“We work online, so we can travel and work wherever we are.” This was our standard line, Drew and I, delivered to everyone we met as we traipsed around the Dominican Republic and Haiti and Mexico. The almost universal response was, “Wow! That’s so cool!”
And there were cool moments, like when I was able to get an email containing a signed contract for a new gig while we were in the back of a pick-up truck headed to the closest town for groceries. When Drew was able to sidetrack a loud innkeeper long enough for me to make a phone call from the hotel lobby. The pro bono project that came about because I chatted up an NGO worker in Port-au-Prince, who was amused at meeting “backpackers with business cards.” And the week we found ourselves in a cheap but perfectly nice hotel in Santo Domingo with not only fast and reliable wifi but also a big and quiet lounge area so we didn’t have to work crammed on top of each other. This also coincided with two very civilized clients who didn’t have any fire drills and let me work with low urgency.
But there were many, many shitty moments as well. Never any big, dramatic, “good story later” type shitty moments. Just things that made me feel like I was constantly pushing a rock up a hill. Not having work for 3 weeks when we first got to the DR. The client who finally pulled me out of the drought — with a two hour turnaround project, on a day I had promised Drew we would go to the beach. The time we were stuck on a bus (aka nightclub on wheels) with two minutes to go until I had to get on a conference call with a new client. The time Drew had a heap of deadlines and the power went out, leaving him with no choice other than an all-nighter to get it all done. Having to leave a picturesque but mysteriously wifi-less town to backtrack two hours and hole up in a shithole town for three days to work and eat nothing but lukewarm rice and beans. Being nearly out of money and knowing that three checks were waiting for me back in New Orleans.
All these issues left me wondering if working while traveling was even worth the hassle. In the week after we returned home, I got more work than in the two months we had been gone. Working on the road seemed so dreamy: we would get up early, work out, work for a few hours, hit the beach or grab a bus to the next town. It was never, ever like that– not one day. There were days with last minute calls and days with client emergencies and slow wifi days and no cell service days.
The thing is, I really, really want it to work. I want to figure out a way to get just the right amount of work and condense it all to the same 4 hours every day, or three days every week, and have technology work the way it is supposed to and be with Drew and be happy. I picture us staying in a bright, breezy house with plenty of space for us both to work and lightning-fast wifi. I fantasize about clients who give me plenty of lead time and rarely need conference calls, who value me enough to fly me back to the States for groups or meetings. I imagine being able to turn down projects that correspond with planned trips, consistently outsource to reliable people, and trust myself enough to fit work into whatever amount of time I allot for it.