Is this Digital Nomad Thing Working Out? (Looking Back on Year 1) - Intentional Travelers

08 Jul Is this Digital Nomad Thing Working Out? (Looking Back on Year 1)

Flash Back to July 2014

One year ago, Jedd and I had just begun our journey of being digital nomads and we were getting ready to attend our first World Domination Summit in Portland. Having completed 2+ years of Peace Corps volunteer service just a few months earlier, we were unsure about what the future would hold.
WDS 2014

Volunteer Ambassadors at WDS 2014

We knew we wanted to try working online and continue traveling for a few months, just to see if we could make it work. We plotted out a way to live off our Peace Corps readjustment allowance from May through December, and made two commitments to ourselves for the remainder of 2014:
1) Live rent-free, and
2) Avoid dipping into our savings before the year was through.


I’m happy to announce that we made it through 2014 successfully achieving both of those goals. Not only that, we also spent a month in France, three weeks back in Jamaica, and visited friends all over the States.Eiffel Tower - Paris, France Jumping Jedd | Intentional Travlers

Visiting family in Paris and the Loire Valley #JumpingJedd

Reggae Marathon, Half-Marathon & 10k in Negril, Jamaica | Intentional Travelers

After a 10k race in our former Peace Corps host country 

Visiting Cohasset (and Boston) | Intentional Travelers

Our first time house-sitting with horses during a farm stay near Boston

How did we do it?

Thankfully, we came out of Peace Corps with a monthly social media contract for a non-profit in Jamaica to get us started. Paired with house-sitting gigs, a long camping road trip, and friends and family willing to host us, we were able to live on about $750 (or less) per month, whether we were at “home” or traveling. Our new travel hacking skills got us the nearly-free flights. And eventually we picked up a few more clients – helping our favorite Swiss restaurant do a rebrand, updating a website for a non-profit in DC, etc.

I can honestly say I have no regrets. Yes, we had to make sacrifices, like the following:

  • No steady paycheck with benefits
  • Living out of a suitcase
  • Coordinating our living situation and use of a car with various hosts
  • Extra time and effort learning the ropes of travel hacking
  • Inconsistent connection with our home community (this is probably the biggest one)


But in exchange for these sacrifices, we benefit in the following ways:

  • Freedom to determine our own daily schedule, allowing us to prioritize exercise, home-cooked meals, and time to be spontaneous
  • Flexibility to attend family gatherings, visit friends, or be available to help anyone anywhere in the world without having to use “vacation time”
  • The chance to reconnect with distant friends and family in 10 states and 4 countries throughout the year
  • Learning new things every day through a wide variety of work projects
  • Hanging out with fun dogs and cats without the long-term responsibility (by pet-sitting)
  • Joining two amazing teams of passionate people working on meaningful projects: World Domination Summit and Wayfinding Academy
  • Avoiding the hassle of commuting to work (or having to wear work clothes!)

I can still remember one year ago, as we were about to help with World Domination for the first time as volunteer Ambassadors. Attending that conference, suddenly my dream of becoming on online entrepreneur – a “digital nomad” – became undeniable. At WDS, we were surrounded by people who were making it happen. They were not only living an unconventional life but making a meaningful impact, too.

Since Then

WDS was a big catalyst for us. Afterwards, one of the event organizers recruited us to help her for the 2015 summit (taking place this weekend). Learning from her and being a part of the planning team this past year has been an incredible experience. The same person also brought us into the start-up team for her legacy project: Wayfinding Academy, an alternative college. We’ve been working hard on a crowd funding campaign for that, which also launches this weekend.

After our post-Peace Corps experiment in working online ended, we realized we were no longer in temporary “sabbatical mode” and we started to own the long-term “digital nomad” identity. We were able to make another big international trip – our very first visit to Asia – where we stayed with friends in Vietnam and Jedd’s parents in Japan. Then we landed two long-term house-sitting gigs which allowed us to be in Portland for most of the summer.

I can’t imagine what our lives would have been like if we didn’t take the risk to follow our own path. If we had taken cushy jobs and settled down. If we hadn’t volunteered at WDS last July. I’m so thankful for this past year.

What’s Next?

As far as we can tell, our experiment in nomadic living is proving to be sustainable. We would appreciate having more of a “home base” where we can build community, grow things in a garden, and host people. We can’t necessarily afford our own place right now, but we have some ideas to get around that, and we think it will come soon. Either way, we’re not planning to give up long-term travel.

After this year’s WDS weekend, we’re heading back to Europe for a wedding and family reunion. We’ve extended our trip to include our first ever bike tour from Bruges, Belgium to Amsterdam; then we’ll be in Copenhagen for a house-sit and brief farm stay. Beyond another family wedding and road trip through California, our plans for the next year are still shaking out. Ideally, we’d like to try living abroad for another month or two – somewhere we can afford the rent, like SE Asia or South America.

Business-wise, we’re hoping to slowly start the transition away from freelance web services as our travel services and online products grow. We’ll see where it takes us…

So that’s our story, and we’re sticking to it. (Actually, we’re not stuck. We’re flexible!)

Here’s to another year of adventure, growth, and who knows what else!

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  • Karen
    Posted at 16:40h, 08 July

    Thanks for sharing! I always find your blogs so inspirational!

  • Kathy @ SMART Living 365
    Posted at 16:28h, 10 July

    Congratulations Michelle and Jedd! Has it been a year already? You guys have done so much and come so far in just a short year. I can’t wait to see where you’ll go from here. Enjoy your success and everything you’ve learned…it’s a great intentional journey huh?

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