Welcome—

I’m Russell Max Simon.

This is a pic of me on my last trip, which was kitesurfing in La Ventana. I’ve just turned 40. The hairs in my beard are turning white; I have a tattoo that says Do not go gentle; and I’m writing this for me, not you. If you’re cool with that, read on below.


What is What Really Matters?

There are already a lot of folks online who write about money, work, and that ungodly term productivity. There are also a lot of folks who basically write motivational stuff about grabbing life by the horns, living your truth, or some other sort of cliché’d something or rather.

I originally started this newsletter because I had a feeling that most people who wrote about “lifestyle” stuff were dramatically over-simplifying the core problems of modern life. I have no patience for pithy sayings or easy answers. My posts are long, deep, and explorative of meaning, identity, legacy, and the inherent complexities of the examined life.

Just think of this as an antidote to every time you’ve heard someone give advice which begins, “If only you’d just…

All that said, if you’re wondering about questions like niche and brand (or about how to decide those things for yourself), I wrote about that in a long post here:

What Really Matters
I've agonized for years about "What I'm doing with my writing" — and now I have an answer
When I started this newsletter I made two important brand decisions — and for anyone interested in the topic, you might have noticed the two were in conflict. First, I named the newsletter What Really Matters. It was a generalist’s name, meant to provide broad latitude in topic selection and a lot of freedom to take the new…
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Here are some of my favorite pieces that I’ve published:

  1. Metaphors: the ‘Life Path’ and Denali. A response to the common “life path” metaphor; why your life isn’t a story about you, even if you prefer to make it one.

  2. But beware of looking for goals. About Hunter S. Thompson’s Ninth Path letter and why I stopped doing annual goal-setting.

  3. Ability to conform. On how so much of life is about this one particular skill, ability to conform. With reference to Nassim Taleb, Bryan Caplan, and more.

  4. My authentic self. By far my most read post, about the one time in my life I lived alone for 6-months, post break-up, as a young man in Washington D.C.


Why you should pay me

Fundamentally, I make my living as a writer. And as the founder of Substack has so eloquently written, ex-journalists like me have few good options other than the subscription model.

The old model of chasing views in exchange for ad dollars wasn’t just broken — it was soul-destroying for writers, and some would say corrupting for the institutions. It made for cheap content aimed at the masses.

I wrote about this extensively in one of my first posts: The different ways to make money with online content, and what the decision says about your values.

The subscription model is about my direct relationship with you, the reader.

If you think, like I do, that the brightest future for writers doing this kind of work is driven by models like this one, I hope you’ll consider becoming a paid subscriber.

I publish semi-weekly dispatches from my travels and generally more personal stuff for those who pay.