A Conversation on Intentional Time Use and Personal Structure in Retirement

What is my retirement going to look like? I'm excited about making more time available for tennis, art, and dancing. The ability to spread out my tennis to more than just evenings and weekends is fantastic. Currently, my weekends aren't my own to relax and do as I please, as I have tennis commitments. Which is odd as I solely control when my tennis is scheduled. That is 100% on me. So don't think I can't do what I want.

Do we think that way about other things? Even though we think we don't control it, aren't they just commitments that we've signed up for? No one else is responsible for what we say yes to. Just us. And are they things that we enjoy doing?

Flexibility will be the key and the bane of my retirement. The ability to have less structure will be good and a challenge for me. I love structure, so I'll just need to craft a different kind of structure. Will my time-blocking work satisfy my organization's desires?

Currently, as part of my weekly planning session on Sunday, I block out and schedule time to work on my weekly key three. I block out time for exercise, tennis, art, reading, and home projects. Also, having breaks between time blocks will be good.

Will scheduled time blocks be enough of a pull for me now? Will I respect the time blocks? More importantly, what can I do to build rigor and a "stick" into the blocks? I need to appreciate the fact that I have limited time left, and this is a way to live intentionally. Perhaps the focus is on living intentionally, and this is just one of the tools to achieve that.

I'm not focused on time blocking—I'm focused on USING time blocking to live intentionally.

I may intentionally choose to relax in the pool, but that is a choice, not my default position. This will be good. I also view retirement as a reward for all the hard work I have put in. A bit of a reward and an opportunity to spend more time on what I enjoy and love, as well as explore new experiences and activities. The ability to revisit old interests will be fantastic. There is a lot to do, including seeing my kids, grandkids, and in-laws. I have a lot of time on my hands to get after it. Art will be a great release and quiet activity.

Schedules – I don't want to go overboard. I'm a guy who loves schedules, time, spreadsheets, plans, and details. I love details. Vacation is enjoyable for me when everything is scheduled, and I'm doing something. I don't consider relaxing on the beach doing something.

Do I need to push myself to consider sitting on the beach doing something? Something productive? The fact I'm worrying about something being productive is a problem. Relaxing, spending time contemplating, and sitting with my wife on the ocean side is something. I'm doing something. I'm letting my mind and body recover and relax.

I have started identifying one action or task that must be done daily. Now, I am intentional about what I do. And it can be "enjoy the day with my family." Funny how I need to write that down! Do what you need to do to reduce unnecessary anxiety.

Does this conversation resonate with you? Do you have similar conversations? Let us know in the comments below.

From Melancholy to Momentum: Embracing Intentional Retirement

Why is it that I’m thinking about retirement as a daunting 30-year block when I never thought about my work life as a 40-year block?

Why is there such a stark difference in how we view those timeframes?

Why shouldn’t I approach the next five years of retirement the same way I approached my first job—one step at a time?

Instead of sitting in melancholy, I’m choosing to embrace intentionality.

Back in college, my goals were simple: get a job, pass the CPA exam, and see what came next. That took care of my first three years out of school. I didn’t obsess over what I’d be doing for the next 40 years—it would’ve been overwhelming, and frankly, I had no idea what the future held.

Retirement should be the same. What will I do in the first five years? I’ll try out retirement. I’ll refine my health routines, learn how I want my days to unfold, and make time to have fun. I might continue with what I’m doing now or I might completely change it up. Either way, I’ll learn, adjust, and keep moving forward with intention.

One book that supports this mindset is Tiny Experiments by Anne-Laure Le Cunff. Her premise is simple but powerful: treat your life like a lab. Run small, personal experiments to figure out what works for you. Don’t just copy what’s worked for others.

Choose something you want to try. Define what success looks like. Do it for a set time say, 30 days. Then reflect: Did it move you forward? Was it worth continuing? Whether it “works” or not, you’ll gain insight and clarity.

Maybe your experiment tells you to stop. Maybe it tells you to pivot. Or maybe it says, “This is working keep going.” All three are wins.

You don’t need to overhaul your life or commit to massive routines. Start small. Test. Learn. Adjust. It’s a more effective and sustainable approach than New Year’s resolutions.

Living with intentionality isn’t about constraint. It’s about freedom. You’re consciously choosing what matters most to you.

Want to relax by the pool for an hour a day? Great. Make that your tiny experiment: “I’ll sit by the pool for an hour a day for 30 days and track how it affects my stress.” You may love it. Or maybe you’ll realize by day 20 that you’re too fidgety and that’s valuable insight, too.

So don’t think of retirement, or life in 30-year or 40-year blocks. Think in chapters. Experiments. Intentional steps forward.

Your next chapter is just a tiny experiment away.