Why a 3x CTO went back to a 25-person team. From Will Larson @lethain, Imprint CTO and 4x book author. "It's a hard time in middle management, right? There's a lot more competition for these roles. What I found personally very rewarding is getting back into the details of writing software. When I left Carta, my team was around 250. When I joined Imprint, the team I was leading was 25. This a unique moment to actually re-skill. If you're in management, I think right now either you have to get back into the details, or the world is changing so radically that the profession you know will not be valued in three years. You sort of have to decide, am I retiring now or am I re-skilling? I think there has to be some openness to taking a backward step or a lateral step. What I knew I wanted was getting back into the details and relearning how to do software in the current age. That's what I believe is going to be the unlock to the longevity of my career."