I woke up early one morning last summer to turn in a story. I was camping in a trailer in rural Wisconsin, and I intended to connect my laptop to the internet by using my phone as a hot spot. But my phone had no service. No phone, no hot spot, no way to turn in the story.
“Turn in the story” is the single most important task I have as a freelance journalist. If I can’t turn in stories, my business ceases to exist, which made this a problem I needed to solve, immediately.
As my wife and kids slept, I exited the trailer and paced a rut in the dirt as I thought through solutions. I could drive to a local coffee shop and file from there. For that, I’d have to wait more than an hour for it to open. Until then, I decided I might as well take a walk and hope I found cell service. I was pretty sure I was in one of those very small, unpredictable and massively annoying blank spots in coverage. How small, I soon found out. I walked with my phone in my right hand and my laptop in my left. After 60 steps, the phone found coverage, the hot spot fired up and the internet on my laptop sprang to life.
I froze, worried if I took one more step I’d lose coverage again. I found out later I was right. But for now, I had full connectivity. I sat on the gravel road and crafted an email. I heard the pitter-patter of woodland creatures hustling across the forest floor. Somewhere in the distance, a woodpecker hammered its face into a tree. I grinned at this unique setting, attached the story and hit send.
It sounds funny now, but it was a pain in my gravel-covered butt then—not so much because I had to take 60 steps to file a story, but because the lack of connectivity in the trailer meant my wife and I wouldn’t be able to work.
We had planned an eight-day jaunt to Wisconsin and Michigan as a “bleisure trip”—a way to mix work and fun. I planned to write. She’s a lawyer and planned to spend several hours each day researching and writing in the RV and the rest of the time with me and our kids hiking and kayaking and taste-testing gelato across Door County, Wisconsin.
Our best-laid plans fizzled out on the first morning, and the lack of connectivity turned out to be only the beginning of our “troubles.” In Crossman family lore, this eight-day bleisure trip will go down as The Vacation of Whiplash.
I’ll get to that in a second. First, I need to answer a question you’re surely asking: What in the hell is a bleisure trip?
Bleisure is a made-up word smushing together business and leisure. Now that we’re in the middle of this trend, it seems inevitable: More and more people are realizing working remotely gives them the freedom to work wherever they want, whether it’s their office, a coffee shop at the bottom of a ski slope or a gravel road in Wisconsin.
Think of it like becoming a short-term digital nomad—you adopt a more “YOLO” way of living and working, while retaining the comforts of a home to return to. This is #VanLife for people who don’t want to spend their whole lives on the road… yet.
Bleisure trips have been growing since the pandemic, while business travel has simultaneously decreased. In its 2022 travel outlook, Deloitte said it expects both trends to continue: “They should be treated as new but lasting components of travel’s structural reality.”
I used two apps to make our bleisure trip to Wisconsin easier to arrange. One is called Outdoorsy, through which you can rent someone’s camper, trailer, motor home, etc. (Outdoorsy comped my RV alongside the gravel road in Wisconsin and another at an alpaca farm in Michigan.) The other is Harvest Hosts, a membership-based network of unique campsites such as museums, wineries, farms, etc. I paid a yearly fee and now can camp at more than 4,000 locations for free. That number is nearly quadruple what it was when I first discovered the app in mid-2020 (1,046).
Jennifer Young, co-founder and CMO of Outdoorsy, said reservations slowed to zero at the beginning of the pandemic and exploded as the world reopened. Their reservations grew for many reasons. The emergence of bleisure trips is one of them, as more people recognize RV travel as a way to take advantage of the freedom of remote work while also exploring the outdoors. “What we’re seeing is a more blended approach for how they might relocate for a month at a time or plan their life on the road and figure out how they work in that period of time,” Young says.
I’ve been taking bleisure trips since before the word existed, including to Columbus, Ohio (twice); Branson, Missouri (also twice); Des Moines, Iowa; Colorado; and Michigan (many times). All of those trips went fine, many of them went great.
Our trip to Wisconsin did not.
We kept laughing: Every time we left the trailer to explore Door County, we had a blast—kayaking in Lake Michigan, skipping rocks in it, hiking alongside it, visiting a lighthouse on its banks—and every time we returned to the trailer, something went wrong.
In addition to the internet problems, water backed up into the shower (my fault; it’s easy to drain, but I didn’t check the level). I shattered the glass cover on a stove (my fault again; I didn’t know I was supposed to lift the cover before I turned on the stove, and the glass exploded because of the heat). And a dog pissed on my backpack.
Right in front of me!
He just lifted his leg and let loose!
I’m just relieved I wasn’t wearing it at the time.
One morning, I exited the trailer to go for a “problem-solving” run along an isolated road lined by green fields. I planned to spend that time thinking through what to tell you about The Vacation of Whiplash. How would I write about the challenges of bleisure trips without understating them and making it seem easy—or overstating them and talking you out of trying it? As I worked to solve that problem, a greater truth about bleisure trips revealed itself.
My feet pounded the soft grass as I noodled on a paragraph that started like this: You’ll have the same problems as you would during a regular workday or a regular vacation, and it’s how you overcome them that determines how…
A fluff of brown movement grabbed my attention. I stopped running, looked to my right and watched four deer play their version of leapfrog. I’ve seen thousands of deer, but I’ve never seen them do that. By the time they scampered into the forest, I had forgotten about the internet, the shower, the dog.
Anyway, what was I talking about before I got distracted? Oh, yeah: Problems are inevitable on bleisure trips. Your phone won’t work, the museum will be closed, traffic jams will make you miss your reservations.
But magic and inspiration will arise when you least expect them, too. Young made a stirring case for toggling between a recreational adventure life and work life, and that the former will make the latter better, even if—especially if—a dog pisses on your backpack.
“You’re really leveling up your life, because you’re realizing the benefits that Mother Nature affords you that there’s no way any office—whether it’s your home office or work office—could ever provide,” Young says. “Your productivity is better, your anxiety is low, you’re inspired by life. You’re grateful for the opportunity to be able to flex a little bit in and out of it. Not to mention the cumulative benefits of just being more active.”
My family treasures these Whiplash memories; even as they were annoying us, we knew they made the trip special in a way it wouldn’t be without them.
If given a choice, I’d rather file a story sitting on my butt on a gravel road then sitting at my desk in my home office. Having said that, if a dog never pissed on my backpack again, I’d be good with it.
This article originally appeared in the January/February 2023 Issue of SUCCESS magazine.
