My Digital Nomad Dreams Crashed & Burned – And I'm So Grateful
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My Digital Nomad Dreams Crashed & Burned – And I’m So Grateful

Two days after moving out of my San Francisco, rent-controlled apartment and putting my stuff into storage I received notice that the company I was planning to travel the world with as a new Digital Nomad for 12 months was officially out of business. Along with my $5000 deposit.

I’ve said, “my head was spinning” before but in reality, I didn’t know what it felt like until just then.  What?? A giant curveball in my new life plan 48 hours into it?? I mean, I had a plan.  A plane ticket. A company that was going to take care of all the planning and logistics. Now what the F do I do?


The Pivot

Exactly one year to the day later I can tell you I am so grateful for this universal redirect and here is why.

In the month following, I was on phone calls with other companies and with people who were going to start a new company from the ashes of the dozens of people who were stranded or screwed over. I had an instant crash course in the industry of Digital Nomads and discovered so many options and different approaches to providing services for those of us who craved adventure and location independence.

Feeling scared and scarred I took a closer look at Hacker Paradise because, well, they offered a deal for us orphan travelers. I spoke with Sara on a video-call from the living room of her place in Costa Rica. I could see some nomads hanging out in the living room with her. It seemed a little Real World (which was awesome) and she was professional and as warm as can be. After being assured they were nowhere near going out of business and I didn’t have to pay a deposit, I made the decision to join them for 3 months in two locations starting in September.


I would be going to Split, Croatia for 6 weeks and then immediately to Cape Town, South Africa for 6 weeks.

As I write this in Vietnam I can’t wipe the grin off my face. Sometimes the universe needs to redirect you and sometimes it costs a pretty penny. Zooming out and reflecting on the dozens of friends I made on two continents and the half dozen I have already seen since on another continent  . . . is pretty freaking amazing.


Almost immediately I became an advocate for Hacker Paradise, or HP as we call it. I feel like I could write several pages about my experience so I’m gonna go bullet point style to keep it brief. Then when you’re an alum like me we can gush about how great it is over drinks on another continent.


What sets HP apart from other companies:

  • You get to choose your own adventure. The commitment is as little as two weeks or as much as the 4-8 weeks they sit down in a certain location. (But please don’t do two weeks.) They have at least two trips happening at any given time so you can create a schedule that fits in with your location needs and desires. This is huge for a lot of us because we have chosen a life of freedom and flexibility and don’t want a company dictating our path.
  • There’s a culture of radical inclusion. Have you ever read the rules of Burning Man? My first big lesson in this was one of my first nights in Croatia and I was planning to meet a couple people for dinner. Sara encouraged me to post it on the Slack channel (which becomes your social lifeline) and get a bigger reservation. I’ve been in event planning and am a social butterfly so I really wasn’t interested in navigating a big group dinner but . . . I did what she asked me. It, in fact, was a bit of a hassle calling a couple times to increase the reservation BUT I ended up sitting with a crew that became my besties for the rest of the three months. Who knew? Maybe Sara did.
  • Being an alumnus has value and not just the intrinsic kind. Since finishing my first trip in Croatia I was added to the Alumni Slack channel. There are fantastic resources and threads for researching your next trip, meeting up with fellow HPers AND there is a jobs channel. We have a culture of wanting to support other digital nomads and keep each other on the road as long as possible. Helping each other fill in the pipeline and share opportunities is super valuable.


This may not be the right group for you if:

  • You aren’t looking to meet people and would rather hang solo in your place. The social element is a lot of what you are paying for. Introverts are absolutely welcome. There are so many weekly events though — it would be strange to not take advantage of at least a couple.
  • You enjoy researching apartments, negotiating with landlords in foreign languages, and having no network of support when life goes awry. HP takes care of all of this. Plus, I know one fellow traveler felt so much better when Sara was by her side in the emergency clinic.
  • You don’t have actual work to do on the road. HP requires that you have some work. Or at least a project like writing or developing your own business if you’re on sabbatical. As much social and fun as we have, we spend a lot of time at the co-working space. The weekly workshops and other digital nomad speakers will add to your skill and knowledge base.

Full Circle

The last thing I want to share is for anyone hesitating that you’re “too old” for this experience. I am still personally working on letting go of the social rules and judgments about age. One of my first questions to Sara was the age range and average. In the end, I developed a sweet friendship with a woman in her late 50’s. And then my roommate in Cape Town was one of the youngest in the group at 26. It’s true what they say, age is just a number.

What has more weight and value with HPers is our common lifestyle choices. Since we are all living outside the box there is a camaraderie and connection; something that many of us don’t feel amongst our corporate suburbanite friends back home.  Many conversations turn to dream trips, best locations and tricks for online flight purchases. Or to wishing our families would join us for the holidays instead of us having to come to them. Compare that to your friends’ common topics and it may just be a breath of fresh air for you too.

I am happy to connect with anyone who has questions about the Hacker Paradise experience or getting your start as a Digital Nomad. My passion has evolved from inspiring people to live and travel healthy into helping people create a life by design and how to ultimately have more choices.


Hope to see you in a new country soon!

Kendra Cannoy — Virtual Health & Side Hustle Coach

Catch up with Kendra on your next Hacker Paradise trip! Check out where we’re heading next!

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