I think a lot of it was career envy.

You see people who you hired as young developers end up, years later after going the management track themselves, in regular face to face interaction with the CEO or senior corporate executive VP or whatever.

Their peer group seems to have more control over their own destiny or more power or however you want to frame it, while they're still stuck bootstrapping yet another CRUD framework for the nth time and answering to a department head who's now younger than they are and getting younger every day.

I think, when that inflection point comes, you have to decide if you're okay with being in that position, and if working with the tech is enough for you...for some people, they honestly don't care about the careerism bit and just simply enjoy the bit twiddling and never get tired of doing it. You really have to decide if you're one of those people and it can be really hard to do so.

One mistake I see often is people, hitting that inflection point, conflating the pride they have in the effort they put into gaining the knowledge they have as being the same thing as the love of the art. And also the fear of jettisoning that life-style (and yes, development quickly becomes a lifestyle), for something entirely new and different with an entirely different set of skills that often have to be learned from scratch.

Big companies try to have career paths for technical people. They claim "Distinguished Engineer" is the equivalent of a VP. However, it's really hard to get promoted to the few coveted DE positions, whereas a fresh batch of VPs are anointed every Monday.