While I agree he made the right decision, and I also agree that Taleb has interesting things to say that bear on career choices, I don't think he needed Taleb's

While I agree he made the right decision, and I also agree that Taleb has interesting things to say that bear on career choices, I don't think he needed Taleb's ideas on risk to make this choice. In programming, becoming obsolete is not a risk, it is guaranteed. This is just short term pain vs. long term pain. Which is also a difficult decision, but not one you need to have read "Fooled By Randomness" or "Black Swan" to understand. Losing your job (eventually) if you become obsolete isn't tail risk, it's the most likely scenario. And losing your job right when everybody else is losing their job is also not tail risk, it's the most likely scenario. So, if you're not learning anything new, you aren't at risk from a black swan, you're doomed. If anything, it relates more to the idea of "Antifragility"; many small shocks strengthen you. The small shock of learning a new technology (and feeling underproductive while you're on the steep side of the learning curve) is the small shock that makes you stronger. Don't let yourself avoid those small shocks for too long.