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Win the Retirement Game: Joy, Gratitude, Humor, and Purpose

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July 25, 2026 By ESI Leave a Comment

Today I’m continuing my thoughts on the great retirement book,  Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy

So far, here are the posts in this series:

  • Win the Retirement Game, Introduction
  • Win the Retirement Game, Fighting Boredom 
  • Win the Retirement Game: Take Control of Change and Move Beyond the Status Quo 
  • Win the Retirement Game: Connect Socially
  • Win the Retirement Game: Be Creative
  • Win the Retirement Game: Defeating Expectations
  • Win the Retirement Game: Beating Uncertainty, Complacency, and Obligations

If you missed any of those you may want to go back and read them as they all build upon each other.

And we’ll be giving away a copy of the book at the end of this post. Be sure to check that out if you’re interested.

Today we wrap up the book by giving highlights (and my thoughts) from chapter 10 (which is about joy, gratitude, and humor) and chapter 11 (which is about fighting off drift).

Let’s get to it…

Joy, Gratitude, and Humor

Here’s how the book introduces our first topic:

There are three other things you’ll want on your side in retirement, besides financial security, of course. The first is joy. You’re surrounded by it if you know where to look. Take the time to notice, appreciate, and celebrate things. Did you ever notice how easy it is for kids to express joy in the moment? Somehow, we lose that. Try to notice those small moments in daily living. They are special, and retirement gives you the space and the pace to enjoy them fully. You own your time. Fill it with joy as much as you can.

Let me just say that retiring in and of itself will produce a lot of joy in your life.

Once the shock of retiring wore off me (which took a week), JOY came in big-time! I couldn’t wait to get up and seize the day! I was up at 5 am or earlier every day, well before the sun came up. I was greeted by my Christmas tree already shining bright (I had it on a timer), grabbed a cup of coffee, and fired up my computer. A couple hours later I was on my way to the gym and then my day just unfolded from there.

I remember the birds singing louder, the colors looking brighter, and the whole world shining. Hahahaha. Ok, so that’s a bit over the top. But it was a joyous time that I often compare to “Christmas morning” as a kid (remember how great those were?) Retirement was just like that. I didn’t need to search for joy — it oozed out of everything!

The book continues…

The second one is gratitude. Appreciate the gifts you have. Reflect on them often. Some of my friends who have had so much good fortune waste a lot of time complaining about minor things. And frankly, there’s plenty to complain about as you get older. But I think it’s better to approach each day with gratitude for what you have. It doesn’t take much time. Then go off and live the day. You won’t be able to do that forever.

I actually have a recurring to-do on Todoist simply to take time and be thankful. I usually only spend a minute or so on it every morning, but I do like to begin my day that way.

Then throughout the day I’ll see or experience things and be thankful for them. For example, today I was at the pool swimming and they had our dome open to the sky/sun. It was very bright and beautiful. How could I not be thankful for that?

And the third one:

The last one won’t surprise you. It’s humor. Lighten up. Don’t take things so seriously. Especially yourself. Get over yourself and see the comical side of life, especially when things go wrong. When others complain, you can laugh instead. There’s an entertaining angle in most situations. I also urge you to experiment with things until you find what you truly love. It sounds easy, but it’s not. Look back at what you used to love and wish you had time to do. Now you have time. Take advantage of it.

I’m generally a happy person and I like to laugh, so this comes fairly naturally to me.

As for the suggestion of looking back at what you used to love — I can say yes and no to that.

On the yes side, I used to love playing tennis, so pickleball is a great option now. That works (not exactly the same but close.)

On the no side, I used to love skateboarding, so…no. Hahahaha.

Plus I think your preferences change over time.

I’m a bigger fan of searching big lists of activities (like this huge list of retirement activities) for ideas. Or do what I did — have a chat with ChatGPT and ask for suggestions. Tell it what you like and see what it comes up with.

More on Gratitude

Before we get into their summary points for this chapter, let me share a few more thoughts on gratitude, starting with this:

Gratitude has been found to increase positive emotions, decrease negative ones, and reduce dysfunctional behaviors. Scientific evidence shows It’s associated with enhanced psychological and physical well-being. It helps relieve stress and reduces frustration. It also keeps you away from social comparison, which leads to toxic emotions such as envy and regret. It’s also been found to reduce materialistic strivings by helping you focus more attention on the gifts you already have.

I love when something makes you feel better AND has positive health benefits to boot! (Volunteering is like this as well.)

Now, some thoughts on “how to do gratitude”:

Many things about gratitude are counterintuitive. First, it is not necessarily something you have to do every day. Research shows journaling two times a week raises well-being more than if you do it every day. Reflecting on your challenges and failures, along with your successes, will lead to more gratitude than if you only concentrate on successes alone. And thinking about the things you treasure produces more gratitude if you imagine their absence from your life rather than their presence.

That is some interesting stuff.

I may need to adjust my gratitude practice.

I’m not big on journaling, but I might need to give it a try. I do enough writing as it is, adding another thing to write might push me over the edge — and make me much less grateful. Hahahaha.

Finally, there is this:

I was surprised to see so many other effective gratitude practices. Two, in particular, stood out to me. Gratitude letters and visits. They benefit both the sender and the receiver, but especially the sender.

The practice involves making a list of the people who have had a positive impact on your life and writing handwritten letters thanking them for the difference they’ve made. Research showed presenting gratitude letters in person had a more lasting effect on happiness, especially if you read it out loud as a testimonial.

I have done this a couple ways:

  • I have written gratitude letters and sent them to people. These tend to have very positive results and people respond very well to them. They have made me feel better as well.
  • I haven’t delivered a letter in person, but I have met with a person and told them about the positive impact they had on my life and thanked them for it. It was a pretty emotional time for both of us and I felt great afterwards. 🙂

I highly recommend both of these. I need to do a few more myself actually.

Takeaways

Here are some of the key takeaways the author had from this chapter:

Notice what gives you joy. Savor the big moments and the surprising moments, but don’t overlook small moments of joy. they’re all around you in your daily life if you look for them.

Basically, pay attention. I can find joy in walking around the track at the YMCA if I just stop my mind for a second, take a breath, look around, and realize how calming, nice, and reassuring the place is — and how I’m thankful for it. This then brings on joy.

I guess thankfulness can lead to joy, huh?

Learn what takes away your joy and address it.

Yep, drop these things like a hot potato. You don’t need that stuff in your life.

Practice gratitude. Find a regular way to appreciate what you have. You can start by building a new habit for it.

I’ve already told you what I do. It can be as simple as that.

Or you could journal, which I know works for a lot of people (including my wife.)

Get a Purpose

Well, you knew we’d get to it right? The dreaded “purpose” in life.

But we already talked about a “calling” in Win the Retirement Game: Beating Uncertainty, Complacency, and Obligations, so how is this different?

They’ll get to that in a minute, but I warn you, it won’t clear up much.

Let’s begin with what purpose is…

Purpose is a self-organizing life aim that stimulates goals, promotes healthy behaviors, and gives meaning to life.

There are four parts to purpose, and each one leads to the next:

    1.  a self-organizing life aim
    2.  clear goals
    3.  healthy behaviors
    4.  Meaning

So far I think I’m ok with “purpose” (as opposed to “calling”.)

Purpose is simply “a new driving force in your life.” It helps you structure your days and spend your time. And it helps you defeat the enemy in this chapter: drift (more on that in a moment).

So this doesn’t have to be a save-the-world purpose. It’s simply is something that excites you and gets you out of bed. Something you can add to your day to create structure.

My suggestion is to see if any of my top seven retirement activities meet the definition of a purpose for you. If they do, that’s a BIG win.

The Drift

Next they bring in this chapter’s enemy…here’s what the book says:

Drift is the downside of the freedom of retirement. Just like a leaf floating along a stream, when you’re drifting in retirement, you’re not in control of the direction you’re heading in. And while the ride may be pleasant, you might not like where you end up. You’ve experienced this. You go from a structured, dynamic environment with forces pressing on you to a life with lesser demands. It’s nice to live without the structure for a while, but it can be unsatisfying. For a lot of us, our purpose has been defined primarily by work, partially because that’s where we have spent most of our time.

I feel like they’ve said this ten different ways, and this time it’s under the name of “drift.”

If you simply let your life unfold in retirement, it’s probably not going to go well.

Said in my favorite way, if you go-with-the-flow you get go-with-the-flow results (which are generally bad.)

This (once again) is why you need to make a plan for your time BEFORE you retire. You need to test it out so you’re pretty sure you direct your retirement life in the way you want it to be.

See my series on the book Retirement Starts Today for specifics.

Here’s an example of drift that is really scary:

Drift leads people away from finding a new purpose. Sadly, the average retiree ends up watching forty-eight hours of television each week, according to Nielsen audience data (and that was before the pandemic).

That is a crazy number. Forty-eight hours? I can’t believe it.

So I googled it and got this:

The average retiree watches a substantial amount of television—typically clocking in at 4.5 to 7 hours per day, which equates to roughly 30 to 49 hours per week. This makes watching TV the single largest use of free time for Americans aged 65 and older.

Ok, this seems to say that 1) the average is below 48 hours and 2) it’s still very high.

I wondered if this was truly TV or if it was all screen time (including phones, computers, tablets, etc.) and I couldn’t find a reliable source.

But even if the numbers above represent everything, they are still very large. And quite sad IMO.

That said, I stepped back to see where I stood:

  • I probably watch two hours of TV a day that’s not tied to any other activity (I do watch TV when I life weights in my home gym and sometimes when I eat after getting back from the gym — but those are more to just make another activity more interesting.)
  • I then play an hour of video games a night (when I have a game I like.) If it’s a game I really like, it’s way more than an hour. But there are times of the year (most of the year actually) where nothing is out that I like so I don’t play at all.
  • Then I do my brain games every day (chess puzzles, NY Times games, Sudoku, etc.) which is another 30-45 minutes.
  • I then spend somewhere between 3 to 4 hours a day in my office…writing, tracking my activities, talking to ChatGPT about this project or that project, managing our finances, answering email, reading, and so on.
  • Throw in another 30 minutes a day for doom-scrolling Instagram (which I do when there’s nothing else going on) and reading the news on Apple News+.

All that adds up to 7 to 8 hours a day on a screen of some type!

I wondered if it made a difference what type of screen time made up those hours, so I asked Gemini this:

Is there a difference in screen time impacts based on activity? For instance, is watching 8 hours of TV a day the same as spending 8 hours writing articles on your computer?

Here’s its response:

There is a massive difference between those two scenarios. While 8 hours of any screen time introduces physical considerations like eye strain or a sedentary lifestyle, the cognitive, psychological, and neurological impacts of passive consumption (watching TV) versus active creation (writing articles) are worlds apart.

It went on for quite a bit (as it tends to do), but this is the summary of its thoughts.

Ok, I feel better now. Back to the book, which notes that if you avoid the drift and find something to live for (your purpose), it can have positive health benefits:

There’s a growing body of research indicating that leading a purposeful life may have significant health benefits. For one, it can help you stay sharp. Studies by Patricia Boyle at the University of Chicago have suggested people who report a strong sense of purpose have a 30% slower rate of cognitive cline. Having a sense that your life has purpose has been found to support the health of the central nervous system and to increase resilience in dealing with adversity.

Purpose leads people to be more engaged in activities promoting physical and mental health, contributing to a better overall quality of life. It’s linked to higher levels of physical activity, involvement with community-oriented goals, and higher levels of social engagement. A study from the University of Michigan of over 7,000 people 55+ found a stronger purpose was associated with decreased rates of mortality.

So, there are HUGE benefits to finding something you love in retirement and going for it!

For me, I’ve had a few things that I’ve loved:

  • On the “keep life challenging and interesting” side there have been all the businesses I’ve had — ESI Money, Rockstar Finance, and MMM. These have been enjoyable, mentally stimulating, creative, financially rewarding, and have helped thousands of people (everything on ESI Money and Rockstar Finance are/was free, after all.) As I’ve talked about many times, there are a lot of benefits to working in retirement and I have reaped many of them.
  • On the “make life fun” side there’s pickleball, of course. This also has the side benefit of creating a social circle for me (plus adding some health benefits to my normal exercise routine.)
  • On the “meaningful” side there is my family. I have spent a lot of time with my wife as we are both home now. And we have spent and still spend a good amount of time with our daughter and son-in-law. In just the past week they were over for dinner on Monday, we went to Costco on Thursday, and we have a birthday celebration this weekend. Pretty cool.

Now my next challenge is “what’s next?” What else can I add to my life that will make it better (which means not overwhelming as well)?

I have a few ideas. Time will tell where I go.

The Benefits of Volunteering

The book continues talking about purpose, but moves it into the context of finding purpose through volunteering. It makes these comments:

Purpose is all about meaning, but what’s meaningful to you may not be meaningful to someone else. Furthermore, everyone lives a new purpose in different ways. A study of people 65 and older found that retirees are setting goals in multiple life areas, including wellness, personal growth, and learning new skills. The most common focus is on relationship goals, which older adults find most personally meaningful. Volunteering and service are also significant areas for goal setting. Retirees actively involved in volunteer activities report a stronger sense of purpose, happiness, and self-esteem.

Such activities also can have positive impacts on health. Volunteers have a lower risk of hypertension, delayed onset of physical disability, and enhanced cognition. A study indicated 29% of baby boomers expect to volunteer in retirement.

A few thoughts from me:

  • I 100% agree — what’s meaningful for someone else may or may not be meaningful to you. You need to find what works for you and do that. Don’t let others influence you into doing what they feel is meaningful — you do you.
  • I have goals in many areas…but I wouldn’t consider several of these to be my purpose. For example, I have physical fitness goals, but exercising is not my purpose.
  • There are a TON of benefits associated with volunteering — I highly recommend it! I “volunteer” in two ways. First, I consider part of what I do at ESI Money as a volunteer effort — spreading solid financial information to thousands free of charge. Second, our giving, which is substantial, is a form of volunteering. I focus on it more because I can impact more lives giving than I can physically volunteering.

And there’s another activity that some do as a volunteer effort (and I do as part of the MMM forums):

The pandemic highlighted the value of intergenerational relationships and mentoring. It’s a way for experienced people to pass along their knowledge and wisdom to the next generations.

Mentoring offers a good fit between supply and demand. One study noted that 50% of people 50 and older in the US want to be mentors, and more than half of the people under 50 are interested in being mentored, with 2/3 of gen Z wanting mentors. Best of all? True mentoring isn’t one directional. Both parties learn from each other. It’s mutually beneficial.

I know that I get a lot out of mentoring — both by contributing as well as the feedback I get from others (mentors and members in MMM.)

It’s an AWESOME way to spend some time every day. It’s totally flexible (can be done on any timeframe) and the impact can be amazing as people are getting truly solid ideas, sometimes at times of great need.

Calling Versus Purpose

Next the book gets to the question we had up above:

What’s the difference between a calling and a new purpose?

They’re related, but a calling tends to become a singular focus. Some people get stuck looking for a single purpose. Most people’s lives are multidimensional. When they retire from their primary career, that doesn’t change. Most feel a need to replace the central purpose work provided, but not necessarily with one thing. Think of it as creating a portfolio of interests. You can decide which are primary and secondary, and you can set goals in each area.

Uh, that certainly clears it up, right? Hahaha.

I’m more confused now than before they asked the question.

Anyway, let’s move on…

Find Your New Purposes

This chapter ends with a section that gives several steps you can use to identify new purposes in your life. It begins with this step:

List your core values. Dig a bit deeper than the things you may usually cite. Challenge yourself to list five specific things that matter most to you now. Ensure your mindful of things that may have been central in your full-time career years (like status and advancement) that may be less important to you going forward.

And the process ends with this:

Draft a one paragraph mission statement for your unique retirement the reflects what your new purpose could become.

I prefer my method of looking at lists of potential activities, trying the ones you think you might like, keeping what works, and tossing what doesn’t.

But I can see how this would work as well.

As we close out our coverage of this book, let me share the last sentence of the book to take us home:

You may be retiring, but you’re not done yet. It’s your time. Create the new life you’ve earned with imagination, experimentation, and a sense of adventure. 

Well said.

That’s it for this book. What did you think of it?

——————————————

As I said above, I’m giving away a copy of Win the Retirement Game on every post I do about the book. Here’s how to you can enter:

  • Leave a comment below telling me what you liked best about this post, what you think you can use, or something you learned from it. Basically just share anything meaningful related to the content above (note: “please enter me to win” and similar comments will not be considered out of pure weakness! At least put a bit of effort into it!) This should be fun!
  • Be sure to leave your email address when you leave the comment so I will know how to reach you if you win (the email address will not be visible to anyone other than me).
  • The winners will be selected by me at random a few days after this post goes live. I’ll announce who wins in my own comment.
  • I’ll email the winner, get their address, and send them a book from Amazon.

As with most giveaways, there are rules. Here they are.

Good luck!!!!

Filed Under: Books, Retirement

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