Working to the West [and Back]

Wide open Wyoming at Bighorn National Forest
Wide open Wyoming at Bighorn National Forest

It was probably somewhere between the 254th and 255th time someone said "Web Developer, that's great. You could practically work from anywhere" that my wife and I thought it might be an interesting idea to take everyone up on it.

I'm sure I followed up that comment with my usual "For sure, just like everyone assumes that you will work from ANYWHERE and at ANY TIME" but inside, the wheels were churning.

We hatched a plan in late 2011 to take a road trip out west in the Summer of 2012 and see all the states we'd never visited and generally absorb the massive landscape our country has to offer. The added benefit—which quickly became the primary driving force—was that we had nearly a perfect curve of family and friends starting in Northwestern Washington State, winding down the West Coast and ending in Louisiana.

Happy Campers in Orcas Island, WA

An itinerary was gradually drawn up to include stops every 200-300 miles, allowing for a tolerable amount of driving every day or so, enough time to catch up with the folks with whom we were staying, and, of course, an appropriate amount of time to keep up with our current work loads. We settled on a westerly route that included a lot of camping the first month and less the second to combat potential exhaustion. Particular attention was paid towards routes that kept us in cellular data range and only pushed us off the grid on weekends.

Doing the Damned Thing

There's a saying regarding best laid plans and mice or something like that. Well, whatever they say about that definitely applies ten-fold to working vacations. Fortunately, we didn't plan all that much.

Well, we did, but it involved a camping trailer, driving through the state of Nebraska, visiting San Diego, and a whole heap-ton of other things that didn't happen.

I'll tell you what did happen. We drove, we ate, we slept, and we worked. Oh, how we worked. We worked everywhere. 

Coffee shops, rest stops, and hotels? 

Worked there. 

The morning ritual at Cup of Joe in downtown Cedar Falls, IA

In tents and laundry rooms at campgrounds? 

Damn right. 

The finest cooperative workspace the Black Hills has to offer.

Hell, I got a day's work done in the passenger seat at 85mph down I-90 through South Dakota and took a conference call on a island ferry north of the Puget Sound.

We launched a website in the Black Hills during a hail storm, signed a new project in the vineyards of Sonoma, and submitted the artwork for a national print campaign somewhere along I-5 between Seattle and Portland.

Yes, there was a lot of hard work done and to many of our clients, it may have seemed like we hadn't even left [we hope]. It wasn't always haphazard circumstances either. I logged plenty of hours at plenty of desks in perfectly reasonable settings.

And there was also fun. Everyday when quitting time came around, we were somewhere completely new to us, with thousands of possibilities. We could haul off to see Mt. Rushmore, head down to the beach, hit four new vineyards to do some wine tasting, or hang out with friends whose new homes we'd never seen.

The stress of working on the road can easily match and surpass that of a day in the office, but the therapy of your enchanting surroundings is up to the task of keeping your life in balance. For every work day that ends at 1am in your tent, there's a thousand mile Arizona sunset across a sky bigger than you've ever imagined [unless you're from there].

Man, You're Crazy Man

To some, the entire trip may have seemed outlandish and even irresponsible, and I assure you, it could well have become just that, but it can and did work. It takes a strong desire to make things work regardless of the circumstances and it requires constant affirmation of your goals for the trip. 

No matter how certain of our plan we were, there were always times when you felt like you should be doing more in the new areas you were visiting. The sense that being in a new place means that you're on vacation is tough to shrug. And for most, being on vacation means that you aren't working. So when you find yourself in yet another coffee shop in the middle of another gorgeous new place you've never been before, it's easy to ask yourself what the hell it is you're doing and why aren't you exploring.

Avenue of the Giants at Humbolt State Park (left). Friends, poolside in Santa Cruz (right)

For us, we stated from the outset that this was to be a working road trip. We made time to keep nearly normal office hours every day and made sure to balance those seemingly endless work days by also seeing tons of new places, catching up with friends and family, getting a great overview of the parts of the United States with which we were unfamiliar, and figuring out which we'd want to visit again. 

So if you're interested and have the flexibility, I have nothing but encouragement for you to hit the road, let your hair grow and don't let your clients bug you about your beard length on video chats. If you're motivated to make it work, you can't go wrong.