3 False Myths Of The Workationer Lifestyle

I recently went to Algarve and even more recently returned from Seychelles a couple weeks ago but literally haven’t found any time to write about either trip. You see one common mistake people often make when they see my instagram feed is that I don’t work much. In fact when I get asked “bro do you ever work” I chuckle a bit to myself. So I figured I would write a post on the realities and myths to being a workationer aka digital nomad.

1. Easy life

I won’t argue that living a workationer lifestyle isn’t glamorous, it absolutely is. Living a 3rd of the time in 5 star hotels and business class cabins is a dream come true but easy is the last word I would use to describe the lifestyle.

First, even being audacious enough to convince yourself that you could break with conformity and be able to pull off this lifestyle is a tough sell. But then comes the harder part, actually pull it off. Whether you have an online business or like me have a traditional business you have to be pretty confident of yourself that you can run a successful business while simultaneously running around the world because you will fail and then you will doubt yourself several times. You’ll win a little bit and then you’ll fail again and doubt again before you win. No question about it!

You see, there are many people online claiming that it’s easy to live this lifestyle but the truth is that many of these so called workationers aka digital nomads are broke or making money teaching online classes on how it’s so easy to be a digital nomad. Spend some time going through their social media pages and it’s obvious that they are marketers. So think about it, would they be able to sell a lot of their ebooks and/or courses if they honestly told their prospects how tough it was? Probably not. Now some of the less misleading digital nomads are usually in places like Thailand and Indonesia where the cost of living is dirt cheap so they can easily make the lifestyle work by doing odd jobs here and there and that may work for them but if you are reading my blog I doubt that that kind of lifestyle would appeal to you. No, you’re probably like me and understand that while money can’t buy happiness, it can buy 6 nights in an oceanfront villa at one of the best hotels in the world and that will absolutely inspire a big grin on our faces.

So, living a workationer lifestyle jetsetting around the world is incredibly tough to do and even tougher to maintain but if a stuttering first generation immigrant that dropped out of community college can do it, well then maybe I’m exaggerating the difficult level just a bit 🙂

2. You Hardly Work

It’s called a workation for a reason. Despite the misconceptions, living this kind of lifestyle and doing it properly requires tons and tons of work. I’m constantly working; in the airport, on a plane, at a fancy restaurant, in the pool, at the beach, and definitely in bed. Recently my amazing girlfriend and I sat down to have dinner at a high end hard-to-get-a-table sushi restaurant in Oslo and right when we were ordering I received a phone call from a potential new hire. I spent the next hour on a telephone interview while the sushi got cold and poor Eszti ate alone. You see while it was the evening time in Oslo it was still business hours back in Washington DC and the business world doesn’t care that I’m hoping from country to country. My competitors still want to eat me alive, my customers still need delicate handling, my staff still need me to be the foundation of our business and the new candidate still needed to be interviewed. It’s business as usual and in order for me to thrive and grow I have to act like it and most importantly work like it.

While most people work 8 hour days, workationers that are doing well are working around the clock and dealing with a whole host of issues like slow wifi, jet lag, time zone changes and a whole host of other things that ensure that we have to work harder just to be as effective.

And when I’m home for a brief 2 week period I aim to optimize my time at the office so it’s very common for me to spend 14-16 hours days 6 days a week working at the office doing everything I can to complete all the tasks that require my physical attention. In fact, one of my good friends started doing some consulting work for my insurance agency and after spending 2 weeks in my office told me “if only people knew just how hard you work”.

It’s work, and tough work but the reward is having freedoms to have an overwater bungalow in Maldives as an office for the week. So if you have to work twice as hard for the corner office, you have to work 10x as hard to get the bungalow.

3. You Can’t Work Effectively

I’m not going to lie to you, the first couple months I went full pledge workationer it was tough to focus. I was like the freshman in college, fresh out his mama house and just been exposed to a life of freedom.

I was partying, pool lounging and wasting a bunch of time but then reality set in as I expressed in myth #2 and I soon had to adjust (or get called to the principles office 😂) so I set out to organize and soon found out that I can be a heck of a lot more effective and efficient while working remotely.

Before going workationer I had multiple offices of my business yet I was physically in one location so I was already working remotely but it seemed easy because all my offices are on the same voip business phones so someone in one of my offices could easily call my extension and get me in the other office with ease. When I needed to have break out meeting I could easily make the drive to each of my offices and have face to face meeting so it was workable but I soon found out it was very inefficient.

Being all over the world and having to manage my offices and staff was going to be much harder so I searched out for tools, apps and software to make life easier and I found Slack Messenger and Zoom video conference. My two go-to apps that make my virtual self as, if not more productive and efficient than the static office version of myself.

The truth is that if you are dedicated to your career, you can definitely get a lot of work done and there are tons of tools and apps to help you do so.


Workationer/Blogger/Traveler/Digital Nomad.