What Is A Workationer? 

Okay so most of us know what a jetsetter is but a workationer? Hmm that’s a term that many may not have come across although you could kind of get the idea, but let’s dig a bit deeper  shall we?

A true workationer is the 2017 version of a nomad, a digital nomad if you will, a wanderer that has no static place he or she would call home. This new version of a nomad isn’t wandering looking for better pastures, instead they are traveling in search of new experiences while performing tasks that generate revenue; a job. There are those that travel from place to place finding gigs in different cities but if you want to be considered a true bonafide workationer than your revenue generating duties travel along with you and you can generally perform these tasks via the Internet.

“If you are  even smarter you’ll head over to Thailand where your 6 figure salary would afford you the lifestyle of royalty.

You can be a business owner or even employed by a company that lets you work remotely therefore workationers decide to take the show on the road. I mean why the hell not? If you are gonna have the freedom to work remotely than why don’t you truly become remote? Think about it, I mean even if you didn’t want to travel weekly or monthly for that matter, you could still take your Manhattan income and go buy a home in the carribean and live there while working for your Manhattan firm that lets you work remotely. If you are  even smarter you’ll head over to Thailand where your 6 figure salary would afford you the lifestyle of royalty.

As for me, I travel approximately 250k miles per year and I’m home in Washington DC for no more than 2 weeks out of the month. I figured out a couple of years ago that my physical presence in the office had  more of a symbolic value than it did have a true added value to my duties in the company. As a matter of fact once I began workationing I was surprised to realize that I was getting more substantive work completed and the most significant reason was that I was able to complete tasks unabated. When I’m in the office I can’t sit down for 10 minutes without someone having a question and/or needing something from me which in most cases they already had the solution or answer to but they are just so attracted to bouncing these thing of of me. It flatters me to know that my team has that level of confidence in me however it does come with some negative consequences.

The frequent interruptions stagnate my work flow thus it takes me longer to complete tasks or stay focused. The opposite is true while I’m out of the office on a workation, I have very few interruptions and perform shorter bursts of work intense work. Instead of a straight 8 hours of average energy and attention, I spend about 2 hours of centralized focus and high energy spats of productivity before I go to a massage or jet skiing and come back for another hour or so of another burst of highly productive work. It’s the old adage of working ON your business instead of IN your business. The numbers don’t lie, my business has seen substantial growth as my frequent flyer mileage increases.


It takes a lot of work to be this chill. I had no other reason to use bold letters in the previous sentence other than to emphasize the fact that IT TAKES A LOT OF WORK. especially in the beginning, when you decide to untether yourself and begin to transition to develop your digital workation lifestyle, it’s gonna be tough. The fact that you have your toes dipped in white powdery beach sand won’t help you retain that valuable customer that just emailed you a contract termination request, or just because you are watching the sunset from your ocean view private pool villa that doesn’t mean that you are immune to the daily shit storm that arise from running a business and managing employees. Shit still happens, I’m just sipping a pinna colada when I’m putting out the fire.

In fact it takes a lot more work to workstation. You sometimes have to work at odd hours to be up during business hours of your local time zone. You have to be very organized and create good processes and infrastructure that will enable you to sustain while on the go. In short, it ain’t easy, but if it was easy then everyone would be doing it.

“I predict that workationing will become more and more common as people free themselves of ideology that one must be at a designated place of work to earn a living”

Although it makes all the sense in the world most people just don’t get it and so I’m frequently asked this pesky and annoying question, “do you ever work?” primarily because people see me constantly traveling and they just can’t grasp at the simple logic of what I do. As if first class tickets buy themselves and hotels are just handing out free 5 star overwater villas. Questions like that and the puzzled look people get when I explain to them what I do confirms that we are still a long way before workationing becomes a mainstream phenomena however I predict that workationing will become more and more common as people free themselves of ideology that one must be at a designated place of work to earn a living.

The more people understand and embrace the powers of the Internet and wireless technology and all the other advances that are allowing us to unplug ourselves yet stay connected, the more Instagram pictures we will see of someone floating in a pool on a donut with a laptop on deck.


Workationer/Blogger/Traveler/Digital Nomad.