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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