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Digital Nomad for a Decade: 33 Lessons Learned About Life and Business

by Sean Ogle | Last Updated: August 30, 2021

Last week I was sitting in the lobby of the Hoxton Hotel in London, settling into answer some emails after a crazy two weeks of traveling.

Normally I’m pretty good at getting work done on the road, but this trip with my wife and various friends through Paris, London, and Amsterdam had taken its toll on me.

Each night we were checking off boxes on our very weird quest to go to the top 100 bars in the world (58!), and each day we’d be sightseeing and walking 10+ miles around the city.

It was one of the first real vacations I’ve had in years.

The impetus was because it was my sister Courtney’s birthday, and was going to Europe for the first time. So with a little planning, my wife and I decided to join her on the trip!

Only catch was, she didn’t know we were coming ūüôā

The surprise went off without a hitch, and we spent a week in Paris with family and friends exploring a city I’d never experienced before.

Courtney and Sean at Eiffel Tower

My sister and I in Paris after surprising her for her birthday.

But while I was sitting down during that 90 minute stretch on a Wednesday morning in London, I noticed something.

The date.

May 8th, 2019.

Random day in May, right?

Well actually, that day in particular holds a lot of significance for me.

Why?

Because it marked the 10 years anniversary of me starting this blog.

10.

Years.

I’ve had a lot of pivotal moments throughout the years.

But with the exception of getting married, starting this blog may have been the single most important thing I’ve ever done.

Simply put, had I not done it, the chances are good that none of those things above would have happened.

Fun fact about me, I’m one of the most nostalgic people you’ll ever meet.

So in one of the few sessions to actually get work done on this trip, I found myself mostly just soaking in everything around me.

Hoxton Hotel London

Sitting in the Hoxton Hotel in London on my 10 year blogiversary.

Where I’ve been, how I got here, and where I’d like to go.

Digital Nomad Lifestyle: What I’ve Learned

Today I’m going to share some of the most important lessons I’ve learned in the decade that I’ve been building online businesses.

I’m also going to throw in a few photos and stories from the trip and my travels, because well, even after all of these years travel and adventure is still at the core of our brand.

So without further ado, here are some of the most important lessons I’ve learned in 10 years as a digital nomad, blogger, and lifestyle entrepreneur.

If video is more you’re thing, here’s the vlog I shot for it while I was in Paris:

1) Remember: Preparation + Luck + ??? = Opportunity

They say luck plus preparation equals opportunity.

I’d add one more part to that equation: luck + preparation +¬†readiness = opportunity

I think that we all get half a dozen or so big chances, big breaks, and big opportunities in life that can be life altering.

Moving to Thailand to work with Dan was a big one for me.

I prepared myself to be in that situation. I got a little bit lucky. And the opportunity presented myself.

But it wouldn’t have meant anything if I wasn’t¬†ready and willing¬†to take a leap.

Always be on the lookout for those rare golden opportunities, and then be willing to take a little bit of a leap, and act.

Because those are the things that can truly facilitate great positive change.

2) A morning routine can work wonders…but only if you have a plan

I’ve never had much of a problem with waking up early.

My problem is knowing what to do with my time.

Waking up early doesn’t mean much if you don’t have a plan. I can easily spend an hour in bed on social media, watch some You Tube videos, and before I know it, it’s¬†10 am¬†and I’ve got nothing to show for it.

But if you know exactly what you’re going to do the night before, and you have a plan – you’ve discovered one of the secrets to a productive and happy life.

My current morning routine consists of:

Sometimes breakfast or exercise is thrown in there, but knowing that as soon as I get up,¬†those¬†are the things I’m going to do has helped both my productivity levels and my happiness levels sky rocket.

If you struggle with this, check out 31 Things You Can Add to Your Morning Routine to Increase Productivity.

3) A key secret to business success is “play”

At least once a week I’ll take an entire afternoon off to go golf. And my business is better for it.

How?

Because play is one of the most important components to business success.

Doing things I enjoy on a regular basis gets me away from my computer, allows me to remember¬†why¬†this lifestyle is so beneficial in the first place, and gets me refocused and more excited to go back to work when I’m done.

It also helps me stay sane, reduce overwhelm, and generally help to keep me a happy person.

4) It doesn’t have to be difficult to be worthwhile

Recently I was listening to a podcast and this quote came up:

“It doesn’t have to be difficult to be worthwhile” and man did that strike a chord with me.

None of the businesses I’ve created have been difficult or elaborate.

I’m not solving extremely complex problems with crazy technical solutions.

I simply solve a basic problem or fulfilled a need, and consistently put in the effort every single week over a long period of time.

Consistency¬†is the key to success, and you don’t need to try and save the world with your business idea. Just solve one small problem, for one small group of people, and do it consistently, and you can have a massively profitable business.

5) Everyone should have a blog

Starting a blog changed my life. Plain and simple.

It’s the single most valuable thing I’ve done, as if I hadn’t of started Location 180 (what this blog was called at the time), I never would have met the people or followed the path I’ve gone down.

Here are 56 reasons why I think starting a blog is so valuable.

Here’s exactly how to do it.

And read chapter 3 in this book, for more insight on how I was able to leverage the blog in the early days.

6) It’s important to have a quest.

I’ve found this to be true for so many reasons. Having long term goals and something to work towards can give you purpose, fulfillment, and it can make travel so much more beneficial and rewarding.

Right now I have three quests:

So often tourists who don’t have much of an agenda visit cities and just go see the postcard sights – without¬†really¬†being invested or caring much about them.

As I’ve experienced more golf courses, I’ve been able to study and educate myself about various aspects of golf and course architecture.

The Old Course Hotel at St. Andrews at Sunrise.

Sunrise on the most famous golf course in the world last October: St. Andrews.

I’ve experienced some of the best cocktails in the world, and with every city I visit I seek out bars on this list, or other highly rated cocktail bars.

It adds structure to my travel, while also boosting my IQ in each of those fields with which I have a passion.

Having a quest adds purpose and an extra sense of accomplishment to everything you do.

Le Syndicat Paris MWA

This drink at Le Syndicat in Paris is called M.W.A. It uses only French spirits, and was themed around Disneyland. There is cotton candy flavored helium in the balloon that changes the way the drink tastes, and then makes you sound like, well, Mickey.

7) Experiences trump things.

Simple and true.

I spent 22 pounds on this Martini at Connaught Bar (the 4th best bar in the world).

They brought it out on a trolley and gave me my choice of 7 different “tinctures” that added a unique flavor to the drink.

The famous Connaught Martini

The famous Connaught Martini

I flew on one of the most decadent and extravagant flights in the world.

I lived on a tropical island, and visited Cuba to smoke a cigar.

All of these things cost money, but made memories I wouldn’t trade for anything.

8) Don’t be afraid to spend money on things that bring you joy.

Echoing the point above, don’t be afraid to spend money on things that bring you joy.

I’ve learned that everyone has their thing.

A lot of people think I’m insane for spending $500 to play a round of golf at Pebble Beach.

But I loved every second of it.

My buddy Dan and I on the 7th at Pebble Beach.

My buddy Dan and I on the 7th at Pebble Beach.

Regardless of whether or not it’s an experience or a material item, if it truly brings you joy, buy it – and don’t feel guilty about it. Life is too short for that.

And who knows, when you drop $500 on that round of golf, or whatever your equivalent is, you might have a chance meeting like this:

Steph Curry at Pebble Beach

Let’s try and forget about the fact he is pummeling my Blazers right now…

9) There’s usually a way to get 90% of the value for 10% of the cost

So often we fall into a trap of saying “when I do this,¬†then¬†I can do this.” Or in more specific terms, you might say something like “When I make a million dollars, I can drive a Ferrari.”

Or “when I get that big promotion,¬†then¬†I’ll take that truly exotic vacation I’d always wanted.”

There are a¬†lot¬†of lessons we can glean from statements such as those, but for the purposes of this point, I just want to say, you don’t have to be rich to do most of those things.

I’d always wanted to drive a Ferrari. For a hundred bucks I got a few laps in a 360 Modena.

Crossing "Drive a Ferrari" off the bucket list

Crossing “Drive a Ferrari” off the bucket list

90% of the value (much less than) 10% of the price.

My Suites class flight. Retail value: $10,455.

Cost me about $300 in fees and a bunch of miles that I was able to get from a single credit card sign up.

In that case, it was 100% of the value, 3% of the price.

My golf quest is another great example. Recently I played a course that has an initiation well into six figures. Monthly dues are over $2k.

How much did it cost me to play?

$100 for the caddie, my greens fees were comped due to my golf blog.

I was treated like a member for a day, got to have the same incredible experience that their members did, but I did it for next to nothing.

Or there was this week, courtesy of Lexus:

So remember, if you have a hobby or something you love to do, but don’t think you can do it until you’ve “made it” – start getting more creative.

We teach you how to do this in our “Make Money Blogging” course inside the Academy.

10) Focus on the micro, not the macro

These days with the current political climate and so much negativity in the news – it can be all too easy to let the “macro” run your life, your mood, and your happiness.

It’s easy to get caught up on headlines about trade, the environment, and our current administration, but if you really think about it, on a day to day basis, how much do these things¬†actually¬†effect you.

Very little – as long as you don’t let them.

Focusing on the micro, rather than the macro will allow you to give more energy to the things that are most directly relevant to you and your life.

11) You can have anything, but not everything

Pretty simple concept that can be tough to grasp. If you want something bad enough, chances are, you can probably have it. But, what are you willing to give up in order to have it?

I talk all about this in my 31st birthday post a few years back.

12) You don’t have to be an expert. You just have to be a relative expert.

Do you think most guitar teachers are as good as Jimi Hendrix?

Does your tennis pro beat Roger Federer on a regular basis?

Of course not.

It’s easy to get sucked into thinking that before you can provide a service or teach someone, you have to be an expert.

You don’t. You just have to be an expert¬†relative¬†to the person your teaching.

Am I the world’s greatest guitar player? Not even close. But could I teach someone how to play a few basic chords? Absolutely.

Expertise isn’t necessarily important. Relative expertise is.

13) There’s no such thing as too many hobbies

If there’s one piece of advice I’d give to kids right now, it’s this:

Do more things.

I’ve¬†always¬†had a lot of hobbies: tennis, skiing, guitar, rock climbing, golf, travel – the list goes on.

I like to do a lot of things, and while I’m not amazing at any of those – I’m pretty good at them all. Good enough that I can enjoy them or hang with people much better than me.

Not only can they help in social and business situations, but many help keep me in shape, provide stress relief, and allow me not to get bored with life.

So if there’s something you’ve wanted to try – go out and do it! You never know, it may turn into the passion you never know you had.

14) I owe a lot of my best traits to tennis

I grew up playing competitive tennis. I know, not exactly the most “digital nomad” friendly hobby.

I played most days after school, tournaments on the weekends, and with a lot of the adult members at the tennis club I played at.

Doing this, taught me so many life skills.

Sportsmanship, composure under pressure, manners, how to talk to adults or people more successful than me – the list goes on.

I’m not¬†exactly¬†sure what the lesson for you is with this one, but as I’ve made the transition to playing golf and talked with younger golfers, I see them learning the same skills I learned as a kid – and I think they’re incredibly valuable.

15) Don’t grow for growth’s sake

As an entrepreneur, the rhetoric is almost always the same:

GROW!

SCALE!

HUSTLE!

GO BIG OR GO HOME!

And I think that kind of motivation is great; you should always be trying to make yourself and your business better.

But, it’s also important not to grow for growth’s sake.

For instance, for years my business had been at about the same size.

You could call it a plateau:

Or you could call it recognizing my priorities.

My life is great. I have everything I need, and all the free time to enjoy those hobbies I mentioned above.

So here’s a question:

Would you rather have a $300,000/year business with two part-time employees, relatively little stress, and lots of free time?

Or would you rather have a $3 million/year business with ten employees, 60 hour work weeks, much more stress, and an extra $100k a year profit for you personally?

For me, I’d choose the former. Sure, it’d be nice to have a little extra money, and the ego boost of saying I have a seven-figureHow to Get Anything You Want in Life (The Complete Guide) business – but my lifestyle is much more important than that.

Don’t be afraid to¬†not¬†actively be trying to scale your business if you have it in a place you’re happy with.

Not enough people talk about that.

16) …But also don’t be complacent

I think there’s truth in the saying “if you’re not growing, you’re dying.”

So if you’re not actively trying to scale your business, make sure you are growing in other ways.

Updating your content and services, focusing on your personal goals or health, creating experiences that enrich your life.

Whatever it may be, try to be as aware as you can of what you want, why you want it, and how to get there without being complacent.

17) You can’t do it alone. But more importantly, you wouldn’t want to.

It’s easy to think that being a “solopreneur” means doing everything by yourself.

The reality couldn’t be farther from the truth.

We all need help. Whether it helps with work, help with accountability, help with mentorship – whatever it is, don’t fool yourself into thinking you can or should do¬†everything¬†on your own.

Plus, it’s way more fun when you get to create things with other people.

18) In a digital world, analog wins

These days the art of the personal touch has all but disappeared.

In a digital world where our day to day lives revolve around smart phones and computers – we rarely see the personal attention to things that have the power to truly surprise and delight someone.

Send an unexpected gift.

Write a hand written letter, and mail it. 

Make a phone call rather than sending an email or a text.

In a digital world, it’s often the people who go analog that win.

19) Learn to recognize when a decision is ego based

Recently I found myself debating whether or not to go to a conference.

It was expensive, ten times more than I’d ever spent to go to an event.

I certainly would have gotten some value out of it. Who knows, maybe a ton of value of out of that would have far exceeded the cost.

A handful of my most successful friends were going as well.

As I debated attending, I came to a realization.

My main motivation for wanting to go,¬†wasn’t¬†because I thought it would truly help the business.

It was so that I could be included in that group of successful friends, and receive a big ego boost.

That’s the¬†wrong¬†reason to do¬†anything.

Anytime you’re considering buying or investing something, try to be real with yourself, is it because it truly brings you joy (#8) or is it simply a way to boost your ego?

20) There’s a very significant difference between can’t and won’t

Everyone has excuses. Way too many of them.

I wish more people would take ownership of their life, and stop blaming their own faults or inactions on outside circumstances.

I wish I were better about it, as well.

It’s not that you “can’t” go to the gym after work because of _______.

It’s that you “won’t” find a way to go to the gym despite _______.

There is always a solution. If you truly want to do something you’ll find a way.

And one of the best ways to start making progress in this regard is, to be honest with yourself and change your language.

Instead of saying I “can’t” do this, say I “won’t” do this.

My guess is once you start phrasing things that way, the I “won’t” will quickly transfer to I “wills.”

21) Music makes everything better

Seriously. Happy, sad, angry, motivated, lazy – you name it, music is a powerful thing for any emotion.

Get Spotify and listen to your weekly discover playlist or any number of the daily playlists it creates for you.

I’ve discovered¬†so much¬†new music lately.

As a digital nomad, this has always been one of the few ways I’ve been able to have consistency no matter where in the world I am.

22) Write everyday

If you want to grow as a person and grow your business, write every day.

Simple, yet true.

Struggle with getting going? Start with this post.

Don’t think of yourself as a writer? Watch this:

23) Read everyday

Same thing as above. The most successful people I know write every day and read at least 20 minutes every day.

I could include a cliche quote about the benefits of reading, but you already know it’s good for you.

If you’re not excited to read, it’s probably because the book isn’t good enough. Move onto something else until you find something that grabs you.

24) If there’s one habit you build, it’s the “default action.”

How many times do you find yourself finishing, and then running into a death spiral of social media and You Tube videos?

It used to happen to me all the time.

This is why it’s so important to have a “default task.”

The one task you always default to when you don’t know what to do.

It could be something like answering emails. Or it could be something to get you refocused, like doing 20 pushups or jumping jacks.

But it’s important to have a productive default task to keep you from those spirals of unproductively.

25) Habits Will Make or Break You

When you have a day job, some habits are forced upon you. Showing up at the same time for work everyday. Hitting certain deadlines that you know will get done no matter what.

Going to the gym everyday on your lunch break, to escape the monotony of everything else.

But when you start working for yourself, your routine changes. You lose the accountability of your boss, and having to show up everyday.

And if you’re not careful? That will be the end of you.

Positive habits will help you thrive, negative habits can quickly spiral into a giant heap of un-productivity.

Do yourself a favor, implement these 5 strategies for building a habit – and then buy Atomic Habits. You won’t regret it.

26) Treat life as a privilege, not an entitlement

I’ve been fortunate enough to have been living a pretty flexible lifestyle for the last 9.5 years. But I try to remind myself every day that I’m the exception – not the rule.

This lifestyle is a privilege, and it can disappear at any time if I take it for granted, become complacent, or don’t keep moving forward (#16).

So never treat it as thought you’re entitled to it. You’re not. Work hard, be humble, and good things will happen.

27) I can see why so many writers become alcoholics

I’m going to let you in on a little secret about being a solopreneur…

And no, it’s not that I’m an alcoholic.

But the secret is that as a solopreneur, you can end up with a lot of time.

You’re by yourself with no one to look over your shoulder or hold you accountable (why #17 and #25 are so important).

I often wake up early and finish my work early – as do many writers.

So if you finish work by 1 or 2 every day, and¬†don’t have hobbies¬†(#13) or a plan – then quite frankly, you can find yourself getting, well…bored.

Which is why I can see how so many authors or writers have become alcoholics or turned to other negative behaviors over the course of history.

So the moral of the story here, is use your free time¬†wisely.¬†Have a plan for what to do with all of that time you’ve made for yourself and use it for productive things, rather than destructive things.

28) “Why Not” can be a powerful phrase

In relation to that point above about having a plan and doing more, remember that “why not” can be a powerful phrase.

“Want to travel all over the state and film a cool video about Location Rebel?”

Sure! Why not?!

“Oh, and want to blow up a desk at the end of it?”

Sure! Why Not.

“Want to come to Hong Kong to make your daily vlog more interesting?”

Sure! Why not?

See where I’m going with this?

29) Happiness wins

What’s the point to life?

To be happy. That’s it. As long as it doesn’t harm someone else, you should seek out the things that make you happy.

Working on your happiness is the single best thing you can do for every other aspect of your life.

Here’s how to be happy.

30) Travel

This is a huge part of my digital nomad lifestyle.

Plain and simple. More so than just about any thing in my life, my experiences traveling the world have been some of the most fulfilling, memorable, and worthwhile.

Do it more. Even if it’s just exploring some place in your home state.

Here are some more of my travel posts.

31) Be Nice

Here’s an embarrassing little fact about me. My senior year of high school I was voted “nicest guy” by my graduating class.

How’s that for the kiss of death? Or at least I thought it was at the time…

Now, I’ve been amazed at how powerful simply being nice is.

When I can have a positive interaction with someone, simply because I was nice, it makes me happier.

People who are nice, generally get more of the things they want. And while it may often be the assholes that become billionaires, I think one of the best ways to become successful on a smaller scale, is simply to be a nice person to be around and do nice things for others.

Will this be true for everyone? Maybe not, but it certainly has been for me.

32) Heredity can be overcome, but you’ll need to try harder

I get it; you’re not a morning person.

You’re not organized, or you have total ADD, or procrastination always gets the best of you.

We all have natural tendencies and traits that we wish we didn’t.

The good news?

All of these can be overcome, you just have to try harder – and most importantly, be¬†willing¬†to make that effort, because it’s never easy.

33) The person who wins, in the end, is the one with the most stories

Everyone is going to have a different definition of success.

But at the end of my life, I think the person who wins is the one who has the most stories, memories, and experiences.

What are you doing today that is going to create a story worth telling tomorrow?

Hopefully at least one of these resonated

This turned into a long post, but it was worth it if at least¬†one¬†of these things that I’ve learned has been beneficial to you and sparked you to take action.

Thank you again for continuing to read this site and these sometimes rambling accounts from me.

If the lifestyle and things I talk about in this post resonate with you, I highly recommend you check out our 6 day series that walks you through the best way to start building a lifestyle business. Following these steps has truly changed not only my life, but the lives of thousands of others over the last 10 years.

If you’re up for doing something a little against the grain, taking a chance, and truly pursuing the life you know will make you happiest, then I’m ready to help you!¬†

Here’s to the next 10 years!

This post was originally published in May 2019, and has been updated periodically to fix links and remain relevant.

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.
Build a Lifestyle Business Giving You Freedom You've Always Wanted

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