To Retire or NOT to Retire… That is the Question


In my work as a leadership coach, I am encountering more people every year who are considering retirement… often with angst. Why?

After all, they have the money to retire!
They have the interest in retiring! And yet…

They resist retiring because…
THEY DON’T KNOW WHAT THEY WILL DO!

Are you a successful person who keeps on working because that seems to be the easy answer? After all, you DO know how to work!

If you are facing this dilemma, I encourage you to consider this:

1. When you were a Freshman in High School, you had no idea how High School was really going to be for you.
2. When you were a Senior in High School, you thought you had it all figured out… and it seemed a lot easier than it looked like, as a Freshman.
3. Then perhaps you became a Freshman in College, or Technical School, or a Trade, or a New Job. You started over. And everything seemed “difficult” and “confusing” again.
4. Then, a few years into that experience, you “graduated” into something new and, in retrospect, those earlier years seemed easy.
5. Now, at the precipice of retirement, you are a FRESHMAN again! And that means it WILL seem new, and confusing. You will likely feel unsure and ungrounded. That’s OKAY!

So give yourself some time and grace to “figure it out” as you go. You didn’t have your entire career all figured out before you embarked upon it. And you won’t have retirement all figured out before you embark upon it. Just take your time. Stay curious. Try new things. Meet new people. And accept that you will “wander” through retirement just like you have wandered through your whole life. The real trick is to ENJOY the wandering!

Remember: Life is not a Do-It-Yourself Project. Life is a Do-It-Together Adventure. One uncertain step leads every Freshman into the promise of an exciting new adventure, even in retirement! Enjoy the journey!

© Copyright 2026 Lemke Leadership, Inc., Karen K. Lemke