From Bohemian Writer to AI Captain: My Journey Back to the Page

It's Friday morning so I'm finally taking a deep breath to sit down to write.

Writing is one thing I no longer do. Like at all.

In 2010, I graduated university with an unmatched enthusiasm to finally be able to live the lifestyle of a bohemian writer: wake up, practice yoga, smoke cigarettes and drink coffee as I tap away on my laptop until noon, go work out after lunch, continue writing until it's time to start pounding beers and smoke more cigarettes.

Yes, you could say I read a little too much Bukowski as an undergrad.

For 4 years, I lived this way throughout Europe, the USA, Mexico, and even southeast Asia, (this last one seeing me as an English teacher of 6th graders). I obviously have guardian angels watching over me because sometimes I reflect and wonder in amazement how I made it out of some of those escapades alive.

In 2014 I started feeling called to discover a sense of purpose. Whether I liked it or not, I was growing out of this hedonistic lifestyle and wouldn't admit to myself that I didn't want it anymore. My medieval high fantasy epic just wasn't enough to change the consciousness of the world and I didn't DARE learn how to do the work to make it better, or find an agent, self-publish and market it, etc. (Work was for non-free people)

So I stopped writing as a lifestyle, and thus stopped writing.

(instead, I pulled out the old dusty video camera to make content and figure out a way to make passive income, working for myself for the first time with the intention to make money, but that's a different story altogether...)

But what I really miss about that writing lifestyle was the freedom--not just the physical freedom but the mental freedom--to allow myself to sink into the words without any other care in the world. I either wrote my novels, started memoirs, or let my consciousness stream out... It didn't matter what it was specifically; it was a new world I was entering and creating.

As you can imagine, this was very therapeutic... and by the time the evening arrived it was no wonder that I wanted to party--I felt productive and creatively satisfied. And I was in my early 20s.

But the issue was income. My savings from college dried out like cigarette ash in the wind, and despite being a pretty good worker on projects I like, I really hated finding the work and so I much preferred to stay broke and write instead.

That was stressful though, because despite the psychological contentedness coming from a writer's lifestyle, it can't heal an empty bank account juxtaposed against a craving for adventure.

And so it's been for the last 11 years that I've been on a completely different mission, to build that same lifestyle from the opposite direction. I want money to come in with the highest leverage (i.e. lowest amount of non-desiring effort), and I want so much peace in my life that there would be no reason whatsoever to not get up and spend the morning writing, reflecting, pontificating... even if I don't smoke cigarettes or drink beers anymore.

(The irony is that my kids will never let the morning be peaceful--but that's why we're on a long time horizon here!)

Sitting down today is my reflection on this whole writing thing; Fridays are generally my "day off" after a hard 4 days in the creator space of content, vibe coding, email sequences, and God knows what else.

It makes me very happy to sit down and write this email without a trace of AI help (for you see, in another tab I have Opus 4 ghostwriting my newest Substack post)... just pure expression.

Anyway, I've spent almost 6 weeks without this little ritual, so allow me to catch you up on what's been going on:

• I've been creating videos for Venice AI. They are a privacy-focused AI company that resonates quite strongly with my general mission in life (not to mention decentralization-focused), so there's a chance I'll be working deeper with them in the coming months.

• My own YouTube channel has kind of taken a backseat as I build out the courses in the new AI Captains Skool. I've finally figured out that what I am teaching is hardly AI, but rather clever ways to employ AI to do human-desired things (such as build apps or plan community calls).
  
  The Skool hasn't been officially launched yet but the 3 main courses are finished and there is plenty to learn in there for any normie wishing to build their own app one day.

There's a lot of potential with this AI education stuff. I won't reveal my master plan just yet but my Substack will subtly start to reveal it in the next few posts.

In personal news...

We've got 2 more weeks on the West Coast before it's off to Hawaii to see how the homestead life treats us in 2025. We'll be living island style for a couple months before heading off to Argentina to see the [other] fam.

What comes after that is anyone's guess...

It's a shame the world isn't more stable right now, but in truth it's really a blessing. It may have been a tough 10+ years but I'm grateful that things are finally coming together to allow me to earn income online and "work" from anywhere.

Getting closer and closer to that writing lifestyle 2.0.