What feels like fun to you and like work to others?: The Best Question for Figuring Out What to Do With Your Life

Jackson Kerchis
2 min readFeb 3, 2022

Are you in your 20s or 30s and struggle with “what should I do with my life?”

Me too. I’ve obsessed over this question. And concluded that 90% of advice is bullshit. There’s no hack, recipe, or secret formula for finding your thing.

The best way is to answer: what feels like fun to you and like work to others?

1. Doing work that’s fun removes risk.

Imagine. You hate marketing. You spend two months researching copywriting, e-commerce, and digital ads so you can launch an online store. You do it. It flops.

Don’t imagine. Because that story is me. It sucked. I wasted my time.

But what if I spend those two months writing a book about a topic I love. Every Sunday I have a cup of coffee and write all morning. And when the book is done guess what?

It also flops! Not a single copy sold. That’s me too.

But it wasn’t a waste of time, because I enjoyed it. It was terrific. I’m doing it again right now.

When you do work that’s fun you have a win-win: it’s a success and you enjoyed it — or you just enjoyed it.

2. Stamina wins.

Pretty much every success story is the same shit. “Guy or girl keeps trying and trying and trying. They never quit. And finally they break through.”

The reason it’s so cliché is because it’s true. That’s how it works. Stamina wins. If you don’t find your work fun how the hell are you going to hang with your competition?

It’s Thursday at 7 pm. You’re exhausted while they can’t wait to get back at it. It’s Saturday morning — you want to sleep in. But they want to get up early — there’s nothing they’d rather be doing.

The secret to motivation isn’t willpower. It’s doing shit that’s fun.

3. Strengths are nature’s competitive advantage.

From 1 to 10 how much do you like doing stuff you’re absolutely terrible at?

We tend to enjoy what we’re good at. What you’re naturally good at is your competitive advantage. My body type — skinny fat. I’m also slow. It wouldn’t be wise for me to focus on making the NFL.

But I’m a big time nerd for psychology and mindfulness. So maybe I should study and teach about happiness (that’s the plan).

Think about things that are fun to you that others hate and you’ll hone in on your natural strengths.

Then do those things for fun and you’ll eventually put in more work than everyone else (stamina wins).

And even if you’re a flop. You still had fun. You’re still happy. Does anything else really matter?

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Jackson Kerchis

I’m an ex startup CEO and zen monk who created the first Happiness degree. I write and speak about happiness in work and life. 50K+ have read my essays