How to Pick Your First Remote Work Destination

I meet a lot of people who dream of the “work from anywhere” life but have no idea where to start. Their first question is often “how do you decide where to go first?”

The answer: the intersection of easy and dreamy.

Start with dreamy. When you daydream of that moment when you’re THERE, when all of the struggles of your current situation are a distant memory, where are you? For me, it was always an empty beach, whales breeching, gentle breeze. No phone buzzing, nowhere to be, nothing but time. What’s the fantasy in your mind’s eye that represents your “freedom”?

After taking a year to travel around the world in 2013, and deciding there was no way I was “going back”, I pitched my husband the “let’s keep going” idea. He was all for it and also at a total loss on how we would figure out remote work or get clients who didn’t care where we were located. Through creativity, tapping into our networks and some iteration (a subject for another post) we both found consulting jobs. The new challenge became where exactly would we be doing this remote work from?

We had spent our year crossing the Sahara by camelback, scuba diving in remote places such as the Solomon Islands and eating our way across Thailand. None of those locations sounded particularly easy for working with US based clients for the first time. So I did what I do best, I made a spreadsheet.

Decide What You’re Optimizing For

First, I listed out criteria for the ideal remote work location for us, such as:

· Time difference to our US-based clients

· Strong wifi

· Cost of living

· Surf conditions ;)

· Community/Friends

· Language (we are biased to a location where we could learn another language)

· Visa requirements/ entry or length of stay restrictions

· Weather/Seasonality

Brainstorm Dreamy Locations

We then brainstormed all the places we were excited about living in, which included Sayulita and Puerto Escondido, Mexico; Lisbon, Portugal; Bali, Indonesia; Costa Rica and Puerto Rico.

I then created a scoring system for each criteria, we scored each location, tallied it up and DING DING DING - Sayulita, Mexico scored highest. The funny part is that at the time I was feeling pretty meh on Sayulita. Who knew that 8 years later we would own property there and it would become our home base!

Your first few locations will come with plenty of new and unexpected challenges to work out, so I strongly suggest you choose a location that makes life as easy as possible. We chose Sayulita because it was an EASY place to start that met our criteria.

Here, the time difference is manageable, we have some friends and local contacts to shortcut us to valuable information, and the cost of living is low. Use your criteria for selecting a location that is easy, and your life will be a whole lot smoother. Give yourself the gift of having extra time and money to play, explore, to do things without stressing. Trust me.

What are your ideal location criteria? What activities or seasons do you want to optimize for? What would make it EASY for you?

Looking to make the LEAP but don’t know where to start? I can help. This is what I do.