Ask HN: How to think long-term in terms of professional life?

It's good to have a direction of travel, but don't overdo it: You want to make God laugh? Tell him your plans.

Every few years, my wife asks me "What do you need to learn for the next five years of your career?"

I think that question is enough. I don't know enough to plan ten years out; technology moves kind of fast. But five years out I can often see the rough shape of what's coming.

The trick is remembering to ask the question every few years...