What Changes When Retirement Stops Being “Someday”?

My retirement from teaching has now moved from “someday” to a specific expiration date.

For me, that date is May 26, 2027.

It didn’t happen all at once. I’ve been seriously thinking about retirement for about three years and I actually came pretty close to pulling the trigger each of the last two years. Each time, though, there was still something holding me back. Sometimes it was because of financial insecurities and at other times, it leaned more toward the emotional side of things. Sometimes it was simply that feeling that maybe I wasn’t quite ready yet.

This year feels different.

For the first time, I feel ready both financially and emotionally. Once that happened, retirement stopped feeling like a distant possibility and started feeling like the beginning of something new.

For years, retirement can live mostly in the world of numbers. How many years of service do I have? What will my pension be? When can I afford to leave? What will health insurance cost?

Those questions matter, because at some point they determine whether retirement is even possible. But eventually, the numbers stop being the whole story.

My financial guy once said something that stuck with me. I could keep working, and every year I did, I’d probably enjoy seeing that pension estimate climb. The number would keep getting better. But that didn’t automatically mean I should keep going.

That helped me look at retirement a little differently. Instead of asking only, “Can I retire?” I started asking, “Am I ready to retire?”

You can always find a reason to work one more year if the only thing you’re watching is the number. At some point, though, you also have to think about what another year of work is worth compared with another year of your own time.

Getting both of those things aligned can take time. For me, apparently, it took a few years.

I’m extremely excited about what comes next, even though I’m not completely sure what “next” looks like yet. Surprisingly, I’m okay with that.

There is something exciting about reaching a point where the next chapter doesn’t already have every page written. After spending so many years working within school calendars, schedules, meetings, practices, deadlines, and responsibilities, having some control over what comes next feels pretty appealing.

At the same time, I know there will be things I miss. Students, certainly, and the teachers and coworkers who have become friends over the years.

After 31 years in education, it’s hard to separate the work completely from who I am. Walking away from the daily routine of school means leaving something that has helped define a huge part of my adult life. I don’t think that disappears just because you retire.

I know I haven’t always thought about retirement that way, but lately that part matters more to me.

When retirement is still far away, most of the questions are about timing. When can I retire? Will I have enough years? Will the pension make sense?

As the date gets closer, though, the questions start to change. I find myself thinking less about when I can leave and more about what I want life to look like afterward.

I’m still answering that one myself, and I think that’s okay. I don’t believe you need to have every detail mapped out or know exactly what you’ll be doing five years from now. But I do think it helps to start paying attention to what you want more of.

Maybe that’s more time with family, travel, another career, part-time work, volunteering, better health, or simply enough room in your life to figure out what comes next.

I’m still figuring out what my own answer looks like.

I’ve probably talked about retirement to death over the last few years. Most conversations with fellow teachers usually began by asking how long we had left, as if it was a prison sentence or something. One thing I’ve learned over the last few years is that retirement preparation doesn’t really begin with the paperwork, a pension estimate, or even a date on the calendar. For me, it started with conversations. Talking it through with people I trust has helped me sort out what I actually want and, in some ways, helped make the decision feel more real.

Sometimes another person sees a concern I hadn’t thought about. Sometimes they ask a question that sticks with me and sometimes simply saying something out loud helps me understand how I really feel about it. That’s why I think it helps to talk with different people like family, friends, coworkers who are thinking about retirement themselves, people who have already retired, and financial professionals who can help with the practical side.

They won’t all see things the same way, and that’s probably a good thing. You don’t have to follow every piece of advice, but hearing different perspectives has helped me get clearer about my own. I’ve found that I understand what I want better when I actually talk it through with other people.

If retirement is getting closer, these are a few things worth having on your radar.

For me, “someday” now has a date attached to it. That still feels a little strange to say. But I think that’s part of what makes all of this feel real now.

See you Friday.