Three People Working Outside the Box: Part 1
What do a liquor distributor, a pizza store manager, and a tour guide in colonial garb have in common? Interesting jobs and good attitudes to start, but that is certainly not all...
So, a liquor distributor, a Dominos manager and a tour guide walk into a bar…
It reads like the start of a joke, but no. These are the unique professions of three people I had the good fortune to “talk shop” with in my 2024 travels. They didn’t actually walk into a bar, but I bet the three of them could have some fabulous conversation if placed at the same social table.
Even in Biblical times, people asked the annoying question most people don’t love answering: “So, what do you do?” Okay, so it was phrased a little differently, like in the story of Jonah when the mariners in the storm-tossed ship asked Jonah, “What is thine occupation?”1
In my approaching-mid-life rewrite, that question has become one of the least interesting questions to ask or answer. Why? Well, I suppose because it’s so often asked to determine a person’s social or economic status, and this tells us exactly not much about a person’s zest for life, character development or contributions.
That said, the subject of work remains very interesting for me to talk about—it’s a big part of what we’re here to do, and a critical way we stay engaged in this whole living thing. More than ever, I know that the goal of life is not to do nothing.
More than ever, I know that the goal of life is not to do nothing.
Having spent most of my 30s working in technology doing knowledge work, I find myself endlessly interested in people who do things outside the that realm. With no further ado and without much commentary, please enjoy meeting three people working outside “the box.”
There will be a Part 2 to this article, featuring more interesting people with interesting jobs; subscribe to receive it and other More to Your Life posts in your inbox.
The liquor distributor
“Willie” was the parking attendant who gave me a couple hours of free parking near a Wilmington, North Carolina, beach. His name is not Willie, but in order to protect his identity and generosity, let’s just call him that.
Here’s why we need to protect his identity: Like a real live O.Henry story, a colleague of Willie gave me a $75 ticket; this after Willie generously authorized me to not pay for parking. At the end of our lengthy conversation, I was scanning the parking sign to pay when he said, “Don’t worry about it. You’re good for the rest of the day.”
I responded to his generosity with delight and appreciation. I responded to the ticket on my windshield with much less delight, but I did still laugh out loud. The humor of the situation was too good to not appreciate. And never fear, I managed to—in the friendliest fashion possible—track down Willie and his golf cart days later to have the ticket waived. Thanks, Willie!
Our original conversation started with affable hellos, a question about the beach parking situation, and my genuine interest in whether he enjoys his work as a parking enforcement officer. He loves it. We talked about his son moving west to do more snowboarding, my writing and travels, Wilmington in general, and even politics.


Willie is happily retired and happily married, but his wife made it clear that, in order to remain happily married, he needed to get a part-time job. Hence, the parking enforcement gig. They’d moved in the past couple years to Wilmington from New York City to spend retirement in better weather, and a more laid-back beach town.
For most of his working life, Willy worked for decades as a liquor distributor. His customer list was comprised of upscale restaurants throughout the city, and the staff and owners at these restaurants had become his friends. He’s Irish, I believe, as I recall him sharing this fact when he joked that he was only too happy to sample his wares along with his clients as they made their spirits selections. According to him, he never really worked a day in his life.
He enjoyed not being tied down to an office and loved working with people—it was all about relationships. In his current work as a parking enforcement officer, he similarly loves that he’s not tied to an office and gets to be out-and-about in a place he loves. It reminds me of a CPA I read about on Reddit who quit 70+ hour-per-week job, got his CDL, and delivers fuel around town. He absolutely loves it.
The Dominos Pizza manager
Newly arrived in Colorado Springs and hoteling it for two more nights until my furnished apartment opened up, I had a hankering for Dominos pizza. On the menu: stuffed cheesy bread. I recommend you not knock until you try it.
While paying, I asked the guy at the register, “So, how’s your day been?” and was surprised by his peppy answer. “It’s a great day after the craziness of yesterday (Memorial Day). I’ve had caffeine, I slept more than 5 hours last night, so it’s a good day!”
I laughed, but my curiosity was piqued: “Are you busy doing good things or just don’t sleep much?” He could’ve also laughed it off, but didn’t. “I’m in school full-time, and I work here 45 hours a week,” was his frank and proud answer.
If my memory serves, our friend Josh is pursuing a masters degree in social work. Managing a pizza place doesn’t directly correlate, but it’s obviously working for him. He seemed to genuinely enjoy what he does. He wasn’t just friendly with me. He grinned broadly at the customers after me and, as I waited for my order, I appreciated just how dang cheerfully he helped his coworkers. Josh was like the born-again Ebenezer Scrooge in A Christmas Carol, but I doubt his goodwill attitude was preceded by a miserly chapter.
The tour guide
I’m thrilled to finally introduce you to my friend Stacy, a passionate tour guide at Colonial Williamsburg. A self-proclaimed “historical nerd,” this woman literally hopped with enthusiasm at one point in our conversation. I was a cheapskate who hadn’t bought the fancy pass granting interior access to all the buildings, and was thus not allowed to go in. This, in retrospect, proved to be an accidental good decision—had I been there for an interior tour, I wouldn’t have been able to talk at such length with this marvel of a person.


Our exchange began innocently enough when I asked her, “I bet you know what that coat of arms means.” Did she ever—she knew all about it and so much more. But not in a show-off sort of way. She was rather an explorer excited to share her discoveries with another explorer. She was almost more ecstatic when she didn’t know the answer to one of my questions, and told me how excited she was to dig into it with one of her colleagues later that night.
When someone is this passionate about their work, you’ve simply got to know more. Stacy was happy to be asked and to share. This bundle of enthusiasm for American and British history has known since girlhood—age 7 to be exact—that she wanted to be a tour guide at Colonial Williamsburg. She decided at the same time she wanted to attend William and Mary College as part of that pursuit.
And that’s exactly what she’s done. She received a full-ride scholarship to William and Mary College, and spent an hour every day in Colonial Williamsburg on her own. She exuded enthusiasm and vigor as she shared the rule she’d made for herself: “If I hadn’t talked to a new person or learned something new I couldn’t leave!” She wanted to be part of the Colonial Williamsburg mission—“That the Future May Learn from the Past”—and that is exactly what she is doing. With gusto.
As people, Willie, Josh and Stacy don’t seem to have much in common. But in their out-of-the-box work we see some common threads. There seems to be little connection between their title and their feeling of self-worth. They like to be busy and they like their lives. They don’t swim upstream, so to speak, but work with their passions or talents—talking with people, being out-and-about, being able to learn endlessly. Providing for themselves in a way that was satisfying to them seemed to be a much higher priority than making gobs of money.
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/If you liked this, you may also enjoy this related post, about a cobbler in Raleigh: https://www.moretoyour.life/p/be-your-own-person