Oscar Funes

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June 29, 2026

Weight of Old Decisions

Hey!

Welcome back to another week of musings. I’ve been trying to rest more before I burn out with several incidents and migrations going on at the same time. As well as playing “Tag” with all the projects to avoid becoming a bottleneck.

In the background, I’ve been enjoying the World Cup! I hope you had a great weekend and managed to rest for the week ahead.

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Things I enjoyed in the past week

  • Vercel released its AI agent framework, eve. I’ve been using Strands, but I’ll take this one for a spin this week.
  • Make AI Boring Again by Charity Majors, not much to add, go ahead and read it!

Lately, with all the migrations and re-architecture we’ve been doing, I’ve had the chance to revisit many old decisions that no longer work in the current context.

Things like technology choices with no one left to maintain them, or simply a design decision like an API contract, or a “quick hack” that has been around for 10 years. Also, as part of these migrations happening, some other teams want to sunset some internal frameworks, and I remember hearing about them, or listening to someone present about them, getting a promotion, and then leaving the company.

On the flip side, I feel some other teams never move as fast and are now taking a chance to migrate their stacks to newer technologies. It’s becoming chaotic very quickly, and we can only maneuver through the chaos, not control it.

In any case, all of these past choices can make it easy or very hard to replace or evolve them. Sometimes the weight is so great that you can only leave them in place for a bit longer. No replacement in sight, and you no longer want to actively maintain it, so we’re in limbo, waiting for the owners to replace it, which is hindering productivity.

Other times, I feel that there’s so much “gravity” behind an internal project, that it becomes impossible to replace even when off-the-shelf products have caught up to what is being built in-house. Especially if they’re big orgs with Directors, etc.

Inertia is a real thing, and also teams protecting their work or “space”, so migrations or “cleaning up” things not only involve technical decisions or data but also require dealing with people and selling them on different options and your view of the world in the present.

Your Turn!

Have you stayed so long at a company or team that you have to live with the consequences of past choices? Tech Debt left for later? Let me know your thoughts by replying to this email.

Happy coding!


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