Work Life Travel: The Fantasy and the Reality

A few months back when I first contemplated a two week trip overseas, I accepted that I’d have to put in some work-time in exchange for a prolonged holiday. Even so, I envisioned waking up a few hours sipping a cafe con leche on the balcony and watching the sunrise, while tapping out a blog post or responding to a client email.  Or maybe for the heck of it, I’d check out a co-working space for a couple of hours for the experience of working alongside local entrepreneurs. Then, with my work done, I’d shut down my computer, turn off my phone and join my daughters for a museum exhibit, a shopping trip, an afternoon on the beach or late night tapas with Sangria. And just before going to sleep, I’d dispatch some tweets or Facebook posts to my relevant social circuits to keep on everyone’s radar.

Of course, the myth of work life travel isn’t at all like the glamorous location independent lifestyles  that you read about online.  Despite the best planning, it’s often impossible to get away completely. Let me share some of the biggest fantasies about work life travel and the reality.

Cases don’t always go the way you plan.  Before this trip, I did everything right – or so I thought. Scheduled hearings and meetings to be completed either before I left or put them off until after I returned. Arranged for contract lawyers to handle small matters and filings that might come up during the trip. Yet even with all of these systems in place, I couldn’t predict the huge break in one of my cases three days into my trip – that allowed us to finally settle a six-figure matter. Great news for the client; but the deal involved two afternoons of last minute details and drafting that couldn’t be done on the beach. Same development in another matter a week later – necessitating a 2 am phone call that set me back the next day.

Some work is just harder than other work.   Many of the “location independent” crowd earn money from blogging or online product sales. Sure, that’s work – but as I know from my own experience, blogging is quicker and easier than negotiating a complex deal or drafting a motion. On this trip, I banged out a couple of blog posts in a morning without disturbing the day – but I needed a full afternoon to review and redraft seven different settlement documents.  I wasn’t going to be able to do that kind of work on the beach.

Even the best tech set-up isn’t as efficient as your daily set-up.  In the office, most of us work off dual monitors, with easy access to printers and scanners. Granted, most tech-savvy lawyers don’t use all of those tools all of the time – but they’re great to have if you need them. On the road, I didn’t have access to Adobe professional, so I had to mark-up a document using a free mark-up tool. If I need to print or scan, I’ve got to do it through a hotel desk, or by taking pictures on my phone, page by page. Unless you want to bog yourself down on a two week trip with a ton of heavy equipment, you need to accept that you may not be able to work as quickly as you might back in the office.

You’re only human.  Though you might envision yourself blocking off chunks of time in the morning and evening to work, even planning and discipline may not suffice to overcome the forces of nature. At the beginning of my trip, jetlag and fatigue from intensive touring prevented me from always rising early and getting my work done. And if I wanted to make up the work at night, I had to forego the alcohol with late-night meals – one of my traditional vacation indulgences – so that I wouldn’t find myself proofing a document for a six-figure transaction while drunk.

Ultimately, lawyers can successfully take long breaks from the office. However, the secret isn’t great technology or support staff, but to lower your expectations. Assume that you will have to work during your vacation. Recognize that you may need to miss out on a couple of sangria’s or sunset.  If that’s the admission fee for a two week trip overseas every few years, then it’s a cost that I’m willing to pay.  Are you?