That boundary tends to become more and more fuzzy as you grow in your career. I think that’s where the feeling comes from. When you’re a software engineer it’s easy to know if you’ve failed or not. When you’re a CTO it’s often a matter of perspective and depends on what will happen in the future.
As tough as it is, I think it's best for your development to be in a space where you're screwing up regularly.
This is one thing that we should lament about AI generating all the code. You never get to look back at your own "hand crafted" work with the distance of time. Progress or perspective, it does not matter, one would probably find something they could have done better.
I think I'm actually going to miss that feeling.