Last Updated on February 23, 2022 by Janine

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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.”

Do they make you feel duped?

I’ve been feeling duped by headlines like that for the past few months. Actually, I’ve been feeling this way ever since starting what I call my “digital nomad journey” last May.

Headlines like that one one (and the articles that come along with them) made me believe that creating an online business and living a location independent lifestyle was easy. They also made me feel like a failure because I have yet to achieve a “win” like that. They’re the reason that it has taken me nearly 10 months to even write anything about my digital nomad journey. And why it has taken me almost as long to realize that I’ve already passed the threshold from “location independent hopeful” to being a fully-minted, successful digital nomad… even though I don’t even have a palm tree mansion…or 10k days, weeks, or even months.

You see, this digital nomad lifestyle is messy, and confusing, and presents many challenges. It doesn’t happen overnight and it isn’t as easy as it looks on paper. Of course it isn’t! 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 on digital nomadism — 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.

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!

My goal in sharing this 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
  • Dreaming of Location Independence?

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      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 blog!), 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.


      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.


      Comparing your success to that of others is one of the pitfalls of a digital nomad lifestyle.

      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].


      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).

      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.


      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!).

      Time management is a crucial skill when it comes to leading a digital nomad lifestyle.

      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!


      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!

      What are YOUR biggest struggles as a digital nomad? Let me know in the comments maybe we can find a solution together!

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      Living a digital nomad lifestyle definitely isn't too good to be true. It's a dream to wake up every morning knowing you have the freedom to spend your time however you wish! However, as rewarding as this lifestyle is, it's not without challenges. These are some of the biggest challenges I faced in my first year as a digital nomad (and how to handle them). Surprisingly, none of them have to do with packing! Click through to learn more. #digitalnomad #locationindependent #workonline #travel