One career metaphor is the ladder: you're on one rung and you work to get to the next rung. You climb as high as you can, and then you climb higher.
But I've been thinking more about a boring old scale - weight on two sides balanced by a fulcrum. With the scale metaphor, there's no winning, only balance.
I've always loved working hard. And I doubt I'll ever figure out how to be satisfied without challenging myself on something. I'm not much of a slacker, and I've been rewarded for that work ethic.
But after a career full of hard work and luck, I think I'm good. I don't think I'm thinking about the ladder much these days. I just see balance. And I'll still feel like I'm "winning" as long as that balance is maintaned.
PS I'm closing down Design Dare.