Choose Your Favorite Westenberg Piece (and Tell Us Why)

Cast your vote for Westenberg’s best work and explain your choice. Share the title (and link if you have it).

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My pick: “Why The Smartest People I Know Set Constraints, Not Goals.” (link)

This piece hit me the hardest and made me a follower. It resonates with the simulation-for-entertainment theory, which is my current best theological hypothesis. Elon Musk seems to be on board with it (see his tweets bellow). I just left this comment under the video explaining why I liked it so much:

If life is like a movie God’s watching, setting rigid goals is basically dropping spoilers (or trying to sit in the director’s chair). And as Elon once tweeted, “the most entertaining outcome is the most likely,” so of course God will gleefully sabotage your plans. Trade goals for constraints, improvise with the chaos, and keep the story fun (for Him) and fruitful (for you).

Here are some Elon’s tweets about the simulation-for-entertainment “theology”:

“The most entertaining outcome is the most likely – my variant on Occam’s Razor.” (Nov 20, 2022): https://x.com/elonmusk/status/1594078009954570240 X (formerly Twitter)

The most entertaining outcome is the most likely. (Feb 10, 2021): https://twitter.com/elonmusk/status/1359612035374473217 X (formerly Twitter)

Most recent, May 12, 2023: https://x.com/elonmusk/status/1656914397141278720

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Difficult. I have something like 42 essays bookmarked in Readwise Reader.

If I had to pick one, it would probably be The Erosion of Critical Thinking Will Doom Us Long Before AI (video - I believe this is the text version: The Death of Critical Thinking Will Kill Us Long Before AI.).

Mostly because the topic is critical. I see it daily. People just aren’t questioning anything at all, particularly if it aligns with their pre-conceptions. Thinking (and reading) has become too much like work, and unfortunately, certain people are more than willing to take advantage of our laziness. I was the one who asked “how do we get people to think” in the most recent Q&A, because it feels like the question of the decade.

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My personal favourite is the death of critical thinking.

It’s one of the pieces I’m proudest of having written.

Thank you for caring about it as much as I do.

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The hardest part of course - is that when the constraints are self imposed it’s easy to break out of them. Matter of willpower. I fail all the time - but the attempt is always made.

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I think it was before this incarnation of the site, but How I’m building a Trump-proof tech stack will always live in my heart. Lot of useful recommendations and it helped nudge me to where I am now, tech wise, with a lot more self-hosted and open-source stuff.

More recently, I deleted my second brain resonated a lot and got me thinking about how I use things like Obsidian, Sublime, etc. And I think The danger of Stoic sadism was v well considered.

Self-imposed “constraints” aren’t constraints, they’re goals in disguise. The only constraints in our game are set by Nature and the Free Markets. As Naval Ravikant puts it: truth-seekers take feedback from nature (planes have to fly) and free markets (customers have to buy). Everything else, especially the artificial, well-meaning self-imposed “constraints”, are not real constraints and belongs in the “goals” bucket.

Why The Smartest People I Know Set Constraints, Not Goals ? Because “Man plans, and God laughs”. And self-imposed wannabe ”constraints” are the funniest jokes.

I think this conflates two different types of constraints that serve distinct purposes.
Yes, physical laws are ultimate constraints. But self-imposed constraints are often enabling constraints that make complex work possible.

IE: a haiku’s 5-7-5 structure. This isn’t the same as a “goal." It’s a framework that forces creativity, focus, and decision-making. The constraint itself becomes a tool…

  1. Goals define what you want to achieve
  2. Constraints define how you’ll operate while pursuing those goals

Sometimes the constraint is the strategy.
Nature = the final arbiter, sure. But between vision and reality, self-imposed constraints turn good ideas into actual working systems.

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This is the one that caught my eye. I don’t know if there’s a text version, but I’d love it if there was. There were some punchy one liners here that i found impressive, and it was the gut punch i needed to stop relying on AI for so much. Then I ran into the boredom one (https://youtu.be/bXvWK6ElK1I?si=agHTup4N5IJah_wc) just as I started doing something similar for myself and found that the video was saying what I was feeling more eloquently than anything I could ever do.