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Escaping Corporate America During a Pandemic

Do you have a dream, that when you reached it, it just was’nt what it was cracked up to be?

Since I was in college studying accounting, my dream was to have an office with a window and “real” walls to hang my diploma next to a picture of the nighttime skyline of Minneapolis.

Unfortunately, after achieving those goals 20 years later, I realized they weren’t as fulfilling as I thought they would be.

So, a couple years ago, I started planning my escape from corporate America.

I wanted to start a new chapter in my life that was full of travel with just enough work to support my travelling lifestyle.

Life in 2019

In the hopes of making this escape a reality, I started reading blogs and watching YouTube videos from full-time travellers.  I also spent a lot of time researching places around the world and understanding the various costs of living.

My two biggest concerns were:

#1 My career

I wanted to keep my current “brick-and-mortar” job, but transition it to 100% remote so that I could do it from anywhere.

Since my current employer was not very amenable to remote work arrangements, I knew I needed to have a backup plan in case they said no to my request to work remotely.

Therefore, I addressed my finances (see #2 below) in case I had to quit my current job and either find a new job that was 100% remote job or take some time off unpaid like a sabbatical or mini-retirement.

#2 My finances

Addressing the financial aspect was pretty straightforward to me – I had to increase my savings.  So, I made two major moves:

  • I sold as many of my possessions as I could and put the proceeds into a savings account.
  • I significantly changed my lifestyle and monthly spending habits so I could put more money into my savings account each month.

Pushing Boundaries

By February 2020, I decided I had enough money in the bank in the event I was out of work for a while.

Also in February, I did something I didn’t think I could do…

I hiked down to the bottom of the Grand Canyon, across the bottom, and then back up to the top – ALL IN ONE DAY!

It was during this hike that I came to the conclusion that I needed to take REAL action on my travel dreams so I set a target date of April 1st to ask my employer about making my job fully remote.

Kristie all packed and ready

The Arrival of COVID-19

As everyone knows, the COVID-19 pandemic struck in mid-March 2020 – about two weeks after my big hike in the Grand Canyon, and about two weeks before I was going to request to work fully remotely.

Like many other companies, we closed our office and sent all of our employees home to work remotely.

Deciding to hold off on making my job change request for a bit, I focused on not putting to much pressure on myself. The world was so unstable and I wanted to see how things with this virus played out.

So, for the remainder of March and all of April and May, I continued to successfully work remotely from home.

During those ten weeks of working remotely, I realized a couple things:

  • Our company seamlessly transitioned to remote working, barely missing a beat.
  • As a leader in Customer Success at our company, I observed similar successes in remote working among all our customers.

It didn’t take me long to recognize that remote working actually works and it was absolutely going to be the future of work.

In fact, most of my colleagues (me included) raved about how much they enjoyed working from home.  Many realized the value of being more independent and autonomous when they had more freedom and flexibility around where and when they work.

This got me thinking:

“We just spent several months proving we can work remotely (thanks to the pandemic), so why couldn’t we work remotely from somewhere amazing?”

Early June 2020, there was no end in sight for returning to the office so I decide the time was right to email to my leadership about making my job permanently and 100% remote.

Wheels in Motion

My direct leadership was immediately very supportive of my request.

However, it took a few weeks before I heard back from senior leadership – which came in the form of a meeting invite for the next day, a Friday afternoon at 4:00 pm.

While we often joke about people getting fired on Friday afternoons, I had a weird feeling this might not be joke…

When the meeting time arrived, the COO started off the conversation by asking me to take a couple deep breaths because this wasn’t going to be an easy conversation.


The boss then told me they decided to eliminate my position in the company and I had two options. I could:

1) Sign a separation agreement and take a severance package or

2) Accept a newly-created position in the company that was 100% remote. This new position was nearly identical to my current position but came with a significantly smaller salary.

I asked for the weekend to think about it, which he totally understood and agreed.

It was a Saturday morning when I woke up and my decision was crystal clear: I was going to go for it, separate and take the severance package for these key reasons:

  • A strong feeling that a higher purpose was intervening with this situation and pointing me in the direction of my travel dreams.
  • I didn’t really have to worry about money (at least for a while) since I had just spent the past year or so building up my savings. It was also comforting getting a severance package too.
  • For more personal and ethical reasons, and perhaps a dash of egocentricity, I was somewhat offended that my employer basically offered me the same position. But with a lot less pay. In my mind, I felt like; if I accepted that “new” position, I was basically saying I had been overcompensated the whole time. I was too stubborn to accept that suggestion! ????

In the end, I signed the separation agreement and my last day was July 31, 2020.

FREEDOM & Uncertainty

A feeling of freedom and a degree of uncertainty was present, I had no idea what I was going to do for work, but with enough in savings to travel for a while, I decided I would just figure it out as I go!

In mid-August, with my belongings in a storage unit, I boarded a flight to Serbia to start my next chapter!

Shortly after arriving in Serbia, I started a travel blog to document my travels and share my experience with others. If interested, please check out A Path To Travel.

Enjoying different cultures

One Year Later…

I’m happy to report that I’m still a full-time traveller and living out my dreams in different places around the world – typically staying for one to three months at a time.

Over the past year, I’ve been blessed to travel to Serbia, Croatia, Montenegro, Bosnia & Herzegovina, Italy, Hungary, Turkey, Mexico, and the United States.

With the combination of advancements in technology and the growing acceptance towards remote working in the corporate world. More and more opportunities are opening up for corporate professionals to travel and live wherever they choose while working online.

Therefore, I started a private online community with the sole purpose of helping corporate executives figure out how to travel while working remotely. Not for a weekend but for extended periods of time so they don’t have to sacrifice their careers.

Kristy living and working on a yacht

Oh Yes! and then this happened… “me living and working from a Yacht in Croatia”!!

Global Accommodations

One of the biggest pain points I’ve encountered during this past year of travel has been finding suitable accommodations for my husband and I around the world.

It is such a time-consuming process!

My husband and I both work remotely. He runs a real estate investment company and I manage my travel blog and online community, so we need two comfortable workspaces with reliable internet.

We’re also not luxury travellers but we’re not on a shoestring budget either. We look for places to live and work that are safe, clean, comfortable, have the creature comforts we want, and offer good value for the price.

As such, we spend a lot of time researching and verifying potential accommodations. Spening so much time scouring property listing descriptions online, pictures, and reviews. We also sometimes message and communicate with the hosts if something isn’t clear.

Before we commit to an accommodation (especially if it’s a monthly stay), we need to be sure it meets all our needs and can comfortably support the two of us working remotely.

Because of this time-consuming (and somewhat risky) process, I was super excited to learn about Nomad Stays.

Nomad Stays has such a great approach to helping digital nomads (like us) find accommodations. They basically help you find your accommodations first which then determines where you are going to travel next.

It’s a brilliant time saving concept and perfect for digital nomads who can travel and work from anywhere but have specific needs and wants from their accommodations. It saves time and money, Their point of difference is that they are fit for purpose with 100%, Wifi, Afforable and best value for money, Convenience and you can book instantly. They partner with the tourism industry rather than compete. Nomad Stays hand pick their Stays making sure they have a strong relationship the the members and the Stay owners and coworkings spaces near the stays. It’s a no brainer!

Now in 62 countries around the world they aim to be the goto for digital nomads and the future of travel.

See other blogs on this topic: 15 Amazing nomad hotels

Finally, putting it all together

Throughout my travels and jumping into entrepreneurship head first I realised I was so much more capable than I realised. Travelling to other countries while exploring the world in such uncertain times just highlighted the opportunities that are out there.

As I continue on my journey through change I also realised nothing stays the same and that’s ok because I am willing and able to adapt and change. I hope you enjoyed my story and if it resonates then please connect, I would love to hear from you.

In closing, if you want to learn more about our community, please check out Executive Remote Worker and Sign up now to join the waitlist for when we re-open the doors again in January 2022!

With Love – The executive remote worker!

Kristie guest blogger profile photo

Hi, I am Kristie the founder of The Executive Remote Worker. I am currently living and working in Mexico.

“I am passionate about helping corporate executives figure out how to travel and work remotely for extended periods of time without sacrificing their careers in order to live a more free and independent life.”- Kristie Sullivan, founder

Connect with me

If you have any questions or are interested in connecting with me, please feel free to email me at or find me on LinkedIn.

You can also follow me on my travel blog, and/or check out my private online community

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