Three Essential Skills to Success as a Digital Nomad


in Productivity, Travel

[Editors Note: This is a guest post by Sean Ogle of Location180]

I remember the moment in January of 2010 that I stepped off the plane in Bangkok, Thailand to begin my new life: I was clueless.

A few months prior, I’d quit my job as a financial analyst with only two goals in mind: to travel and run my own business. I had grandiose dreams of living on a tropical island and making money in my sleep–you know, the same illusion every other cubicle dweller as at some point or another. Now, nearly three years later, I look back and can see just how young and naïve I was.

From not knowing how to order Pad Thai on the street, to getting my first Thai massage and not knowing what to do, it’s safe to say I was the worst digital nomad in the world. Luckily for me, things have changed: I’ve been able to create a business that allows me to travel wherever I want, whenever I want, and as Maneesh would say, I’ve become pretty good at “hacking the system.”

If you’re reading this, my guess is you’re on a path to do something similar. But how do you go about doing that?

Obviously, there are a limitless number of ways to approach it, and what worked for me may not be work for you. However, in my three years of working from anywhere and building online businesses, I’ve discovered three skills the most successful lifestyle entrepreneurs I know have in common.

Skill #1: Discipline (yes, this is a skill)

The reason I chose Thailand is because I scored an “internship” of sorts that would pay for my basic living expenses in exchange for helping them market their business. It was called an internship, but it was essentially the most flexible working situation ever.

OLYMPUS DIGITAL CAMERAThe two partners of the company both showed up, and we hopped a flight to Krabi, Thailand (at right) where we proceeded to spend the next three weeks hanging out with friends, drinking buckets, and engaging in now-banned fire antics. Apparently, they wanted to “get to know me”, and what better way to get to know a new employee than to hang out with him in the most debaucherous place on Earth?

I couldn’t believe this is what my life had become. Then at the end of all of it, I had to make a choice. Dan and Ian (the bosses) were going to Phuket for a couple days before flying out of the country. My friends were all going to the Full Moon Party, something I had always wanted to do. My bosses said they “totally didn’t care” what I did, and looking back, I really don’t think they did. However, instead of heading off to another massive party, where I would get no work accomplished, I went with them and really got down to business.

It was the disciplined decision. Had I gone to the party, I think the next six months would have taken a drastically different turn. I wouldn’t have learned the skills I needed to be successful. I believe that after those first six months were up, I’d no longer be working with the Tropical MBA crew.

Do you have any idea what it’s like to spend 10-12 hours a day working, while living in an exotic foreign country, all while a civil war is raging right outside your doorstep (more on that in a minute)? I do. If you want to be a successful digital nomad, you have to learn to block out all distractions and get the work done.

When you first hit the road, I can promise you this: you’ll have more opportunities than you know what to do with. If you don’t have the discipline to choose to work when it really matters, you’ll have an awesome vacation but be crying about your wasted opportunity when you’re back in your cubicle six months later.

How to Apply This
Most new entrepreneurs struggle with discipline the most, so here’s a few ideas to help:

  • Set solid working hours, even if it’s only 3-4 hours a day. Creating a solid schedule was absolutely essential both then and now.
  • Plan something fun. If I know at 2 in the afternoon I’m going out to explore a city or do something fun, I’m much more motivated to get my work done before I leave. I never want that hanging over my head.
  • To make that last point more effective, create solid deadlines. If there’s someone else counting on me getting that work done by 2pm, I’m much more inclined to actually do it.

Skill 2: Flexibility (yup, also a skill)

This skill applies to both traveling and business. Recently, my site about HDR Software got hit with a Google penalty (bonus tip: make sure you trust the people you hire for SEO work). Many people would give up, call it quits with the whole Internet marketing thing, and do something safe, like flip burgers at Wendy’s. But by being flexible, you understand that things out of your control will always happen…it’s how you respond and shift course that will define your success.

manilaRemember that civil war I was talking about? On May 19 , 2010 it all came to a head. Bangkok was in flames, and everyone was forced inside their homes during a government-mandated lockdown. That didn’t seem very conducive to a good working environment, so I hopped a cab to the airport. Where to? Hm, Manila looks cool, I thought.

Eight hours later, I was kicking it in the Pines’ while my Bangkok brethren were locked inside their apartments. The ability to change course at any given moment, roll with the punches, and still maintain discipline and focus are key attributes as a digital nomad. Having trouble with either of those? Maybe you should just hire someone to slap you in the face every time you screw up. (Image credit of Manila skyline.)

How do you gain flexibility?
Everyone can think of ways to become more disciplined, because it’s mostly just common sense. But how do you specifically become more flexible? This might not be as obvious, so here are some pointers:

  • Put yourself in uncomfortable social situations. The best way to become flexible is to set yourself up to have to change course. Go to a meetup about a topic you know nothing about — by yourself. You’ll probably have to change your approach a couple times before you’re comfortable talking to new people.
  • Go somewhere that people don’t speak English. I first noticed my ability to be flexible when I was in Thailand and my attempt to order a specific Thai dish was just not happening…time to adapt.
  • Be aware. Do you find yourself getting frazzled when someone interrupts your focus? Do you stress out when you don’t have full control over a situation? Be conscious of these things. By simply recognizing when you’re having issues, you can more consciously adapt to them.

Skill #3: Copywriting (Didn’t see that coming, did you?)

qwertyIt doesn’t matter what you do in life –you’ll always be selling something. Whether it’s an idea, a product, or yourself, we’re always selling. Copywriting is the art of crafting persuasive text. It might be through a blog post such as this one, on a sales page, or a script for a video. If you can effectively communicate and persuade others into seeing things the same way you do, you’ll never struggle to make money.

You can create products of your own, build a freelancing career, and market affiliate products–the options are limitless. All of these things are particularly great if you’re a digital nomad, because you can do them from anywhere. However, if you can’t persuade people to buy your products or hire you for work, you don’t have a business, you simply have a vacation. That’s why copywriting is more important than any other basic or technical skill online. (Image credit.)

How to Apply It
Copywriting is one of those things where practice absolutely makes perfect. That said, there’s a few things you can do to get started:

  • Read Breakthrough Advertising and Influence. These two books have helped me improve my own copywriting prowess and got me thinking about the psychology involved.
  • Check out Copyhour. It costs a little bit of money, but I haven’t found anything that matches its super simple approach to learning the craft.
  • Practice. Find a product you like and write your own sales page for it. Then do it again, and again. Best way to become a good copywriter is lots of practice.

Now you know the secrets to success. Develop these three skills and you’ll be a master digital nomad in no time. Just remember those copywriting skills mean nothing if you don’t have the discipline to do the work, and the flexibility to adjust your strategy if it’s not working.

Taking the Next Steps
Once you have these skills, one of the hardest things to do is actually follow through with the “nomad” part of being a digital nomad and quitting your job. I’ve put together a special package just for Hack the System readers to help. Use this link to get two free guides: “How to Quit Your Job” and “Location Rebel Arsenal: Everything You Need to Work from Anywhere”.


TheWellnessActivist January 31, 2016 at 5:37 am

Informative posts. I especially found your writing on copyrighting to be invaluable. This one I intend to learn more on and implement some tips on my personal development/life hacking blog. So glad I stumbled upon your posts. Lot’s of wisdom here.


best cleaning November 30, 2013 at 10:06 am

I do consider most of the concepts you’ve got provided within your article. They’re effective and can definitely work. Nonetheless, the actual posts are extremely small for novices. Could you please extend these a little bit via next time frame? Thanks for your publish.


Snoesje August 30, 2013 at 6:02 pm

Great post! I like the part about flexibility.Digital nomadic lifestyle in its nature,is about being free from restraints and being utmost flexible.


Bernard Hanna March 20, 2013 at 10:31 am

Hi I’m just trying to spread the word about this site, I think some fellow Digital Nomads Could find it useful, Its an online community for Digital Nomads, with Forums and articles on The Digital Nomad lifestyle and a rowing accommodation section listing monthly rates of apartments and hotels around the world
The idea is to connect with other Digital Nomads or learn to become location Independent from those who are already. Its free


Alicia January 28, 2013 at 1:09 pm

great post, currently working towards the exact same goal, time to get my copywriting game up! lol


Susan @ Travel Junkette January 25, 2013 at 11:34 am

Great post, Sean! For me, discipline is by far the toughest. Setting deadlines does help a lot!


Paige | Simple Mindfulness January 17, 2013 at 3:48 pm

Great post! I would argue that these are critical skills in life, regardless of what you do or where you do it. As I’ve honed my copywriting and marketing skills for my site over the past couple years, I’ve realized how transferable those skills are in all aspects of life.

My day job is as a CFO (I actually enjoy it since I’m in a great environment with great people) and I see that so many of my daily interactions are basically sales/marketing/copywriting situations. I’m reading Daniel Pink’s latest book, To Sell Is Human, which brings to light that we’re all selling at least 40% of the time. He defines selling is basically getting other people to do what you want.

Want your kids to clean their room? Want to negotiate a remote working situation with your boss? Want people to buy your products? Think of what’s in it for them and why they should do what you want. It’s all sales and, whether it’s written or verbal, it’s all copywriting and being flexible.


Carlo January 15, 2013 at 7:16 pm

Another excellently written post Sean. Great information contained in it.


Pauline January 13, 2013 at 4:46 pm

Great post Sean. I would put flexibility first. I have been location independent for three years as well and life has taken me places I would never have guessed, personally and professionally.


Eyleen January 13, 2013 at 7:11 am

I’m working on a startup and all these tips are awesome! I’d love to have a video chat meeting with you sometime.


jimmy January 12, 2013 at 2:54 pm

maybe off topic, but super interesting… The whole minimalist & automation stuff.

“Take Albert Einstein. It has been reported that the famous physicist bought several versions of the same grey suit because he didn’t want to waste brainpower on choosing an outfit each morning. Now—decades later—President Obama does the same.”


Ami Sanyal January 10, 2013 at 5:22 pm

Completely agree about all three points, particularly the copywriting bit. There’s a craft that any ambitious person should become familiar with!


Shamus Mac January 10, 2013 at 4:24 pm

Copywriting… you are very astute. That was a surprise, but a totally sensible one. Thanks for the post, it is a great reminder of where to put our focus. 12 years nomadic, going sketchy and strong as always!


R.C. Thornton January 10, 2013 at 2:30 pm

Excellent article Sean. I really like it when people are open about their early entrepreneurial experiences, and elaborate on what they learned along the way.

Funny that you mention feeling clueless…that’s how I felt when I started my startup, and looking back, I now know how naive I was too! 😉 But you just keep working at it, stick with it for the long run, and success will come.


Tania Dakka January 10, 2013 at 1:31 pm

Thanks much for this. I’m working on my discipline as we speak – as well as the copywriting. James Chartrand’s Damn Fine Words really, really helped with that. Thanks for this post!


Ben January 10, 2013 at 10:30 am

Nice post. Thanks for sharing copyhour. I just signed up. Why? Because I’ve heard several times that writing ads out by hand is one of the best ways to get better at copywriting. I’ve heard this for months. BUT I have yet to copy out even 1 ad by hand yet. Looks like a great system to hold you accountable.


Sean January 13, 2013 at 12:31 am

Awesome Ben. I’ve been through a lot of copywriting resources, and Derek’s the best in my opinion because it forces you to actually start writing. You can read all the books in the world, but until you start actually getting pen on paper, it’s not going to do much.


Henry January 10, 2013 at 8:53 am

Is this Maneesh writing or Sean?


maneesh January 10, 2013 at 8:55 am

sean wrote this


Craig Anthony January 10, 2013 at 11:38 am

Great article Sean.

People have no idea how valuable that link to Breakthrough Advertising is. I hope everyone follows your suggestion to read it!


Sean January 13, 2013 at 12:45 am

Its not the easiest thing to read because of the quality, but when you look at the fact a hard copy of it is a hundred bucks these days, its a great deal!


christiano kwena January 10, 2013 at 8:09 am

I agree. Discipline is crucial and that is part of what I am focusing on this year as a build my resources towards setting up a side business.


Leave a Comment


  • { 2 trackbacks }

    Previous post:

    Next post: