Openings & Closings

A trip to the car dealership, a storytelling retreat, and other exits and entrances

Stories Riding Shotgun

I hadn’t bought a car since 2015 when I picked up my sensible Subaru Impreza with all-wheel drive on a frigid January day in Columbus, Ohio. My first mistake? Not springing for the remote starter. Then, my logic was consistent with my personal brand: Why pay an extra $500 for a fancy key just to start the car from a distance? The answer — obvious to every Ohioan that winter except me — because in the Midwest, you set the heater to full blast before turning off the engine, so when you remote-start it on an icy morning, the car defrosts before you get in.

A decade later, on a sunny fall day in Oakland, CA, the Impreza met its demise. Its driver took a left turn. An oncoming truck had a different vision. No one was hurt. The insurance company declared it totaled. I thanked it for its service.

Car shopping ensued. And I wished my dad was around to help me navigate the rapidly changing world of automobiles. He loved cars — thinking about them, test-driving them, negotiating the price, and engaging in all the theatrics that came with it (“Let me go to the back and talk to my manager, Mr. Smith”). Then Lou Smith would bring the car home, park it in our driveway, and spend hours reading every word of the owner’s manual of his new toy.

I enjoy the car-buying process about 10% as much as my dad did. And I missed him 100% when, for the first time in my life, he wasn’t riding shotgun.

But life is a circle, not a line. And this time, I had a new co-pilot: my 13-year-old son, who shares many traits with his late grandfather — including a love of cars. He made me a list of models that fit my criteria, joined me for most of the test drives, and, like my dad, grew impatient and irritable when we had to wait too long for a salesperson. Once we got their attention, he peppered them with questions — just like his Pop Pop would have.

My kid wasn’t with me the day I visited a sprawling dealership in Fremont, CA to check out a few cars. Unlike many of the slick young sales bros hustling to get me behind the wheel I’d encountered at other spots, this place seemed to be run by old-timers in no rush to wheel and deal.

“Jimmy will be with you in a few minutes,” the manager said.

Twenty minutes later, Jimmy finally strolled out of the break room, a newspaper tucked under his arm. He was a big man with a slow gait and a cool hat. It took him a while to find a car for us to test drive, but once we got going, I liked how it handled and all its modern amenities — a heated steering wheel, beeping sounds before you hit something, car manual accessed by QR code — we live in an age of wonders! But the best part of the ride was Jimmy, a natural conversationalist, comfortable in his skin, and in no hurry at all.

“Let’s head back and see the best price we can get you,” he said.

And then the game began. As the manager “worked out the numbers,” Jimmy waved me over to the chair by his desk.

I joked that if my boy was here, he’d haggle with Jimmy’s boss and asked Jimmy if he had any kids. He told me about his own son. His boy, now in his thirties, was a public high school principal. (“Can you ask him if he knows about Six-Word Memoirs?” I might have said.) He got his commitment to education from his mother — the first of Jimmy’s four wives — who taught special ed in the Bay Area school system for decades.

And Jimmy? He was a lifelong musician who played the sax. As he scrolled through his photos, his face lit up, revealing snapshots of his younger self playing alongside jazz legends like Chick Corea and Art Blakey. I told him about my dad’s love of jazz — how he took me to see Miles Davis and Sonny Rollins at Philly clubs when I was in high school.

Eventually, a manager emerged, waving printouts filled with numbers, financing options, and other bits and bytes of information. I received it like the wah, wah, wah sound of adults in Peanuts cartoons. The moment I said, “I’ll think about it,” he grimaced and walked back to his office, knowing he’d never see me again.

“Jimmy,” I said, “I’m not buying a car today, but I’m really glad I came in because I loved hearing your stories.” He stood up, extended his large hand and an even larger smile, and said, “The stories are part of the sale, my friend. It was a pleasure to meet you.”

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Crafting Your Story at Midlife: My Workshop in Santa Fe

This Way In: I’m here with my co-facilitator, Mary Hofstedt, at the 7 Directions art installation at Rising Circle Ranch, home of MEA’s stunning and inviting retreat center in Santa Fe

Modern Elder Academy (MEA), the brainchild of “zeitgeist surfer” Chip Conley, is the world’s first science-backed midlife wisdom school dedicated to sharing wisdom and navigating life transitions together. I’m thrilled to be leading a five-day workshop called Tell Me More: Crafting Your Story at Midlife at MEA’s breathtaking retreat center in Santa Fe, July 7–12, 2025. You are invited to join me in a deep-dive exploration of your life’s stories, gain tools that will increase your capacity for self-expression, and empower you to envision the stories to come. As a student of MEA myself, I can tell you that you will learn as much from your fellow students as you will from your instructors, find the space to do so in an absolutely gorgeous setting, and enjoy one delicious meal after another.

I have a few 20% discount codes to readers of this newsletter and MEA offers a range of scholarships. Send me a note if you want to hear more.

Men Can Talk About the Hard Things

Eleanor Tweddell, the creator and host of Another Door podcast chose the above words as the teaser for our conversation. Originally designed to guide individuals through career transitions, the podcast has since expanded to explore the many exits and entrances we navigate in life. I was honored when Eleanor — who I met through my cherished professional peer community, Sidebar — invited me onto her show. Here’s the thing: men often struggle talking about the hard things. I’ve learned that when I answer the casual “How’s it going?” with genuine honesty instead of the automatic “Good,” I open the door to meaningful conversations — both with men I’ve known for years and those I’ve just met (as well as with everyone else).

In this episode, Eleanor and I delve into some of my pivotal life moments —relocation, divorce, career shifts, blending a family — and the importance of embracing change while, always, trusting the process.