Living Richly: Music, Travel, Discomfort, and Growth in Tuscany

Introduction

Greetings and Salutations! Welcome to the third installment in the psychological richness series. In Part 1, I introduced Shigehiro Oishi’s concept of a psychologically rich life—one filled with interesting, perspective-changing experiences. In Part 2, I put on my skeptic hat and reengaged the theory: praised what works, critiqued what doesn’t, and pointed out the political and philosophical baggage riding along in the sidecar.

Quick refresher:

• Hedonia = pleasure, comfort, enjoyment.
• Eudaemonia = meaning, purpose, coherence.
• Psychological richness = variety and novelty that change how you see things when you reflect on them.

If you are just joining us: I’m not endorsing one of these over the others – or even 2 of the trio. All three matter. None of them, alone, is enough.

Recently, I had a chance to put all of this into practice, whether I meant to or not. My wife and I spent a week in Italy: part vacation, part blues guitar workshop, part pilgrimage to my family’s roots, and part “let’s see what happens if I actually do the things I coach people to do.”

Only after I got home did I realize: this trip was a case study in psychological richness.

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Old Strings, New Story

I’ve played instruments since third grade—violin first, then guitar as a teenager. I spent most of my musical life as the classic lead-guitar side man. Rhythm was for suckers, and singing wasn’t even on the table. My best friend once told me, “You’re so far off key you harmonize.” People later upgraded that to, “You should only sing in church; God will forgive it.”

So for decades I happily hid behind the amp.

After I retired from the Army, I decided to reclaim music as part of my life instead of leaving it filed under “past self.” I’m hardly unique as a middle aged reborn wanna be rock star. The struggle is real when it comes to G.A.S. (Gear Acquisition Syndrome).  My daughter smirks at asks “So…how many guitars is it now?”, and the windowsill of my office turned studio is a pedal storage.  I also accumulated books, online courses and went on some guitar destination trips, meeting some amazing musicians that I enlisted as guides on my transformational journey. Some of them at my annual blues camp trip with my daughter have been consistently encouraging me and inspiring me to push the edge of my comfort zone (Thanks Jontavious!).  

One of the two gents that are formal teachers, Doug, lovingly dragged me into musicianship, not just guitar-playing. He had me sing scales, arpeggios, and melodies as I played them. He called what I did “humbling”—a combination of humming and mumbling that was startlingly on pitch but not yet public. It was funny. It was accurate. And it was the first crack in the “I don’t sing” story.

Then I met Seth, a blues guitarist and teacher I connected with at a workshop in Tennessee. During one of his sessions he explained a way of seeing the pentatonic scale that connected dots first put on the paper 35 years ago. Later, when we jammed, I suggested we play “Highway to Hell.” He smiled and told me he’d actually started guitar after seeing School of Rock as a kid and hearing that song. It was the first time he’d ever played it live. Instant inside joke.

Fast-forward a bit. I start studying blues with him online. I tell him my goal is simple: get competent enough to improvise at real-life speed. Seth, being a professional nudge, casually suggests that actually playing at a blues jam might be the best way to know if I’ve gotten there.

Then he announces he’ll be teaching at a workshop in Tuscany and offers his students first crack at the spots.

Tuscany. In truffle season. With a built-in excuse to play guitar loudly and call it “study.” Sold.

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Rome: History, Hedonia, and Humility

We flew into Rome a few days early to do exactly what you’d expect: hit the Colosseum, the Forum, the Trevi Fountain, the Spanish Steps, and Via del Corso to do some damage to my wallet in the name of Italian leather.

Rome is one of those places that makes your grasp on world history feel embarrassingly underpowered. Every way you turn, you are standing at the literal crossroads of Western civilization; suddenly it makes perfect sense that our democracy is modeled on Greece and Rome, our currency has Latin and pyramids on it, and monuments to our founders look like they were commissioned by Augustus.

Rome is a constant reminder that some ideas persist for thousands of years because they’re durable and true…and some persist because we’re stubborn and afraid of change. That tension—what to conserve, what to reform, what to abandon—was buzzing in the back of my mind the whole trip. (Put a pin in this, we’re going to explore psychological richness as a means to political/cultural bridge building in our last installment.)

In the meantime, there was language, food, and the kind of everyday novelty that richness thrives on.

My wife and I learned just enough Italian to be dangerous. Between my five years of Spanish, a career in medicine (Latin everywhere), and osmosis from growing up in an Italian family, I could fake my way through simple conversations—right up until all four languages collided and I started speaking gibberish.

At one store I almost asked, in Spanish, if all the faldas were the same size instead of using the Italian gonne. The shopkeeper was gracious, and managed to understand my pidgin Italian. A small but real bit of humility: accepting that you might sound ridiculous but going ahead and trying anyway.

We ate outside at a restaurant where taxis passed a foot from my elbow while the servers didn’t blink. Everything came with truffles, except dessert—a lemon and sage panna cotta so good I briefly considered ordering a second.

On the way back through Rome after the workshop, we visited the Vatican Museums and the Sistine Chapel. That was a bit more profound a moment of humility.  Staring up mesmerized, you feel simultaneously insignificant and safe—tiny, yet somehow seen. It’s eudaemonia turned up to eleven.

Reviewing “The Good Life” travel checklist:

• Hedonia: phenomenal food, shopping, boots, leather, glass, coffee.
• Eudaemonia: family roots, Rome, the Vatican, centuries of philosophy and faith.

But the most transformative layer—the richest part—came in Tuscany.

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Tuscany: Psychological Richness in 12 Bars

The workshop was held at an agriturismo in the hills outside Montepulciano. Our hosts, Pierpaolo and Marianna (one plays drum, the other sings karaoke…coincidence, I think not), grow olives and hops and run a small brewery with a stage and PA in the taproom. Nine of us, plus a professional rhythm section from the local conservatory, spent the week learning nine blues standards and rotating trios so everyone had to stretch.

Here’s where things got interesting.

When Seth sent the advanced song list, a few of the tunes sat in a vocal range that suspiciously matched mine. He mentioned his goal for the workshop was not to sing everything himself. When I told him I wanted to focus on the one instrumental on the list, he casually suggested I also learn the melody and lyrics for two of the vocal tunes.

Did I mention my teacher’s superpower is “The Nudge”?

By the end of the week, I’d sung on half the songs—four out of eight—in rehearsals. For the final show, Seth assigned me two Albert King tunes to sing and play, plus lead guitar on “Crossroads.” I was officially out of hiding.

We found out partway through the week that this wouldn’t just be a “friends in a room” recital. Pierpaolo invited family and locals to the taproom for a semi-public show. We had a real audience, a drum kit miked up, and a setlist that had only existed in our hands for a few days.

We pulled it off. Was it flawless? No. Was it good? Yes. Was it rich? Absolutely.

At one point during the show, I completely forgot to give the cue to end a song. The band kept playing. I realized my mistake, took a solo, and then gave the wrap-up signal on the next pass. Afterwards, Seth told me nobody noticed it had been an error because I just rolled with it instead of panicking.

That’s psychological richness in miniature: Novelty → mistake → improvisation → recovery → story → growth.

And it didn’t stop there. After our set, the taproom turned into an open mic. A couple of my workshop compatriots played acoustic numbers. Then Seth turned to the organizer, Richard (who prides himself on having a Robert Plant adjacent voice), and to Pierpaolo and said, “you guys should do ‘Highway to Hell.’” When they asked who was going to play guitar….

Seth looked at me.

We had never rehearsed it together. Different singer, different band, same shared inside joke from Tennessee. We counted it in and went. It wasn’t perfect, but it was loud, fun, and honest. For the kid who’d been told to never sing outside church, fronting an AC/DC tune in a Tuscan brewery definitely qualifies as “perspective shift”.

After the show, Seth said something that stuck: he was surprised—in a good way—by how naturally I’d taken on the “front man” role. Calling tunes, assigning solos, managing endings, staying present with the crowd and the band. Our lessons have shifted since then. We still work on theory and technique, but now we’re building repertoire with the assumption that I’ll be singing, not just hiding behind the guitar.

Psychological richness didn’t just make for good stories. It altered my sense of who I am as a musician.

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A Different Kind of Richness: My Wife’s Week

While I was spending my days up to my eyeballs in 12-bar blues and imposter syndrome, my wife was having her own psychologically rich week—one that looked very different and was no less real.

She’s an introvert. Her idea of a perfect evening is an empty house, a bubble bath, a glass of wine, and a novel. She enjoys music but has zero desire to make it. Her artistic side comes out in visual art and nature -sketching, photography and as chief designer of our gardens and landscape.

Before the trip, I bought her a small travel watercolor kit as a surprise. When we arrived, she struck up a conversation with our host about hiking. For someone who recharges alone, initiating that conversation was a definite comfort zone border incursion.

It paid off. He pointed her to a European hiking app, handed her the back-gate key to the property, and shared his collection of the best local trails. While I was in the rehearsal room, she was out in the Tuscan hills—hiking, painting, taking in the autumn light, doing exactly what fills her tank.

She also connected with Richard’s wife, Barbara. They explored the nearby town together, did some shopping, and found my new clocka (or two). She bought herself a pair of boots our daughter later dubbed “Italian Cowgirl Chic.” She wore them to the showcase and was told more than once that she and the boots stole the show.

It was a joy to watch her work the room at the taproom—quietly but confidently talking with Pierpaolo’s family and the staff who’d been harvesting olives all week. Not bad for a “recluse-level introvert.”

Her version of richness involved fewer guitar solos and more elevation gain, but the ingredients were the same:
curiosity, small risks, new experiences, reflection afterward, and a slightly expanded sense of self.

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So What?

It’s nice that we had a great trip. It’s nice that I played some blues and my wife painted some hills. But why should you care?

Because psychological richness is one of the most practical ways to get to both pleasure and meaning—especially when you feel stuck.

You often don’t know whether something will be meaningful or enjoyable until you do it. Richness is the willingness to experiment. Try the thing. Go to the place. Have the conversation. Learn the song. Hike the hill. Speak the mangled Italian. Then—and this is the critical piece—reflect on it.

Richness without reflection is just noise and novelty.
Reflection is what turns “that was wild” into “I’m different now.”

This post is, in many ways, a formal act of reflection. My sense of myself as a musician has shifted. Our sense of what we want from retirement has shifted—we now know that travel isn’t solely luxury; it’s part of how we want to live. My understanding of how pleasure, meaning, and richness braid together is deeper.

It’s also hard to keep them neatly separated once you start looking. Was that moment in the Sistine Chapel hedonic (awe), eudaemonic (connection to something larger), or richly perspective-changing? Yes. Were the leather boots pleasure, meaning (my wife and daughter bonding thru humor), or just variety? Yes again.

Plato said the unexamined life wasn’t worth living. Oishi’s model, at its best, gives us another angle on that:
A life rich in experience, processed with humility and curiosity, is one of the most reliable ways to build a life that is not just happy and purposeful, but interesting—to yourself and to the people you care about.

You don’t need Tuscany, a taproom, or a blues workshop to do that. You just need:

• a little humility (“I don’t know it all”),
• a little curiosity (“I wonder what would happen if…”)
• enough reflection to let the new experiences change you.

The rest is just practice.

If you’re curious what psychological richness might look like in your own life, might I suggest: Start small. Pay attention to the experiences that have already nudged you, unsettled you, or surprised you—and take a few minutes to reflect on what they changed. Psychological richness doesn’t require chasing novelty for its own sake; it often begins by noticing where curiosity has gone quiet, where humility might open a door you’ve been walking past, and where a small shift in perspective could deepen a life that’s already underway.