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Sunday Letters

How to think like a programmer, letters to my younger self, and system thinking

Newsletter · By Sam Schillace · English · Official site

Indexed issues, last 90 days
13
Latest publication
Sep 27, 2026
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Earliest in this view
Jul 5, 2026

Latest issues

  1. Issue · Sep 27, 2026

    Do More By Knowing Less (opens the original)

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    There is a contradiction in working with AI that I want to dig into: we have to learn ways to trust the work without seeing all of it. On the one hand, as we’ve discussed, your personal attention is now the most valuable, critical resource. It’s easy to get the computer to do work for you - it’s harder to pay attention to that work and make sure it’s right. As we try to scale the return on our attention - the amount of useful work that gets done per unit of us paying attention - that validation

  2. Issue · Sep 20, 2026

    You’re the Executive Now. (opens the original)

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    Working successfully with AI at scale feels a lot like being an executive leading a large organization. If you lead any kind of larger organization, particularly a technical one, you quickly realize that it’s not possible to know all of what is being done in it. For a while, it can be possible to stay fairly close to the work, but eventually, enough is being done that you can’t even read or see all of it. This isn’t surprising - if one person could do everything, you wouldn’t need the team in th

  3. Issue · Sep 13, 2026

    Are we just Sharpening Pencils? (opens the original)

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    I spent some time with my team of 10 programmers this week, at a programming offsite. This is a group that has a lot of experience with very advanced programming tools, access to cutting edge models, generous budgets and no real restrictions on what they build. What magical new thing did they (including me) mostly gravitate to? Building ever better tools for building more software faster. Developer tooling. Every “power user” or technologist I know, when they’re not worrying about AI safety, see

  4. Issue · Sep 7, 2026

    Everything Will Be Code (opens the original)

    Excerpt · Positive tone

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    Almost a year ago, as we were struggling to work with earlier versions of AI and agentic harnesses, I wrote “Code Goes First”. In that era of AI skepticism (“what is it good for, anyway”) I argued that code was uniquely shaped to be accessible, and useful, to AI before anything else. I feel pretty good about that - I wrote it right as models were starting to get good at coding, and as we know, the progress over the last year has been astounding. But I think that idea is much bigger than I initia

  5. Issue · Aug 30, 2026

    Attention Ergonomics (opens the original)

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    What is the point of a team? In any kind of work, the point of a team is to do more work than one person can do alone, somehow. With some kinds of work, that scaling is straightforward: if the task can be done in parallel, it’s easy to just add workers and get more done. There are coordination problems eventually, but to a first approximation, you can just add people and get more done. That works for many kinds of physical work, but it’s more complex for mental work. The software world has known

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