Kari's Workationing Story: How This Adventure All Began

When I first got the idea for workationing, I was a freelance writer – after working in advertising post-college for a little more than a year, I’d untethered my life at 23 years old. That was more than a decade ago, and yet somehow I’m still only 27 😉

My boyfriend at the time also worked from home, but his tech job frequently required travel. Wherever he went, I went, both of us working and collecting hotel rewards points along the way. Eventually we got married, and I decided to ditch my work from home job to suit up at a local startup, where I was hired to start and staff their content writing department. The CEO of the company happened to be Kelly’s fiancee, which is how we originally met and became friends.

I left that startup in 2010, and within a week I’d created my own digital PR agency. I still own and operate The Content Factory, and about a year ago I hired Kelly as a digital strategist – we’d remained friends, even though our lives had changed a lot.

In the time between when I left the startup and when I hired Kelly at TCF, I moved from Pittsburgh to New Hampshire as part of the Free State Project. I got divorced. Kelly was back in Akron, Ohio. She broke up with her fiancee. I bought out my business partner, who I started TCF with. A lot can change in five years.

One thing that never changed was my love for working on the road, because it enabled me to see more things and have more experiences. When you can work from anywhere, why wouldn’t you?

Pool time, palm trees and perfect weather. #calivibes #californialove #westhollywood #workation

A photo posted by Kari D. (@karidephillips) on

As I grew TCF and began to hire more people, I decided early on to keep our operation remote. I could find better talent if I wasn’t limited to a very specific geographic location, and working from home is awesome. I wanted a particular lifestyle, so I engineered it for myself – and by extension, for my employees as well.

When I was 22, my mom died of cancer. I could go into a bunch of sad details, but instead I’ll just say that she never lived up to her potential. She was brilliant, beautiful and could’ve done anything she wanted, but when some roadblocks got in her way she couldn’t quite figure out how to get around them.

An alcoholic, abusive husband got in the way. Being isolated in a small town with few opportunities got in the way. Kids got in the way. Health problems and bills got in the way. Life, in general, got in the way.

My mom died without having seen or done as much as she could have and should have. She certainly wanted to have more and better experiences, she just didn’t manage to get there in time.

It breaks my heart to know that her story is a common one. I don’t want it to be my story, too.

To her credit, my mom did eventually get out. She moved out of the house she bought with my dad, and went to live with a sister. I wish she’d done it sooner, so she could’ve experienced more freedom. A few months after she separated from my dad, my mom died at the age of 42. That same day, my dad received the divorce papers in the mail.

Basically, at a young age life came at me hard – and I became hyperaware that life is fragile (I’m not going to live forever!) and wasted potential can lead to some of life’s greatest regrets. Making jumps can be scary, but if you stay where you are forever you’ll never know where you can go.

All this leads up to me resolving, at some point, to live as intentionally as possible. I need to be able to work from anywhere, because I want to see everything I can before I die. I want to meet fellow travelers, eat weird food, bask on beaches and cross as many items off of my bucket list as I can before I actually kick that proverbial bucket. The photo collage at my funeral is gonna be siiiiiick!

Next stop: San Francisco!

A photo posted by Kari D. (@karidephillips) on

But in order for me to have these things, I need to design my life a certain way.

Enter workationing. With the exception of about two years of my professional career, I’ve always worked from home and workationed, but never really defined it. I travel a lot for conferences, client events, business meetings and just for funsies, and occasionally I take employees with me. My team has workationed in San Diego, Puerto Rico, the Dominican Republic and Mexico (twice). It’s kind of embedded in our company culture at this point.

For a variety of reasons, a few years ago I started seriously considering how I would go about taking a year-long working abroad trip. In the last year, I’ve worked from 10 different countries, the longest of which was a 2-month stint in Europe. I didn’t want to come back from that trip.

It’s taken me a while to build my life up to the point where I think it can handle such an extended adventure. Four years later here I am, about ready to do it. But getting to this place hasn’t been easy.

Here’s the thing: traveling solo as a female in her mid-to-late 27s seems dangerous, and personally I’m not that into it. I’m not necessarily worried I’m going to get kidnapped and sold into sex slavery, but there are a variety of potential risks that are greatly mitigated by traveling with a companion you trust. And that’s not exactly something I felt comfortable Tindering.

Here’s the other thing: not everyone can work from anywhere. In scrolling through my mental Rolodex of potential people I could con into coming on this adventure with me, the list was short. VERY SHORT.

This list was so small it only contained one name, and she’s an employee. Sure, Kelly’s also my friend, but in my life business always comes first and I didn’t (and don’t!) want to jeopardize our working relationship. 

When I first approached Kelly with this idea for an extended workation, I wanted to do it in a way that wouldn’t scare her off. On the surface, it’s weird that an employer would be like, “Hey, nice job on that blog post…want to run around the world with me for a year?”

At the same time, Kelly and I have been friends for years – before I even started TCF – and we’ve already workationed together in Mexico and the Dominican Republic. We’ve always sort of clicked on that “insta besties” level that rarely happens but when it does, you know you’ve got a friend for life. Weird or not, I was going to ask her if she wanted to come with me. 

I mean, how could I not? Look at this queen.

Fuck your beauty standards.

A photo posted by Kelly Chase (@kell_of_the_brawl) on

The big ask was about to happen during a call on July 31st, and I couldn’t even explain the full concept to Kelly before YAS GIRL YAAAASSSS came out of the other side of Skype. She’d been thinking the exact same thing, and also hadn’t figured out the travel companion side of the puzzle – we were facing the same problem, and were each other’s solution.

Kelly, on our Skype call.

We gave it a few days, and a few weeks, and occasionally asked one another if we were “still in.” After a month of nothing but answers in the affirmative, we started mapping out our workation adventure.

As I’m writing this, it’s October 23rd – almost three months since Kelly and I decided to go on an extended workation together. Screw five years. A lot can change in three months, and a lot has. Namely:

  • 2 cats have been rehomed
  • 1.5 homes have been moved out of (working on my other half next week)
  • 1 boyfriend has been broken up with
  • Lots of furniture has been put on Craigslist and Facebook
  • 2 storage facilities have been rented
  • Many tears and at least 3 panic attacks (so far)
  • 2 plane tickets to Puerto Rico have been purchased (leaving 1/1/17)
  • 1 month in an Airbnb in Aguada has been booked, for all of January
  • Holy shit, we’re really doing this

I keep telling myself that progress is often painful. As I’m going through the process of untethering my life so that I can live the way that I want to, there have been times where the progress has been excruciating. I’m 20% sure I’m making some sort of horrible mistake, but 80% sure I’m about to have the time of my life.

#currentmood #skydeck

A photo posted by Kari D. (@karidephillips) on

There are definite risks associated with untethering your life and becoming a digital nomad. But for me, the greatest risk is wasted potential. It’s a lesson my mom learned the hard way, and I don’t intend to.

I’d be lying if I said I wasn’t absolutely terrified. I am, and Kelly is too – but all big jumps are scary. Pushing through that fear is how you know the reward is worth the risk. At the very least, I’m going to come out of this with a few killer stories to tell at cocktail parties.

There’s nothing fearless about me or Kelly – trust me when I say there’s a lot of fear here. But right now, I wouldn’t have it any other way.

Side note: having a friend to go through this with has made it all infinitely easier – hats off to you badass ladies who travel solo, because I don’t think I could do it. I hope to meet you on the road, so I can buy you a beer and celebrate your bravery.

A photo posted by Kari D. (@karidephillips) on

Why We’re Workationing(.com)

The purpose of this website is to document our workationing adventure, and show others how they, too, can untether their lives and travel the world – while accomplishing goals along the way. Workationing isn’t for everyone, but those who want it should know how to get access to it – Kelly and I are going to teach you how, as we learn how ourselves.

AND, we’re going to do this up classy. The term “digital nomad” conjures up all kinds of images in my mind – like crowded hostels, dirty clothes and lonely nights, filtered through the lens of low levels of productivity and next to zero accountability. Kelly and I have our own spin on how this going to work, and it’s going to be fun.

Each of us is always going to have our own bedroom and bathroom. Most of the places we’ll be staying are either within walking distance to a gorgeous beach, or have its own pool (OR TWO!). Our Airbnb wish lists are swanky and affordable, to the point where we’re nervous about whether they’re legit or not. Either way, we’re going to document the process and share our experiences with you.

My favorite part of this whole workation adventure is the fact that we’re going to goal our way around the world. Each location will have a work goal, a personal goal, and some items that we’ll be crossing off of our bucket lists.

Kelly and I are going to be tackling hairy business goals, learning how to surf and swimming with sharks…and that’s just the first month. We’re also going to do it all on a budget, which we’ll share with you and keep updated on an ongoing basis. Because, accountability.

Stay tuned and stay scared,


P.S. – If you’re interested in our story and what happens on our journey, check out The Workationing Podcast (subscribe and rate, and we’ll be your besties forever). If you don’t have iTunes, you can find us over at SoundCloud.

Turns out, we made it out of Aguada alive and Medellín, Colombia is next! Kelly and I talk about our adventures on the road, travel hacks, technical difficulties and the local flavor of each city we Workation at.

Update (February, 2019): I’ve now workationed on five continents, and have had some incredible adventures and experiences along the way. I’ve flown a plane over the Netherlands, cage dived with sharks in South Africa and swam in Puerto Rico’s bio bay…to name a few. And I’m nowhere near done yet.

You may also like

12 Things To Look For In An Airbnb

12 Things To Look For In An Airbnb

Ashley’s Workationing Story

Ashley’s Workationing Story
  1. Oh Kari, absolutely loved reading this!
    Your Mother would be so so proud of you, I know I’m proud of you! Have a fantastic time and be safe!

Comments are closed.

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}