Why I’m Starting Diary of a Retiree

Retirement used to be something I’d think about someday. Lately, someday has started looking a lot like next year.

I’m less than a year away from being eligible to collect Social Security at 62. That doesn’t mean I’ve decided to claim it then, or that I’ll suddenly stop working. But it does mean a decision that once felt far away is getting close enough to deserve some serious thought.

And that’s why I’m starting *Diary of a Retiree* now—while I’m still figuring it out.

A working life with a few turns

My first career was computer programming. Over the years, I moved into real estate, working with buyers and sellers here in Maine. More recently, I’ve been winding down that chapter and finding my way back to programming, building software and exploring what work might look like going forward.

I’ve also been doing gig work to help pay the bills. That might not be the retirement lead-in you’d find in a glossy financial brochure, but it’s where I am.

My working life hasn’t followed one straight line, and I don’t expect retirement to either. I like creating things and solving problems. It’s hard to picture a future where I put all of that aside just because I reach a particular birthday.

What I would like is more control over how much I work, what I work on, and how much of my life work takes up.

Our family is changing, too

Patti and I have children, now teenagers and adults, and we’re grandparents. After years of raising a family, we’re approaching a different stage of life.

Parenting doesn’t end when your children get older. The conversations change, the needs change, and you start thinking about your own future alongside theirs.

For us, that includes time together and the chance to travel. We’d like to see places we’ve talked about for years while we’re able to enjoy them. We also have a real budget, so part of this story will be figuring out what we can reasonably make happen.

The Social Security question

As one of the oldest Gen Xers, I’m reaching a milestone that still feels a little strange to say out loud: I’ll soon be old enough to collect Social Security.

Eligibility is one thing. Deciding when to claim is another.

I’m weighing what that income could mean, how much I’ll continue working, and what makes sense for our household over time. There are numbers involved, of course, but there are also questions about time, freedom, and how we want to spend the years ahead.

I haven’t settled every question. I want to document the process while those decisions are still in front of me.

Why start before I retire?

Because this part counts.

It would be easy to wait until I had a retirement date, a settled budget, and a clear plan. But the uncertainty, conversations, and course corrections are part of the experience. Recording them now gives me something honest to look back on—and might help someone else facing the same questions.

This diary will follow the transition into retirement and, eventually, life on the other side. I’ll share what I’m considering, what we try, what works, and what needs adjusting.

I’m writing as someone living through it. There will be money discussions, travel plans, family life, probably some work, and hopefully a few laughs along the way.

For now, I’m still working, still making plans, and still figuring out what retirement could look like for us.

That seems like a good place to begin.