The 6 Biggest Challenges of the Digital Nomad Lifestyle
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Raise your hand if you’re sick of seeing articles titled “How I made 10k from my palm tree mansion on my first day of being a digital nomad.” Only if it was this easy. Below, I’ll provide my experience AND give you recommendations on how to get started on a similar journey so you can learn how to be a digital nomad.
How to Create a Digital Nomad Lifestyle for Yourself
While I’m technically a digital nomad living in Mexico in the Riviera Maya and earn money solely from working on my laptop, I’m very skeptical of these types of stories.
Actually, I’ve been feeling this way ever since I started my “digital nomad journey”. I started to reflect on the past 9 years of me living this type of life and I thought how I should provide my blueprint and steps as to how to be a digital nomad. This way, you’ll be able to learn more about what is involved in the Digital Nomad Lifestyle.
You see, this digital nomad lifestyle is messy, and confusing, and presents many challenges. It doesn’t happen overnight and it is most definitely is not as easy as it appears like on paper. When you give your entire life a makeover, it takes time. Even after doing this for a year, there is SO much that I don’t know how to do. I’m learning new things every single day and being confronted with new challenges every single day.
I’m not sharing this to be down how to be a digital nomad. I think it’s an amazing lifestyle and I have zero regrets about quitting my 9-5 to pursue location independence. Literally zero. The only thing I regret is not doing it sooner!
I’m writing this because I think there are two sides to every story, and I know it would have made ME feel better back at the beginning to hear this one. Sure, the palm tree mansion version is more glamorous and sounds a lot sexier, but it’s also the easiest version to write. But for one, mansions aren’t all they are cracked up to be, especially in Mexico. Living in Mexico, has taught me to be one to blend in and not try to attract attention to yourself. It really comes from the conservative culture here. Living in an oversized home is the opposite of having a Digital Nomad Lifestyle.
It’s easy to share share and celebrate wins, but it can be uncomfortable and difficult to share struggles. It’s important to me to share this side of the story — this section of MY story, because the wins are SO much sweeter when I look back on the hard parts.
Even though I sometimes feel like a total amateur at this lifestyle for not having all the answers at any given moment, the truth is, I’ve had a lot of success and I have a lot to be proud of! And, I think you can do it also as long as you don’t give up on your goal.
My intent with this article is to remind you, whether you’re currently a digital nomad or planning to become one, that it’s important to celebrate ALL of your successes, even the little ones! Give yourself a gold star for every accomplishment — you deserve it! And always remember, the only way to fail is to quit. So never give up. As Marie Forleo would say, everything is figureoutable!
That said, here are some of the biggest struggles that come with this digital nomad lifestyle, and my best advice on how to handle them, based on my own experiences.
Related Reading:
- How To Quit Your Job and Move Abroad
- 7 Online Jobs That Actually Pay
- Is November the Best Month to Visit Mexico?
Digital Nomad Mindset
Your mindset will make or break you in your pursuit of your dream lifestyle. Up until recently I was proud to say that I had never read a self-help book. My mindset was great, thank you very much. Until, after someone mentioned “limiting beliefs” for the 8 millionth time, I decided to put some thought into it.
Holy crap do I have a lot of limiting beliefs! For months I thought I was just being kind of lazy about building my business (and my website), but I did some digging and it turns out that my perceived laziness is actually a side effect of a deeply ingrained (like, since childhood) belief that nobody could ever make money as a writer. So there I was binge-watching Club de Cuervos, lamenting how lazy I was for the 8th day in a row, while deep down my subconscious mind was saying “you’ll never make any money as a writer so, like, why bother?”
And of course there I was, not bothering.
Don’t be shy about mindset work. It is seriously important. Maybe your mindset is already great, and that’s fantastic news. You’ll probably be killing it as a digital nomad in no time!
But if you have doubts, worries, or blocks about anything, don’t be shy. Talk about them, journal about them, find a way to confront them and work through them. It will help you immensely!
There are tons of people, books, and other resources out there to help you with this, but if I can make one suggestion, it would be to read You Are A Badass by Jen Sincero. It is the perfect intro to self-help books for those of us who don’t need read self-help books.
Comparison-itis and How to Avoid it
Comparing yourself to others is a great way to feel like crap about yourself (ie. palm tree mansion posts and feelings of despair). It’s way too easy to look at someone with a pretty Instagram feed or the perfect, most cohesive website, and think “dang, she’s way better at this than I am.” Or worse, it could make you think “dang, I’m way better at this than she is,” which will make you feel even more awful for judging someone you don’t even know. Avoid it at all costs. Your journey will be unlike anyone else’s.
DO NOT COMPARE.

We’re all in our own realities. The other people you see on the internet, they’re dealing with their own demons, fears, mindset issues, financial struggles, whatever it is… everyone has something.
I know you already know this, but social media is not always an accurate representation of reality. Focus on yourself and your goals. You’ll be happier, more productive, and more successful.
And always remember, there’s room out there for every single one of us to be successful in whatever way we dream. [graphic about other people’s success].
Marketing Yourself and Creating Your Brand
Knowing how to market yourself is understandably critical to your success online.
Imagine this: you put all your time and energy into coming up with awesome service packages, branding, and building a beautiful website that your future clients are totally going to love. And then you find yourself sitting there wondering “but like… how do I find a client?”
Not ideal. Trust me, I’ve been there.
Then, once I realized I needed to learn some marketing principles I promptly became overwhelmed by all these people out there on the internet telling me what I was doing wrong and what I should do instead to get clients (usually starting with buying their course). This led to complete paralysis in growth (at least for me).
The best pieces of advice I’ve heard related to accomplishing goals is this: Lots of individuals will and are going to tell you that you’re doing things wrong, or what steps you should actually be taking to reach your goals. But ask yourself, “is this unsolicited advice from someone that has actually achieved the goal that you’re trying to accomplish?”
You’ll notice that 99% of the people who give you unsolicited advice haven’t accomplished what you have and for that reason, learn how to tune them out.
Marketing is essential to your online business, but it doesn’t have to be a huge, impossible obstacle (which is how it felt to me). You just need a few ideas about how you plan to get yourself in front of the people you want to work with.
Start by figuring out who they are, then figure out where they are, then engage with them. It can be as simple or as difficult as you want it to be. And, if your first attempts don’t work, adjust and try again.
Naturally, I set my marketing to MAX difficulty, because where’s the fun in doing things the easy way?!
Shiny Object Syndrome
This is a toughie. Everywhere on the internet there are people yelling at you to “download this freebie,” or “participate in my challenge,” or “opt-in to my email course.”
It kind of feels like going to a crowded street market where all the vendors are yelling at you. You get so anxiety ridden that you either leave and curl up in the fetal position, or, you feel guilty and try something from every single vendor just to make sure you weren’t missing out on anything!
The same is true of the internet — everyone has an offer for you.
Stay focused and steer clear of the freebies.
Don’t get me wrong, some of them are actually super helpful, but the majority of them are a waste of your time because they aren’t helping with what you actually NEED help with. How many free Instagram challenges do you think you need to do? How much of a role does Instagram even play in your overall marketing strategy? Do you even have an Instagram account? If not, you probably don’t need the email course.
That said, some freebies ARE awesome and can absolutely help you. This is why it’s critical to have a business and marketing strategy in mind. If you know what your immediate goals are, you’ll be able to filter out the offers that don’t make sense for you.
ONLY DO THINGS THAT SERVE YOUR IMMEDIATE GOALS!
If your goal is to get clear on your mindset, overcome your limiting beliefs and kick ass in your business, definitely take part in a mindset challenge. But say NO THANKS to someone else’s Instagram email course because it’s not serving your mindset goal and will only distract you (and possibly create even more anxiety/FOMO).
Focus is important when you’re starting out online and you’ll get where you want to go much faster if you can cut through all the extra noise.
Time Management
Time management is a really critical skill to have when you’re pursuing a digital nomad lifestyle. Some people are very good at it, while other of us could use some work.
It’s very important to set deadlines for yourself, and I don’t mean with client work (that’s a given — always deliver client work on time, or early!).

When you’re your own boss it’s really easy to put off the tasks you don’t really enjoy (umm, accounting!), but these are often some of the most important tasks in your business. Set deadlines for business related tasks to ensure that you make progress on your to-do list. If you continually say “I’ll do it later” the next thing you know a year will pass and you still won’t have made progress.
That said, it’s also important to be flexible. Sometimes you might be too stressed, or too tired, or maybe you just want to go to the beach. It’s okay to be flexible with yourself, and allow yourself to fully live your life! After all, that’s why you chose this lifestyle in the first place! Don’t forget to live it up just because you haven’t, say, scheduled your Tweets for the week. The Tweets can wait!
Location
Anyone who lives this lifestyle will likely agree that the location independent designation is followed by an enormous asterisk. Like it or not, as soon as you choose this lifestyle, you are taking your commitment to your wifi connection to the next level. In the beginning you might think “oh, me and wifi, we’re totally chill, I can do whatever I want in my free time and it’s cool.” Until the ONE time wifi doesn’t text you back, and you’re running around like a dog that’s never been off-leash at the beach before, just trying to find ONE bar.
Orrrr maybe that’s just me.
The point is, you can’t really run an online business without wifi. And, while I highly recommend taking breaks from wifi on occasion, your quality of life will likely be a lot better if you have a reliable connect…ion.
These are important lessons to learn, and the sooner the better.
Always remember, your success is not dependent on whether or not you live in a palm tree mansion. It doesn’t matter whether you have $10k months, or you’ve only been to 2 countries, or if you’re not even sure what to name your business.
YOU get to define your version of success. It might not look like anyone else’s and that’s totally fine! Maybe your version is staying home with your baby, or never having to wear slacks again, or selling all your stuff and living in a tiny house. Or maybe it IS making boatloads of money and living in a palm tree mansion (there’s nothing wrong with that at all)!
When you’re clear on your vision it is SO much easier to block out all the noise and chase your goals.
But don’t forget that when you’re in pursuit of something you’ve never done before there are bound to be struggles, blocks, and fears. Don’t be afraid to admit that you’re struggling. It’s normal to get hung up on things, face self doubt or face imposter syndrome.
You might feel frustrated because things aren’t progressing as quickly as you thought they would, or be afraid to raise your rates and actually charge a reasonable price for your services in fears that you’ll never sign a client. All of these feelings are normal, and you are SO NOT ALONE in any of them.
Always give yourself credit for your accomplishments, no matter how tiny they might seem. Pitched a client on Upwork? Congratulations! Posted on Instagram? Amazing! Rewrote your website copy? You’re unstoppable!
Sometimes the best way to get past a roadblock is to ask for help, so don’t be afraid to reach out to someone else who has been in your shoes. A quick pep talk might be all you need to push through!

How to be a digital nomad in Mexico FAQs
Here is what you will need to live the digital nomad lifestyle
What is required to be a digital nomad?
To be a digital nomad, you need the following:
A remote job or freelance work that can be done online.
Reliable internet access for communication and work.
A durable and new laptop or device necessary for your work.
A flexible mindset to adapt to new environments and cultures.
Basic budgeting skills to manage finances while traveling.
Travel insurance for health and safety.
A plan for accommodation, whether it’s short-term rentals, hostels, or co-living spaces.
Knowledge of visa requirements for different countries.
A network or community of fellow digital nomads for support and resources.
What jobs qualify as a digital nomad?

Jobs that qualify as a digital nomad include:
Freelance writing
Graphic design
Web development
Social media management
Virtual assistance
Online tutoring or teaching
Digital marketing
Content creation (blogging, vlogging)
Software development
Remote customer support
Data entry
SEO specialist
Affiliate marketing
Consulting
E-commerce management
Are digital nomads allowed in the Mexico?
Yes, digital nomads are allowed in Mexico. In fact, many digital nomads already reside in Mexico, especially in areas close to the beach and in Mexico City as well.
What exactly do digital nomads do?
Digital nomads work remotely, often traveling to different locations while maintaining their careers. They typically engage in jobs that allow for flexible work hours and locations, such as freelance writing, graphic design, programming, consulting, and online marketing. Their lifestyle allows them to explore new places while continuing to earn an income.





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What a breath of fresh air! Loved this post <3 thank you
Glad you liked it Kim. Thanks for your comment!
Hey Janine,
As a digital nomad of 5-6 years I can let you know there is a deep dark side and a whole host of issues that you haven’t even touched on. However saying that this lifestyle can reward you in ways that are simply not possible in a 9-5 role or that may take a lifetime to achieve.
I have been embarisingly blessed but I am now hanging up the backpack and this year is my last year of travel. Funnily enough it looks like I will be settling in playa del Carmen (it’s a toss up between there & Turkey ha!) so if you are around we can grab a beer 🙂 otherwise you will catch me in my place in Wales 😉
Keep on fighting keyboard warrior ??
Regs
James
Hey James,
Thanks for your comment. Six years is a long time to be on the road1 I’m sure there are many obstacles I have yet to face in my DN journey.
I’ve recently moved on from Playa– the tourist scene was too much for me, but it’s a beautiful place none the less. I hope you enjoy it.