Although I now have four tattoos, calling myself a “tattoo guy” would be an insult to legitimately inked-up gentlemen everywhere. I’m still a white-collar nancy boy who hails from the suburban-est of roots. Also, I don’t really like heavy metal or rockabilly. But to the dismay, perhaps, of many authentically etched souls, I’m evidently morphing into a body art wannabe.

I got my first one, a question mark on my shoulder (pictured above), four years ago, at 41. The reason I did it—other than the midlife crisis—was…

Okay, the midlife crisis was pretty much it. I wanted to shake things up a bit with a symbol of who I am. (I ask questions for a living, I’m always searching for answers, and so on.) Yes, it hurt—the pain is similar to getting scratched repeatedly by a cat—but needles don’t really bother me.

Some people told me tattooing is addictive, but I wasn’t planning to get into it. What surprised me was how quickly I started thinking about getting another one. My process was to test an idea for a while to see if it stuck, and if it did, go for it. Using that guiding principle, over the next few years, I added two more to my other arm (both of them short, inspirational phrases). I’m a word guy.

My latest (pictured, above), started with a theft. My friend Jennie Dorris, a writer and musician, had mentioned getting the Denver skyline tattooed on her arm as an ode when she and her husband—former 5280 editor Patrick Doyle—moved to Boston. I’m from Chicago, and I’ve lived in San Francisco, New York, and now Denver, so I started contemplating ways to fuse those four iconic skylines into a single drawing. (This is the first she is hearing of this, so I hope she’ll be flattered that I’m honoring the old saying that good editors borrow and great editors steal.)

I ran the plan by my father, a Chicago-area artist, who noodled around with it, came up with the globe concept, and helped me choose the structures from each city to include: the Golden Gate Bridge in San Francisco, Denver’s Cash Register building and Speer Boulevard bridge, the John Hancock building in Chicago, and NYC’s Chrysler and Empire State buildings.

I was still searching for a way to put them together into a single design when I happened upon the work of local artist Talia Swartz at the C.C. Opiela Gallery on Santa Fe Drive. Swartz’s cityscapes have an exuberant, almost childlike quality that seemed like a perfect match for my skyline mashup idea, so I asked her to design it for me. (Swartz may want to consider a side gig as a psychic, because after a quick meeting, she returned about a week later with exactly what I’d been picturing.)

Now, it was time to find the tattoo artist who could execute it. (Actually, now was the time to get together the money that would enable me to execute it; between design fees, tips, and the inking itself, this cost me just under $500.) As a tatted-up friend once warned, the wrong artist can screw up a dot, so I returned to Sol Tribe on Broadway, where I’d gotten two previous tats. Here, I found the portfolio of artist and recent Denver transplant Missy Rhysing.

Rhysing was down, and the rest is history. Her finished product mimicked Swartz’s design just as I’d hoped, and it landed on my arm precisely as I’d envisioned. They say it takes a village, and in the case of my tattoo, it took a bunch of them.

The question for me is, what’s next? Because it turns out I may be addicted after all. I plan to add some stars around the question mark to unify everything a bit more. And I’m contemplating finding a spot somewhere else for my favorite Simpsons character. My girlfriend isn’t so excited about that one, but as I’ve reminded her, it’s my body, and pro-choice means pro-choice. Although I may still be the weeniest tattoo guy around, I hope I’m at least inking my way toward something resembling cool.

Thinking about getting your own tat? Check out Tattoo-Pedia, from the editors of Denver-based, and comb through designs for everything from angels to zodiac symbols.

—Image courtesy of Jeff Panis.