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Choices presented:

  1. management
  2. entrepreneur
  3. bigger company with bigger problems
  4. become junior in new thing
Of those, 2 or 3 seem the best for me (currently in 3), I've already seen enough to not want to go 4. Doing 2 would only make sense with cofounders who were interested in the biz/marketing side more than I am, otherwise fail for sure.

I wonder about 1. I get the sense that as soon as I pick that option, my mind will age at a phenomenal rate. Certainly growing in 'soft' skills but I value staying sharp too much.



Unfortunately most roads lead to management in tech. Tech knowledge is a decaying asset with a half life of 5-7 years. Eventually, you have 10-15 years of experience and your skills are decaying as fast as you can learn new ones. You look up and realize you are the oldest person on your team still writing code. Suddenly you fit in more with the other managers than with the developers. Such is life at most companies.


I am already the oldest person on my team by a decade or two and still solving the hardest problems. The solutions don't depend much on tech as most tech can do the common things that a problem can decompose to. It depends a lot more on how the problem is conceptualized and broken down, separated and recomposed. Then there's tech that hasn't changed a whole lot, like SQL/transactions/isolation levels. Retooling with new syntax isn't that hard. The problem really is that the problems are not that interesting or challenging at most companies. I'm now writing Ruby+Sorbet that looks like the Java/Scala that I wrote about a decade years ago.


I’m almost 15 years in now and feel like a) there’s still a lot to learn before I could be effective as management and b) very few companies I’ve worked with or interviewed with seem to want to support management skills or values that I’d want to develop or embody.

As a result I can only see myself going into management in bad faith for a higher salary. I already earn more than enough, so I’d be effectively kneecapping my professional development along with my job satisfaction and personal happiness.


> going into management in bad faith for a higher salary

I think you might do better than many managers who are incompetent and don't know it. I think it would only be in bad faith if you had no intention of trying to be good at it.

I can certainly see the ob satisfaction and personal happiness difference angle. A viable in-between could be some sort of educator/mentor/evangelist role.




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