To be fair, I also work in the tech industry and could afford snazzier equipment, but I leaned toward keeping everything cheap and cheerful so I didn't worry too much about it getting stolen in town, or busted up when taking some questionable cross-country "shortcut". At the end I donated all my gear to a local co-op, then bought a new bike in the next country, so it also helped me feel more free and not bound to a pricey piece of hardware. I feel like spending money makes you need to spend more money - now you need a better lock, now you need a storage unit, now you need to take your bike on the plane etc. For me that's just more stress that would get in the way of my goal, which was to travel carefree.
I get your point about the utility of electronics, though. I'm not anti-tech, I guess I just tend toward cheaper and simpler solutions unless there is a very strong motivation. I don't think I'm especially unique in that sense - I think a lot of people (even those who own bicycles) would be surprised to hear that some cyclists nowadays are using electric shifters! I'm sure at some point the tech will trickle down to the mainstream, but in the context of this thread which was about someone thinking of retiring to become a bike mechanic but worried it'll just be like retiring to do the same tech job they just left... I think that future is still far enough off in the distance that it's not something people who are thinking about retirement at the moment need to worry about.
