It Won’t Happen Overnight

Don’t kid yourself.

Going from office-first to traveling while working remotely doesn’t happen overnight.

In fact, I spent the past 10 years perfecting the workation lifestyle.

Here’s how I took baby steps to acheive geography freedom:

Step 1 – Continental USA

In 2014, I accepted a great job opportunity that moved me across the country from Minnesota to Virginia.

I was newly divorced & eager for a fresh start but also very concerned about losing touch with my family & friends back in MN.

That’s why I negotiated with my employer for the ability to periodically travel back to MN for 3-4 weeks at a time.

I was the only one at our company doing this so I was very appreciative of their flexibility.

From 2014-2020, I took 2-3 workations each year in MN.

Step 2 – Non-continental USA

In May 2019, I achieved one of my biggest career goals:

👉 Having my own “real” office with a window!

However, I was also having these thoughts:

1. Taking 1 or 2 vacations each year wasn’t cutting it for the amount of travel I REALLY wanted to do.
2. A few months prior, my friend Beth passed away from ovarian cancer at age 42. We were the same age. While in hospice, she said her biggest regret was not traveling more. At that moment, it became very clear to me that tomorrow isn’t promised to any of us and I needed to take more action!
3. I had been periodically traveling back to MN & working remotely from there for the past 5 years so figured there was no reason I couldn’t push the envelope a little further related to traveling while working remotely.

Motivated by tragedy and the fear of similar regret on my deathbed, I started moving faster towards my dreams of travel!

I took my workation one step further by going outside the continental US. This time I headed to the Hawaiian islands of Oahu & Maui.

From my employer’s perspective, I just took a typical vacation – using 5 days of PTO.

But…

What they didn’t know was that I spent a good chunk of time thinking about & testing things out for remote working suitability.

After a week there, I concluded that there was absolutely nothing different about working remotely from Hawaii than working remotely from MN!

Step 3 – Outside the US – Central America

After my remote working success in Hawaii. I wanted to push the envelope a little more and do a dry run outside the US but in a similar time zone.

So…

In October 2019 (5 months after my Hawaii trip), I headed to Costa Rica, specifically Puerto Viejo de Talamanca on the Caribbean coast.

I heard Costa Rica was a pretty safe & well-developed country in Central America with lots of expats & digital nomads from the US. Therefore, I figured it would be a good destination for my first international workation test-run.

Similar to Hawaii, I took a typical 1-week vacation from work and used my time there to dry-run living there while working remotely.

During this trip, I uncovered a few things that required remediation when I got back to the States and/or special consideration for future workations:

1. VPN

   . One of my side businesses required downloading data from data providers and government entities back in the US. I found out I couldn’t access any of their websites from an IP address in Costa Rica. Therefore, I would need to use a VPN to get a US IP address if I wanted to do that work outside the US. As I would also find, VPNs are also very helpful in mitigating cybersecurity risk. My solution was to subscribe to NordVPN.

2. Two-factor Authentication

   . I did not have an international cell phone plan at the time so my iPhone with my US number was useless in Costa Rica. The biggest impact of this was that I couldn’t receive any 2-factor authentication codes when logging into my bank & investment accounts online. Luckily, this was only a 1-week vacation so logging into these accounts wasn’t 100% necessary. [SIDE NOTE: 2-factor authentication has become even more popular & important since 2019 – going beyond banking & investments and into social media accounts and online tools.] My solution for this was to find a US cellular service provider that supports wi-fi calling & texting when outside the US. I currently use the low cost carrier, Tello, for $5/mo.

3. Backup wi-fi

   . As any remote worker will tell you, reliable internet is crucial! Even though Costa Rica was a relatively developed country, I experienced internet outages at both the resort & at the local coworking space. My solution was to buy a global hotspot with both virtual & physical SIM capabilities. I found it on Amazon HERE. With this hotspot, I could pre-load the virtual SIM with enough data to ensure I had internet immediately upon landing in a new country and until I found a local, more affordable physical SIM to have internet back for the duration of my stay in that country.

4. Accommodations

   . While this was only a 1-week vacation, I learned that hotel-like accommodations are not suitable for longer-term workations of more than a week. As a traveling couple, we both couldn’t work comfortably & privately from our hotel room at the same time. We ended up rotating workspaces: our hotel room (quiet & private), the communal area at the resort (loud & not private), a lounge chair on the beach (sand & glare), & going to the coworking space in town (time-consuming & more expensive).

   The other reason hotels aren’t good for workations longer than a week is they lack kitchens for cooking your own meals. It turns out that it’s very time-consuming & expensive to eat all your meals from restaurants or cafes and it very much adds up after a week. Therefore, given all that… I came up with a new rule: stay only in vacation rentals with sufficient workspace and a kitchen unless it’s only for a week or less.

 Step 4 – Outside the US – Europe

After 5 months of ‘forced remote working’ due to the COVID pandemic, I had enough and pushed the remote working envelope one more time.

This time, I headed to Europe to spend at least 2 months in Croatia.

With backup internet, VPN, and 2-factor authentication sorted out and the knowledge on what to look for in accommodations. The biggest new issue I had to deal with in Croatia was the time zone difference.

Croatia was 6 hours ahead of the US east coast.

This meant I had to work 3pm to 10pm in Croatia to perfectly overlap with the business day in the US.

As it turned out…

I LOVED my work schedule from Croatia!!

I was able to wake up without an alarm, do a little independent work in the morning as I sip on a coffee, go for a hike in the mountains or a swim in the sea. Then buy some groceries or try a new restaurant for lunch, and then return to my apartment in the early afternoon to start my workday.

The only other issue I encountered in Croatia (which turned out to be relatively common all over the world) was getting fast & reliable internet when my accommodations were in a multi-unit building and the modem & router were not inside my unit. Internet signals struggled to penetrate thick concrete floors & walls. Luckily, I was able to resolve this issue by having my global hotspot for backup internet. Getting local data is usually very affordable. In Croatia, for example, I got a local, 1-month physical SIM card for my hotspot for around $10 USD and never ran out of data.

Conclusion

Starting with my trip to Croatia in 2020, I became a full-time traveler. I basically rotate around spending equal time in North America, Central America, and Europe while working remotely.

As you can see, though, my workation journey was a slow progression starting in 2014.

Transitioning from office-first to traveling while working remotely doesn’t happen overnight.

I’ve spent many years refining my workation craft and want to help so you don’t have to spend 10 years figuring it out too.

Want to take your first short workation before Summer arrives?

I’ll personally walk you through everything you need: getting approval at work, planning logistics, knowing the best things to do there…

ALL OF IT!

DM me and let’s talk!

Click Here to send us a message

 

[p.s. I might make a small commission on purchases made using the embedded links above. However, my actual use & opinion of these items is not affected by this small affiliate commission. I REALLY use this stuff!]