How To Find Fulfillment In Retirement

Have you ever wondered “How To Find Fulfillment In Retirement?”  

Shortly before I left on sabbatical, I had a phone call with an impressive man named Ashby Daniels.  He makes his living advising folks on personal finance,  retirement readiness issues, and answering the question “How to find fulfillment in retirement”.  He reached out to seek my advice.  He’s a professional advisor and wanted to learn directly from someone who experienced a successful transition into retirement, hoping that those learnings would, in turn, make him a better advisor for his clients.

I respect that.

He also maintains his own blog (Retirement Field Guide), and he’s a good writer with a strong mind.  He thinks a lot about what we can do to ensure a good retirement, and his thoughts are worth hearing.  I explained that I was going to be taking a sabbatical for the summer, and asked if he’d be interested in writing a guest post.   He accepted the offer and followed up with a hand-written note of thanks a few days later.  Nice touch, too often lacking in our society today.

As I said, he’s an impressive person, and I’m pleased to share a few words from him today as we continue our RV adventure through the Pacific Northwest.

(BTW, if you’re interested in how our trip is going, see “An Update From Fritz” at the bottom of this post…).

contentment in retirement

How To Find Fulfillment In Retirement

The philosophy of “more more more” is America in a nutshell. Most of the time it’s more money or more stuff. And that philosophy is riddled with irony. The idea of “more” is complicated because deep down we know money is not important. If it was, people would talk about it on their deathbed, but they don’t.

If More Money was important, people would talk about it on their deathbed. They Don't. Here's how to find contentment in retirement. Share on X

At its core, money is a tool, nothing more. But it doesn’t seem that way because that would be ignoring the concept of ego. And ego is a touchy subject for many people because nobody wants to be labeled as egotistical. Instead, we re-label wants as needs and material things as fulfilling to somehow justify our feelings. 

To be clear, I am not judging or coming down on enjoying your material success or desires. By all means, you should! And I can’t judge because I deal with the same things. In fact, I struggle with this issue on a regular basis. 

For example, I have a business that many would be envious of and yet, I think all the time about how I can grow it bigger and faster. Why? Is it my own innate healthy desire or due to external forces (society)? If I’m honest with myself, it’s mostly external. I know that, and yet the desire persists.

If society pressures us to want more, what can we do to find true contentment in spite of societal influence? Share on X

There is a great story that I want to share in its entirety that so clearly explains this disconnect. You may have heard it, but it’s so relevant, I had to share it.

how to find contentment in retirement

The Banker and the Fisherman

An American investment banker was taking a much-needed vacation in a small coastal Mexican village when a small boat with just one fisherman docked. The boat had several large, fresh fish in it.

The investment banker was impressed by the quality of the fish and asked the Mexican how long it took to catch them.

The Mexican replied, “Only a little while.”

The banker then asked why he didn’t stay out longer and catch more fish?

The Mexican fisherman replied he had enough to support his family’s immediate needs.

The American then asked “But what do you do with the rest of your time?”

The Mexican fisherman replied, “I sleep late, fish a little, play with my children, take siesta with my wife, stroll into the village each evening where I sip wine and play guitar with my amigos: I have a full and busy life, señor.”

The investment banker scoffed, “I am an Ivy League MBA, and I could help you. You could spend more time fishing and with the proceeds buy a bigger boat, and with the proceeds from the bigger boat, you could buy several boats until eventually, you would have a whole fleet of fishing boats. Instead of selling your catch to the middleman you could sell directly to the processor, eventually opening your own cannery. You could control the product, processing, and distribution.”

Then he added, “Of course, you would need to leave this small coastal fishing village and move to Mexico City where you would run your growing enterprise.”

The Mexican fisherman asked, “But señor, how long will this all take?”

To which the American replied, “15-20 years.”

“But what then?” asked the Mexican.

The American laughed and said, “That’s the best part. When the time is right you would announce an IPO and sell your company stock to the public and become very rich. You could make millions.”

“Millions, señor? Then what?”

To which the investment banker replied, “Then you would retire. You could move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siesta with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos.”

Everyone can understand the wisdom of this parable and yet we ignore it in practice. Myself included. Do you want what you want because you want it or because the world wants you to want it?

Here in America, where opportunity and wealth are abundant, I’ll guess that most of us don’t actually need more or even want more. We want what more represents. A higher social status.

We can argue that all we want, but at the end of the day, that is what our wants represent to a large degree. And it’s a slippery slope. Yet, no matter how much we attain, more rarely leads us to happiness. If this wasn’t true, there wouldn’t be miserable billionaires.

how to find contentment in retirement

Redefining More in Retirement

Imagine if you had more money than you could ever spend, what would more mean to you at that point? The goal of retirement for most people isn’t having the most stuff or passing along the largest inheritance. It’s finding fulfillment in your daily life. 

Our goal for retirement shouldn't be about having more stuff. Rather, it should be finding fulfillment in our daily lives. Share on X

What makes this such an ironic post for me is that, as a financial advisor, many people assume that my goal or job is to help them accumulate more. More money. More stuff. More trips. I politely disagree. 

My goal is actually quite different than that. Simply stated, I want each client “to lead a fulfilling life” – however they define it. And that’s different for each person.

Finding Fulfillment That is Unique to You 

When is the last time you sat in a quiet place and thought about what you truly want out of your life? Or what a successful retirement actually looks like for you? 

If you boil retirement down to what’s truly important to you, it probably takes less than what you’ve envisioned in your grandiose plan. 

To be very clear, I’m not discouraging stuff, or travel or anything like that. By all means please buy/do those things if they add enjoyment to your life. 

I am, however, encouraging getting in tune with yourself to identify what might make your retirement truly fulfilling. What might you do in life that would cause you to feel that you have led a life well-lived? 

I’ll bet what leads to a feeling of a life well-lived are the quiet moments. Spending time with your children or grandchildren. Having dinner with friends. At the core, it’s time with those we love no matter the activity.

Taking Action

If there was one takeaway from this post, I hope it’s that you’ll take the time to find a quiet place to ask yourself those two questions:

  • What do you truly want out of your life?

  • What does a successful retirement look like for you?

You may find that you’re closer to your retirement goals than you initially expected and well on your way to a more fulfilling retirement. 

Thanks for reading!
Ashby Daniels

Related Reading: A Letter to Grandparents

An Update From Fritz:

I appreciate Ashby sharing his advise to “find a quiet place” to determine what you truly want out of life.  It’s essentially the same advice I gave in A 10 Day Retirement, and I can speak from experience of the value gained from this exercise.  If you haven’t done it yet, give it a try.

The sabbatical has gone even better than I’d hoped, and we’re truly enjoying the luxury of “slow travel” through our beautiful country.  For those who are curious about how the trip is going, I’ve edited a short video of the first few weeks of our journey, and have decided to share it with you above.  Yes, I’m taking a break from writing, but I’m enjoying keeping the “artistic” side of my brain busy as I teach myself video editing.

I’m currently sitting in our RV in Olympia, Washington (see pic to left). We spent the month of June traveling cross-country, and are now parked a few minutes from my daughter’s home, enjoying a month with her, her husband, and our precious 7-month old granddaughter, Octavia Rose. 

“The ladies” are out at the moment getting their hair done (and, hopefully, having some good Mother-Daughter bonding time), so I took a short break to load up Daniel’s post and write this brief update.  


Today's post includes a special feature: A short video summarizing the first few weeks from our Great American Road Trip, a 3-month cross-country RV trip with 4 dogs! Share on X

Enjoy the video – we’ll be back in Georgia in another month or so, and I look forward to sharing more thoughts with you upon my return.  Until then, enjoy your summer!  We’re certainly enjoying ours…

We made it to the Oregon coast (the dogs and the humans are loving the adventure!)


  1. The ‘ole Mexican fisherman tale is a wise one indeed and really shows the somewhat absurd end-state of the “bigger-better-faster” mentality when it comes to a career.

    I hope I’m close to achieving my proverbial state of ‘fishing all day in a small coastal village’.

    1. Bigger-better-faster is so hard to overcome mentally – especially when we have an ingrained “high-achiever” mentality as so many of us do. I’m working hard to overcome it. I appreciate the comment!

  2. I often think of my early retirement goals as returning to the grad student lifestyle, biking everywhere, reading daily, exercise daily, and socializing. The ironic thing is I dropped out of a Stanford PhD program so I could go start my career and make money, although the end goal is to get right back to that same lifestyle! Sure, we added some things along the way like owning a home and having a child, but our daily lives now look so similar to grad school that new neighbors often ask us which department we’re in at the university!

    1. Isn’t that ironic?? I was just talking with my wife the other day about how when we were in college and had $100, I might as well have had all the money in the world. Getting back to our roots and the things we truly find fulfillment in is what life is all about. Thank you for your comment!

  3. Having been “retired” (free!) for 9 years and counting, I can relate to both the Mexican Fisherman and the achiever mentality. I just got a book recommendation called “The Obstacle is the Way”, which points out that we find our happiness and greatest fulfillment through challenges. I personally enjoy the variety and challenge myself to try new endeavors that last 6 months or a year, which has worked well so far.

    I recently found myself wanting to roll my Roth to a self-directed account and start learning to do real estate loans. Meeting people in the FIRE community gets me spun up, but also makes me re-ask that age old question, if I am the Mexican Fisherman or if I want more, more, more!

    1. Funny you mentioned the Obstacle is the Way – I’m a big Ryan Holiday fan! Also love “Ego is the Enemy” if you haven’t given that a read already!

  4. Thank You for this insightful article! Soooooo True!.
    I retired from a long career about 3.5 years ago in order to create more margin in my days, flex in my weeks, work that I love and projects that interest me. Some call it REWIRING. I like to call it ENCORE-PRENEURSHIP = Embracing the time freedom to pursue what matters most in the second half of life.


  5. Everyone has to find their own path. I enjoy the slower pace of life, but I still continue to blog. I enjoy being busy and producive for a few hours every day. You just have to find the right balance for yourself.
    We all change as we age anyway. Travel was a lot of fun in my 20s and 30s, but it’s not as much fun now.

    1. When I ask people what they plan to do in retirement, the #1 answer BY FAR is travel. I always jokingly ask what they plan to do during the other 48 weeks per year?

      To your point, striking a balance is the key! Thanks for reading and commenting!

  6. Are those Hillsdale College shirts?? I graduated from Hillsdale College in 76′. A great institution for learning, leadership and freedom from government.

    1. They are, indeed, Marc! I grew up in Hillsdale, my Dad was a professor there for 38 years (you likely know him, Professor Arlan Gilbert – History). While you were there in the mid-70’s, I was a 9-13 year old kid who spent the majority of my free time buzzing around campus on my bike and/or skateboard. I suspect we’ve seen each other at some point, possibly even in that grand old field house. If I recall, wasn’t “Comstock” the QB in the early 70’s? If so, I remember watching you play! Small world. And yes, a great college, a true shining light in today’s increasingly dark world.

      1. Fritz~I grew up in North Adams, attended Hillsdale College (played QB and captain in 75′) and coached Basketball/Baseball for five years at Hillsdale College after graduation. I absolutely remember your father. I’m currently going into my final year of teaching (elementary PE) in Adrian. Will retire with a pension, my healthcare, planning on taking SS at 66 (65) now, yes Medicare and have a annuity that will provide some monthly income. Hope to continue coaching basketball, part-time teaching and some public speaking. Any advice?? Thanks for responding. It is a small world!!! Blessings!!! Marc

  7. I remember a night tent camping in Palo Duro Park – huge thunderstorm and flash flood. Mrs and kids ended up sleeping in Suburban. We were up higher in park to avoid the floods, – but even the rangers had left and roads were closed. Fantastic experience.

    It was like I was fishing in a coastal village.

    1. I can’t imagine being down in the canyon during huge thunderstorms, those shallow dry riverbeds had signs all over the place warning of flash floods, I can’t image what that place must have looked like when you were there! Beautiful canyon!

  8. A fishing story I have seen on several other blogs and all over the internet and find a quiet spot. Boy I miss Fritz.

    1. Perhaps a well known story, but I think the message Ashby was stressing is the most valuable part of the post. The most frequent advice I give folks when they ask me is to take some time before you retire to disconnect and think about what you really want your retirement to be. An important message we would all be well to heed. Thanks for missing me, tho! As Douglas MacArthur said when he left he Philippines, “I’ll be back”…

  9. NOW I understand how you could take 4 big dogs with you. That caravan/rig is HUGE!!!!
    I was talking with a friend at work today about travel and he said he’d go back to America in a heartbeat, particularly Sth Texas. He said it was amazing.

    1. Huge by Aussie standards, for sure. Pretty common out here in the American West. As big as ours may appear, I’ve often astounded by some of the truly HUGE rigs you see out here! And your friend is correct, America IS an amazing country for extended travel. We’re fortunate, and thankful, to be able to do what we’re doing.

  10. I love this line, “At its core, money is a tool, nothing more.” I completely agree. Additionally, I always enjoy that parable. Great post, Ashby. Great to see your video, Fritz.

  11. Nancy, I also walked away before “maxing” my pension, and have no regrets about the decision. It’s important to know when Enough Is Enough. Thanks for the kind words on the video, I’ve been enjoying teaching myself how to edit video!

  12. The story has been around for quite some time, but I find it ironic that we don’t see that the whole IB community never comes up with an original idea, it’s always some one else’s dream that they piggy back on. Of course that is a form of entrepreneurship that is sometimes required, but most times not necessary. I love the work that I did, and I owned my own company for 36 years and raised 3 lovely girls and sent them all to college and one to medical school and they never had a student loan. (Yes this might be enabling)
    I sold my business 5 years ago and 2 years later I was asked not to show up at the office anymore. That was difficult I am still a consultant (a guy without a job that gets a paycheck) and now on the board, but I am bored bored bored. I volunteer with SCORE and that is rewarding, I am on the finance council at my Church, but I am bored. I am one of the strange ones I would go back to work in a heartbeat. So thank God that we all live in America (the greatest country in the world) and me the son of a mail man can live in the mc mansion, drive my Tesla and do whatever I want whenever I want. I am starting a new business with my SIL and hopefully that keeps me busy.

  13. JJ, I appreciate the honesty of your comment! While I cannot currently relate to that situation yet, I have a feeling I’ll feel similarly as I don’t know what I’d do without work. I love every second of it and can’t imagine filling it with golf/fishing/volunteering 24/7. It’s just different for some reason. Congratulations on your successes and I hope the new business is a cure for the boredom!

  14. Good article. Surely retirement is about having the time to do the things you wanted to do but could never find the time? If work defines you and you gain fulfilment from it, don’t retire. Keep working a few days a week or volunteer etc. Retirement should be about freedom not about being a prisoner with no purpose.

  15. There really is a fulfillment curve and unfortunately, the table shifts and recognizing the shift takes a huge amount of self-awareness. Then there’s the challenge of responding to the shift.
    Whether you are working, at FIRE or recreationally employed, fulfillment continues to remain a process of growth, appreciation and resetting the table.

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