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Laptop? Check. Cell phone and charger? Check. Mindset to work productively from the road during the family’s extended summer road trip? Uhhh…

Preparing to take a “workation” from the road is not as simple as it may sound. Think of it as “mind over motel” – you have to find that place where your creative spark feels comfortable igniting, even if it’s a place you’ve never seen or been before.

As our family heads out on a three-week road trip from South Florida to Northern California, I’ve promised myself not to work too much. But, in addition to the “slob gene” I wrote about previously, I also bear my father’s habitual early rising. So while they slumber, I’ll surf or work.

I’ve read with interest Rhonda Hughes’ dispatches as she’s driven some 4,000 miles from California to Massachusetts. As a four-year teleworker, she’s accustomed to working outside the traditional office. But working from the road? “My experience will no doubt teach me new skills,” she wrote.

Indeed. I’ve workationed before in an adventure we call Home Office Highway. Each year, we take an extended road trip, usually in an RV – to the Carolinas, the Jersey Shore, Henry David Thoreau’s Walden in Massachusetts, even Toronto and northern Ontario.

Before each journey, parallel preparation is launched. My wife packs the food and family supplies. She shops for road gorp like we’re heading on a three-week walkabout in Utah. My kids (hopefully) will pack all their clothes and belongings. What they’ll definitely bring along are their laptops and smart phones. Chargers? One can only hope.

I focus on the tech. Packing for a road trip isn’t just about having the stuff you need to work. It’s about having the right stuff, where it belongs, so you’re mentally prepared to work from the road. Think of it as Jack Bauer (24) meets George Clooney (Up in the Air). Whether they carried a messenger bag or a TravelPro suitcase, both were packed before each adventure.

My trusty Oakley knapsack is my TravelPro. It’s been my pop-up office-on-the-road for the better part of a decade now. Even when we take a weekend away, I just grab it and go. It’s like an expecting couple’s hospital bag; pre-packed with clothes and toiletries, it’s good to go when baby says, “It’s time.”

This time, it’ll carry:

  • My Verizon 4G Mifi broadband wireless mobile hotspot. Mobile Internet has proven very handy indeed when on the road previously. Unlike the USB mobile Internet I once used, with the Mifi, five devices can log on at once (i.e., five people, five users). For a dad who wants to work, or a mom looking for a hotel, restaurant or tickets for a whitewater outing, mobile Internet is golden. Even if you get a short-term agreement, if you plan to work from the road, this is the way.

  • A power transformer. We’ll have to charge the laptops, tablets, iPods, phones and Kindles along the way (alas, one at a time, folks). The Town & Country we rented actually sports a 115v outlet. So I’ll pull out and plug my Belkin mini, four outlet surge-protector / power strip in and we’ll have all the power we need.
  • USB headset for Skype calls home. The kids’ Macbooks have iChat. But this’ll allow dad to chat with family or clients from the road.
  • Flash drive and card reader. I’ll use these to transfer pictures to my laptop, then upload them to Picasa in the cloud. Data portability is important. More important, I’m not keen to wade through and download 1,000 pictures when I get home. I’ll clear the camera’s card (and delete bum shots) along the way – ensuring they’re protected, should something happen to the camera. The camera’s replaceable. The pictures are (hopefully) priceless.
  • Carbonite account updated and all my stuff backed up. In journalism parlance, they call this “burying the lead” (putting the most important detail toward the end of the story). People who use online back-up generally enthuse about its effectiveness. Sure, I’ll upload key files to Google Docs. But if I want to reference or work on something on my hard drive back in the home office, backup-to-the-cloud is invaluable. Just renewed this month. It’s easily the smartest $54 I’ll spend over the next 12 months.
  • Laptop cable locks. Another permanent item in my Oakley. Think of it as insurance. You can never be too safe. Alas, people will be people.

Some added possible accessories: Motorola walkie talkies, if we split up somewhere in the Utah countryside; an LED flashlight, strong and powerful, it cuts through the blackest night; a GPS locator (part compass, part GPS, you mark a spot and it’ll guide you back to that spot – not matter how far off the path you venture); my laptop transformer and camera and BlackBerry chargers (of course); a bottle of Excedrin and a toothbrush.

And I always stash a couple of pens and a notepad. Hey, typing is productive. Journaling is cathartic. Just ask Mr. Thoreau.

What will you take on your summer vacation?

Photo Credit: dbaron

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