The Writing That Woke Me Up

Before I even realized I was asleep, I wrote the words that shook me awake.

My 2023 post.

Not a full year in review, but an attempt to open up about how and why I made the change to start writing and sharing my thoughts and creative work online this year.

---

I wrote the below six months ago.

I had been trying to write something original for the better part of a year, but struggled to create something that felt like me.

But nothing was working. Nothing worth sharing.

Everything came off feeling too distant. Too cold. Too “smart.” Too self-serving. “Hey look at me and all my success! You, TOO, could have this incredible knowledge!”

Something was off.

Maybe it was imposter syndrome. Maybe it was long-term writer’s block.

Something was in the way.

And yet, something brave welled up within me. I wrote this, half-proud, half-ashamed.

I didn’t want to post it. But the very act of confronting these words, in private, allowed me to (finally) be honest with myself.

And while I didn’t share this with anyone (til now), I had nicked an artery and all this other, related stuff found its way out. I posted them online.

After posting just two writings online ever, I’ve written and shared 50 pieces. Jokes, essays, confessions, advice, and childhood memories.

And that writing has re-opened up the world for me.

• It led to starting this Substack account. (thanks for subscribing to these meanderings btw)

• It led to stopping a 2,000-day drinking streak.

• It led to founding a new secret company.

• It led to the bravery required to get back up on stage.

• Haha I wrote about getting a colonoscopy. I forgot that I did that.

• It led to countless renewed relationships and meaningful conversations.

So here’s the writing that started a Renaissance, exactly as I wrote it six months ago.

You’ll note the sadness in there, which—sure—I still feel, only lessened. The sting is no longer debilitating.

I had long felt an incongruence between “trying to be me” and “trying be a successful business executive.” Scratching that painful itch allowed others to see it for themselves and share in my story.

All this started by writing the scariest and most honest thing I could.

I didn’t know I was asleep, but these words woke me up.

“I’ve Been Sleeping”

< June 20, 2023 >

“...But we were sleeping. I've been sleeping. And I've been turning away from the truth I wanted not to face…. There is a wound that won't heal… there is a darkness reaching, like rust, into everything around us. We let it grow, and now it's here. It's here and it's not visiting anymore. It wants to stay… Perhaps it's too late. But I'll tell you this, if I could do it again, I'd wake up early and be fighting those bastards from the start!”

No spoilers, but ladies and gentlemen, I present to you: Maarva’s moving speech from season one of Andor. It’s an amazing series that I’ve watched multiple times now. It’s the best Star Wars since the original trilogy, hands down. I’m not going to fight you on this. I’m just right.

But this isn’t about galaxies far, far away. It’s about me, and what I’m actually rather embarrassed to admit.

I’ve been sleeping.

Asleep. In plain view. Not myself. Trying my best but deep in my soul, asleep. Trying my best to look smart, fun, assertive, and successful, but privately admitting defeat daily by allowing distraction, doubt, and fear creep in.

The irony is that I take so much pride in founding, growing, and selling a company. My identity is “success,” but I feel like anything but. Am I the asshole who had all this success and is secretly (and ugh, now publicly) WHINING about how hard life is? Another bro having a hard time at his creative work while millions seem to find contentment while doing much harder work? 

The War of Art calls this “the Resistance”—the overwhelming, crafty power that stops you from doing the good, important work you were meant to do.

I had lunch with a new friend the other day, and he called it “a long, dark tunnel” — for him, it was SIX YEARS of struggle.

I’ve dodged the issue by jokingly calling the past few years my “very reasonable midlife crisis.”

But it’s more than that.

I’ve been sleeping.

For longer than I like to admit. Maybe for a full decade and if I’m asking myself to be honest, right here in public, this is the hardest, most honest thing I can say.

I don’t want to be asleep. I don’t want people to know that I’ve been struggling. I’m embarrassed to have spent so many years on my back foot, like I haven’t done my best. Like I wasn’t honorable in my work. Worried that they’ll feel like I’ve cheated them or been dishonest in some way.

But hey, I’ve been asleep.

The source of this veiled darkness is self-doubt, and I can tell you the exact day it overtook me.

It was a decade ago. A client didn’t like my approach to dealing with their team (in retrospect, I was trying to be helpful, but maybe was coming off too pushy?). They told Alan (my longtime friend and business partner, for those who don’t know) to have me pull back from the work we were doing. Didn’t say it to me. Said it to him, and then he said it to me. “It’s okay. I don’t care.” But I did.

I told myself that this client knew I couldn’t handle the direct feedback. That’s why they couldn’t say it to my face. And worse, my decade of self-imposed decay proved that they were right.

I started pulling back. I let people at my company take the spotlight. I focused on keeping everything organized and others supported. It was good to let others win. Good for them, good for the company.

But I knew the truth. I was letting myself hide.

I didn’t let myself get too close to the creative work. Before too long, no clients knew me. I went dark. Behind the scenes. I organized things. I literally changed my title from Creative to Operations. “Order” was easier than putting myself out there.

I’ve been sleeping.

I recently spent five weeks going through Jason Sperling’s Creative Directions book with members of my team, and in the final pages, he asks a bunch of famous creative people what they got wrong early in their careers. 

As I thought of my own path, I quipped this — “I’ve spent the past decade valuing and encouraging order, when I should have been cultivating rebellion.”

There it was—that Andor speech. Plain as day.

Rebellion.

I should have been brave. I should have fought. I should have stopped the darkness from advancing. But I didn’t, and now it’s here, and I’m drowning in it.

My worry, of course, is how this will make me look. Like I’m doing a bad cry for help, on social media.

I don’t have anything wise to say, other than to admit defeat, and commit to writing more about it.

This is my story. I’ve been asleep. And I’m trying to wake up.

---

That was six months ago, but today is today, on the cusp of a New Year.

Less order.

More rebellion.

Seems like a great goal for 2024.

What do you think?

Thanks for following along this year. Hope you have a wonderful new year and are feeling brave for the future.

Here we go—