A Decade of Freedom: 10 Activities That Have Enriched My Retirement, Part 3

In 2026 I hit a milestone that seemed like a distant, foggy dream back in my corporate days: the ten-year anniversary of my retirement.

If you want to go to the beginning and get the details on that blessed event, check out I Retired! There are some fond memories for me in that post!

Anyway, my plan to celebrate this momentous occasion is to write several “10 Things” posts about retirement.

So far, here are the articles in this series:

Today I’m continuing a series that started with A Decade of Freedom: 10 Activities That Have Enriched My Retirement and continued with A Decade of Freedom: 10 Activities That Have Enriched My Retirement, Part 2. If you missed either of those posts, I suggest you go back and read them as they contain the first seven activities in this list.

And as for this post, let’s jump right into it with this…

8. Daily Games and Puzzles to Keep My Mind Sharp

Not every enriching retirement activity has to be big, deep, or highly productive. Some of them can simply be small daily habits that are enjoyable and useful at the same time. That’s how I think about games and puzzles.

I’ve found that doing word games, challenges, and puzzles on a regular basis is a good way to keep my mind engaged. They are fun, they provide a small daily test, and they force me to think instead of just passively consuming whatever happens to be on a screen in front of me.

That last point matters. One of the easiest ways to waste retirement is to slide into passive entertainment as a default setting. A little of that is fine. Everyone needs downtime. But if you are not careful, it can quietly take over. Hours disappear, days blend together, and the only real accomplishment is that you finished another round of content someone else created.

Games and puzzles are a much better use of that sort of in-between time. They require focus. They make you recall words, spot patterns, think strategically, or solve a problem. They are not a massive achievement, of course, and I’m skeptical of the exaggerated claims people sometimes make about brain games as if they are some miracle cure for aging. But I do believe regular mental activity matters, and this is one easy way to build more of it into a day.

I also like that puzzles provide quick wins. Retirement has fewer obvious scoreboards than working life. You are no longer closing deals, hitting deadlines, or wrapping up projects on a daily basis. In some ways that’s a relief. In other ways it means the days can feel a little less defined. A good puzzle gives you a small challenge and a clear finish line, which is satisfying in its own right.

Here’s what I do every day:

NY Times Games — Pips
Chess.com — Two chess puzzles and a game against a bot
LinkedIn Games — Mini Sudoku, Patches, Zip, Queens, Pinpoint
Apple Games — Sudoku (regular version with daily challenges)
I usually do these first thing in the morning.

Then at night my wife and I do the following NY Times games together:

Wordle
Mini Crossword
Connections
Strands

In addition to all the other benefits these games provide, they’re just enjoyable. That matters too. Not everything in retirement has to be profound to be worthwhile. Sometimes an activity enriches life simply because it adds a little fun, a little challenge, and a little rhythm to an ordinary day. Daily games and puzzles have definitely done that for me.

BTW, I still play video games too. But I have very specific types of games I like. When one of those comes out, I’m into it big-time (I put over 300 hours into Assassin’s Creed Shadows), but unfortunately those games are few and far between. So when I’m done with one, I usually have to wait a few months for the next one.

9. Building a Flexible Daily Routine

This may sound boring compared with other activities, but it has been hugely important.

One of the underappreciated challenges of retirement is that too much freedom can become its own problem. When every day is open, it’s easy for days to become shapeless. You putter. You delay. You drift. Before long, a week disappears and you’re not sure what you did with it.

That is why some form of routine matters.

I do not mean a rigid schedule that turns retirement into another job. I mean a flexible framework. A rhythm. Something that gives order to the day without choking the life out of it.

For me, having repeatable anchors in the day has been very helpful. I like a group of activities I want to accomplish that is generally set (I say generally because you can always change them) in the morning, then using the rest of the morning and the day for whatever else I want to do.

For me that means exercise in the morning — swimming, walking, running, and StairMaster. It’s about a two-hour cycle from the time I leave the house until the time I get home (we live a 5-minute drive away from the YMCA). I have to go at different times on different days based on the pool schedule, but the latest I get back home on any day is 11 am. I then eat a meal and have the rest of the day to do whatever I want.

The reason this has enriched retirement is simple: routine reduces friction. When the basics are built in, you spend less time deciding and more time living. You maintain momentum. You avoid the odd fatigue that comes from too many unstructured choices.

This is one place where retirement advice often gets weird. Some people act as if routine is the enemy because it sounds too much like work life. I think that’s backward. Bad routine is the enemy. Good routine is a support system.

Human beings generally do better with some pattern to life. We sleep better, eat better, move more, and accomplish more when there’s a loose framework in place. Retirement doesn’t change that. If anything, it makes it more important because external structure has been removed. (FWIW, we eat dinner at the same time every day. We also have a set bed time.)

This is also why I think a successful retirement has more in common with a well-run household than with an endless vacation. Vacations are enjoyable partly because they are temporary. Retirement is life. Life needs rhythm.

Building that rhythm has been one of the smartest things I’ve done.

10. Enjoying Simple Everyday Pleasures

I’ll end with the most ordinary item on the list, because in some ways it’s the most important.

A great retirement is built on simple pleasures.

Yes, big events are nice. Trips are nice. Milestones are nice. But most of life is not made of milestones. It’s made of normal days. So the quality of retirement depends heavily on whether you can enjoy those days.

In fact, that’s sort of my “make retirement great” plan — have a good/great day today. String enough of those together and you have a great month, a great year, a great decade, etc.

This has been one of my clearest lessons of the last 10 years. The activities that enrich retirement most are often not dramatic. They are walking into a room you like. Sitting down with a book. Having a good conversation. Sharing a meal. Working on a post. Exercising. Taking care of something at home. Laughing with your spouse. Enjoying a quiet evening. Petting your cat (or having him sleep on your lap).

That may sound small, but it adds up to a very large life.

In fact, I think many people miss this because they approach retirement with a consumption mindset. They imagine retirement as a series of peak experiences. Then real life shows up, as it always does, and the gap between fantasy and reality creates disappointment.

The better approach is to build a life where the baseline is high. Then the big moments become a bonus instead of a requirement.

Sometimes retirement turns out better than people expected not because it is glamorous, but because it is calmer, simpler, and more satisfying than they imagined. The daily grind is gone. The pace is better. The stress is lower. The little things get bigger because you have time to notice them.

That has certainly been true for me.

And maybe that is the biggest surprise of retirement. Not that life becomes exciting every day, but that ordinary life becomes enjoyable enough that it doesn’t need to. And what’s not to enjoy? I get to do things I like and I don’t have to go to work!!!!!! Hahahaha.

This can be a hard activity for a high-achiever to master. Mainstream culture tells us that if we aren’t “doing,” we aren’t “being.” We are conditioned to feel guilty if we aren’t productive.

I have spent ten years learning how to be “productively idle.” This doesn’t mean being lazy; it means having the space to think, to reflect, and to simply exist without a deadline. Sometimes the most “productive” thing I can do is sit on my deck, look at the woods, and let my mind wander.

I wouldn’t say I have this mastered, but I’ve done better over the past 10 years than I would have guessed. And I’m still improving even today. So I’m happy with where I’ve been as well as where I’m headed.

BTW, this is often where the best ideas come from. The idea for a new blog series, a solution to a family conflict, or a realization about a financial strategy often emerges during periods of quiet. In the ESI framework, we talk about “buying back your time.” If you buy it back and then immediately fill every second with “busyness,” you haven’t actually gained freedom; you’ve just changed bosses.

Learning to enjoy a show, a long lunch with my wife, or a quiet afternoon of people-watching is a skill. It requires unlearning decades of corporate conditioning. But after ten years, I can say that time affluence is the true mark of wealth.

The ROI of a Well-Lived Retirement

When you look at this list, you’ll notice a common thread: almost none of these activities are expensive. Walking, blogging, reading, mentoring, and playing pickleball are all relatively low-cost.

Mainstream financial advice tries to sell you the idea that you need millions more than you actually do because they assume your retirement will consist of high-cost consumption. They want you to believe that happiness is something you buy at a travel agency or a luxury car dealership.

I’ve found that the most enriching activities are those that engage your mind, your body, and your community. They are the activities that allow you to continue Earning (in spirit and sometimes in dollars), Saving (by avoiding the traps of buying junk you really don’t want), and Investing (in your health and your legacy).

Retirement isn’t a destination; it’s a decades-long on-going experiment. After ten years, I’ve found that the math of retirement is simple, but the life of retirement is a masterpiece that you have to paint one day at a time.

If you treat your time with the same respect you treated your money during the accumulation phase, you won’t just survive retirement. You will thrive. You will find that the ESI lifestyle doesn’t end when the paychecks stop; it just moves into a higher, more fulfilling gear.

If you’re planning for retirement, I’d encourage you to think about activities the same way you think about money.

Don’t just ask, “How much do I need?” Also ask, “What will I do consistently that makes life good?”

That answer does not need to be exotic. In fact, it probably shouldn’t be. The activities that enrich retirement most are usually the ones you can return to again and again without needing perfect conditions, lots of money, or a burst of motivation.

For me, those activities have been the ones detailed in this series.

The Second-Decade Activities I May Want to Pursue

Several of the activities mentioned in this series have morphed over time (to grow more or less important.) I assume they will continue in this pattern with some expanding and others going away completely.

But what about new activities? What does the next ten years look like?

One of the encouraging things about retirement is realizing that even after 10 years, the story does not have to be finished. In fact, one of the best parts of this stage of life is that there is still room to grow, explore, and add a few new dimensions to life. Retirement is not just about maintaining what you already enjoy. It can also be about leaving enough white space for something new.

So what could I do? There are endless possibilities.

I went to my “friends” ChatGPT and Gemini and simply said to each, “I need a hobby.”

They then offered suggestions (some of which were hilarious) and I told them which ones I might be interested in. We chatted about them back and forth and here’s a list of potential possibilities so far (in no specific order):

1. Local History / Exploration

This is basically studying local history (of the Triangle area and perhaps NC as a whole). I could read about history (both AIs gave me sites to check out) as well as explore towns, trails, historic sites, gardens, and regional culture.

If I wanted to get crazy (which I do not want to do), they suggested I could be a:

Docent — Lead tours or explain exhibits at a historical center/house
Archivist — Offer to help digitize old records, identify people in vintage photographs, or record oral histories from long-term residents
Researcher — Pick a specific local landmark or an old neighborhood and try to piece together its “life story” using library archives and property records

I am a history fan but this sounds high on work and low on excitement. We’ll see.

FWIW, I have read a book on town history, so maybe that’s as far as it will go.

2. Public Service: Town Citizen Committees

Our town is regularly looking for residents to serve on advisory boards.

We have an annual application window for boards and commissions. There are a few which require skills that I developed over the course of my career.

This idea appeals to me because it would be a practical way to contribute to the community while also staying engaged with what’s happening around me. I like the idea of using experience, judgment, and available time in a way that is useful without turning retirement into another full-time obligation.

Plus I’d get a behind the curtain look at how local government functions and a direct say in the future of our community.

This is a solid possibility.

3. Local Travel

I expect/hope to travel within North Carolina during the next 10 years. At this point, I’m less interested in chasing faraway destinations because they sound impressive and more interested in enjoying places that are relatively easy, enjoyable, and worth returning to. That makes trips to the beach (2 hours away) and mountains (3 hours away) especially appealing, along with seeing more local sights along the way.

I also want to check out some sights like the Biltmore (maybe at Christmas), Duke Gardens, and the museums in and around Raleigh. I may want to go to DC again as well, though I’ve been so often I’m not sure what I’d do there that interests me.

That kind of travel fits where I am now. It offers variety, beauty, and refreshment without all the hassle that often comes with bigger trips. And frankly, I think that’s one of the advantages of retirement: you can stop traveling to impress other people and start traveling in ways you actually enjoy.

4. Fixing Up the Back Yard

This is sort of an on-going activity and sort of a one-time task. It depends on how far I take it and whether I do it all at once or in phases.

Our backyard is woods. There are trees only a few feet from our screened-in porch. They run 10 yards or so and then hit a paved greenway trail where people walk the neighborhood through the woods.

I’ve been playing with ideas that might shape that wooded area into something attractive: statues, path markers, benches, bird features, subtle lighting, seasonal displays. Leading candidate is a group of statues (cuts down on maintenance).

BTW, I started by thinking I could do a miniature world with a couple trains running through the woods — then realized the upkeep nightmare that would be. lol

I haven’t decided what I might go with (or even if I do it), but it’s a possibility that might add some joy for both us and the people walking the trail.

5. New Physical Activities

Apparently the more varieties of exercise you participate in, the better your health outcomes I already have:

Swimming
Walking
Running
StairMaster
Weights
Pickleball
Gardening/outside work (yes, this counts)

I’m looking for 1-3 new activities to keep the variety strong and me interested.

Some options:

Racquetball — Haven’t played in years but they have courts at our YMCA
Aqua aerobics — I’m already in the water six days a week, so why not switch it up a bit?
Yoga — Good at building core strength and flexibility
Pilates — My wife does these…also at the YMCA
Tai Chi — Good for joint health and long-term stability
Badminton — Popular here though I’m a complete newbie at it

There could be more, but it seems like this is a good list to start. I’m sure I’ll add a few new exercise activities in the next year or so.

6. Financial Mentoring

I will be with MMM until its dying day, but I also wouldn’t mind some in-person financial mentoring.

I’m just not sure where to find those interested. High schools? Colleges? Workshop at a library? Somewhere else?

ChatGPT says:

“Given your background, I’d consider creating your own funnel. For example, a local ‘money Q&A’ workshop at a church, library, YMCA, or community center can attract people who want help, then the strongest prospects can move into 1-on-1 mentoring. That route is more self-directed, but it often gives you better-fit mentees than joining a big system.”

Hmmmmm…not a bad idea.

7. Starting a YouTube Channel

Hahaha. I’m putting this here to amuse myself.

I have been “starting a YouTube channel” for 3 or 4 years now. Will I ever do it? Who knows.

There are a lot of benefits. YouTube involves many skills — writing, filming, editing, marketing and tech. So it would be a great learning experience. It could also be a way that I “mentor” thousands of people (if not more).

If I could get it to a reasonable size, I could monetize it…and give away all the profits to help others.

What’s stopping me? It sounds like a lot of work…hahahahaha.

New Hobby Possibilities

I don’t know yet if I’ll pick up any new hobbies, maybe I will or maybe I won’t, and I’m perfectly fine with that. I have no interest in forcing a hobby just to say I picked one up. Retirement doesn’t need fake goals. But I do like the idea of staying open to a fresh interest that is enjoyable, engaging, and worth developing over time.

Even if I don’t add any of these (or anything at all), I think there is value in simply admitting that life can still expand from here. Too many people talk as if retirement is one long glide path of gradual narrowing. I don’t think it has to be that way.

If I had to guess I’d say that some of the things I do now will decrease or even fade away totally and I’ll replace those with new things. That’s what’s happened so far, but time will tell if the pattern continues this way or not.

I want to note that hobbies really pair well with the rest of retirement life. They create conversation. They connect you with like-minded people. They sometimes lead to travel, learning, or family time. In other words, they are often force multipliers.

So yes, hobbies belong on my “potential” list. But I’d frame them this way: the right hobbies do not just kill time. They enrich time.

Whether I do all these things, some of them, or none remains to be seen. But that uncertainty is part of the fun. Retirement still has open space in it, and I see that as a gift. After 10 years, I’m grateful not only for the activities that have already enriched my life, but also for the possibility that the next decade may still hold a few good surprises.

I’ll let you know how it’s gone sometime in 2036. 😉

The ROI of a Well-Lived Retirement

The Second-Decade Activities I May Want to Pursue

New Hobby Possibilities

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