To me, one of the most annoying things about working alone, working remotely, and being a "digital nomad" is how people idolize it like it's the most wonderful lifestyle business. It's not. Please, stop pretending it is.

Seriously, there are scads of videos on YouTube trying to lure poor saps into the big lie of "grab a laptop, book a one-way ticket to a tropical island paradise and live your best life working as a digital nomad."

Please, for everyone's sake, stop it with this madness! The whole premise is 95% garbage. For most of the past two and a half decades, I've been able to work entirely remotely. That means I have no dedicated office, and can essentially take my work with me wherever I go since I don't have any sort of headquarters or home base.

The "early days" when I first learned of the magic of being a digital nomad. Working remotely in Mobile, Alabama. (2008)

Working remotely can definitely can be cool...

This ability to "work from anywhere" is something I do appreciate for the most part. But over the years, I've seen a ridiculous amount of romanticizing of this lifestyle and it's really getting old.

Don't get me wrong, I'm not saying I don't appreciate that I can work just about anywhere with a wifi connection and my laptop, no matter the location, environment, or time zone. For the past decade, especially, I have spent many days or even weeks working from various coffee shops, co-working spaces, and hotel rooms all over the USA where my clients have absolutely no idea where I am, or even that I'm gone.

Working remotely from a coffee shop in Jersey City, New Jersey. I didn't tell anybody I left town. (2019)

I currently live in Arizona where it's relatively warm all year long. That's why I moved here. But before that, I lived in Colorado for 20 years, and for at least the past decade, my ability to work anywhere was a huge blessing. More than once, I saw on the news that a massive snowstorm was coming in a day or two, and I bought a plane ticket to Florida as fast as I could, then flew out there and weathered the storm in sunny paradise while my friends back home were shoveling snow, scraping windshields, and rubbing their frozen hands together to stay warm.

Working through dinner at "my office" at DIA airport in Denver, Colorado. It's hot, cramped, messy, stressful, and not ideal. (2022)

My ability to do this, while still remaining self-employed is my superpower. Nobody in my dad's generation had the ability to do this. They just didn't. The mere thought of something like this would have seemed outrageous. But because I can do my work with nothing but a computer and the internet, it matters not where I work. I love that. That is absolutely, positively one of my favorite things about being self-employed. Not only can I go just about anywhere I want, whenever I want, and keep working... I don't even have to ask permission since I'm self-employed and don't have a boss, or a human resources department, or bureaucratic red tape and paperwork to fill out.

I just go. Whenever I want. Wherever I want. That is glorious. But it's not as amazing as it sounds.

Over and over, on YouTube, Medium, Twitter, Facebook, and all the other social networks, I see a constant stream of people that idolize a lifestyle that is 100% movable, and 100% remote, 100% of the time. But let me tell you... that sucks. Nobody actually wants to live completely remotely, logging into random wireless access points at coffee shops in the far reaches of the world forever. It's fun for a while, but it's not a lifestyle.

Please, stop promoting this.

Working remotely on a random Monday afternoon in St. Augustine, Florida. Did any of my clients know where I was? Absolutely not! (2020)

I'm a married man with five kids and a wife. I could not possibly be a 100% digital nomad even if I wanted to. But because the restrictions on my career are so few, I could come very close if I really wanted to, and while there are times I'm sitting on the beach collecting seashells during business hours on a random Tuesday afternoon, let me tell you: it's not all it's cracked up to be. I've worked all over the place, including: Texas, Pennsylvania, California, South Dakota, Nevada, New Mexico, Utah, Louisiana, Alabama, Colorado, Oklahoma, Florida, and Yosemite National Park.

Do I like being able to hop on an airplane with no warning and disappear, and not have to take time off work in order to do it? Yes, absolutely. Is it great that nobody knows I'm even gone and doesn't even think to ask? Yes, for sure.

But is it luxurious? By no means.

Working remotely in a hotel in Phoenix, Arizona, in May 2020. Living out of a suitcase is lame.

Please keep the following in mind:

  • working remotely is still work.
  • working remotely is less than ideal.
  • working remotely often has complications like poor cell phone reception, spotty wifi, slow connections, and lots of interruptions.

When you're sitting at home, or at a dedicated office, you can often sit down for 5, 10, 0r even 15 hours and get a lot of work done. But when you're sitting in the airport in Denver, like I was a few weeks ago, during a layover, you can get work done at the airport bar. But it's a constant stream of activity that can look like a comedy of errors:

  • find a place with a wifi connection
  • get connected to wifi
  • realize you don't have a sufficient charge on your laptop and need to plug your laptop into a power outlet, but realize there aren't any near you
  • relocate to a seat that has a place to plug in
  • start working
  • realize you don't have enough money in your personal checking account to pay for your tab
  • whip out your phone and open your banking app, then deposit a check to pay yourself
  • make sure you're staying on top of the status of your flight so you don't miss it
  • try to work like a maniac while casually sipping a beer and making sure you eat something since you don't know the next time you're going to have a chance to get a solid meal
  • check the phone messages that have piled up when you were on the road or on the plane and decide which ones need a response
  • put on some noise-canceling headphones and try to get some work done
  • get a notification from your iPhone app that your flight is now boarding
  • close your laptop and start packing up so you can head to your gate before your flight leaves
  • realize that you are not going to be able to get any work done, since you'll be on a plane without wifi for the next four hours, and it will be midnight when you arrive at your destination and you're so tired from walking, driving, shuttling, and flying, and you're so jet-lagged that you finally give up and put everything away and just try to sleep on the flight or just watch a movie because your brain is fried

So far, my experience working on the road has only been in the USA. Some people might look at where I've been and say something like "Yeah, but you haven't even left your own country. It's more worthwhile if go somewhere 'exotic' like somewhere in another country." But I totally disagree: that only adds to the misery. Because then on top of that, you'd be adding all kinds of new variables, such as:

  • tropical diseases or issues with food poisoning or unfiltered water
  • immigration/visa issues
  • problems with exchange rates
  • potentially missing flights that are much harder to make up for
  • language barriers
  • etc.
Working on an Amtrak train somewhere in New Mexico. Note: there was NO wifi!

When I was a part-time opera singer, I spoke to a soloist who had made a full-time career out of singing opera professionally for multiple decades. I asked him what a life like that entailed. I thought it sounded kind of fun and glamorous, as he traveled all over the world doing his art. But his response actually surprised me.

"No, way, man... this life gets old really fast. No matter what country you're in, every hotel room looks exactly the same on the inside. And after a week or two, living out of a suitcase absolutely sucks and you just want to go home."

That was an excellent point, I thought.

Working until midnight in a hotel in Boulder, Colorado. (2022).

See what I mean? Being a "digital nomad," is quite similar to that.

In theory, it sounds incredible. It's something that people from my dad's and my grandpa's generation couldn't have even considered.

But in real life, it kind of sucks. You're living out of rolling luggage filled with dirty laundry, constantly chasing flights, constantly negotiating the bizarre phenomenon of changing time zones which will often screw up your phone calls and scheduled meetings no matter how prepared you think you are, and you're always battling the twin beasts of finding a solid wifi connection and finding a place to plug in and charge your gear.

Working late past 8:00 pm at my "other office" in Miami, Florida. (2022)

I've been a "digital semi-nomad" for a decade and a half. Sometimes, it's incredible and life-giving. Sometimes, it's really hard. And sometimes, it straight-up sucks. Please, let's all stop pretending it doesn't.