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Transitioning types of programming
#1
There's a lot of types of programming: web apps, mobile apps, desktop apps, game dev, embedded systems, etc etc etc 

I feel like the difficulty in moving between these is overestimated but how hard is it really? 

Not as much in the sense of technically speaking, but career wise. I think once you learn how to write software the principles get carried over fairly easily but looking at jobs and seeing 5+ years of some technology not applicable to my current field seems like a boundary



#2
It can be tough to transition subfields in programming without proof that you're good at what you're wanting to move to. The classical way around this is to make a portfolio of simple projects that demonstrate the new skill, or to contribute to an open source project in the new area.