The Truth about Your “Working While Traveling” Dream

The Truth about Your Working While Traveling Dream

I spent my cubicle dungeon days dreaming of traveling the world with a laptop and nary a care… And rolling in some serious bank notes.Then Reality slapped me in the face, told me to, ‘Get down from that baby elephant, right NOW, missy!’ and made me wanna break ALL THE THINGS in frustration.

My bf and I spent two months traveling the world when my full-time business was brand spanking new. Spoiler: trying to type a post on an iPad while drenched in enough Thai sweat to make a fish feel ‘too wet’ is no good.

Clearly, these are first world problems.

But when someone sells you the idea of bopping from continent to continent all whilst maintaining status quo they are lying! LIES.

Because if you’ve spent 12 hours a day x 7 days a week working hard. Only to get on a plane and find out that you can’t savor eating arancini in Florence then what was the point?

The ideal? Is to create a business that you can walk away from for a couple of weeks and know that your clients still feel special, the blog keeps pumping out content, and your business keeps growing.

Here’s how you can make the working/traveling conundrum work:

Try planning for a home base.
If you’re hopping from place to place every few days, it’ll be hard to work. It seems like a lot of people who travel and work successfully are those who stay in one place for a month or longer then move again.

Ride the goddamn elephant.
Make your travel the priority. Your experiences are why you started this business so if you can’t enjoy them, what’s the point?

Delegate and hire out.
There’s a lot to do with your business. Try hiring a VA to manage your emails and clients or get a CRM that automatically sends out emails while you’re trekking thru the Brazilian jungles or clacking thru the Roman cobblestones. Your clients are your top business priority.

Book clients for when you get back.
Not during. You’re not going to find it fun to hunt wi-fi down desperately in the middle of the Mongolian hills nor try and conduct a Skype call whilst holding your laptop above your head screaming, “Can you hear me now?!?”

Involve your clients in the travel.
How about taking snaps and involving your clients in your travels? Put them up on Instagram to show them where you are/what you’re doing. Even include a hashtag for them to see the journey. Although unplugging is best, it’s nice to let your clients/possible clients have a insider’s peek into your life (edited of course).

Limit your workload.
Do not commit to anything that takes a lot of computer time. Pretend for the next few weeks that you don’t want to work at all. What would be on your to-do list?

What’s been your experience working while traveling? Yay or nay?


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  • Love this–and this is exactly why when I go to Germany later this year I won’ be bringing my laptop!

    Erin E Flynn
    Reply
    • Perfect, Erin! You won’t regret it. 😀 Where are you visiting?

      Halley Gray
      Reply
  • This is the bomb! Boyfriend and I just decided to take twelve months off to travel around Australia in our 4WD. It wont be for a few years yet but I had these romanticised ideas about getting my biz off the ground before we leave and coaching my clients with Uluru in the background… It would be lovely, right? Then the reality of it creeps in. Much planning to do so as to make it as fool-proof as possible.

    Jess | Just Jess May
    Reply
    • That is FANTASTIC, Jess! I think you should do it! Just know the pitfalls of the working while traveling model and work around it.

      Halley Gray
      Reply
  • Having spent 4 months in Mexico and 4 months in SE Asia last year, I totally agree with you! My solution was sslllloooowwww travel. For ex. an apartment in Chiang Mai on a 3-month agreement. Mostly I worked and then somewhere in the middle of that I took 2+ week “vacation” to Laos and Cambodia. The flow I’m working towards is one month work, week or two as digitally-free as possible. Repeat.

    Shawn Tuttle
    Reply
  • Oh snap! So true – as I am figuring out right now. I was planning to write a post just like this one. It’s totally BS…

    Nell
    Reply
  • So true! I just experienced this myself while visiting back home (not a new country!) Still found it impossible to work. And trying to was just exhausting. I needed to take a break when I went back, totally defeating the purpose of taking a vacation.

    Laura G. Jones
    Reply
    • Yes, travel is so exhausting and if it’s a new country then it takes up even more brain matter.

      Halley Gray
      Reply

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