Note: this map isn’t 100% accurate to my drive, but it covers the general route. I spent a lot of time driving off the Interstates but used Map Quest (classic!) to make this graphic and I really can’t be bothered to retrace every step. This map skips the little bit of Missouri we drove through to cross the Mississippi on our way back to Texas, which was the 14th state we traversed.

If you can work remote and like adventure, consider trying a work-on-the-road trip. I learned how to do it during the summer of 2021 while taking minimal days off.

As a marketer, it let me better understand consumer circumstances across the US. When you can talk to people face-to-face, you can learn a lot more about them.

Work-on-the-road is definitely a practice I will continue to do going forward, but it’s not always easy. Consider this as one-part guide, one-part story.

BASIC PRINCIPLES FOR WORKING ON THE ROAD

Split the trip up into multiple extended stays to cover more ground.
Take your time and avoid Interstates when possible for nicer scenic driving and low-stress road traffic.
Use weekends to do long-haul drives (or take time off for those if necessary), then stay somewhere during the whole workweek to get stuff done.
Stay with friends or family when possible to minimize lodging costs.
Utilize an unlimited data hot spot so you can connect on your computer anywhere with a signal.

BACKGROUND & INSPIRATION FOR MY SUMMER ON THE ROAD

I started working remote in January 2020. I had been living in China for the past 12 years and was home for the holidays for Chinese New Year in Austin, Texas. This was right around when COVID policies were rolled out in China. I decided not to go back, but I kept working.

Now that I’m living in Austin, I still manage to work as if I was in still in Asia. I’ve been working specifically in global brand advertising since 2015, helping Asia-based brands communicate to people all around the world. The US happens to be a key market for many global brands, so it actually works out quite well that I’m in Texas.

My work days are typically split in two segments. When it’s morning in China and Japan, I’m on the phone with people over there. That makes Sunday night my Monday morning. I’m usually on the phone for 3-5 hours, halting any further meetings past midnight, US Central Time. The following afternoon is when I get my busy work done, while Asia sleeps.

This unique work lifestyle suits me. I feel like I can be anywhere so long as I have an internet connection. I don’t like waking up early anyway. I also love driving.

So I made a plan for the summer of 2021. I was determined to do a summer on the road without the need for taking much time off from work.

I’m a sucker for road movies. I’m a sucker for Americana. Much of the inspiration is simply that. I love the feeling of being on the road and I love my country.

This trip wasn’t just for Cruis'n USA. I have a lot of family scattered across the United States. My mother’s family in West Virginia. My father’s family in Vermont. My parents in Maryland. I have siblings and extended family, from the northeast all the way to Texas. My parents made sure to take me to see extended family across the US when I was growing up and I want to do the same for my son.

This set the framework for Summer on the Road, 2021. My son and I hit the road in late-June from Austin, Texas. My wife doesn’t have the same flexibility with her work, so she was not able to join for most of the trip, unfortunately. But this made for some quality father-son time for the following weeks until early-August, when we returned to Austin.

THE TRIP BEGINS

Our first extended stay was planned for West Virginia, where we were planning a bit of a family reunion. Central Texas to West Virginia is no short trip, so we split the drive into 3 legs.

Day 1: Austin, TX to Hot Springs, Arkansas

Day 2: Hot Springs, AR to Lebanon, Tennessee

Day 3: Lebanon, TN to Summers County, West Virginia

Some might scoff at me for taking three whole days to get from Texas to West Virginia, but I don’t personally enjoy spending more than 7 hours in the car at a time. I love the road, but it gets tiring.

I love driving, but I hate Interstates. So taking more time allows me to drive state highways, where there’s few cars on the road, high speed limits, and a little vantage into small-town America every 30-50 miles. These are places forgotten by the Interstates.

You’ll get a much different impression of Texas between Austin and Texarkana if you can avoid driving I-35. It takes longer, but it’s so much more enjoyable.

I can’t stand the irresponsible drivers pulling dangerous moves left and right on the Interstates. I don’t enjoy inching past big rig trucks who are in a constant battle to slowly pass each other while clogging up lanes for the rest of us. It’s a pain in the ass and it’s an energy-suck. Those truckers work hard and I’m just gonna let them have the Interstates. I’ll be one less log in the jam.

Meanwhile, driving an empty state highway with beautiful countryside and quaint small towns scattered across it makes you feel like you’re in a good road movie. It’s enjoyable.

I chose Hot Springs, Arkansas as the first stop because it’s on the way to Appalachia from Texas. It’s a quintessential American lake town which makes you feel like you’re in an 80s movie. It has history too, when big wigs across the nation used to come down for the healing properties of the springs. It’s a place of organized crime folklore as well:

“Visiting Hot Springs, Arkansas, today, it’s hard to imagine the city as a hotbed for organized crime, such as gambling, prostitution and bootlegging. But from the late-1800s through the mid-1900s, especially in the 1930s, Hot Springs was a popular hangout for Al Capone, Frank Costello, Bugs Moran, Lucky Luciano, and other infamous mobsters. The safe, secluded scenic location of Hot Springs made it the ideal hideout. In order to understand how and why they chose this site, it’s necessary to reflect on the corruption that had been going on here for decades.”
- Hot Springs dot org

It’s got more of that vibe than Hot Springs dot org leads you to believe in that excerpt. When you leave Lake Hamilton for downtown Hot Springs, you’ll see the history. The town is full of beautiful art deco buildings, taking me back to that Gotham City feeling you get in parts of old colonial Shanghai.

We didn’t do an extended stay in Hot Springs on the way out east, but we did on the way back. It’s a lovely and inexpensive place to spend time working remote. Both times we stayed at a lakefront rental spot I found on Vrbo for less than $200 per night. The kind of place you can wake up, walk out the back door, and jump into the lake for a refreshing start to the day.

*Our view at our* *stay* *in Hot Springs, Arkansas — right on Lake Hamilton*

After Night 1 in Hot Springs, we had to set out to Appalachia for the family reunion. We had a much less pleasant stay in Lebanon, Tennessee on Night 2, right off the Interstate.

Lebanon, TN is a pretty standard southern Interstate town. The local economy is dependent on Interstate traffic. It’s got a bunch of chain stores in suburban sprawl format (like that meme). We got dinner from Pizza Hut and Taco Bell. I got an oil change at the Walmart Auto Center the next morning. Anyway, we were ready to get out of Lebanon after a suboptimal motel stay — a stark contrast from our previous night on Lake Hamilton in Arkansas.

We moved our way up through the mountains toward West Virginia on Day 3. While I do hate Interstates, they’re usually fun to drive in WV. First off, West Virginia is a gorgeous state and it’s not that crowded, so the roads are open and picturesque.

We arrived at our destination in Summers County. We stayed at what we call “camp.” It’s essentially a family-owned cottage in a mountain valley with access to the Greenbrier River. This is where we held the family reunion and it’s where I began the first extended stay where I could actually get some work done.

WORKING THE EXTENDED STAYS

With three days from Texas to West Virginia, I didn’t get a lot of work done. I did some calls at night, typically after about 8 hours of driving. But I could’t get any real work done during the day.

I was able to mix a weekend with some time off to make this first major leg of the trip. In West Virginia, I was in a place where I could relax and stretch my legs, knowing I wouldn’t need to drive for a while. We had WiFi too.

It’s important to make your extended stay a comfortable one if you want to get some work done. A crappy motel off the Interstate isn’t ideal. A cottage tucked away in the mountains is great so long as you have an Internet connection.

Or pick a quiet place by the seaside if you can. That’s where my parents are in Maryland. I took a Saturday to drive from the mountains of West Virginia down past DC, over the bay bridge by Annapolis, and onto the Eastern Shore of the Chesapeake Bay.

My wife was able to take some time off work and fly over to meet us, where we celebrated the 4th of July on the Bay. We spent another couple weeks on the Eastern Shore. My wife was able to get herself a rare week of remote work to extend her stay with us.

*My son and nephew playing on the Chesapeake*

When you have a comfortable spot to rest your head every night, you can focus on getting the work done during the day like a normal work week. My work weeks are never “normal” with my schedule, but the same principles apply.

But if you’re up for more adventure like me, you’ll keep this work-on-the-road thing going. I did another extended stay in Vermont after a couple weeks in Maryland.

Weekends are critical for long-haul drives, like the 457 miles I drove from Maryland to Rutland, Vermont. I drove up with my son, brother, and nephew this time who had joined us in Maryland. We did yet another family reunion in Vermont (different side of the family).

Another family reunion means another place to stay at no cost. My aunt and uncle put us up in their house. My cousins (their kids) don’t live at home anymore so there was ample boarding.

Rutland is one of those towns that gets listed as a place of major decline in the United States. I liked bringing my money there. I spent time at sandwich shops and cafés in town while getting work done. I had big Italian family dinners at my aunt and uncle’s place.

*Working at the Yellow Deli in Rutland, VT*

There’s town after town in America that’s in decline, especially off the Interstates. Rutland is one of those places that got the short end of the stick in terms of Interstate route planning. But its decline is more than that.

If you want to know what Americans across the country are facing, take a trip to a bunch of towns and talk to people.

If you’re a marketer like myself and you want to understand who you’re trying to reach, go talk to them. Work-on-the-road is an ideal way to make that happen.

Even if you don’t have family all over who can host you, costs are typically a lot lower when you’re off the beaten path. You can get a decent Airbnb or Vrbo stay in idyllic locations that won’t break the bank.

I had reached the farthest location from Austin as this trip took me while staying in Vermont. It was time to start heading back west. This was where I booked some interesting stays that I didn’t have the privilege of staying for free.

DISTINCT STAYS MAKE FOR INTERESTING ROUTES

I wouldn’t do this trip if it meant driving crowded Interstates everyday and staying in dusty Econo Lodges every night. That sounds more like hell to me.

I keep my stays interesting by getting on the Vrbo app, searching a general location where I can finish a day’s drive, then relying on the map feature to find an ideal spot.

Instead of browsing a list of search results, I browse pins on a map. You can find good spots that don’t show up at the top of the list that way. You can find locations far from urban centers and Interstates more easily. There are some very interesting hosts out there on Vrbo.

One great stay was in Rushville, New York. This is in the Finger Lakes region, not too far from Rochester. This was a place I couldn’t commit to doing my work as it was completely off-the-grid. This location was strategically planned for time-off.

The remote glamping location has a number of safari tents surrounding a pond. It has outdoor foot-pump faucets for washing up. It has those solar bag shower devices. They have a relatively sanitary feeling no-flush toilet too.

*Our off-the-grid glamping spot in Upstate New York*

The hosts are a lot of fun and put on a nightly camp fire for guests with gourmet s’mores. We’re talking elaborate homemade marshmallows and fine chocolates out in the middle of nowhere in Upstate New York.

This stay was a very refreshing break from work and a nice place to recharge after being on the move for weeks. If you find yourself around the Finger Lakes, look up glamping in Rushville.

I drove my way down past the Great Lakes toward Cleveland, where I met up with another family member. I have a cousin out there I hadn’t seen in years. We stopped in just to grab a meal and say hi. The next interesting stay was farther down the road in Central Ohio in a small town called Mount Vernon.

I was browsing Expedia instead of Vrbo this time and found a historic hotel that was off-the-beaten-path in Ohio. The Mount Vernon Grand Hotel is a hidden gem in another small American town in decline.

“Walk back in time with us at The Grand. This 46 room boutique hotel will take your breath away with its Victorian décor, beautiful parlor, and Grand staircase. The Grand offers amenities such as a fitness center, complimentary high-speed Wi-Fi, business center, two conference spaces and an upscale breakfast.”
- Mount Vernon Grand dot com

As the description puts it, the place is nice. Experience wise, it’s comparable to other classic hotels in larger urban areas — just a bit smaller and a whole lot cheaper. It’s a lot more quiet in small towns too, so great place to focus and get work done.

The following night, we stayed in one of those comparable hotels — this time in Lexington, Kentucky. My brother and nephew who had joined us in Maryland & Vermont lives there. He had flown home after the family reunion in Vermont. My son and I paid them another visit on our way back to Texas.

The Campbell House in Lexington, KY has a real equestrian vibe. It’s a fancy hotel with fancy horse stuff. Makes sense for Lexington, the Horse Capital of the World®.

*My son, happy to get out of the car at the Campbell House in Lexington*

If I’m not staying at an interesting Vrbo spot, I typically like to choose historic hotels. They’re distinct, unlike the ultra-generic Holiday Inn experience you’ll find in any-town, USA. I like history and I like character.

Staying in distinct locations throughout the work-on-the-road trip was an energizing factor. It’s tiring to do all that driving while staying far from home. These types of stays make make it very worthwhile. They also lead you onto roads less traveled.

Staying on farms is a lot of fun too. Our next stay was spent on some farmland near Jackson, Tennessee. Bear in mind my son was with me on this entire trip. He loves animals. I made things a lot more interesting for him with that. And if you can get a farm with an internet connection, you can really get some work done.

*Saying hi to the horses at our* *farm stay* *in Tennessee*

Some of these farmhouses can be somewhat inexpensive on Vrbo. You might stay in a studio-sized cottage, but you’ll have plenty of land to roam. You’ll have nice views and things to do. Searching for stays on the map feature in either Vrbo or Expedia is critical for finding affordable gems.

FINAL THOUGHTS FROM THE LAST LEG

We set out one morning in rural Tennessee after checking out of the farmhouse. I-40 was looking like a nightmare and there’s not that many places to cross the Mississippi River over into Arkansas.

We took a detour north and crossed a bridge over to that little patch of Southeast Missouri that juts out into what you’d think was Arkansas. We took a breather in the town of Hayti, Missouri before continuing our trip into Arkansas — avoiding as many Interstates as possible.

That drive from Southeast Missouri to Central Arkansas is a lot of fun when you avoid the Intestates. These were some of the most open roads with some of the highest speed limits across the 14 states we had already traversed. These are the kind of roads you wish you had a super car for (Cobra Tate style). I’m driving a Chrysler 300 S-class this whole time, which still makes for a nice ride.

We made it back to Hot Springs, where we did our final extended stay before arriving back in Austin. We got to dip in the lake every morning. My son could play in my vicinity, indoor or outdoor, while I was getting work done in the day. Since I do calls every night, I typically put him to bed first then took my calls out on the lake-view balcony.

*Morning dips in Lake Hamilton, Arkansas*

We’d spent a lot of time away from my wife, which was tough on both my son and myself. My son missed his mom. I missed her as well of course, but I really needed the helping hand.

My son was able to spend a lot of time with family members while on this trip. I wouldn’t have been able to take him on this trip if that weren’t the case. He also did some summer day-camps with his cousin in Maryland during our 2-week stay there.

If you’re going to work-on-the-road with your children, summer is the ideal time to do it as they’re on break. But it’s going to be a handful. Have a plan for making it all worthwhile for them too.

After about 6-weeks on the road, we were happy to get home. We got back to Austin in early-August — just in time for my wedding anniversary.

Since my wife was not with us for most of the excitement, we wanted to include her on one last Vrbo stay. We popped down to Shiner, Texas after returning to Austin for a little anniversary weekend.

It was another farmhouse, this time completely chicken-themed. All the home decor and tableware was chickens and roosters. There’s so many fun spots like this on Vrbo and Airbnb. These rural hosts are typically very charming. I’ve never been disappointed.

*The* *Chick-Inn Coop* *in Shiner, Texas*

So that’s that. I needed a break from the road after the final weekend away from home, but I’m keen to go for round two in 2022.

If you’re looking to do something like I did, I’m sure you’ll be under different circumstances, but I hope my story helps.

FINAL THOUGHT FOR MARKETERS

Get out there and talk to people!

Working on the Road: How I Traversed 14 States in 6-weeks with Minimal Time Off