Looking to Become a Digital Nomad-preneur? Don’t Commit These Blunders
Ethan Drower

The dream of many office dwellers is to shed their winter coats and boots, grab a laptop and flip-flops, and build a riches-producing business while sipping iced lattes on the beach somewhere.

As silly as that image can seem, it’s completely possible. Many have done it, and many more this year will embark on the journey in search of better beaches, cheaper standards of living, and, of course, that all-illusive million-dollar business idea.

Digital Nomad Entrepreneur Building a Lifestyle Business But don’t go putting in your 2-week notice just yet as building an online business while marauding around the globe isn’t nearly as glamorous (or easy) as social media would have you believe.

In my own experience of building CiteMed and “lifestyle” businesses while traveling for years, I’ve certainly made my share of mistakes and naive assumptions. In this article I want to share the common mistakes made by nomad-preneurs that either will drain your spirits or your bank account.

Assuming You Will Work Less than “Regular” Entrepreneurs

The internet will have you believing that financial freedom while nomading around is as simple as setting an e-commerce store with a clever logo, running some ads, and sitting back while the cash flows in.

Unfortunately for aspiring nomad-preneurs, the reality of the online business landscape is that it’s often more competitive than its brick-and-mortar counterpart. It often takes years to build a sustainable and profitable business that replaces your job income. Not weeks. This means that when you set out on your journey, it’s critical that you have the right expectations to avoid getting discouraged and throwing in the towel on month 3.

You may live on the beach but make no mistake — if you intend to build your financial freedom online, you will be working just as hard as anyone else. Hitting the road doesn’t automatically create shortcuts. So do the work and enjoy the process of building something that is entirely your own… while in the destinations of your dreams!

Trying to Outsource Your Entire Company for Pennies

At some point you will need to start hiring and building a team to help you grow your company. Part of this team can indeed be low-priced, offshore talent. However, it’s important to remember that hiring and managing remote contractors (especially lower skilled, cheaper ones) is a skill on its own. You cannot simply hire an army of contractors, hand them the logins to your site, and go take a vacation.

Take the time to research, speak to other digital entrepreneurs, and learn about the fine art of remote hiring and training. It will save you thousands of hours, and tens of thousands of dollars in wasted efforts by hiring the right folks with the right instructions at the right time.

Spending More Time Sharing Your Nomad Business Life on Instagram than Actually Building a Company

There is a constant pressure on newer nomad-entrepreneurs to showcase their newfound freedom and (implied) success that comes with it. We all want to be seen as heroes to our friends back home for coining it in while having the time of our lives abroad. However, far too often I see entrepreneurs on the road quickly turn into want-trepreneurs because they spend all their energy trying to appear successful on social media.

Don’t sweat the process, but embrace it! It’s ok to struggle with your business and still be in a great location. Not every weekend needs to turn into a photoshoot or live stream where you answer questions about “the nomad entrepreneur lifestyle”. Stay focused on your business and your goals and try not to over-compare or compete on social media.

Trying to Sell Online Courses on Subjects You Haven’t Mastered Yourself

There’s nothing wrong with creating and promoting online courses in areas you are passionate about or skilled in — emphasis on the “passionate and skilled” part here. An all-too-common route for a brand-new nomad-preneur is to fire up an online course platform of their choice and spit out an unstructured, thoughtless course on a random topic in the attempts at making a quick buck.

This is not only annoying to those of us that are trying to consciously build real, sustainable businesses, but also, it’s often completely dishonest and misleading to potential customers. I always advise aspiring entrepreneurs to take stock of their current skills, and what the market wants. If your current skills are viably sold to the marketplace, full speed ahead! If you might be lacking mastery, or experience, consider trying to make a go of it on your own before attempting to sell wisdom you haven’t quite earned yet.

Moving Cities Too Often

This is another classic, first-time nomad mistake. Most people are conditioned for “vacation mode” when they’re traveling. This means trying to see all the things, all the time. Trust me, this is exhausting and will leave you disenchanted with traveling after only a few months of whirlwind sightseeing.

My advice is to slow down and get to know a city and a culture for a few months before deciding to move on to the next. Trust me — there is plenty of time once you are off the clock (and off the grid) permanently.

Underestimating the Challenges of Living in New and Foreign Countries

Should you choose to set your sights on less developed nations and/or countries where you don’t have a masterful grasp on the local language (and you should!), be warned. A lot of the easy things we take for granted in more advanced western countries (internet connectivity, interactions with local government, going to hospitals, dealing with landlords) become anxiety-producing and mentally draining in foreign countries.

However, I’m not saying you should be discouraged. The challenges and differences of foreign cultures are what make the nomad experience so rich and educational. But don’t underestimate the possibility that you might lose an entire day or two of work because you accidentally drank the local water, or the entire island’s power went out. Embrace the mess, and always be ready to accommodate the unexpected stressful challenge.

Saying “YES” to Every Opportunity

With an online business starting to hum along and an expanding network of other traveling entrepreneur friends, your WhatsApp inbox will start to light up weekly with enticing invitations to go to new places and do fun new things. Many new nomad-preneurs dive headfirst into the onslaught of freedom-induced trips and events across the globe. Hooray! Except not always.

If you say “yes” to everything that comes your way as a completely autonomous digital entrepreneur, you will leave yourself with zero time to focus on growing and protecting the very thing that gave you that freedom: your business! It’s important to define for yourself how much time you want to spend focusing on work, and spending time relaxing on your own. Come up with some boundaries and try your best to stick to them.

Fear of missing out becomes a serious challenge for the nomadic digital entrepreneur, and the most successful ones find a way to systematically balance a lifestyle of adventure/travel/friends, with work/focus/rest. How much of a balance you choose will depend on your business goals, and personal preferences.

To Wrap It All Up

That is so exciting that you are ready to become a digital nomad-preneur! You can maximize success by avoiding some of the common mistakes that nomadic entrepreneurs commit. These include assuming you will work less than regular business owners, trying to outsource your entire company for pennies, and moving cities too often. Avoiding these pitfalls will help you ensure that you have the best experience possible as a traveling digital entrepreneur.


Ethan Drower is the Co-Founder and Operating Partner of CiteMed. A renowned business expert, Ethan educates others on the fundamentals of launching a successful software product, tips for aspiring entrepreneurs, and more. Twitter: @EthanDrower