Issue #674, 24th October 2025

This Week's Favorite


Team Dynamics After AI
14 minutes read.

I wonder how much GenAI will raise the floor but lower the ceiling for many teams and products: "AI may be giving you a million prototypes, but if you listen, AI is telling you in quite a painful way that being able to get feedback on your artefacts is much, much more important than the artefacts themselves. [...] Disincentivising people from becoming skilled makes niches harder to dig and makes diversity harder to achieve. It makes mediocrity. And it can engender, based on conversations I have had, a kind of existential panic at the way they can run and run and still not seem to be going anywhere."

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Culture


When Your Smart Water Purifier Won’t Give You Drinking Water Because Aws Is Down
1 minutes read.

My humble effort to help you start the weekend with a smile. AWS outage this week was a nightmare to deal with, but also kinda fun(ny) to see the products that broke because of it.

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How to Compete in SaaS
5 minutes read.

To win, you often need to have the best product in the market, but above all, the patience to continue and show up to win customers' hearts (and wallets): "The key trait for competing effectively is not cleverness, but persistence. You need to apply competitive pressure with very little positive feedback for many quarters (or years) to get any sort of return. This is why founder-led companies, or companies with founder DNA, are the best at competition in the long run."

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Do Things That Don’t Scale, and Then Don’t Scale
3 minutes read.

If the cost of creation (and to some extent, maintenance) is going down, doing many small things becomes attractive. There is no need to choose when "or" becomes "and". Adam Derewecki is spot on: "Scaling used to be the point. Now, small can be the point. AI tools make it cheap to create software for an audience of one — and sometimes, that’s the best possible audience."

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Steve Jobs: "Don't Be a Career”
2 minutes read.

Life is not linear, and it feels better to look at our craftsmanship as a journey. Hopefully, with people we appreciate, achieving outcomes we are proud of.

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Peopleware


Note to My Slightly Older Self
5 minutes read.

Yew Jin Lim with such a beautiful take: "Work-life balance is a myth. Work-life choices are real. The conventional wisdom says find balance - that perfect equilibrium where you excel at work and never miss a soccer game. That’s fantasy. Life doesn’t balance. It tilts. Sometimes toward work, sometimes toward family, sometimes toward that project that keeps you up at night because you love it. Mid-career is when you need to decide what success actually means to you. Not the default path that leads to middle management plateau."

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This Is How DJ Shipley Returns Home Each Day to His Wife and Kids. Anyone Trying to Balance Work and Personal Life Should Listen to This.
2 minutes read.

I have three small kids, and so it's so easy to bring work with you when you enter your home. DJ Shipley shares a lovely tip I'm going to try. You may find it helpful too.

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Karpathy Is Wrong. Write That Post, Build That Slide Deck!
4 minutes read.

"I've been telling this to Individual Contributors (IC) I have managed for years: Build and talk. Those two verbs — build and talk — are not opposites. They compound." -- João Alves with a great take. For those who don't like to speak or write too much, you can also show it by considering an apprenticeship where you can lead (as an expert) and have others watch and assist you.

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Inspiring Tweets


@blakeaburge: The happiest people I know don't have perfect lives. But they do have one thing in common: They've mastered the art of moving on. They don't keep score, they don't cling to what if, they don't dwell. There’s a hell of a lot of progress hiding in not staying stuck in the past.

@DemosKratosCA: I have a mental illness that makes me think that people will change their minds if I present the correct arguments with the appropriate facts and data.

- Oren

P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.

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