The 4 Things You Have to do to Stay Happy as a Digital Nomad

By Sean Ogle •  Updated: 09/20/19 •  10 min read

I’ve got news for you, working for yourself isn’t necessarily super glamorous.

In fact sometimes it straight up sucks.

And often it’s the most “digital nomad-y” moments that can be the hardest. Sure it looks great on instagram to be sipping cocktail while over looking the ocean in that super tropical destination.

But what you don’t see are the week of travel behind it, hours at your computer making up for lost time, and the stress that can come with work and travel.

There was a period of time a couple months ago where I didn’t have any substantial income come in for about two weeks.  During that time, I’d just booked a couple of plane tickets and then received two refunds for different products.

When nothing is coming in and a lot is going out, it’s very difficult not to let your mind run a little wild with what might be happening.

No matter how successful you become as an entrepreneur, there’s always this hint of doubt in the back of your mind that says “what if you never make any more sales?” “What if you can’t find any more clients?”. “How are you going to pay your bills?”

While these moments are becoming increasingly less common, it’s taken me three years to learn how to deal with the mental toll that takes.

So in today’s post I’m going to share some insights into how to be happy again and a proper attitude when you’ve embraced the digital nomad lifestyle.

#1) Digital Nomad Happiness: Understanding Stress

Being an entrepreneur allows me to live a much more rich and fulfilled life than I was before.  I’m able to travel more often and experience new cultures.  I’m able to see friends and meet new people much more often.  I can also take time out to really spend time doing the things I enjoy because of the type of business that I’ve created..ahem, golf.

That being said, for all of the joy that entrepreneurship brings, it also comes with an entirely new swarm of of pressure and stress.

If you’re working a 9 to 5 more often than not it doesn’t matter if you’re giving 110% effort or 50% effort.  You’re still going to get your paycheck, you’ll still have your benefits, and you’ll probably be eligible for that 3% raise at the end of the year.

As an entrepreneur, you have to pay self employment tax.  Your health insurance is covered by you, and if something breaks you don’t have an IT department to fix it.

You’re the boss, you’re in control, you deal with the consequences for better or worse.

While I’m extremely fortunate to do what I do, I’ve found there are certain things I need to do on a regular basis in order to stay happy as a lifestyle entrepreneur and digital nomad.

When I don’t do these things stress or anxiety often creeps up and gets the best of me for absolutely no reason.  So whether you’re currently working for yourself and are struggling with this, or you’re just getting going and want to put yourself in the best possible situation to succeed, listen closely as these are the things I’ve learned firsthand about staying happy.

Here are some posts to help with staying in a positive state of mind, while also continuing to get stuff done:

2) You Have to Have Someone(s) to Confide In

Simply due to the unending amount of uncertainty in your life (remember, this is a good thing), you still need to have people you can talk things out with.

Everyday I’m thinking of new strategies for marketing or products – your mind never stops running.

Sometimes things will work out beautifully and you’ll have a big win. The original Launch day for Location Rebel Academy was a HUGE win for me. Other times, something you spent a lot of time on doesn’t work out so well. For instance, the Hobby Hacking launch wasn’t quite what I’d hoped it would be.

If you don’t have people you can vent your frustrations, concerns, and successes to, it will stay bottled up forever, and you’ll constantly be questioning yourself.

One of the keys to happiness is having confidence in the direction you’re moving.  By having a close group of confidantes, you’re able to continually build that confidence regardless of whether or not something worked or didn’t.

How do you do this?

Beginning a mastermind group is one of the best decisions for my happiness I’ve ever made.  We set weekly goals and talk twice per week to help with accountability, mindset, and anything else related to our business.

Oh, and a few times a year we go really cool places together.

This post on mentorship also should give you some good insight into why having people like this around you is so important.

Digital Nomad Happiness: By following the steps in this post, I've been able to generally stay happy after 10 years as a digital nomad.

By following the steps in this post, I’ve been able to generally stay happy after 10 years as a digital nomad.

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3) You Have to Achieve Balance

Arguably the most difficult thing to do as a digital nomad is to find balance.  All too often I find myself bouncing back and forth between extremes.

One week I’ll be putting in 14 hour days hunkered down in front of my computer while hopped up on my free Starbucks refills.

The next I’ll be jetset flying all over Asia with barely enough time to open up my computer.

One week I’ll be completely paleo, others I’ll be a poster boy for McDonalds.

When your time becomes your own it becomes an increasingly difficult balancing act.

When you have a normal job, the balance is easier.  You work set hours, and then you get your own time back.  There’s a clear distinction between work and play.

For me personally it was also easier to maintain a healthy lifestyle at a day job.  I’d work out on my lunch break everyday because I was so excited to get out of the office.

Now there’s always something that needs to be done, and guess what happens? Yep, that mid-day exercise is right out the window.

So how do you achieve balance?

By recognizing you don’t have to have everything right now.  

In fact it takes some sacrifice.  After this most recent trip to Southern California and New York I reached a point where I wasn’t taking care of myself.  I noticed my work was suffering, and I wasn’t as happy as I normally am because I wasn’t achieving the lifestyle balance I needed.

So, how do you do this?

For me, I decided not to take a trip to Asia I was planning on in October (85% sure at least).  I streamlined some of my productivity systems like email management, and I started going to the gym every single day.

General healthy lifestyle habits are one of the first things to go as an entrepreneur.  But regardless of how business is going, good or bad, if you do these things on a regular basis, you’re going to feel great:

Seems pretty basic right? It is, but as I’m sure you know, it’s much easier said than done.
These posts should help you achieve this mindset:

4) You Have to Have Wins

Early on in your entrepreneurial career you’re going to get frustrated.  You’re going to doubt yourself.  You’re going to wonder if it really is possible to make it as a digital nomad.

In order to get past all of that stuff, you have to have consistent wins.  They don’t have to be big, but you have to have milestones both small and large that will show you that you’re on the right track.

Something as simple as getting your first comment, making your first dollar, or getting your first client inquiry are all huge milestones that when recognized, will give you the fuel you need to keep pushing forward.

So, how do you get wins?

Goal setting.  It’s as simple as that.  You can continue floating by, trying this and that and waiting for that big break, but if you aren’t consciously setting business and lifestyle goals for yourself, you’re dead in the water.

If you’re just starting out, create a habit of having 3 goals per week that will move your business forward.  I still do this, and use my mastermind group that I mentioned earlier to hold me accountable for it.

I call this the milestone mindset.

If you just have one big goal of making say $1ok a month and quitting your job, you’re going to get frustrated when it’s been 6 months and you still aren’t there.

However if you have dozens of smaller milestone goals, you’ll see the progress each week which will motivate you to keep going.

More Reading:

Finally, You Have to Actually Enjoy It

The best part about being a lifestyle entrepreneur is the lifestyle!  If you’re not taking time to enjoy everything you’ve worked so hard to achieve, then you’re simply not going to be happy.

I golf a few times a week. I go to happy hours.  I travel. I spend time with friends and family. I help others build their businesses.

I do all the stuff that makes me happy on a regular basis.

So continue to do those things, and remember to always keep this one thing in perspective:

Being a digital nomad is a privilege, not a right. Many people would kill to have this type of lifestyle, so work hard, never take it for granted, and help as many people as you can in the process.

If you do this, staying happy will be much easier over the long term.

Looking for More Help Starting a Digital Nomad Business?

Take a look at these posts:

Grab our free 6 day course all about how to start a lifestyle business.


Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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16 comments on "The 4 Things You Have to do to Stay Happy as a Digital Nomad"

  1. Liz says:

    Hi Sean!

    This is such a great point. Many of my 9-5 friends think it’s so great that I get to do whatever I want, without ever thinking about the fact that doing ‘whatever I want’ is tied into ‘how am I going to live.’
    As a beginner, for me, it’s more unstable than not.
    So what I try to do is remember that I made the choice to do this. When I start getting anxious, I take a step back and remind myself that I could have a 9-5 if I wanted to. I could quit my business right now and get a more comfortable life.
    But I consciously choose not to. I choose to do what I am doing right now.
    I choose to be a blogger and not a photographer. If I hate blogging, or designing websites, I can CHOOSE to do something else.
    It’s crease a sense of freedom in my mind that eliminates all of the anxiety. I know that I’m doing what I am doing by choice, and I have the freedom to change that choice whenever I want.
    I also do all of the above! I just wanted to add one more thing.


    1. Sean says:

      I think that’s an excellent point. The idea that you are the one choosing to do this, and at any given time you can choose to do something else. That freedom of knowing your in control is huge.

      Thanks for sharing!

  2. Hey Sean,

    “isn’t all unicorns and glitter.”

    I actually say “chocolate fountains and rainbow making machines,” but yours is definitely shorter and to the point.

    I agree with you, but then I disagree with you. I’ll give you a few examples to explain…

    Running out of money = Entrepreneurs should keep 6-12 months savings for rainy days. If people don’t have that they could at least be putting a little away per month to build it up.

    Getting stressed = Meditate
    No time to work out = Step one meter to the side and blast out some bodyweight exercises

    McDonalds poster boy = Superglue 90% of your mouth shut and drink smoothies through a straw

    The only reason I think like this is because I always like to have back-up plans. Stuff I can fall back on for anything. Sometimes I think if you plan properly and train your mind (as well as your body) you can overcome the negative things that come up.

    This is coming from someone who spent 2 years with mental fatigue, so I’ve came out of with a few tips.


  3. Financial Samurai says:

    I feel your pain.

    It’s sometimes so frustratingly slow. Just got to be patient and hope for the best.

    How’s the savings from going? This is what I worry about most vs a 9-5 job.

  4. Jeff Bronson says:

    The funny part is, when working for yourself and having all the time in the world, it’s easy to take twice as long to do something.

    Just like if we work full time, and have to get our own projects done with a few spare hours here and there, it’s almost easier than having the full day, which is easily wasted.

    I agree with Jamie Alexander’s comment of having a 6-12 month savings reserve, I’m actually working on a 2 year reserve to make the leap.

  5. Hey buddy, I love this post. It covers a lot of the thoughts I’m starting to experience as I leave my job next week.

    The taking care of yourself is SO important. I had an epiphany (I guess you could call it that) recently where I finally realized, after all these years, that without my health and taking care of myself I have nothing else. I’m not able to enjoy the people closest to me, do the things I enjoy, work on projects I enjoy working on, etc.

    Taking care of yourself so you can experience life is the foundation for everything. I realize this isn’t earth-shattering, it just all became very clear to me last week.

    Keep up the great work here!

  6. Darlene says:

    Hey Sean

    Some great tips there fur sure. I’ve been an entrepreneur in some form since 1991, sometimes full time, sometimes part time. I’d also add this:

    Ignore the nay sayers, and if that’s all your friends – find new ones! I’m totally serious. If you’re constantly surrounded by people telling you that you’re gonna fail and why it’s a far more likely possibility that you will.

  7. Elly Klein says:

    ‘It’s not all glitter and unicorns.’ Love it!

    I like Jamie Alexander’s, too. Mine usually goes like this: ‘It’s not all rainbows and lollipops.’

    Sean, I love your honesty, and found myself relating to – and chuckling over – a few of your struggles, including the importance of having a sounding board, finding balance and not letting your physical health go out the window. As an author-preneur, I totally feel ya. I wrote a similar post about the realities of this kind of lifestyle myself:

    I don’t have a lot of location freedom at the moment – that’s the plan for next year – but I do work for myself from home, and it can be tough-going.

    I really enjoy your blog. Keep up the great work!

  8. Kate says:

    OMG!!! I’m struggling with all the points you mentioned above! (an I’m not even a solopreneur boo oooh). 🙁

    I guess I have to stop, take a deep breath, concentrate and get organized and healthy.

    Btw: as I WOULD like to be a solopreeur (more like a freelancer to be able to travel loads and earn as I go), I thought of practicing translation (which I never studied for but I’m Italian mother tongue and been living in English speaking countries for nearly 10 years).

    What I wanted to say is that, as you are one of my favourite bloggers, I decided to translate one of your articles every day to get started with. Then I will see where all my practicing will take me. Hopefully to a freelance career that pays the bills, a confidant to discuss projects and deadlines with, a healthy body, completed goals and an enjoyable process 🙂

    As always: kee up the work! 🙂

  9. I’d love to have an IT department. I have too many ideas to implement too. Thanks for the reminder to take care of our health. I need to hit the gym or pavement on a more consistent basis too.

  10. Darby says:

    This is a great post, and is something that I really need to work on. I recently became a solopreneur (about 3 months ago) doing SEO consulting, and also a lot of small editing projects because they generate good cash flow. It’s going pretty well and I have a few clients, but I’m also doing 2 part-time jobs teaching English. Even though my schedule is pretty flexible, I feel overwhelmed because it’s very unpredictable and I have a hard time carving out time for exercise and eating well on a regular basis.

    I’m actually looking for some people to start a mastermind group. If anyone happens to be in Tokyo that’s great but I’m totally open to Skype masterminding. 🙂

  11. Joanne Munro says:

    I must have been really brave or really stupid when I went freelance as I took the leap without any savings at all! It actually worked out ok because generally most things do, and if you wait around until everything is perfect then your dreams will never happen. I just jumped and knew it would be fine one way or another.

    I work most of the time in the UK but sometimes work from abroad (France, Rome and Vegas so far) I’m a Virtual Assistant and a CV writer so both things are pretty location independent – especially the first one (clue is kinda in the name there!) However next year I’ve decided to try and work abroad a bit more to see how that goes.

    I’m planning on firstly going away to a European city for maybe 5 days every 6 weeks or so and taking my laptop with me. I will find out very quickly if I can actually carry on making the same living whilst not at home, if that goes well then I plan on doing maybe a 2 week stint, and if that works out then trying a month of working abroad.

    I’m lucky that I already have a good VA client base, I can do CV consultations on Skype, my outgoings are low, I have no dependants, and I already live in Europe. Still pretty scary but if I don’t give it a go then I’ll never know.

    And I can’t have that!

  12. Dude, love this! Thanks for your honesty about how working for yourself isn’t always as glamorous as it might seem and it’s actually an incredible struggle sometimes. I feel exactly the same, and brother, I’ve had stretches of 8 months where everything went wrong, I’ve had to spend my time on righting wrongs, doing the important work (that didn’t pay any money!) and I didn’t have any income coming in. Definitely, I’m so appreciative for the awesome people I’ve met along the way, the good friends I’ve made, the few who are there as partners and as support. Like you say, it’s so important having a few folks you can bounce ideas off of and stay in regular touch with to hold each other accountable and help each other out. It’s a long hard slog at times, but it’s always worthwhile. 😀

  13. Sean Smith says:

    After a long marketing career, the company laid off 20% of it’s staff, including me (their search marketing guy). And while I continue to hunt for a good job, articles like this one really helps me begin to see that the fear I feel at being unemployed for the first time and pondering making it on my own aren’t unique to me. I truly believe it’s not so much our monetary support, but that dark, unknowable fear of chaos in the future that cements our feet to the floor. You’re a real inspiration to this guy that never before pondered being his own boss (and being able to live overseas again!). More posts like this please! I’m one month into this new way of seeing my possibilities and the stress can get a bit much. You make it easier though.

    1. Joanne Munro says:

      Hi Sean,

      As a CV writer, I see a lot of people who are being made redundant and most of them are pretty worried about the future. But once they get a brilliant resume written and have a chat with someone about their options they start to feel excited about the possibilities instead.

      I understand that you must be concerned and anxious, but as long as you do your homework and research all your options, plan your next step, and map out how you can make it happen for you, then you’ve done all you can and nobody can ask more.

      Your work as a Marketing Consultant is perfect for location independence so it’s just the finer details you need to worry about. Go to sites like Freelance Folder and Freelance Switch and learn all you can about how to be a freelancer. My friend has just been made redundant for the 5th time so her ‘safe’ full-time job is actually far less stable than my freelance life.

      Sometimes (in fact always) redundancy turns out to be the best thing that ever happened to someone. You now finally get the push from the Cosmos to go live your dream. Cover your bases, do your research then go for it I say! Good luck.

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