I don't have a five-year plan. I've tried to make one a few times — wrote it down, believed it for a few days, then abandoned it when something more interesting showed up.
For a while I thought this was a personal failing. Most people who seem to have their lives together seem to have plans. They know what they want to be doing in 2029.
But I've noticed that the most interesting people I know don't work that way either. They have directions, not destinations. They follow things that pull them, not things they've optimized for.
The obsession pattern
There's a specific feeling I've learned to recognize. It happens when I'm reading something at 11pm and I look up and it's 2am and I don't remember the last hour. Or when I'm in a conversation and I keep wanting to get back to one particular thread that everyone else has moved on from.
That feeling is information. It's pointing at something.
Most productivity advice tells you to ignore that signal — to stick to the plan, to not get distracted. I think that's mostly wrong, at least for building things or doing research. The obsession is where the energy is. Energy is the thing you can't manufacture.
What following it looks like
Following interesting problems isn't the same as being undisciplined. You still have to ship things. You still have to finish what you start (mostly). You still have to be honest with yourself about whether you're obsessed or just avoiding something harder.
But the direction comes from the pull, not from a plan you made when you knew less than you know now.
I've found that explaining this to people who haven't experienced it is difficult. And explaining it to people who have is unnecessary. They already know.
The version metaphor
I started thinking about my own trajectory in terms of software versions because it captures something that linear resumes don't: you're not accumulating, you're upgrading. Sometimes there are breaking changes. Sometimes v3.0 isn't backward compatible with the decisions v2.0 made.
And the next version is always unknown. You're writing it now.
That's the honest state of things. Not a plan. A direction and a lot of uncertainty about what happens when you get there.
Which is fine. Uncertainty is often a sign you're working on something real.