Hey there. I’m Riley—if you’ve made it here, you probably already figured that out. I’m 36 years old (37 is coming fast), and I’m here because I’ve decided to start over. Completely.
You could call it a rebirth, a reinvention, or maybe just a long-overdue escape. Either way, this is my new beginning.
I’ve spent most of my life in a tiny town in Wisconsin—so small, I jokingly call it the Bermuda Triangle of the Midwest. To many, it’s a beautiful place to live. And I get it. There are people who are genuinely happy there, and I respect that. But I’ve always wanted something more. Something bigger. Something that place could never give me.
Door County, Wisconsin, where I grew up, is steeped in history, tradition, and deep-rooted families who love keeping things just the way they’ve always been. Ephraim, one of the towns there, was known for being the last “dry town” in the United States. You couldn’t even get a beer there until recently. People celebrated that fact—still do, actually. It’s the kind of place that got the iPhone ten years late and didn’t get fast, reliable internet until Starlink came around and embarrassed the local providers into modernizing. That’s the pace of change in Door County—glacial, and often met with resistance.
The mindset there? Outdated. Comfortably stuck in the past. Businesses running on point-of-sale systems from the early 2000s, refusing to upgrade because it would mean spending time and energy—something they had plenty of in the off-season, but couldn’t be bothered to use. It was a strange, backwards place to work and live in.
And the people? Predictable. Uninspired. I could probably tell you where almost anyone in town is sitting at this exact moment, what beer they’re drinking, and what they’re complaining about. Spoiler: it’s probably tourists. You know, the very people who make it possible for them to live there in the first place. But that irony seems lost on most of them.
I needed more. More color, more energy, more life. Door County is grey and brown for 75% of the year. Some folks are okay with that. I’m not. I need fire, not ash.
So in 2024, as the world started to move past COVID but still reeled from burnout, I reached my breaking point. I had a well-paying job—part owner of a retail business with five storefronts and a sixth framing shop off the beaten path (which, surprise, was the only one I enjoyed). But the toxic environment, the outdated practices, the coworkers stuck in cycles of negativity and mediocrity—it all just… broke me. My body started rejecting it. I was exhausted, mentally and physically, and not from working hard—just from existing in that space.
Eventually, someone said, “Just leave. You’re a dread to be around.” That was my cue. No argument. No dramatic exit. I just walked away. And I’ve never looked back.
So, what now? What does a 36-year-old, jobless ex-retail guy do?
He creates.
I want to tell stories. I want to travel, feel alive, chase beauty, and experience culture. I want to meet people who inspire me, eat food that surprises me, and capture moments that remind me what it’s like to be here, now, and awake.
And I want to share that with you.
“This Life of Riley” is about that leap. It’s about starting over in the middle of your life—not because you failed, but because you refused to settle. But the name isn’t just about me. The real emphasis is on This Life. Because we each get one. And whether you’re 36 or 66, stuck or just starting to feel the itch—there’s still time to make it something beautiful.
So, here we go. Let’s see what happens when you stop waiting for the “right time” and finally choose to live this life.
