You're not Simon Sarris.

Castles in the Sky December 20, 2024

Picture of the week: I ran twelve miles and saw a cat walking alone on the bayou last weekend. After the essay you can decide what this picture means for you.

Before I dive into why you're not Simon Sarris, let me start by saying I'm a fan.

Sarris is another writer on Substack who has over ten times the subscribers that I have and writes excellent essays about what he believes in and how he lives his life. He lives an enviable life on a large plot of land in New England that he and his wife cultivate. He works in tech, but he also doesn't believe in having useless gadgets inside the house. The end result is that the lifestyle he writes about is a thoughtful balance of useful modern technology with old-school technology. It’s down-home back-to-the-land type living funded by and in a symbiotic feedback loop with his tech job.

I could have titled this essay using a lot of names, but I picked Sarris for a specific reason: I know so many men who want to emulate his lifestyle. The problem is that they get what's happening wrong. After talking to enough people who admire him, whenever someone tells me, "I want to live the way Simon Sarris is living," I suspect that they misunderstand his way of living.

These conversations remind me of an essay I read over ten years ago that has always stuck with me. I have trouble finding it now¹ but the title was something like, "Be more like Steve Ballmer, not Steve Jobs." The part of the essay that has stuck with me forever was at the beginning when the writer muses about who might be reading the essay. To paraphrase:

"Steve Jobs was a handsome billionaire genius who started multiple world-defining and industry-changing companies in his twenties. Steve Ballmer was the forty-something-th employee of Microsoft without a stellar background who negotiated a great equity package. Which one are you more likely to be? I know which one: you're not Steve Jobs. You know why? Because Steve Jobs would have never been caught dead reading an article on the internet about how to be more like Steve Jobs."

I remember reading it being like, "well shit, he's got me." By trying to become more like Steve Jobs, someone is automatically signaling that they are, in fact, not like Steve Jobs. This is because Jobs had an unshakeable vision and tremendous will to power, plus an enormous bias for action. Procrastinating reading articles on Medium about how to be more like Steve Jobs is ironically something Jobs would never have done.

In the same way, what makes Sarris’s life so attractive is that he has a sort of high-tech pastoral aesthetic. He seemingly combines the best of analog technology and the benefits of being plugged in with tech, and connecting to the world at large but being very rooted in place. The irony is that many who I've spoken to who admire him essentially want to buy a plot of land like he has, fill it with stuff like he has, and live a lifestyle like he does.

I'm not a superfan who's read everything Sarris has put out, but I've read enough to see a clear throughline of reflection, intention, and agency in everything he does. He thinks deeply about his choices, makes a clear decision about what he prefers or doesn't prefer, and then exercises his willpower to bring his own idiosyncratic vision to life.

In an ironic parallel to the Steve Jobs article, someone who wanted to live like Sarris and would do it by unthinkingly mimicking everything he does would automatically be disqualifying themselves from the benefits of his lifestyle. He advocates for a lot of specific things, but the lifestyle he advocates for overall is something that needs to be cultivated from deep within oneself and brought to life through action.

The last time I had a friend who said he wanted to live how Sarris does, he told me that he was basically going to copy his lifestyle. I said that attempting to copy may make him less like Sarris, not more. He need not live on a piece of reclaimed New England land or develop a preference for analog technology. Instead, he should think deeply about the things that matter to him and make them a reality. This is what Sarris does that inspires me. But someone could observe my life and never guess I was inspired by him, because the lifestyle I cultivate after looking within myself results in a very different aesthetic environment and lifestyle pace than Sarris’s.

Copying someone is often a great strategy. It is the best method to find yourself when it comes to, for instance, creating art. Reproducing the outputs of famous artists you admire allows you to learn their processes and measure yourself against them. As you do this, you develop a level of mastery that enables you to make more sophisticated choices and therefore create your own personal style.

Copying someone’s lifestyle is much more complicated because there is no snapshot “result” against which to compare. A lifestyle is not a static outcome but a dynamic thing that evolves and is being continuously recreated. The problem with people who want to copy Sarris’s lifestyle is they want the results of how he thinks and acts, but the only way to get that is to mimic his processes. You can’t purchase that level of combined introspection and agency or mimic the outcome: you have to understand the process and do it for yourself.

My friend eventually accepted that he wasn't Simon Sarris, and after some encouragement, he came to see this as liberating rather than limiting. If you find yourself drawn to Sarris's work thinking "I want that life," remember: the path to the freedom and fulfillment you're seeking doesn't start with copying his choices. It starts with understanding your own values and bringing them to life through deliberate action.

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Notes, News, and Other Thoughts

This is my favorite Simon Sarris essay.

If people hate technology and think it clashes with nature, I find it hard to blame technology. We have careless technology because we are careless in evaluating it. We demand too little of it, or we are willing to sacrifice too much for too little in return.

It is emblematic of this thoughtful approach to things, and I have found it very useful. (Although, following his logic has lead me to draw different conclusions than he did—which is kind of the point of my above essay!)

Careful technology

My most popular essay is about how to be more thoughtful and intentional even if you’re not sure what you want.

I wrote an essay last week you may have missed.

I had been kicking this essay around for like seven months. This is a bit meandering and the response has been small, but a few people have messaged me to say how it captures something they feel acutely. Plus it’s about the dream of an interplanetary immortal proletariat.

1. BIG UPDATE—A reader found the essay! Shout out to

Mayank Singamreddy

for finding the essay on Medium. Please go read it: How to be like Steve Ballmer by David Barnes. It’s got a lot more “actionable” advice than I remember.