I always wanted the laptop lifestyle where I could work from anywhere so long as I had a WiFi connection. I used to sit at a desk job and dream of the day when I could get on a plane without asking my boss for permission. I couldn't wait to bust out of there and start traveling.

I've had this life since I quit my job to pursue my business full-time about four years ago, and now that I travel more than ever for work and pleasure, I'm starting to realize the laptop lifestyle isn't for everyone. The truth is everything has it's downsides and there's always a trade-off.

There is no semblance of a "normal" routine.

If you're the type of person who works better when they have structure and routine, then the laptop lifestyle definitely isn't for you.

For example, I'm flying out to Nashville next week because I've always wanted to check it out. This doesn't mean that I just don't work while I'm there. On the contrary, I'm working from airports, I'm working while I'm in flight and I'll likely have some coworking sessions with a friend I'm staying with. In other words, I'll be sneaking in work while I explore Music City.

This is pretty much the exact opposite of what we're typically told travel looks like. "Normal" people save up their vacation time and then travel while enjoying some time off. That notion doesn't even exist when you run a business from your laptop.

The good news is "normal" is relative. Normal looks different for different people. My normal happens to be booking free flights with credit card points and working from anywhere at strange hours.

You may suffer from a paradox of choice.

A paradox of choice is the inability to make a decision because you have too many options. It's kind of like when you go to the drug store and see 50 different options for toothpaste. How on earth are you supposed to choose just one?

Admittedly, this is totally a first world problem, but it's a problem none the less. In my case, I'm having difficulty deciding where I want to live and lay my roots for the rest of my life. Because of this, I'm pretty much a vagabond for now as I explore new places.

You need to be hyper-organized.

The first year that I was self-employed full-time, I went to eight different cities within the U.S. Some of it was for work, some of it was for family and some of it was just because I felt like it.

During this first year, I came to the harsh realization that I did not have the organizational skills or the systems in place to support this. I remember being on the road for two weeks and only having made $500 in business revenue that month. There was no way I could pay my bills with that.

This realization forced me to take a break from travel the following year so I could focus on setting a good foundation for my business. I needed to get hyper-organized and create systems.

Even though my business is doing much better now, I still need the ability to be hyper-organized when there's no such thing as a routine. Having a team and automated systems helps with this, but I still need to be ready to work at the drop of a hat if need be.

If organization and systems aren't your strong suit, then the laptop lifestyle may not be a good fit for you. That, or you need to hire people to teach you how to cultivate these skills.

It's still worth it.

Even though being able to work from anywhere has it's downsides, I still think it's worth it. I'd rather spend my money on experiences instead of things, and the freedom to travel while still being able to earn money is a privilege I've worked hard for. While this lifestyle may not be for everyone, it's definitely for me.

Published on: Mar 9, 2017
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