Real Talk: Digital Nomad Life Is No Walk In The Park

Real Talk: Digital Nomad Life Is No Walk In The Park

Tips for newbies on how to manage your circumstances when things don’t go your way while traveling, as well as some advice on how to live your best digital nomad life!

I’ve been a self-proclaimed digital nomad for the past three months, and while I’ve been fortunate enough to travel to new places and have incredible experiences, I’ve also experienced the growing pains associated with transitioning into a new lifestyle.

Listen. I was never naïve enough to believe that the #digitalnomad life was going to be primarily comprised of me sipping my almond milk latte while typing away on my MacBook Pro in some quaint little café in the 14earrondissement in Paris. I’m an adult who understands that real life will not always imitate the images populating the work-life hashtag on Instagram. Nevertheless, what I didn’t expect was how difficult, albeit rewarding, this lifestyle can be.

Story Time

Let me take you back to three weeks ago when I was on The Big Island of Hawai’i. After flying for ten hours on an Internet-less plane across most of the United States and the Pacific Ocean, I finally checked into my Airbnb in Kona. The digs were pretty humble, but these days, I’m fine sleeping in a tent on someone’s roof as long as the location’s good and there’s Wi-Fi.

Being the true digital nomad that I am, I made it through the door, dropped my bags on the floor, and hopped on my phone to check some emails. That’s when I noticed that there was no Wi-Fi. I then checked the Airbnb listing in my previously read emails and the DIY welcome book on the coffee table, all of which claimed that there was. I even noticed a power box next to the TV that had a little green light flickering right next to the “wireless” symbol, but I was still unable to connect.

Two hours and a half dozen phone calls between my host and Time Warner Cable later, and it looks like I’m out of luck. No one knows why the Internet isn’t working, and all signs point to me having to go without it for the next four days.

I immediately ran through my list of options and ultimately decided to unpack, get some food, then head straight to a local café that had Wi-Fi to check in with a client. From there I decided to book another Airbnb that was listed as business traveler-friendly (Translation: the Wi-Fi connection there was strong as hell) and pushed on with my trip.


Welcome to digital nomad life. You’re constantly on the road, and unexpected obstacles will always come up. What it all comes down to is how you handle the obstacles thrown your way as you try to live your best life. But how do you navigate the, sometimes, rough terrain of this lifestyle?

Always have a plan “B.” And “C.” And “D.”

It’s always good to have a backup plan in case your travel arrangements fall through at the last minute. However, while most people focus on the logistics, it’s important to cover all your bases. I’m talking about doing the following: insuring your expensive equipment (i.e., your laptop, camera, and anything else you use daily and paid for with your firstborn); backing up your files using a reliable external hard drive; and stashing away a few extra dollars here and there for an emergency travel fund in case you miss a flight or need to book alternate accommodations.

Be transparent.

Initially, I was wary of letting my clients know when I was traveling. I wanted them to see me as someone who was always on the job and easy to access when needed. However, that approach only led to a string of apologies for not answering urgent emails because I was (a) asleep on an 8-hour flight; (b) taking an architecture tour of the Garden District in New Orleans; or (c) buying up all the soap, shea butter, and incense at the open-air market in Oakland.

It’s best to let your clients know what hours you will be available and give them a heads up as to when you will be offline completely before taking your series of trips. (Note: This includes clarifying deadlines to take into account any time zone differences.)

Be honest with yourself.

This lifestyle isn’t for the faint of heart! Focus your attention inward and be real as to whether or not working while traveling is feasible for someone like you. Furthermore, try to design a digital nomad lifestyle that fits your personality.

If you’re the type of person who tends to fall apart when your meticulously thought out plans fall through (don’t worry, I’ve been there too!), then perhaps becoming a full-time digital nomad isn’t your jam. You might want to look into working remotely and traveling only a week or two out of every month.

Let’s say that you’re the type of person who decides to go on that food tour of Montréal before you fly out in two days, rather than finishing up that project for a client that’s due tomorrow. If that’s the case, maybe you should re-think hopping from destination to destination every week and opt for a long-term housesitting job or vacation rental situation instead. Doing so will give you ample time to explore the city you’re in, and you won’t feel the need to prioritize your adventures over the job that’s helping you generate the income necessary to create those memories.

Last Word

Living the digital nomad life is what you make of it. I’ve had some incredible experiences and created some wonderful memories with some very cool people. However, like anything in life, it has its ups and downs. However, real talk: I wouldn’t trade the freedom and sense of adventure that comes with living this lifestyle for anything (except maybe several thousand frequent flyer miles).

 It's Okay to Hate It

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Finding Your Happiness. Takes Guts.

Finding Your Happiness. Takes Guts.