When Your Superfine Mind Comes Undone

This is what I found underneath — 14,000 honest miles on a motorcycle through the Andes. What came back was a more complete version. A roadmap for what being a man in today's world really means.

I named this publication after the Steely Dan song called Any Major Dude Will Tell You.

It’s about a man talking to another man who’s falling apart. Not fixing him. Not lecturing him. Just telling him: I’ve been there. It gets better. Trust me on this.

That’s it. That’s the whole thing.

I’ve been looking for that conversation my entire adult life, though I didn’t know it. I rarely found it. Men don’t tend to talk that way — not honestly, not without performance, not without sarcastic banter, not without the armor we put on somewhere around age fourteen and never figure out how to take off.

This is my attempt to start it. By showing what can be done if you commit to honesty, vulnerability, and conversation.

Here’s what I know about the men I’m writing for.

You’ve built things. Maybe a business, maybe a career, maybe a family, maybe all three. You followed the script — work hard, lead well, provide, achieve.

And somewhere along the way, probably when something went wrong that the script didn’t account for, you looked up and realized you had no idea who you actually were beneath all of it.

Maybe it was a firing. A divorce. A health scare. Another birthday with a zero on the end. Maybe it was nothing dramatic — just a slow, creeping sense that the life you built doesn’t fit the man you are.

We are not alone.

The WSJ ran a piece earlier this year about three new prestige TV shows — Rooster, Your Friends and Neighbors, DTF St. Louis — all built around the same character: accomplished men who are flailing, confused, unable to figure out what being a man actually means in 2026. The critic’s conclusion was that these men never figured it out in the first place.

I’d go further. Most of us were never given the tools. We were handed a script and told to perform it. When the script stopped working, we couldn’t find what was underneath.

This platform is about what’s underneath.

My version of the crisis

I’ve founded companies, led teams, raised capital, built things. I’m still CEO of one. But the one that let me go — that one I chaired — is what cracked me wide open.

I had spent 2023 planning a self-supported 14,000-mile motorcycle journey through the Andes — Colombia to Ushuaia, the full length of South America with a couple buddies. We had shipped our bikes to Bogotá and started riding.

We had flown home for the holidays. Our bikes stayed behind in Colombia.

The CEO of a company I had co-founded and funded took a hard strategic turn that I disagreed with. It was him or me, and I wasn’t going to drop all of my commitments to run a company in a different city. Fuck that, I’m Chairman, and he’s CEO. It was my decision, and it backfired.

Within weeks, I was voted off the board of the company I’d co-founded. A thirty-five-year friendship with one of our VCs cracked in the process. My wife was furious. My internal map — the one that had always told me who I was and where I was going — went dark. I couldn’t name one thing I liked about myself.

Then, I flew back to Colombia, where my bike was waiting. There was nowhere for us to go but south.

Any Major Dude Newsletter

This newsletter is where I’ll share it as it comes together — scenes from Honest Miles, reflections on what the road actually meant, and the larger conversation I think we need to be having about men, identity, and what it costs to live inside a script that was never really yours.

Honest Miles is the memoir I’m writing. This newsletter is where I’ll share it as it comes together — scenes, reflections, the parts of the story that are ready before the book is. This is where I chronicle the lead-up to my collapse, the reckoning, and the awakening I experienced. It’s not for everyone, but if you are a man who is struggling to figure this shit out, then maybe my story will at least show you a path that someone else has traveled.

All in 2026, where masculinity is being shamed and where society can’t even help us define what being a man means.

“No thanks, I’m fine”

Any Major Dude is for men who are done pretending they have it figured out.

Not men who are broken. Not men who are victims. It’s for men who are willing to look honestly at how they got here and what they want the next chapter to look like.

We’ll talk about the road. About career and what it costs when the thing you built your identity around is gone. About friendship — real friendship, the kind most of us stopped having somewhere in our forties. About marriage. Intimacy. About what it means to be a man right now, in 2026, when the old script is dead, and nobody has handed us a new one.

That last part is the one I keep coming back to.

I don’t have a system. I have 14,000 difficult miles and some things I learned the hard way.

Any major dude will tell you.

Subscribe if you want to be part of it, and if you’re done saying “no thanks, I’m fine.” Subscribe if you want a Major Dude to show you what it took for him to find what’s underneath and rebuild.

— Shaun

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