"Where do you want to be in five years?"
I despise that question. My mental answer to queries of that ilk is usually something along the lines of "Not in a room like this answering questions like that!"
Don't get me wrong, I understand why managers feel like they have to ask those questions. They feel a responsibility to motivate the people who report to them to do quality work -- a task that must be akin to herding cats. I certainly wouldn't want the job of keeping people like me motivated and focused! ;)
Here's my true answer to that old trope of one-on-ones across the globe:
I want to have a fulfilling job doing challenging work with a group of people whose company I enjoy.
And guess what? That's what I have right now. If my career is in a similar place as it is today in five years' time, that will be flat out awesome.
What got me started on this rant is chapter 46 of Chad Fowler's excellent book The Passionate Programmer - Creating a Remarkable Career in Software Development. That chapter is titled "Path with no Destination" and posits that a career is not merely a means to achieving a goal or set of goals, but actually is the goal:
So, instead of constantly asking "Are we there yet? Are we There yet?" realize that the only healthy answer is "yes." It's how you traverse the path that's important -- not the destination.
This is something I've felt for ages, but all of my own attempts to articulate it have come off as apathy (at times it probably was apathy, to be honest). The thing is, when I say "right here" when I get asked the five year question, I don't mean working at the same desk, doing the same tasks for the same people. No, I mean getting paid to do work that keeps me as engaged as my work currently does with people who are way more awesome than I am.
What I'm saying is I'm in a really great spot right now and I'd like to be in an equally great spot in five, ten, or twenty years from now.
There's underlying context to that: I've actually worked pretty hard to get where I am. The thing is, if I want my future to be as superlative as my current situation, I will probably have to work even harder in the days to come. The slope doesn't ease off, really. It keeps rising. I need to learn new things from new people and do more and read more and see more. I need to be motivated to improve. That motivation comes primarily from myself, but it never hurts to have effective leadership from others. (Keyword there is "effective".)
So yeah, I have a "five year plan". It's the same plan I've had for the past five years, and the five before that.
It's a good plan. I may not have 100% execution on it, but I'm pretty clear about what it is.
Maybe you should try a plan like mine, too.