A lot has been said about the perks of digital nomad life. So much, that some have been accused of selling a dream.

While it certainly isn’t a nightmare, it’s time to take a more realistic look at digital nomadism. Life on the road is great and does guarantee some unforgettable experiences, but there are some drawbacks that can make this lifestyle a challenge.

Why this blogpost? First of all, I believe in a makeable world; one where there is a solution to every problem. The list you find below may serve as inspiration for professional problem-solvers: start-ups, established companies, and –dare I say it– governments.

Secondly, a list like this can be of great help to budding digital nomads. Rather than imagining a life of cocktails and push-button income, they see what working online while traveling is really about.

If you’re having office problems, I feel bad for you, son. I’ve got 99 problems, but a boss ain’t one.

As you will see, some problems are absolutely trivial, while others are tongue-in-cheek or simply won’t apply to you. That’s what crowdsourcing and editing a long list like this one does (credits at the bottom). Enjoy!

Work Challenges

1. Marketing yourself or your business on social media.
2. Having to explain to your parents that you run a real business.
3. Meeting so many ‘internet billionaires’ that you start wondering where you went wrong.
4. Creativity blocks.
5. Having to decide whether your new pithy idea goes on your personal blog, Facebook, the NomadList forum, or into a new Medium post.
6. Dealing with the stress of not having a steady income, especially for those who are only just starting out.
7. Dealing with the legal aspects of owning a business, especially when you are not in your country of residence.
8. Getting paid in another currency – agree on an amount and then see the exchange rate drop to the ground.
9. Promising a client you will deliver the first draft tomorrow, only to realize their tomorrow is in fact, your today.
10. That freelancer who is willing to do the same work as you for half your price.
11. Weeks without work can feel like a dream because you can focus on travelling, until you start inevitably questioning if you’ll ever get a gig again.
12. And once you do get commissions? Too many to take on.
13. Spending more time looking for work than actually working.
14. Clients who think it’s okay to pay you with referrals.

Work/travel balance (or lack thereof)

15. Temptations, temptations, temptations. Remembering work comes before play.
16. Needing to make a business Skype call pronto while the you’re at is playing Bob Marley’s Stir It Up.
17. Travelling makes it hard to work effectively.
18. Too bad we have to make money in the meantime. Damn that food and shelter crap needed for survival.
19. The urge to travel all the places you visit instead of working from those places.
20. Sometimes you work over 15 hours a day.
21. Finished your work and fancy sleeping in? Chances are that’s the day your phone will ring non-stop.
22. Having taken on too many projects only to realize it’s your last day in the country and you only got to explore the inside of the grocery store in front of your guest house.
23. Feel like drinking cocktails, but it’s only noon and you still have work to do.
24. A lack of routine, which is not necessarily a problem but it can deeply affect your work balance, not to mention your sleep schedule (especially when you are constantly facing jet lag).
25. You are your own boss. This is a problem when you procrastinate as much as possible until you look at your calendar and realize you haven’t done much in a while
26. Hearing other digital nomads arguing about which one of them is running a real business.

Tech Problems

27. Your MacBook has crashed and now you have to travel to the capital to get it fixed.
28. Your charger is dead and you’re in the middle of nowhere and that important deadline is tomorrow.
29. Having to decide which technology will be the most likely to actually work for an upcoming conference call or client meeting: Skype, Google Hangout, WebEx, Gotomeeting, Join.me, Teamviewer, Appear.in, etc.
30. CityMapper and Google Maps don’t work well in many cities. I’ve been lost in my apartment for three weeks. Google Maps doesn’t work well in most countries.
31. You had your computer and electronics insured but once something happens you realize you didn’t read that teeny, tiny text written at the bottom on white letters over a white background that mentions that it doesn’t cover them if you dropped it (or whatever it is that happened).
32. Typing foreign language characters on a regular keyboard is hard.
33. Not being able to work when it rains because it makes the wifi go down.
34. What? No 4G in this town?
35. Being stuck in cosmopolitan cities all the time because remote areas don’t do wifi.
36. Countries that make it hard to get a SIM card.
37. The everlasting search for stable connectivity.
38. Those expensive buses you take because they promise there is wifi on board. However, there is always a “problem” with it and “they apologize for the inconvenience”.

Travel Problems

Documents and Customs

39. When you are asked for proof of employment to get a visa.
40. Having a passport photo that makes you look like a criminal and makes the immigration folks look at you like they can’t decide whether to give you the stamp or put on the latex gloves.
41. Getting asked for an onwards ticket to board a plane. Chances are you don’t have one because the amount of freedom means never having a set plan
42. Visa rules that change constantly or are inconsistently applied. We bemoan the strictness of some countries’ visa policies, but inconsistency (and the often expected bribes at some borders) can get really annoying and drain your time and energy.
43. Having to guard your passport with your life.
44. When you’re filling out a form and they ask you for an address. It is completely unacceptable to state that you’re homeless, apparently.

Getting and Staying There

45. Time stuck in airports.
46. The infamous “chicken buses”, combis, colectivos, you name it – Realizing that comfortable buses are a luxury for a very small percentage of the world’s population.
47. Having to find accommodation everywhere we go.
48. When the apartment you booked looks completely different than the pictures shown on the website you booked through.
49. Jet lag.
50. Arranging gym access when you might be somewhere for a month or less is difficult. In a lot of places they want to charge an arm and a leg for short-term access.
51. Forgetting what seasons are.
52. Staying healthy and fit can be challenging as you have no time to undertake a sport and getting access to a gym can be hard when you’re not staying long enough. Plus, you are constantly trying all the foods from every country.
53. Wanting to do the groceries but finding out it is a national holiday.
54. Trying helplessly to avoid every scam you’ve ever heard of (e.g. the tea scam in China).
55. Climates, seasons and pollution. The cloud that hangs over Las Palmas (Gran Canaria) in July-August, the smoky season in Chiang Mai (February-May), Monsoon season in India, etc.

Cultural Differences

56. In some countries, finding out that ‘now’ doesn’t exactly mean ‘now now’ and that having a local appointment really can screw up your timetable.
57. Being woken up at 5 AM by some random rooster.
58. Forgetting that some things that are considered normal in your homeland aren’t in others (for example, kissing strangers on the cheek).
59. Occasional stomach cramps due to ever-changing food and spices.

Time Zones

60. It’s already beer o’clock in your previous time zone.
61. Having to calculate time zones so your mom doesn’t know you’re awake at 3 AM when you answer her emails.
62. Having to run from the bar for a Skype call to another timezone.

Money, Banks, Taxes

63. Constantly having to figure out how much “x” amount is in your currency to be able to tell if you’re being ripped off.
64. Changing currencies on a regular basis.
65. Bank fees.
66. Budgeting and more importantly, keeping up with your budget.
67. Still having to file taxes for the country in which you have citizenship.
68. High seasons, because prices for everything go up.

Relationships and Socializing

69. Loneliness!
70. Forgetting the last time you had a long-lasting relationship.
71. Your friends keep asking you when your gap year will be over.
72. When you don’t reply to your mom’s email in a week and she starts picturing all these awful scenarios. Her conclusion every time? You died.
73. When you meet your friends back at home, you realize that you can no longer relate to them due to different life experiences and it is hard to maintain a conversation with many of them.
74. You become somewhat unattached to people and even places because everything has become temporary.
75. Forgetting how to speak your native language.

Your Life –and Business– Inside a Backpack or Suitcase

76. Having no dress shoes to wear when you need to attend a formal event.
77. Suddenly realising that Facebook photos of you painfully point out your lack of a wardrobe.
78. Not being sure what to pack. Your plan is to spend 90% of the time in the Caribbean, but what if you get the opportunity to fly to Greenland?
79. Your gadget collection gets heavier and heavier.
80. Having to carry every kind of adaptor there is.
81. Constantly having to resist the urge to buy souvenirs or something nice you saw because you know that in the long run, it will only weigh you down.
82. Missing having your own working space which you can freely decorate.


83. The beer at home tastes better.
84. Missing your country’s cuisine.
85. Missing your momma’s comfort food.
86. Missing out on important events back home like weddings, funerals or the birth of your niece.
87. My friends are organising a party but it’s on another continent.
88. Visiting the ‘home country’ feels like doing a tour and the best way to visit your friends is to surf their couches.

Luxury Problems

It’s Not That Great All the Time

89. The uncertainty of the lifestyle.
90. Working at the beach sounds like a dream but in reality? not so great. The sun makes it hard to discern what’s on your screen, sand gets between your keys (and your eyes!), beach balls hit your head, the list goes on.
91. On many occasions, we are labeled as “bums” and we often have to explain ourselves that we aren’t wasting our lives or ruining our careers by traveling.

But Some Problems, We Are Glad to Have

92. Having to apply sunscreen before going to work.
93. Having difficulty to decide where to go next…Bali, Spain or Costa Rica?
94. The curse of the traveller – always thinking that there must be something more beautiful. But in the end, the beaches are beautiful everywhere in the world, it is the people that make it unforgettable.
95. Having to live in a serviced apartment and having no control over your own laundry as they do it for you.
96. Working while lying down makes your back hurt.
97. Spending the whole day in the pool/at the beach because it’s laundry day and you don’t have a shirt to wear.
98. Preparing for a swim when the electricity or wifi goes down and all you can do is relax.

It Happens to the Best of Us

99. Customs officers that search your bag ask if you always bring sex toys on holiday. (For example, in Thailand they are forbidden, but you can buy them on the markets.)

Let’s end on a high note

Despite all this, being invited to a trip the day before leaving and being able to say “yes” without even blinking; forgetting the use of excuses such as “I can’t go, I have a job to get to”; not having to deal with that dreadful commute to the office every morning; and being able to choose when we want to work and when we want to be outside and enjoy our ever-changing surroundings is pretty darn great.

I’d like to thank the following nomads for their input: Taylor BanksLodi PlantingElmar Haker, Fred Ngo, Martijn Reintjes, Marco Zamboni, Nina Danielle, Alex Rehmar, Damian Reigns, Amy Truong, Jonathan Baillie StrongChris BackeMarv & Jo Abisia, Tom Libelt, Gary Brown, Gary McCaffrey, Johannes Voelkner, Kate Hill, Fabian Es, Chane Steiner, Alex Rehmar, Danniela Ramos, and Björn Nomaam.

The crowdsourcing shouldn’t stop here, though. So let me and other readers know which problems you encountered or which ones you think you have found the solution to.