You are climbing a hill.

This hill represents whatever goal you are going after

Maybe you want to start a company. Or maybe you just want to make a bunch of money. Whatever it is, you're climbing a damn hill.

Let’s call this hill, The Hill of Hopes and Dreams.

Most of us focus our energy on getting to the top of this hill.

Listen to podcasts. Go to networking events. Eat keto. Repeat. Or maybe that's just Silicon Valley.

Regardless, one day, you may get to the top of this hill. And it might be one of the saddest days of your life.


Because you finally realize you were climbing the wrong damn hill.

You realize you weren't climbing the hill because that's what you wanted to do. Instead, you were trying to impress your friends. Or your parents. Or maybe you chose it because it was the easiest hill to climb.

Maybe halfway up the hill you thought about going back down and climbing another one. But something told you it wasn't worth it.

You know what's a waste? Climbing the wrong damn hill.

It's hard though. Because when you're climbing a hill, the Fog of the Future prevents you from seeing how high the other hills are.

But that's no excuse for climbing the wrong damn hill.

Many of us look at career choices as life sentences. "Ah, but I studied English! I can't do something with numbers." Or, "I don't have enough experience for that job. I'm just going to stay on this hill where it's nice and safe."

Career choices aren't life sentences. They're experiments.

Any sound experiment has three components:

  1. Guess
  2. Test
  3. Learn

When thinking about new life opportunities, make your best guess about which one will suit you best.

Just pick one and come up with a small experiment to test that assumption. Maybe you take an online course. Or read a book. Or talk to someone that works in that industry.

Once you've ran your test, reflect on the experience. Was it what you expected? Better? Worse? Why?

From there, make a new educated guess based on your learning. Rinse - for at least twenty seconds - and repeat.

The greatest tragedy is not failing to get to the top of a hill. Instead, the greatest tragedy is climbing the wrong damn hill.

Apr 17, 2020

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