I would have been a better leader if I had been less cocky in my early career, and more confident in my middle career.
When I was 15 I quit school and lived in a Dojo in Japan. Through an accident of fate, I also ended up inheriting a large number of responsibilities. But I was 15. I was a teenager. Mature enough to be living overseas by myself to be sure, but I had quickly grown too big for my own boots. An unhealthy combination of self-importance and fear of failure.
Thankfully, one of the senior students living outside the Dojo sat me down one day and explained politely but in no uncertain terms that I was being a dick. It was one of the most generous things anyone has ever done for me.
I wish I had someone like that when I was a software development “teenager”. Someone to sit me down and explain how, when, and why I should pull my head in. That in the fight to build perfect software it’s easy to lose sight of the people. That empathy is more than just understanding how to solve a user’s problems.
I think if I had, I’d be a much better software developer than I am.