Lots of great answers so far. Consider also that a CTO of a 5 person, 15 person, 30 person, and 100+ person (etc) company is not the same role, despite having t

Lots of great answers so far. Consider also that a CTO of a 5 person, 15 person, 30 person, and 100+ person (etc) company is not the same role, despite having the same title. So I think if you start at 5 and stay CTO as it grows, it is pretty natural to feel like you are always fighting to adapt -- you are. And likewise if the role begins to outgrow you, that's par for the course. In general when I think of CTO I don't think of them as programmers really, but more as leaders who play a role in recruiting, landing deals, setting (broad) technical direction and thinking years out. E.g. "Should we build or buy this thing that will take 2 years to do, based on the market, our competition, and who we have at the company." I think its natural to lose your core development skills. You can always get them back if you want. But that will be a different job of course :) Good luck!