A Decade of Freedom: 10 Activities That Have Enriched My Retirement, Part 2

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. If you missed that post, I suggest you go back and read it as it contains the first two activities in this list.

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

3. Exercising

You knew this was going to be on here, didn’t you? Hahaha.

If enjoying life and health are the top priorities for retirees, then exercise sits at the center of a great retirement plan.

That may not be exciting. It may not sound like a fun retirement activity. But it’s hard to overstate how important it is.

You do not need your body to be perfect in retirement. But you do need it to be functional. That’s the standard I care about most.

A lot of retirement dreams are downstream from health. Travel, hobbies, time with family, social events, home projects, volunteering, even simple independence — all of them get harder when your health deteriorates. Money can solve some retirement problems. It cannot fully solve the problem of not being physically able to enjoy your life.

That’s why exercise has enriched my retirement so much. It is not just about fitness for its own sake. It is an enabling activity. It improves many other activities.

For me, exercise also provides structure. It gets me moving. It starts the day off right. It creates momentum. When I exercise early, the whole day tends to go better.

And beyond the physical benefits, there are mental and emotional benefits too. Exercise reduces stress, lifts mood, and creates a sense of progress. Those effects matter in retirement because even though retirement is better than work in many ways, it is not automatically free of stress. You still have life, aging, losses, relationships, health issues, and the normal burdens of being human.

A MassMutual study found that retirees who were much happier were more likely to be exercising than retirees who were not happier. That doesn’t prove causation, of course. Happier people may simply be more likely to exercise. But in real life, causation often runs both ways. Movement helps mood, and mood helps movement.

And let me be clear (and I know this is not the case for some people), I don’t like or enjoy exercising for the most part. Swimming is about as boring and painful of an activity as you can imagine. All you hear is the sloshing of water. All you feel is your lungs wanting air. And all the while your mind is fighting boredom while trying to count laps. Was that 15 or 10? Ugh. I’ve probably swam hundreds of extra miles because I lost lap count because my mind wandered.

Running/the stairmaster are a bit better simply because at least you can listen to music (yes, I’m aware that there are music options for swimming and I’ve tried a few — there aren’t really any good options.) But they are still painful. My body doesn’t want to do that much exercise for that long. It wants to relax and take it easy. Hahahaha.

What I do like are the results from exercising — better health, feeling better overall, having more energy, and so on.

I compare exercising to taking medicine — it’s something you do because you know it will make you feel better, even though you don’t like doing it. lol.

Of course some exercise can be fun, like pickleball, golf, tennis, and so on. Those are awesome options because you get the health benefits without as much pain (because you are enjoying yourself).

One exercise that is sometimes dismissed for not being difficult enough but actually is amazing is walking.

For the past decade, walking has been a key part of my daily routine. It is a low-impact, high-reward activity that requires almost zero overhead, yet the dividends it pays in physical and mental health are astronomical.

However, even a “free” activity requires the right equipment. Mainstream advice tells you to buy whatever is on sale at a big-box store. I disagree. You need to invest in your “infrastructure.” For me, that meant finding the perfect gear — specifically Brooks Ghost shoes because they provide the support my body needs.

Walking isn’t just about the steps; it’s about the environment. I used to spend a significant amount of time walking outdoors — looking at the mountains. I’d either talk to my mom or listen to an audio book or podcast when doing so. Now my mom has passed and there are no mountains around, but we do have the woods/trees that are beautiful in their own right.

As of this writing, my walking app (which I started using shortly after I retired) shows these stats:

2,986 days (over 8 years) of 7,000 steps (the minimum I set) or more
Over 67 million steps total
Over 30,000 miles walked
Over 41,000 flights of stairs climbed

So yes, I’m a fan of walking. lol

I had goals for years of 20k steps a day, but now I’m ok with around 12k-15k a day. I know, I’m a slacker. Hahaha.

And I can’t move to the next point until I mention pickleball — it’s been such a huge part of my first decade.

I found pickleball in Colorado a year or two into retirement and played it 3-4 times a week for two hours each time for most of the next 5-6 years. It wasn’t until I hurt my back that I stopped playing (for two years). My plan is to return to it, but be a bit more balanced — maybe only a couple times per week.

But I also found it when I was starting to wonder how to fill my time in a meaningful way. Pickleball came along and I had a new sport that was fun, provided extra exercise, and was quite social in nature (I had a gazillion pickleball friends). Those were some great days and I am thankful for them.

4. Spending Time With My Wife and Family

One of the most obvious benefits of retirement is more time with the people you love. But like many obvious things, it is easy to underappreciate.

Work takes a lot more than 40 hours a week from most people. Jeesh, when I was working “only” 40 hours was considered a vacation week. Hahaha.

But even in addition to the time at work, a career takes commute time, preparation time, decompression time, travel time, mental bandwidth, and emotional energy. Even when you’re technically home, work can still own part of your brain (a major part).

Retirement loosens that grip, of course. This newfound freedom gives you the chance to be more present with your spouse, kids, grandkids, extended family, and close friends. For me, that has been one of the richest parts of the last decade.

Notice I said “chance.” It’s not automatic.

More time together does not guarantee better relationships. If anything, it can expose weak ones. Retirement magnifies what is already there. If you have built a strong marriage and solid family ties, retirement gives you more room to enjoy them. If you have not, retirement may reveal the gaps.

This is one reason I tell people not to think of retirement as purely an individual event. It is usually a household event. A couple retires into a shared reality. The daily rhythms change for both people. Expectations matter. Communication matters. Flexibility matters.

What has enriched my retirement most here is not just the quantity of time, but the quality of it. More meals together. More conversations. More shared plans. More margin. Less rushing.

My wife and I have always had a great relationship and retiring made it even better. We have things we like to do separately (which is vital IMO) but retirement also created new things for us — like a nightly walk of 45-60 minutes just to walk and talk.

I also retired when both kids were still at home, so I get extra time with them that I never would have had when I was working. Plus I got to visit colleges with my daughter (and helped her get back and forth a few times) and see my son when he was working in Hawaii.

I got more time with my parents (we vacationed together as well as spent extended holidays with each other). I talked to my mom on the phone quite often (walking home from the gym) and my wife talked to her every day.

We also had time for some bigger family events we wouldn’t have otherwise — like visits from my biological father and some family get-togethers in Iowa.

When you have time and money, it makes connecting with others much easier.

All of this has definitely enriched my retirement.

And before I leave this topic I do have to mention Zeus, our awesome cat. He’s a constant companion for both of us and while he’s not human he does add an element of fun, happiness, life, joy, and companionship to our lives. As I type this he is about three feet away, sleeping on his cat tower in my office.

5. Traveling — But in a Way That Fits Me

Travel appears on almost every retirement wish list. In Transamerica’s survey of middle-class Americans, 67% said traveling was one of their retirement dreams. That made it the top answer.

I get why. Travel represents freedom. It says, “I can go because I want to, not because I got approval.”

That said, I’ve also learned that retirement travel gets oversold. The conventional story is that the ideal retiree turns into a nonstop globetrotter. I think that image fits some people well and others poorly. As with most things, self-knowledge matters more than marketing.

Travel has enriched my retirement, but only when done on terms that match my preferences.

That means I’m less interested in checking boxes and more interested in having enjoyable trips. I’d rather take a trip that is easy, restorative, and actually pleasant than one that looks impressive but feels like a hassle. Retirement has made me more selective, not less. I no longer need travel to prove anything.

That’s one of the underrated benefits of retirement, by the way. You can stop doing things because they sound good in theory and start doing what you actually like in practice.

For some retirees, travel provides novelty and adventure. For others, it provides family memories. For others, it simply breaks routine in a healthy way. I think the important point is not whether you travel constantly. It’s whether you have enough variety in your life to keep it fresh.

In my case, travel has enriched retirement when it has been purposeful, manageable, and enjoyable rather than frantic.

I have been a bit all over the map when it comes to traveling in retirement. I’ll probably miss some trips, but here are some highlights:

Early in retirement we took our first family trip to Grand Cayman (me, my wife, our kids, and my mom and dad).
We liked it so much that we returned the next year. (same group)
We spent a family vacation on the beach in Ft. Myers Beach (unfortunately the house we stayed in was lost in the hurricane a few years ago).
I/we traveled to DC a few times. I went once for a financial conference and various combinations of our family went a few other times as my daughter went to college in the area, plus worked there a summer.
Me, my wife, daughter, and son-in-law went to Hawaii, spent a few days in Honolulu, cruised for seven days (seeing our son along the way), then got home two weeks before Covid locked everything down.
My wife and I traveled to Las Vegas a couple times where my mom was sick, and eventually died.
I went with my daughter to Orlando for a financial conference and we did a lot of fun things during the non-conference times.
Me, my wife, and my dad spent 2.5 months in The Villages, FL. We made a Disney trip during that time with our son, daughter, and son-in-law who came down as well.

In addition to these, there were many smaller trips here and there. In addition we lived in places where people come to vacation — first Colorado Springs and then The Villages — for over three-fourths of my retirement.

But over time we have transitioned as 1) places we wanted to go narrowed, 2) the hassle factor of traveling seemed to increase, 3) we moved to a resort (who needs to travel when the place you visit has fewer amenities than the place you live?), and 4) we worked to make our home so awesome that we didn’t need or want to go anywhere else.

What does the future hold here? I’ll take some guesses later on in this series.

So far I can say travel has been valuable for me. I just refuse to turn it into a compulsory retirement performance.

6. Managing Our Finances and Investments

Managing our finances and investments has remained a meaningful activity in retirement, and I think that surprises some people. After all, once you’ve built the nest egg, isn’t the hard part over?

Yes and no.

The accumulation years are certainly intense. But decumulation, tax planning, managing investments, estate planning, healthcare decisions, charitable giving, and lifestyle spending all still require attention. Retirement does not eliminate money management. It changes the nature of it.

For me, this has been enriching because I genuinely enjoy personal finances. I like making sure the resources we built are being used wisely. And I like the peace of mind that comes from knowing where things stand.

Managing finances in retirement is not about obsessive control. It is about stewardship. The goal is not to spend retirement glued to account balances. The goal is to keep the financial side organized enough that it supports your life rather than intrudes on it.

I also think this activity helps preserve one of the strengths that got many of us to retirement in the first place: intentionality. People who reach financial independence usually do not do so by accident. They pay attention. They make choices. They learn. They adapt. I see no reason to abandon those habits the moment work ends.

Retirement should bring relief from financial anxiety, yes. But it does not require financial passivity.

For me, staying engaged with our finances has been both useful and satisfying.

Overseeing our finances doesn’t take a ton of effort (by design) as I have most of it set on autopilot.

We still track our spending (force of habit more than anything else) in Quicken. Every once in awhile a new financial issue pops up and I need to deal with it. A couple examples: the need to get new wills after we moved to North Carolina and the frustrating episode with Chase.

Plus there are on-going issues like charitable giving, taxes, and Roth conversions.

None of it is too much and I enjoy most of it.

If you enjoy the analytical side of money — as many ESI followers do — this activity is actually fun. It’s like a high-stakes strategy game where the prize is more security and more freedom for your family.

7. Helping Other People

One of the best surprises of retirement is how satisfying it can be to help others when you are no longer squeezed by career demands.

When you’re working, even generous people often feel pressed for time. They may want to mentor, encourage, teach, or give back, but they have limited margin. I volunteered a lot when I worked (on various committees, raising money, and even served as the president of a non-profit for seven years), but it was always a struggle to do everything I wanted to.

Retirement changes that. It creates room for contribution.

This can take a lot of forms. It can be formal volunteering. It can be mentoring. It can be writing. It can be answering emails, sharing lessons, helping family members, or donating time and expertise to causes you care about. The form matters less than the mindset.

For me there have been a few areas of focus.

First, I consider helping people through ESI Money and related efforts to be a volunteer service. I know that clear direction given consistently can change lives. That makes this kind of work worth doing.

Retirees often rediscover this after the initial thrill of not working wears off. Freedom is great. But endless self-focus gets old. A lot of people eventually want to use their skills, money, or experience to benefit someone else. That is not a retreat from retirement. It is often a maturing of it.

Helping other people also has a useful side effect: it keeps your own problems in perspective. When you’re engaged with real people and real needs, you stop obsessing over trivial inconveniences. Your life gets a healthier scale.

Second, I have dedicated significant time to mentoring through the Millionaire Money Mentors.

And it’s not just me. There are scores of great mentors (and members) who help and support each other there. As a result, we all grow — I’ve probably learned as much as I’ve taught. It’s been very rewarding.

We have people with deep experience, insights, and education in a variety of topics. They are very kind to share these freely with others and I know what they contribute make lives better. It’s a privilege for me to be part of it.

Third, we have focused on charitable giving in retirement.

A lot of retirees volunteer by giving their time, and there is certainly value in that. But over the years I’ve come to believe that my own best form of volunteering may be giving. That’s where I think I can create the most impact.

Some people hear that and assume it sounds impersonal. I see it differently. I’m looking for the biggest impact. In many cases, money in the right hands can do more good, more quickly, and on a larger scale than I could ever do personally by showing up for a few hours here and there. A financial gift can feed people, fund ministries, support programs, expand outreach, and solve practical problems almost immediately. That matters.

This is also one place where I think people can get tripped up by sentimentality. They assume that volunteering only “counts” if you are physically present and directly involved. I don’t buy that. Results count. Impact counts. If a dollar can do more than an hour, then the dollar may be the better gift.

For me, giving fits naturally because it aligns with the way I think. I like being intentional. I like evaluating where resources can do the most good. I like looking beyond the emotional sales pitch and asking tough questions: Who is effective? Who is efficient? Who is actually solving a problem instead of simply talking about it? In that sense, giving is a lot like investing. You are allocating resources where you believe they will produce the best return. The difference is that the return is measured in changed lives rather than a higher account balance.

It took us quite a while to determine what sort of problems we wanted to help solve, finding organizations that did that, vetting those organizations to make sure the dollars were effective (you wouldn’t believe how few charities actually have data on how well they address the issues they are trying to tackle), and then giving to them.

We are now connected with 4-5 charities where we give 95% of our funds (through a DAF). We now have “major gift” contacts at each of them who keep us informed of what happens with our money, how much impact our donations have, additional giving opportunities, etc.

Giving has also enriched my retirement because it keeps me outward-focused. One danger in retirement is that life can slowly narrow until it becomes centered on comfort, convenience, and personal enjoyment. There is nothing inherently wrong with enjoying retirement. We worked hard to get here. But I do think retirement is better when some of what you’ve built flows outward to help others.

That is one reason I view giving as a natural next step in the ESI formula. You earn so you can provide. You save so you can build margin. You invest so you can grow wealth. And then one of the great joys of success is being able to give generously and strategically. At that point, money becomes more than a number on a spreadsheet. It becomes a tool that can actually bless people. (Anyone remember Invest, Give, Enjoy?).

As noted in the IGE post linked above, we are now in the last year of a commitment to give away $100k a year. I’m not sure what we’ll do next year, but my guess is that we’ll just stick with that amount until we decide on a different direction.

For me, giving has become one of the most meaningful parts of retirement. It turns financial success into something more useful than personal consumption. It reminds me that money is a tool, not a trophy. And it allows me to contribute in a way that fits my strengths and, I believe, multiplies my impact.

That’s it for this post.

Stay tuned as we’ll soon wrap up this series.

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