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3 Painful Lessons I Wish I Knew In My Early 20’s

“Shit, shit, SHIT.”

I said this to myself as I boarded a plane to Mexico yesterday.

I was scared.

Not for my safety. Not for COVID. I was scared because of my elementary knowledge of Spanish and how I could only speak the most basic of sentences.

Every time I hear someone speak Spanish, I feel like I’m listening to the linguistic equivalent of the Indy 500. Words echoing around the mouth at light speed. That’s how it is with all languages that are initially foreign to you, though.

The point is, I was scared.

Being in a new place with new people that speak a new language is daunting to say the least. You’re staring loneliness directly in the eye, and loneliness is one of the scariest adversaries there is.

As I walked down the aisle I realized something really important, though.

Pain means I’m growing.

I’m 28 years old right now, and I still haven’t totally learned that lesson. That’s the first thing I wish I knew when I turned 20.

1. Pain Means You’re Growing


Jocko Willink is one of my favorite human beings. He’s an ex-Navy Seal commander who fought hostile forces in the dangerous city of Ramadi.

You should read his book, “Extreme Ownership

My brother and I love this one video from him where he rhetorically asks the audiences whether they’ve gone through a variety of different hardships. Then, after a pause, he says “Good.”

It’s easy to take a video like that and spoof it. My brother and I love to send ridiculous statements back and forth to each other “Did you get your arm chopped off recently? …. GOOD.” “Went skydiving and the chute didn’t open? …. GOOD.”

You get the picture.

Jocko’s point, though, is that pain and hardship shouldn’t always be met with resentment and fear. Maybe pain and hardship should be looked at as an opportunity to grow.

That’s why he offers that classic response that’s made him an even bigger legend in the eyes of my brother and I:


I wish I knew earlier that pain means you’re growing. In my case as a traveler, many times it means I’m outside of my comfort zone.

Reframing awkwardness, pain, or hardship in this way can be quite powerful. It gives you what I’d like to call “spiritual body armor.” You’re taking what should be a weakness and turning it into jet fuel for yourself.

When you feel pain, it means you’re headed in the right direction.

Good. Now lean into the pain more.

2. It’s Not Going To Be Perfect

I’ll walk off the plane in Mexico, get greeted by crowds, see everyone smile at me from door to door, and have a great conversation with the taxi driver (in Spanish) on the way to my Airbnb.



When you set high expectations, it’s a certainty that you’ll be let down. I’m an optimist by default, so I tend to expect every moment in my life will be filled with joy and opportunity. The reality is that life sucks a lot of the time, and that that’s okay!

I love that scene from 500 Days of Summer where the main character goes to an event, and it shows two squares side-by-side for the duration of the scene. One square is titled “Expectations” and the other square is titled “Reality.”

Two versions of the evening play out — one joyous scene set in the main character’s psyche, and one scene set in bitter reality.

You can watch this for yourself in the video above.

What makes it so powerful is that we’ve all been there. We’ve all expected something would be way better than we thought, only to be let down later.

The better mindset to have is to expect nothing!

When you embrace pain and expect nothing in life, you stop yourself from ascending too high in the roller coaster of life, only to be let down faster than a cartoon character who just ran off a cliff.

It’s nice to expect more from life. It’s good to be optimistic. It can fill you with loads of energy and fleeting joy. But when you rely too much on high expectations, the inevitable crash will be devastating.

3. Handicap Yourself For Growth

While listening to the Lex Friedman podcast the other day, I came across a remarkable mindset from his black-belt guest.

They were talking about some influential figure in the Brazilian jiu-jitsu scene, and going on about how he “handicaps” himself in practice to focus on specific situations.

In plain-English, he decides to NOT use all the techniques in his arsenal so that he can deliberately put himself in danger and work on his responses in various situations.

It’s sort of like if Steph Curry decided to not shoot the 3-ball in practice. That’s his bread and butter — but by handicapping his game he now gives himself space to work on defense or passing.

My first point “Pain means you’re growing” is a really good mindset to cultivate. This point, though — “Handicap yourself for growth” borders on the masochistic.

I’m urging you to create pain for yourself.

Damn Tom, can I enjoy any part of my life?

I get it. I’m focusing on pain a little too much here. However, if your objective is to grow in life, you need to introduce yourself to pain, much like soldiers introduce themselves to boot camp to become harder, more battle-ready men and women.

What does this strategy look like in real life, though?

For me it’s traveling. It’s diving into a country where I know next to nobody. Traveling is a hell of a crucible for personal growth. People love to think of travel as leisure and fun — and it is when you’re going with other people and staying at resorts — but when you go alone it changes the dynamic entirely.

The essence of this strategy boils down to this:

What are you really good at? What happens if you took that away from yourself on purpose?

I take comfort away from myself by traveling.

Are you stubborn as fuck like me? What if you took your stubbornness away by having a conversation with someone who has drastically different views than you? What if you challenged yourself to not say a goddamn word the whole time?

Do you have a problem checking your phone a billion times per day like me? What if you locked your phone in a fucking box and buried it in your backyard for a week?

Okay, weird example.

You get my point, though.

Many times the most meaningful personal growth happens via subtraction.

Take something away from your life every now and then — be it alcohol, comfort, or technology. See what happens.

If I knew these three things when I was 20, I’d have saved myself unthinkable amounts of heartache. I hope they can help you now, too.

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