Raw honesty about my life

No fancy words. Just reality.

This week’s newsletter is a little different.

Usually, I take a lesson from history and apply it to life.

This week, I’m taking a lesson from my life. And I hope you’ll apply it to yours.

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When’s the last time your life felt surreal?

Since I quit my job in May 2022, I’ve felt like I’m starring in a spinoff of The Truman Show.

Over the last 20 months, I've taken a sledgehammer to the building blocks of my identity.

I stripped it all away — the money, the security, the status, the lifestyle, the comfort — to start from scratch with a new career in a new place with new people, no assurances, no clients, and no income.

I made a decision to blow it all up, and then I swung as hard as I could at the bricks in the foundation of my identity.

And you know what happened?

• I beat myself up.

• I went into free fall.

• I worried about money.

• I woke up at 4:30 a.m. racked with fear.

• I wondered what the hell I had done.

• I questioned myself.

• I spiraled.

• I sank.

And you know what else happened? 

• I learned to surf.

• I got hired to write a book.

• I filmed a game show in Los Angeles. 

• I worked as a tour guide on a Hawaiian coffee farm. 

• I was taken on a private tour of the Vatican Museum. 

• I did black-gloved research of long-lost Belgian letters in dusty Italian archives.

• I made lifelong friends with people I would’ve overlooked before.

• I checked off my bucket list item of visiting all 50 states.

• I built my dream job as a freelance writer.

• I skydived over the Pacific.

• I lived.

It feels like every day is a new episode, and the screenwriters are laughing.

“He’s not gonna believe what happens this week!”

And you know why this all happened?

This all happened because I tore it all down.

Because I did something that was 100% the incorrect decision on paper.

Because I left a comfortable finance career that promised more money than I ever dreamed to chase a dream that refused to promise me a single cent.

I’ve lived more in the past 20 months than in my previous 29 years combined.

So much of it has been bottom-of-the-barrel awful.

So much of it has been touch-the-heavens incredible.

And all of it — every second of despair and every minute of elation — has been so, so raw.

And that rawness has felt so real.

And that realness has felt so surreal.

And that sounds confusing, but the reason the most real moments feel surreal is because we so rarely get an opportunity to press ourselves against the nakedness of life.

And we build up these barriers — these shields — that grant us so much comfort that we’re saved from feeling the harsh sandpaper rawness of what it means to live a human life.

And because we protect our skin from anything that can make it less beautiful, we make it waxy. And dull. And inhuman.

And the realness of life slips away until the real is so rare that it becomes surreal.

So what does this mean for you?

To be honest, I don’t know.

I don’t know your life, your experiences, your situation.

But I do know this:

If you think you know yourself, you need to challenge that.

You need to find a building block, and you need to destroy it.

You need to force yourself to meet yourself — without the shields.

You need to live.

And life will reward you.

(P.S. You may notice that this landed in your inbox at a new time. We’re an 8:00 a.m. EST newsletter family now.)