Life on the Road as a Freelancer
I’ve been doing the freelance travel-life thing for almost six years now, mostly bouncing around between coasts, mountain towns, and the occasional city when I get tired of being surrounded by pine trees. People always say it must be “the dream,” and sure, it has its moments — the midweek powder days, off-season Airbnb rates, working from cafés that don’t have a Starbucks sign on the front. But when you’re constantly on the move, the smallest things can derail everything.
Transportation is one of those things.
No one ever talks about it, but it’s probably the number one reason I’ve shown up late to shoots, missed meetings, and once had to hike a mile in the snow because my rideshare driver bailed halfway through. So now, anytime I’m traveling to a place I’ve never been — or haven’t been in a while — I dig into how people actually get around. Not the glossy, official travel guides. I want the Reddit threads, the locals-only blog posts, the buried recommendations in random Instagram captions.
Heading to Aspen for a Campaign Shoot
That’s exactly how I ended up in Aspen last February. I was hired to shoot a three-day campaign for a boutique outdoor brand. They were launching a new winter line — all rugged textures and muted colors, real “mountain-core” stuff. They wanted the backdrop to feel authentic, but not too commercial. Aspen was their pick, not mine, and to be honest, I hadn’t been there in years. Not since I was a kid on a ski trip with borrowed gear and frozen fingers.
I didn’t want to mess this one up. The client was a repeat, and the rate was solid. I had gear to carry, locations to scout, and a pretty tight timeline. So I flew into Eagle and started lining up everything I’d need on the ground — a cozy little cabin just outside of town, two portrait sessions planned around golden hour, and all the permits locked in. I had one job left: figure out how to get from the airport to town and back without turning it into a circus.
Why I Skipped the Rental Car
Normally, I’d just rent a car and call it good. But the forecast had snow coming in for two out of the three days, and I didn’t want to risk trying to drive rental wheels with all my gear in the back while half-watching Waze for black ice warnings. I needed someone who could get me there, let me work, and not become part of the stress. So I spent the better part of a night reading forums, asking a few folks on Instagram, and eventually found a small transportation company that felt like the right fit.
I booked this car service in Aspen mostly because someone in a photography group I follow mentioned using them for a winter elopement. Their post was simple — “These guys were lifesavers. Roads were garbage. They still got us there.” That was enough for me.
A Ride That Made All the Difference
They picked me up right on time, even though my flight landed early and the weather was already starting to turn. The SUV was warm, clean, and thankfully massive. I had three cases with me — lights, cameras, boots — and it all fit without any creative stacking. The driver gave me the rundown on the weather, made a quick stop so I could grab snacks (because I always forget to eat on travel days), and didn’t make me feel rushed at all.
There was this steady, calm vibe the whole ride into town. The snow was falling in that quiet way it does in the mountains — heavy but soft. It would’ve been a nightmare to drive through on my own. But in the back seat, I just stared out the window, going over my shoot notes, and felt this rare thing: relief. Like, the kind of relief you don’t even notice until you realize your body isn’t clenched anymore. It hit me that I wasn’t behind, I wasn’t stressed, and for once I had built in a bit of breathing room.
A Smooth and Successful Shoot
The shoot itself went great. We got lucky with lighting, the snow was perfect, and the clients were beyond happy. One of the models actually said it was the smoothest shoot she’d ever done in a mountain town, and I think a big part of that was how seamless everything around the shoot went. We weren’t dealing with parking issues or late arrivals or trying to dig a car out of a drift. We just… moved. From location to location, on time, warm, dry. It was one of those rare work trips where everything clicked.
Returning Home with Peace of Mind
On the way back to the airport, I used the same service. Same experience — reliable, relaxed, no drama. The driver even remembered what snacks I liked. We talked a little about the tourism shifts in Aspen post-COVID, how the summers were getting just as crowded as the winters now, and how more people were flying into smaller airports to avoid the Denver mess. It didn’t feel like small talk. It felt like I was catching up with a local, which in some weird way made me feel like less of a tourist.
Why Transportation Can Make or Break a Trip
Since that trip, I’ve been thinking more about what makes a work trip go well versus just “not fall apart.” Everyone talks about planning and prep and communication, and sure, those matter. But I think transportation — the in-between, the transitions — that’s where the trip either flows or doesn’t. That’s where you’re either saving energy or bleeding it out one delay, one wrong turn at a time.
So now, Aspen’s in my rotation. It wasn’t before. But it is now. Not because it’s trendy or because the photos did numbers on social, but because the whole thing just felt doable. I had room to work, to focus, to breathe. That doesn’t happen by accident. It happens because you set things up right — and for me, that started with finding real, local Aspen private transport that actually understood what I needed.
Final Takeaway: Quiet That Fuels Creativity
Next time I go back — and I will — I won’t even think about driving myself. I’ll just book the ride, load up my gear, and enjoy the quiet on the way in. That quiet? That’s where the real creative work starts.
Lynn Martelli is an editor at Readability. She received her MFA in Creative Writing from Antioch University and has worked as an editor for over 10 years. Lynn has edited a wide variety of books, including fiction, non-fiction, memoirs, and more. In her free time, Lynn enjoys reading, writing, and spending time with her family and friends.
