How to Handle the Development Conversation?

I try to make it a policy not to discuss my job or employer on this blog, but I could use some advice so I’m going to break that rule. My post today is a question that I’m posing for other bloggers who are planning to retire early: How are you handling development conversations with your boss?

Every few months, I have to meet with my manager to discuss development and talk about where I see my career headed. Although I’m 10 years out from my planned retirement, it could be closer to 7-8 years if there are no major financial surprises and I decide that the time is right. I realize that this is still a decent amount of time to be working and my career is nowhere near over just yet. But as time goes by, I’m wondering how people who are closer to their early retirement dates have handled these development discussions themselves.

I have a good relationship with my manager and we’ve had some honest conversations. She’s never held anything I’ve said against me but I’m wondering just how much I can and should tell her. After all, most people assume that I’ll still be working for another 25 years, which makes it seem like I’m still in the first half of my career, rather than approaching the end.

Any advice regarding how to handle these conversations? I would love to hear how other people have handled this without announcing their retirement plans.