? If it’s to spend your day doing what you love, I’m not the guy to listen to. My goal is financial independence, to spend my time doing what I want to do, and to have all the free time to do whatever it is that I love.
You have to ask yourself a series of questions as you consider the games of your career:
Is the game fun to play?
If yes, it’s probably a bad decision to go after it. It will draw passionate people who are not in it for the money, and it’s very unlikely that it adds value to other people. It’s a selfish way to look at your career.
How good do you need to be to win?
What percentage of people playing this game are winning? And how good are these people? In pro sports and a ton of other fun industries, very few people doing it can make good money. In sweaty startups, there are a lot of dumb people making great money and winning. People join these businesses not because they’re fun, but because they’re opportunities.
What does winning look like?
Look at somebody who has won and what their life is like. Are they happy? Do they have free time? Are they financially free? Do you want your life to look like theirs someday? If the answer is no, you’ll probably never be happy on that path.
Who are you trying to impress?
Are you going in a direction because society says it’s awesome and really glorifies it, or because it gets you closer to your goals? The ego is your enemy.
What kind of action is rewarded in the game?
People get burned out by the politics of corporate America because winning is more about who you know than what you’re doing. You want to understand what it takes to win and if that’s something you’re willing to do.
Do you want it all right now?
People who win for the most part are people who think 5 years ahead. For the first 3 years of my career I was hauling boxes and answering customer calls, but now that I’m 10 years in I’ve been able to transition to doing what I want and accumulate generational wealth.
Can you avoid the golden handcuffs?
People fall victim to the golden handcuffs because as they earn more money, they spend more money, and they work more. They become addicted to the paycheck, leaving them trapped in their job with no flexibility. Most people spend their money on consumption, but winners spend their money on assets that make them more money.
The big problem is that most people don’t think about these things. They’re told by schools to follow the course and chase their dreams, but that’s not how you win. You win by being opportunistic. Winners try out a lot of different things and explore different opportunities, trying to find the path of least resistance to their goals.
Some people will get partway into one game and realize it’s the wrong choice. The money isn’t there, they’re working too much, or it won’t lead to their goals. The hard part is having the courage and guts to make a change. There’s no easy way to win, but you can explore options while not giving up while you have. You need to have the courage to make a better life for yourself, get out there, and find a game that you want to play.
Three Key Takeaways
- Chasing what you love is a selfish approach to your career and has an incredibly low chance of success.
- Your career can be thought of as a series of games, and you get to pick which one you compete in. There are a lot of unskilled players making a ton of money in easy games!
- The game you pick is important, and it’s okay if you decide to pivot partway when you realize you’re on the wrong path.
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