I’m Not On Vacation

So I’m on a trip.

A road trip.

A road trip that’s currently taking me all over Florida.

A road trip on which I’m getting to see lots of friends, some of whom I haven’t seen in months or even years.

A road trip that has no set itinerary, no final destination, no boss to call me back to work after two weeks, and no limits of location or time.

So I’m on vacation, right?

Not so fast. For starters, let’s not forget that someone has to pay for this trip, and that someone is me. Since I’m a freelancer, that means I spend a lot of time working on my laptop, either getting gigs done or looking for new ones. And since my goal is to have a self-sufficient business, that also means that when I’m not doing the work that pays my immediate bills, I’m developing my skill sets, reading entrepreneurship resources, reaching out to contacts, working on this website, blogging, journaling, and doing the hundred and one other things that find themselves on my business-building to-do list. So while I do make time for self-care (exercise, naps, time with friends, reading), this lifestyle, despite taking place on a road trip, is most definitely not a vacation.

In a recent guest article on Sean Ogle’s Location 180 site, entrepreneur Mike Harrington wrote about several traps that new location independent solopreneurs tend to fall into. One of these traps is thinking like a backpacker. Says Mike, “Backpackers employ the ‘short timer’ mentality.  This means they’re trying to pack in as much fun and experience before loading up their packs and moving on to the next stop on the backpacking trail.” Now, I am moving from place to place a lot on this trip, but if I focused solely on the fun activities I wanted to do in each place instead of the work that sustains my travels, I’d run out of money and be stranded in about three days. Does that mean that I don’t have a goal of being able to go somewhere amazing, take a week off working, and just enjoy some great relaxing time? Hell, no! You bet your asbestos I’ve got that goal.

But “goal” is the operative word. I would love to think like a backpacker, but I know I’m not one yet. First and foremost I’m a word coach, a business builder, and a long-distance driver, which means most of the things that don’t support those activities take a backseat (yes, that pun was intentional) to the things that do. Case in point: I just spent a week in Orlando, with free tickets to both Disney and Universal parks available for the asking from my host family, and I didn’t go to either one. I had work to do. And I was okay with that, because I’m not on vacation.

But when I take an actual vacation, I’ll be back. Because that’s the goal.

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  • http://www.careerdeviant.com/ Mike Harrington


    Getting stranded with no money is NO FUN, and cuts an end to the “Wheeeee, I’m on vacation” mentality pretty quickly.

    Don’t get me wrong, this lifestyle is killer, but it’s all built on the foundation of doing the damn work.

    Looking to seeing more of your progress, James.

    • James M. Ranson


    • James M. Ranson

      Thanks, Mike! Really glad you saw this. Looking forward to connecting more with you soon!