It took me 35 years to write this email


What I know at 35 I wish I knew at 20

Missed last edition? — catch up on the archive here​

Hey Reader,

“Everyone lives two lives, and the second begins when you realize you only have one.”

I don’t think that really hit me until my 30s.

And having just turned 35 last week, I’ve been reflecting on how the most expensive lessons you learn in life don't cost you money… they cost you years.

Cue the existential crisis lol.

I actually wrote out ten of these for a video I’m making later this month. But ten is a lot to put on somebody on a Saturday, so I cut it to my three favorites.

Enjoy!

1. You’ll never feel ready, so do it anyway

“I’m not ready” is almost always “I’ve never done this before”

Of course you haven’t. That’s the whole point.

Where’s the fun in living a life where you just keep repeating what you’ve already done?

The best things in my life came from doing things I didn’t feel ready for:

  • I wasn’t ready for my first dog, but he ended up being perfect.
  • I wasn’t ready to up and move to Arizona, but it stuck.
  • I wasn’t ready to launch my youtube channel, but it turned into my career.
  • I wasn’t ready to launch my first coaching program, but it became the most successful thing I ever did.

As the OG of positive psychology, Abraham Maslow said it best:

"In any given moment, we have two options: to step forward into growth or to step back into safety"

Readiness is just a nicer word for your comfort zone.

We don't feel ready because we're obsessed with needing clarity.

In my experience, clarity doesn’t come before action... it comes THROUGH it. You do something, and then the clarity you're seeking starts to reveal itself to you.

The people I’ve watched get left behind aren’t the ones who failed, Reader. They’re the ones who kept waiting to feel ready first.

Whatever you’ve been putting off (you already know what it is)

ask yourself:

"What would be the first step I'd do if I were fully ready?"

Then just go do that this week.

2. You’re chasing a feeling, not the thing.

It’s not the thing, it’s the thing behind the thing.

Nobody actually wants a million dollars. They want the feeling of what they think 1M will give them: more security, not having to stress over bills, looking at a menu without checking prices.

Take it from someone who spent seven years working to get a million subscribers. I thought what I wanted was the gold play button.

And don’t get me wrong, the award is cool. I feel proud every time I look at it.

But after the initial high wears off, it hit me what I was really after: the feeling of being seen. That my voice could impact people. Waking up every day with a purpose and doing something creatively rewarding.

And when I lose sight of that and start chasing views and metrics, my motivation tanks.

(To be clear Reader, I still love goals. I set them every year. And this point isn’t stop wanting things.)

What I've learned is that if you never name the feeling underneath the thing you're after, you can chase something for years, finally get it, and feel empty.

But the good news is that once you know the feeling you’re after, there might be a quicker path to it than the gigantic version you built up in your head.

You probably don’t need a PhD to write your first book.

You probably don’t need to be single-digit body fat to start dating.

You don’t need 5M in the bank to feel like you can relax and enjoy life.

So get honest about the feeling behind the thing… then chase THAT instead.

3. Stop letting people you don’t respect run your life.

When I was 18, someone told me:

Never care about the opinions of people you don’t respect.

Then in college, I got my first shot to actually live it.

I was posting drum covers online. But I couldn't decide between a drumming or fitness youtube channel. So my big idea was to combine them: take my shirt off and hit the drums as HARD as I could as the workout.

It was exactly as bad as it sounds lol.

My videos were so bad that they started circulating around campus. I’d be eating in the dining hall and would hear people laughing as I walked by because they’d found my videos. I went back to my dorm room ready to delete my whole channel.

But I’m so glad I didn’t.

Because eight years later, one of those videos got me discovered by a band. That led to touring around the world, playing Warped Tour, even performing on Conan.

The reason I’m telling you this:

My childhood dream of touring in a band ONLY happened because I didn't delete the videos.

And it's wild to think I almost let people I didn't even know, and would never see again, block my dream from happening.

So picture the biggest thing you want, and the people you’re afraid will judge you for chasing it. Then ask if you’d actually trade places with a single one of them.

If the answer’s no, then who cares?

Because at the end of your life you don't regret the things you do, you regret what you didn't do.

That’s three of the ten:

  1. You’ll never feel ready, so do it anyway
  2. You’re chasing a feeling, not the thing
  3. Stop letting people you don’t respect run your life

Might send the rest when the video’s out.

Welcome new readers!

Lots of you came in from my recent video around self-sabotage that just hit over 1M views. So if that’s you, welcome!

This is my (almost) weekly newsletter where I talk about big ideas worth sharing. Some weeks it’s a quick personal story, other times it’s a deeper dive into one topic.

You can find all previous editions on the archive here.​

My latest video

How can you get addicted to doing hard things in our modern brain-rot dopamine culture? Here’s a chart video where I break down 3 problems and 3 solutions to that question.

video preview​

​How to Get Your Brain Addicted to Hard Things, Not Cheap Dopamine​

What I'm reading

Notes From Underground by Fyodor Dostoevsky

​https://link.amazon/B08W3Sf6t (affiliate)

Been on a Dostoevsky kick this year. He's not the easiest to read, but he puts things in a way that sticks with you. This one's about a guy who's so self-aware he overthinks himself into a hole he can't climb out of.

See you saturday,

CK

P.S. Feel free to "reply" if you got something from this newsletter. I can't respond due to volume, but I love reading your replies.

P.P.S. Looking for your next watch? Here are my 3 most popular videos from 2026 so far:

  1. ​Give me 17 minutes, and I'll eliminate your self-sabotage​
  2. ​Quit drinking alcohol timeline: Day 0 to 365 (exactly what to expect)​
  3. ​7 habits that changed my life after 30​

Clark Kegley

​

600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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