Ep 71: A career is a series of games

Take a second to think about the most successful people in your town. They probably aren’t Steve Jobs or Elon Musk, they’re the people in your neighborhood that spend time at the country club and eat at nice restaurants. They live a great life, but they don’t get news articles or case studies written about them.

That’s how you should envision success. Success if when you have enough money to spend your time doing what you want, it’s when you stop needing to trade your time for money. Success doesn’t have to be about becoming a billionaire, developing a new invention, or getting famous. The north star is freedom with your time and your money.

So how do you get there? Think about your career as a series of games. You want to be a poker player, not a roulette player. Roulette is a game of luck, poker is a bit of luck mixed in with a lot of strategy. Your resource, your poker chips, is your time, and you should be wise in how you allocate it. Once you’re firm on your goal, you want to take the path of least resistance to get there as fast as possible.

There are too many smart people playing the wrong games with stiff competition and crappy prizes, and they wonder why it’s so tough to get ahead. There are a set of questions you should ask yourself before you chase after any opportunity hoping it will help you reach your goals:

Is this game fun to play?

Is this a passion for people? If so, it probably adds more value to you than others, and that makes it a selfish game. Even worse, your competition will play even if it doesn’t make a lot of money because they find it fun. Things like being a pro athlete or opening a restaurant are fun but so saturated that it’s nearly impossible to win.

How good do you need to be to win?

Very few people get rich in professional sports, but a lot of dumb people make money in real estate. I’d rather compete against rich, lazy people than hardworking, passionate people.

What does winning look like?

Are the successful people in this field working long and demanding weeks? Are they happy? You’d be surprised how many successful people are miserable and still tied to their desk.

Who are you trying to impress?

Are you taking a new career step because of what society says is good or cool, or because it helps you take the path of least resistance to your goal?

Does the game reward the right kind of action?

Many games don’t reward competence, you see this in any office. People get burned out playing politics and grinding away for hours, and they can’t get ahead. If you’re the best, will you be paid like the best? In small businesses, you get compensated for what you do well.

Do you want it all right now?

The shorter your desired turnaround, the worse your odds. Folks who can think 5 years ahead and are willing to delay gratification will do the sucky work right now so they can do the fun stuff later. Ten years ago I was in a warehouse loading boxes while my friends had cushy office jobs, but now I get to do the fun stuff and have made generational wealth.

Can you avoid lifestyle creep?

People get addicted to higher paychecks and end up making no real progress financially. Once you’ve accomplished your goal, it’s important to step back and avoid unnecessary risk. Winners have a balance in their life.

If careers are mountains, the winners take a few steps up 20 different paths before finding the one that works for them, the path of least resistance. People that never find success may go up halfway on a few different trails before giving up for one reason or another because they didn’t plan ahead.

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I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.