11 Years of writing + a confession

I want to tell you a story about why I write about Stoicism when I'm a firm believer in Machiavellianism. Because standard philosophy failed me when my back was against the wall.

Thirteen years ago, my dad made some bad calls, and then he left the country instead of dealing with them.

Everything fell apart over the next few months. The bank took the house. The loan sharks took up permanent residence outside the one we were renting. My phone rang at every hour with men who wanted what they were owed and didn't much care how they got it. Some of them had worked for my father once — men thrice my age, who showed up to our door, demanding answers.

Nobody stepped in to help. There wasn't a mentor, or a friend, or a plan. I kept hoping my father would return. The situation was so dire that I never got the time to lament what we were going through. I didn't care about status, building a business, or making money. My only priority was keeping my family fed, safe, and alive through the next week.

I did what I thought was best. What any young kid would think was the best. Either sell drugs or find a job. I did find a job. For a while, I thought the answer was going to be in a book somewhere. The owner had a stack of self-help books on his table. He knew my story. He told me I could read the books after I finished the job. But the books felt like they were written for men with far more ordinary problems than mine. None of them had anything for a broke kid getting cornered by a man who wanted real money he didn't have. I wanted a book specifically dedicated to the exact problem I was going through.

For a long time, I was just angry at my dad. Not in some reflective, philosophical way. I hated him. That kind of anger doesn't go away on a schedule. I just learned to keep functioning with it sitting underneath everything else I was doing.

The books I was reading angered me further. Because I wasn't finding a solution anywhere. I started writing my own dialogues against the authors of the books I was reading. And by some incredible twist of fate, I fell in love with writing. I started keeping notes and maintaining a diary, mostly just to make sense of what was happening to me. Putting the mess into sentences was the one thing that felt like it was mine to control, on nights when almost nothing else was.

I started picking up freelance writing work not long after. Small jobs at first, then more of them. It turned out to be the one thing in my life at that point that paid me for something I was actually good at, instead of punishing me for something I hadn't done. That income is what actually chipped away at the debt. There was no system. Just years of writing for other people during the day and writing my way through my own life at night.

I'm not going to pretend it was some clean redemption arc. Most of it was just grinding through the same problems over and over until I finally understood them well enough to stop losing. But by the end of it, I bought a new house, every debt was paid off, my dad came home, and the same men who used to show up at my door now talk to me differently. Careful. Respectful, even, in a way I don't think they'd admit to.

The freelance work paid the bills. But the notes I kept for myself the whole time were a separate thing — nobody was paying me for those. I wrote them because I didn't want to forget what I was learning while I was still in the middle of learning it.

Right now, I write like a Stoic because my life is calm enough to afford it. That wasn't true for most of the past decade. Back then, my default setting wasn't calm acceptance of anything. It was pure, unsentimental Machiavellianism, because that's what the situation actually required. You don't out-Stoic a loan shark. You out-think him.

I ended up calling the whole collection The Prince of the Streets. It reads like what it is — notes taken by someone who needed them, not a book someone sat down to write.

Most of it didn't survive going back through it later — half-formed ideas, stuff that only made sense to me at 2 a.m. What's left is what actually held up when I reread it with a clear head. It's denser than anything I send out publicly, and a lot less careful about how it lands.

I've been writing play scripts, emails, publications, cold emails, and newsletters for more than 11 years now, and I meant every one of them. But there's a version of what I write that doesn't really belong on Instagram or YouTube. I believe algorithms will dull the density of it.

My brother suggested that I sell the notes on Amazon for $47.

Instead, they're free if you join the Stern Stoic Premium Publication Pass.

If your life is calm right now, this probably isn't for you yet, and that's fine. Save it. You'll know when it's for you, because you'll recognize the exact rooms I'm describing.

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