On The Road With: Justin Kaplan

Justin Kaplan spends more than 40 weeks per year working on the road.  Justin took a minute to share his story with me.

Eric Murtaugh: Your job seems to take you around the globe.  What is that like for you?

Justin Kaplan: The experience has been and continues to be humbling and awesome at the same time. You realize how tiny you really are when you’re surrounded by people. All the cultures, the people, the sights; this is definitely the best thing that’s ever happened to me and even when I get down, I remember how lucky I am to be in this kind of position—helping people make their lives better.

EM: How many countries have you worked in thus far?

JK: 9 so far, more coming soon—Australia (x4), Costa Rica, Brazil, Singapore, London, Sweden, Germany, Japan, and Mexico

EM: What is the paperwork process like with the countries you work in?

JK: Most of these have been painless or have small hoops to jump through (Singapore and Australia simply require filling out a website and paying a fee), but Brazil is like pulling teeth. Between the notarized letters of intent from both my company AND my customer, the letter stating you’re not a financial deadbeat, and then having to actually physically send in your passport to the consulate— yeah, 3 weeks later it was a huge sigh of relief.

I was told it’s like that for almost anyone coming to America though, so I suppose turnabout is fair play.

Justin, holding it down in Australia.

EM: How did you score such a sweet gig, anyway?  Could you describe what it is you do for work, and how long you’ve been doing it?

JK: Pure blind luck combined with a lot of hard work, great networking, and tenacity. I started off at an insurance company doing Helpdesk and moved into Performance Management. About 3 years later when I was itching for a change I took the chance and submitted my resume through some of the people whose product I had used and lo and behold, they took a chance on me.

Nearly 4 years and more than 500,000 miles later it still makes me proud to come to work. The company I work for now does Performance Management software (making sure websites are fast, servers are up, etc.) and I am charged with creating and, to a lesser extent lately, the delivery of that curriculum.

I also help manage a network of over 60 partner/contractors and enable them to deliver the majority of our Training and Implementation. Since we’re a smaller company by nature (though we were acquired by a conglomerate a little over a year ago), I’ve gotten to wear many hats and have loved (almost) every minute.

EM: What is your favorite piece of gear on the road?

JK: My Packers jersey. Everything else is technology and I have developed a love/hate relationship with technology—at least with my jersey I always have a shirt to wear and it really pisses off the Bears fans when I travel through Chicago-O’Hare (which I frequently do).

EM: How do you overcome language barriers?

JK: Thankfully I had great instruction in Spanish and French growing up and that’s helped immensely. I’ll admit it gets scary sometimes when you don’t know what things mean, but most of the time I stick to the straight and narrow in countries where I am not fluent.

EM: You obviously spend a lot of time in airports. Any tips?

JK: Never lose your cool, realize early on that “we’re all in this together” and never put on a front just because you get an upgrade or something. Also, remember that gate agents are not gods and sometimes you just miss your flight. Always respect the people around you that make your travel possible. They’ll appreciate it, and in some cases return it.

"All the cultures, the people, the sights; this is definitely the best thing that’s ever happened to me." Thumbs up to that.

EM: When you travel for work, do you tend to pack light or heavy?

JK: I’m a horrible packer. I overpack often and yet still seem to find ways to forget things—for example, this week I remembered to get books printed, grab my passport and both my phones but forgot my charging cable and melatonin.

EM: How long do you typically work in each country? Does it vary?

JK: Usually a week or two, I’ve spent 3 weeks in Australia twice but nothing longer. It’s rough because you never really “settle in” to a place before you leave, but good because I’m never gone for more than 3-4 weeks at a time (gotta have the home time to love up the pooch and do laundo).

EM: How do you stay in touch with friends and family back home? Where is home?

JK: Facebook is my lifeline for most of my social interactions. For family and close friends I carry two phones just in case one or the other has no service. “Home” is up in the air, but I hang my hat in SE Wisconsin since ’07 when I moved back and took over the mortgage payments when my dad lost his job. Kind of a feel good story there, but it’s just part of the pattern of life.

EM: Any good stories and/or wild experiences you’d like to share?

JK: So many I could (and may someday) write a book. Highlights would be the celebrity sightings: Jamie Pressley, Flava Flav, Cheech AND Chong (separately), and Sinbad. That and the time I got a first class upgrade wearing shorts and my Packers jersey and was seated next to the “guy who single handedly negotiated the GM and Chrysler bailouts” who said I “didn’t belong” in first class.

Funniest part of that was the fact he got pulled off the plane by Federal Air Marshalls for making drunken threats to the flight crew before we even left Chicago. And then, to top it off, I got his driver to take me to Wilmington from Philly when this guy didn’t make it to Philly.

And then there was the time I gave up my seat on a Christmas Eve-eve flight so that a serviceman could get home to see his family while on short leave. That one just felt good.

EM: For you, is there any distinction between business travel and personal travel?

JK: I hardly ever travel for fun anymore. Vacations become time spent at home resting. I travel over 40 weeks a year usually and outside of Dega in the spring and tubing in the fall, I’m fine with home-stay-cations. I do try to work in an extra weekend here and there to “enjoy” a new place as the work days are usually 12+ hours during the week.

EM: How often, if ever, do you become home sick?  How do you overcome the feeling?

JK: Not often, but it happens. Now that I have a steady girlfriend back home, that doesn’t help much. To overcome I usually drown my tears in beer, but other than that just mental toughness—leaving yourself no option but success is a great motivator.

EM: Any tips for someone who plans on being on the road for an extended period of time?

JK: Do it for the right reasons, not for the money or for the travel—but for the people you get to help. That’s #1.

Second would be pick a couple loyalty programs and stick with them. I can’t tell you the last time I paid for a hotel, rental car, or airfare including when I do some of that mysterious “personal  travel” I hear everyone mention.

Third is developing a routine, no matter how simple, and stick to it. The whole world can change around you but as long as you stay firm and steady you’ll be unshakable. Getting there is a whole other story…

On The Road With: is an ongoing series where I chat with a fellow wanderer about life on the road.  If you are interested in participating, please contact me here.

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