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

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:

Great Activities Make Retirement Great

Reaching a decade of financial independence is not just a victory for the balance sheet; it is a profound test of one’s ability to manage the most finite resource we have: time.

As I’ve written many times, the ESI formula gets you to financial independence. Earn enough. Save a bunch. Invest wisely. But once you’re retired, ESI is no longer the whole game. You still need the financial piece, of course. Yet at that point the challenge shifts from accumulation to allocation. Not just how you allocate money, but how you allocate time, attention, energy, and relationships.

And that’s a very different assignment.

Mainstream financial “wisdom” (yes, that’s in quotes — BIG quotes) suggests that once you hit your number, you simply ride off into a sunset of endless margaritas and golf.

The reality is far more analytical. If you don’t have a plan for your time, retirement will bankrupt your spirit long before it touches your bank account. Over the past ten years, I have approached my retirement activities with the same scrutiny I applied to my asset allocation. I wanted a high ROI on my hours. I wanted activities that contributed to things I value like health, wealth, and happiness.

That doesn’t mean you need some grand mission, a color-coded bucket list, or a consultant to help you “discover your authentic second act.” The retirement industry loves to overcomplicate things because overcomplication sells. The truth is usually simpler. A great retirement is built around a handful of activities you genuinely enjoy and want to repeat over and over again.

I’ve seen that the happiest retirees are not always the ones with the biggest portfolios. They’re often the ones with enough money plus a repeatable rhythm of life they enjoy. They have things to do, people to do them with, and a reason to get out of bed in the morning.

Consider this: people approaching retirement often imagine they’ll be happier than they actually end up being. A 2024 MassMutual study found 77% of pre-retirees expected to be happier in retirement, while 67% of current retirees said they actually were happier. More telling, the retirees who were much happier were more likely to spend their free time on loved ones, exercise, hobbies, and travel.

That’s a useful finding. Retirement doesn’t make you happy automatically. It gives you room. What fills that room determines a lot of the outcome.

My Retirement Activities

I have talked a lot about activities in retirement (especially in this “10 Things about 10 Years in Retirement” series). Two of those posts that all potential retirees should read are The Top Seven Retirement Activities and Huge List of Awesome Retirement Activities. If you haven’t read those, I’d encourage you to check them out. And pass them along to people you know are planning for retirement, in the process of retiring, or already retired but might need some help with activities.

This post will be a bit different than past ones though…and a bit more personal. This one will detail the 10 activities (in no particular order) that I have used to create a great retirement. Hopefully they can add to those other posts and give potential retirees ideas for what they can do to make their retirements happy.

And once I got started writing this post, I couldn’t stop myself. So I’m turning this into a three-parter!

These are 10 activities that have enriched my retirement. This is not a list of what retirees should do. It’s not a “best activities for seniors” article written by someone who thinks pickleball and birdwatching are the universal answers. This is simply my list: the activities that have improved my retired life, kept me engaged, and made the last decade much richer.

And yes, I know I’ve mentioned these before (off and on), but I wanted a post devoted just to them so that others could dig into them a bit. Plus, not everyone reads every post (though I don’t know why that happens, lol) so they may have missed me discussing these previously.

Some are obvious. Some are probably less so. A few may sound ordinary. That’s part of the point.

After 3,650-plus days of “freedom,” I’ve distilled the activities that actually moved the needle. These aren’t just hobbies; they are the pillars of a successful Life 2.0.

And remember, a great retirement usually isn’t built on dramatic moments. It’s built on satisfying ordinary days. That will be apparent in this list.

Here are my ten activities…

1. Writing and Running Businesses

I initially had these as two different activities. I was going to list “writing” as one activity and “running businesses” as another.

And that’s fair because they are two distinct activities.

But after I thought about it they are both so intertwined with each other (at least for me) that I didn’t think I could separate them. Plus I wanted to keep the list to 10 things, so there is that. lol

That’s why I’m listing them together and it works for me. For those reading, perhaps you are interested in one but not the other. That’s fine too. Including them both just gives you more choices/options to consider what might work for your retirement.

Now, after all that blabbing, let’s get to the actual activities. I’ll co-mingle them throughout this section but also try to give each task it’s spotlight.

Let’s get to it…

If I had to pick the single activity that has most enriched my retirement, writing would be near the top of the list.

In one sense, this is funny. I retired from full-time work, and then I voluntarily gave myself another form of work. But it’s a completely different experience when the work is chosen, flexible, meaningful, and fully under your control. Those are the key distinctions many people miss. Retirement does not require the total elimination of productive effort. It requires freedom from mandatory effort. There are reasons working in retirement is on my list of the top seven retirement activities.

And for those of you pooh-poohing the idea of work in retirement, just remember we’ve already defeated the Retirement Police. More than once.

Writing has given me structure, purpose, creativity, and a platform to help people. That’s a pretty strong combination. And it’s done so for more than 20 years now — I’ve blogged for 20 years and did freelance writing well before that. So why would I give those benefits up in retirement?

To me, writing offers an ROI that goes beyond the dollar. It provides mental stimulation and a sense of purpose. One of the strangest cultural assumptions is that after decades of building knowledge and solving problems, the ideal endgame is to stop stretching your mind. That is a recipe for cognitive decline. By writing long-form posts, analyzing millionaire interviews, and engaging with the FIRE community, I keep my analytical gears grinding.

In addition, writing is where I process ideas. It’s where I test them, sharpen them, and organize them into something useful. It’s where I sort out what I REALLY believe (because once you put it in print, it’s out there). It’s also served as a way to hold myself accountable. You can rest assured that if I say I am doing something (like investing in index funds), then I’m doing it. It’s a virtuous cycle: the more I write about wealth, the more I refine my own wealth management strategies.

Over the years I’ve written about earning more, saving more, investing smarter, giving better, and navigating retirement itself. I’ve also had the privilege of publishing hundreds of millionaire interviews, which has exposed me to an enormous range of stories and strategies. That alone has been one of the great hidden gifts of my post-work life.

Writing also fits retirement well because it is scalable. I can do a lot of it or a little. I can go deep when I want to. I can take a break when I want to (I often write in spurts and get 3-4 months ahead in posts, then move on to other activities for some time before coming back to writing). It can be solitary when I need quiet, or interactive when I want feedback and conversation. It’s mentally engaging without being physically exhausting. And unlike many hobbies, it creates assets. Blog posts, books, emails, and ideas compound.

That last point matters to me because I still think in ESI terms even though I’m retired. I like activities that produce more than a momentary experience. Writing does that. It creates leverage. A post written once can help people for years. An email sequence can keep working while I’m asleep. A book chapter can clarify my own thinking and help thousands of readers at the same time.

There’s also a broader lesson here for retirees. Productive outlets matter. Not because you need to justify your existence with output, but because many people are wired to feel better when they are making, building, teaching, organizing, or contributing something. The FIRE community figured this out early. Many people retire from traditional employment only to blog, consult, teach, create content, volunteer, or start passion projects. That isn’t failure to retire. It’s often success at redesigning life.

Writing has been one of my best redesign choices.

BTW, I don’t only write for ESI Money. I probably write more words on the Millionaire Money Mentors (MMM) forums in a given week than I do for this blog. And when I owned Rockstar Finance I did some writing there as well (though it was admittedly more editing and curation than writing).

Separately from the act of writing, there’s the business side of writing. Blogging forces a level of discipline that many retirees lose. It requires an editorial calendar, research, and a commitment to quality. Even when I “only” edit millionaire interviews, there’s a lot that goes on. I’ve told many people that editing a document someone else has written can take me much longer than writing an original piece myself.

Then there’s another side of running a business: building things. Retirement is not about shutting down every productive instinct I have. It’s about having the freedom to choose what I build, how I build it, and how much time I want to devote to it.

That’s why continuing to run businesses like ESI Money, Rockstar Finance, and Millionaire Money Mentors has enriched my retirement so much. These are not jobs in the traditional sense. No boss is setting my priorities. No corporation is requiring me to attend meetings that shouldn’t exist in the first place. No one is handing me work I don’t care about and expecting me to pretend to be excited about it.

What these businesses do give me is the best part of work: purpose, challenge, creativity, and the satisfaction of building something useful. They also happen to line up perfectly with what I already care about. ESI Money helps people earn more, save more, and invest better. Rockstar Finance helped to spotlight the broader financial world. MMM creates a place where people can learn from those who have actually built wealth. That’s not random busywork. It’s a natural extension of the ESI framework.

This is one reason I think many retirees get retirement wrong. They assume the only alternative to a full-time career is pure leisure. So they spend years dreaming about a life with no obligations, no structure, and no responsibility. Then they get there and discover that endless undirected free time is not nearly as satisfying as they imagined. It sounds great in theory. In practice, it can get old fast.

Meaningful effort is different. It gives shape to the day. It creates momentum. It provides feedback. It lets you make progress on something that matters. For me, these businesses do/have done all of that. There are articles to write, ideas to develop, products to improve, emails to answer, and communities to build. That keeps retirement from becoming soft and shapeless.

Even now, after all these years, I have an excel spreadsheet with over 800 lines of personal finance article ideas. Hahaha. I’m sure there’s a lot of trash in there and some things are listed more than once, but however you look at it, plenty still remain. It just shows how much I enjoy the topic, which is another great part of writing/running these businesses: fun.

Another benefit: running these businesses keeps me engaged with sharp people and real-world ideas. It prevents retirement from becoming too small. I still get to think, analyze, write, challenge assumptions, and help people buy their lives back. That’s a pretty good combination. For me, running these businesses has been one of the best parts of retirement because it gives me the upside of productive work without the nonsense that usually comes with it.

But the biggest thrill I get from writing and running personal finance websites is when I get comments like this — which I just recently received:

“I’ve been reading your blog since the days of FMF, and your articles are part of the reason why my husband and I are millionaires now.”

I almost tear up when I read stuff like this. And these emails are only the people who let me know I’ve helped them. How many others (hundreds? thousands? tens of thousands? more?) have benefitted from one of my articles that they’ve read here and there and didn’t contact me? It’s mind-blowing in some respects.

This is why ESI Money is as much of a volunteer effort as a business — because it helps people with zero expense for them. It’s been one of the most rewarding efforts of my life and I can’t imagine not bringing it into retirement where I can lean into it.

Now maybe you don’t have 20+ years of blogging, but my guess is that if you’re reading this, you can write. So maybe in your retirement you write fiction stories. Or you have a gratitude journal you write in every day. Or maybe you write detailed responses to help people on Reddit. There are lots of ways you can enjoy writing in retirement.

And as for running a business, there are a gazillion ways to turn a love into a small business that you could do on your terms. A few that come to mind: pet sittting, bicycle repair, coin collecting, etc.

2. Reading

Reading has mattered to me for a long time (I remember really getting into it in grade school with the help of two very awesome second and third grade teachers). Retirement gave me the time to do more reading and to enjoy it without constantly feeling like I should be doing something else.

When you work full-time, reading often gets squeezed into leftovers: 20 minutes before bed, a few pages on a plane, a chapter on the weekend if nothing else gets in the way. Retirement changes that. It returns large blocks of uninterrupted time, which is ideal for deep reading.

I’ve found that reading enriches retirement in several different ways.

First, it keeps the mind active. That sounds cliché, but it’s true. One reason many people struggle after leaving work is that their jobs provided a steady stream of mental stimulation. If they do not replace that, life can flatten out surprisingly fast. Reading is one of the easiest and cheapest ways to stay intellectually engaged.

Second, reading feeds everything else. It gives me blog ideas, investment ideas, perspective, vocabulary, stories, and questions. Good reading spills over into good conversations and good writing. It expands your range.

Third, reading is one of the most portable activities in the world. You can do it at home, while traveling, early in the morning, on a rainy afternoon, or before bed. It doesn’t require a team, reservations, or perfect health. There are not many retirement activities with that kind of flexibility.

And reading has another subtle advantage: it helps prevent retirement from becoming shallow. One risk of retirement is drifting toward an easy but empty routine — entertainment, errands, meals, and repeat. There’s nothing wrong with relaxation, but too much passive consumption can make the weeks blur together. Reading adds texture. It gives the mind something substantial to chew on.

My reading has morphed over the course of 10 years in retirement…

At first, I read books. In fact, I read many books about retirement (AFTER I retired). Hahahaha. They let me better understand what made for a good retirement (which helped me personally) plus also gave me content ideas for ESI Money.

Over time, more and more of my reading has been online. I read articles (mostly money related but others too — I have Apple News+) as well as thousands of words daily on the MMM forums.

When I do find a book I like, I often buy the book and the audio version. I listen to the audio when I’m at the gym, then re-read that portion (in the book) when I get home. I take notes in the book as well, so the notes stay with the book and are always accessible.

I also “read” a lot of podcasts (do we consider listening reading? Maybe not, but it certainly is another way to consume content.)

That’s it for this post! We only got through two activities!

Stay tuned as I’ll soon be back with another post in this series!

Great Activities Make Retirement Great

My Retirement Activities

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