I just posted a comment over at Fred's blog; his post was about going out on top. The rest of this post is mostly from that comment.
Retiring from software crosses my mind from time to time. I used to imagine doing something else, so I tried. It didn't work so well.
I don't think the question is about going out on top. It's about what your life's work is. The perception or reality of whether you're going out on top or not isn't nearly as important.
A few years ago, the Times ran a story in the Sports section about a guy named Chongo. He's an artist and a writer, but mostly he's a crazy expert climber. And homeless. He lived in Yosemite, mostly stayed out of trouble, and climbed the cliffs around the park with equipment he either made himself or collected from his climbs.
You have to read the entire article to come to the conclusion I did: this was his life's work.
(incredible article, well worth the read)
I asked myself, "what's is my life's work? Software? Fucking software?" At that point I was burned out and driving the company into a brick wall, so I was also cynical. I wanted to do something more meaningful, I thought.
Turns out my life's work is helping people. And I love doing it through software. Software is only the context, but I really enjoy life most when 1) the bills are paid 2) I'm helping other people and 3) I'm able to spend time with people I care about and who care about me.
Yes, I love the win, I love creating things, and I love creating a huge amount of value. But I'm only happy when I'm doing it in the context of helping people. I'm happy to be working on something that will help a lot of people, if even in a small way.