6 Things No One Tells You About Running a Business While Traveling Full Time

By Sean Ogle •  Updated: 10/17/14 •  9 min read

I had one goal in mind when I joined Location Rebel back in 2012, to build a sustainable online business that would allow my girlfriend and I to travel the world.

Fast forward to today, October 2014, and I’m writing this post on a bus traveling to La Paz in Bolivia with three separate online freelance businesses under my belt.

The past 2 years have been an absolute dream come true for us.

We’ve been able to call ourselves ‘location Independent’ and travel the world wherever and whenever we wanted.

The bus where this post was written!

The bus where this post was written!

There are many perks to this sort of laptop lifestyle, but this post isn’t going to highlight them.

Instead, I’m going to talk about the six things that can be viewed as negative issues when it comes to both owning and running your own online business while travelling full-time.

Obviously the advantages far outweigh the disadvantages; otherwise it wouldn’t make sense to pursue this lifestyle.

It may seem laughable to consider that there are downsides to a location independent career, but like everything in life, there are pluses and minuses.

Please bear in mind that while some of these points below may seem a little stressful or “not worth it” – we’d definitely never consider trading it for a regular 9-5.

1. Your Travel Perspective Changes

What I mean by this is that the excitement that’s usually felt with going on a trip, the “travel buzz,” can somewhat diminish.

Before we started working online, the anticipation of an upcoming trip was a really special feeling. These feelings can change when you’re travelling full-time.

That’s not to say that we don’t enjoy the whole travel experience, far from it.

It’s just that sheer feeling of adventure is somewhat lessened due to the fact that earning an income online allows us to travel wherever and whenever we like. This may seem a like a perfect scenario for most people and it is for us too.

But, it does take away the raw travel feeling for us from time to time.

2. A Stable Internet Connection is a MUST

I’ve talked about this before, and it’s probably the number one annoyance when it comes to working online whilst traveling: having a decent Internet connection is literally our lifeblood.

When we travel, we have to make sure that we have a strong enough connection to send and receive emails, as we don’t want to have to deal with missed deadlines, which inevitably causes angry and dissatisfied clients.

This can be a constant hurdle to overcome, especially here in South America where we’ve been travelling for the past four months.

In some small towns we’ve literally walked for hours on end to find either a café that has Wi-Fi or an Internet café that has a good connection to get our work done.

This can quickly turn into a very unproductive day when you consider the time it takes to just find somewhere to work from.

Getting a mobile sim card is a good option, but only if you’re going to be in the country for at least a week or so. Even then, mobile Internet in some countries is so erratic that it would drive you crazy trying to tether it up to your laptop.

When we check into a hotel or hostel the first thing we check (even before the room) is the Wi-Fi. If it’s slow or non-existent, then we’ll probably try somewhere else.

A great way to do this is to get the Speed Test app on whatever mobile device you have.

Note from Sean: While I was living in Bali the internet was extremely unreliable. I had a rotation of about 5 places within a mile of my house where I could go if the internet was down at one spot. It’s good to have options and be flexible. Get to know the area you’re in!

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3. You’ve got to find the Perfect Balance Between Work and Play

Without a boss or restrictions it can be very easy to let your social life tip the scales – leaving work commitments high in the air.

For people travelling full-time this can easily happen due to the amazing places they get to visit and are working from.

You may think because you’re the boss that you can just work when you want.

This isn’t the case for the majority of us that work online.

Client commitments, pending orders and other projects that need to be seen to must get completed – that’s if you don’t want to lose business in the long run.

Sean’s written about this quite a about both work and play in the past.

Check out:

And you’ll get a good idea of what I mean.

4. Maintaining Focus and Will Power is Essential

Imagine looking out of your bedroom window and seeing the sparkling Andes mountain range in Mendoza, Argentina or lush vineyards in Tuscany, Italy and having to find the will power to flick open the laptop and get some work done.

This may seem like an ideal situation to be in and it is, but some days it can be an absolute torment to go online and work when all you want to do is explore your new virtual office surroundings.

Focus and will power are a must if you’re going to keep things afloat online!

We constantly have to remind ourselves that if we don’t continue to complete our work schedule, our lifestyle dream won’t last.

This lifestyle is a privilege, not a right.

So treat it as such and don’t take it for granted.

It’s also not enough to just make enough money to get you by. You need to think about putting money aside as a form of savings so that you’ve protected yourself in the short term.

This can be quite difficult to do initially, but building positive habits from the beginning will go a long ways.

5. Having a Hectic Schedule Isn’t Always the Best Move

Enjoying a life of hectic travel while working online can present problems for some people.

Full-time travel (like you’d do on a typical backpacking trip) will quickly zap every last piece of energy AND productivity out of you leaving you feeling drained and unmotivated.

It’s vital that you find a balance between traveling and basing yourself in a location long enough to see your business progress forward. We personally like to base ourselves somewhere for a few weeks, where possible, before peppering in a few short bursts of travel.

The advantage of this method is that you can catch up with work and also plan things for your next bout of travelling adventures.

6. There’s NO Guaranteed Paycheck at the End of the Week!

Here’s where a lot of people have the biggest issue when it comes to working online for themselves.

Unlike a normal 9-5 Mon-Fri job where you receive a guaranteed pay check at the end of each week or month, an online business doesn’t afford you this stability.

The amount of money you earn depends on how many hours you put in and how much effort you give – simple as that.

Put no effort in and you’ll get nothing out.

Travelling and working around the world for a prolonged period of time is only going to work if you work hard to maintain the lifestyle that you’re living.

Sightseeing, accommodation, tours, food, drink and other expenses quickly add up and take their toll on ones bank balance. You’ve got to do your very best to ensure that the majority of months will see your income far outweigh your expenditures.

Making the decision to go out on the town when you have work that needs to be attended to will only have one outcome – your journey will come to a sudden halt at some point or other.

Unfortunately, due to the nature of the online beast, it’s next to impossible to predict what your monthly income will be. You can mitigate this some by bringing on clients who pay a flat fee each month or by having a monthly subscription service as one of your offerings.

All this can be a difficult thing to deal with while on the road.

Give it up? Never!

Not having the guaranteed income each month is the number one deterrent when it comes to people holding back on their dream of working online.

Yes, it can be scary living without the certainty of a regular pay cheque, but with hard work, commitment, and strong will power, you can carve out a lifestyle and career that make you happy.

Travelling and working full-time may seem like the perfect example of ‘living the dream’ for many people. And for us, it certainly is.

While it’s all rosy the majority of the time, we wanted to let you in on some of the things that very few people talk about when it comes to running a business online while travelling.

Yes, it’s awesome to be experiencing the beauty of the world while working from a laptop, but there are some elements of this lifestyle that are difficult to deal with.

But in the end, do any of the above factors put me off living a location independent lifestyle?

Let’s think about this for a second. Hmmmmmm…absolutely not 🙂

Carlo Cretaro (@carlocretaro) is a travel blogger and online entrepreneur. Along with his girlfriend Florence, they runs multiple online businesses which fuel their location independent lifestyle. Their travel blog – NextStopWhoKnows is a combination of all things travel, photography and lifestyle design.

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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30 comments on "6 Things No One Tells You About Running a Business While Traveling Full Time"

  1. Thanks for the opportunity Sean to be featured on the blog that literally has changed my life.

    Back to my hammock I go 🙂

    1. Sean says:

      My pleasure man! Hopefully it isnt the last time 🙂 Enjoy that hammock!

  2. Ray says:

    That is some sound advice, Carlo! And applicable to just about anyone who is thinking about becoming an Entrepreneur — whether their plan is to travel long-term or not.

    Any particular countries/cities you feel are worthwhile for other travel bloggers to base themselves in based on cost of living , culture/attractions and Wi-Fi reliability?

    1. Hey Ray,

      There are definitely a few countries that spring to mind that I’ve lived in that lend themselves to a location Independent lifestyle.

      Thailand – both Phuket and Chiang Mai are really solid places to base yourself in. I wrote a post about the cost of living in phuket – http://www.nextstopwhoknows.com/cost-living-phuket/

      Bear in mind that Chiang Mai is much cheaper overall than Phuket.

      Vietnam – Saigon/HCMC. I only spent a week there last year but there’s a super digital vibe there and the cost of living is pretty good.

      Indonesia – Bail. This is another digital hotspot in South East Asia where decent WiFi and overall expenses make it an attractive option.

      Paraguay – Asuncion. I spent a month here in July this year and it was magnificently cheap for day to day living. The WiFi was solid but it could have been better. But it was still a great spot to focus on work.

      Columbia – Medellin. This is where I’m off to next week for a month. I’ve heard great things about Medellin. I’ve a few mates there who say the cost of living it excellent and the WiFi is lightening – just the combo that I like. 🙂

      I’ll be blogging about it anyways, so I can let you know how it goes 🙂

      Hope this gives you some insight Ray. Thanks for the comment.

  3. Carlo,

    This is a useful reminder for the digital nomads and aspiring travelers. You need to put in the effort to get something out. Nothing great comes easy – That’s what makes it great!

    Love how you check the WiFi before you check the room. Great tip I need to try!

    P.S. Beats the 9 to 5 without a doubt.

  4. Haha, yeah the WiFi is the top priority for sure. Although my girlfriend doesn’t have the same opinion sometimes 🙂

    You hit the nail perfectly when it comes to getting out what you put in.

  5. Great stuff here Carlo. Thanks for your honestly and the heads up on what to think about and consider when traveling full time while running a business. You’re right, these are definitely the things few people talk about when it comes to running a business online while travelling. These are all incredibly important to understand and realize, especially the whole issue with having a stable internet connection. You’ve definitely given me lots to think about and consider as I plan my round the world travel. No question it can be scary living without the certainty of regular income although what’s more scary to me, is working a 9-5 desk job the rest of my life. Now that’s scary. Thanks again man, cheers!

    1. Hey Mike,

      Yes, for most people the thought of having an “unstable” income is too much of a barrier to cross.

      Luckily for me, it never really held me back. What motivates me is having plenty of time to enjoy life – yes you need a certain amount of money in order to get by, but having all the money in the world is no good if you don’t have the time to enjoy it.

      So that’s where my priorities lie.

      Thanks for the comment mate. 😉

  6. Tate says:

    Carlo, great article on the realities you will face out there traveling. Awesome to see you featured on this site! Keep up the great work!

    1. Cheers Tate,

      Thanks for the kind words.

  7. Lise says:

    Awesome article Carlo – hats off to you and Flor for facing the fear and doing it anyway!

    Whether you travel full-time or not, checking the wi-fi is also my number one priority when checking out where to stay – I’m addicted to wi-fi and nothing pisses me off more than not being able to connect! Will definitely look to stay at the places you’ve recommended along your SA travels that had great wi-fi!!

    And amen to NEVER working a 9-5 again! Now, when are you guys coming down to Australia and NZ?!

    1. You should definitely get to S.A at some stage Lise. It’s tough with the long distances between cites etc, but the sights are fantastic.

      We’ve a few more countries to tick off the list before we head over that side of the world again – but it will happen at some stage that’s for sure 😉

  8. This is a great post and you’re spot on with every single point.

    But all I’m giggling about is the fact that you guys GOT A SELFIE STICK! My hubby will be thrilled that he’s not the only one that does that on the bus!

    1. haha – yeah Tracey the selfie stick combined with the GoPro has proven to be a great combo. Although out here in South America everyone seems to have a selfie stick so we don’t look too out of place. 🙂

  9. Derek W says:

    Hey, nice article, nice to hear one from this perspective.

    The key if you want reasonably stable income in a business is recurring revenue from your customers. (membership website, software subscription, etc.) The fact that you have to keep working a lot to stay afloat is a result of the TYPE of business you’ve chosen to enter. (freelance)

  10. I totally agree with you Derek. I’m still less than 24 months in the digital game so I’m learning pretty quickly the value behind having a recurring stream of income.

    I’ve a few possibilities lined up to diversify things and hopefully flex over to the semi-passive side of the coin soon enough.

    However, I do like working on the business side of things. 100% passive income would definitely not mean I’d sit back – I’d still want to be involved in something to keep me sane 🙂

    Thanks for the words mate.

  11. I don’t travel full time but this post still resonated with me. 4 and 6 are things that I run into when working online. It can be difficult to maintain that productivity and focus at times when you have a ton of free time. I also have found that number 6 is an issue if you allow yourself to get too stressed and anxious when things aren’t going as well as you’d like. You just need to work hard and the results tend to work themselves out in the long run.

    1. Definitely number 6 is what scares the hell of out of most people Sebastian – especially when starting out.

      And it’s totally understandable to feel like that. When we’ve a bad month we naturally think like that instinctively. But as you said, as long as you continue to push the boat out and hustle the results pan out over the long term.

  12. Chas says:

    Although I enjoy travel, unplugging from the ‘9 to 5’ matrix, has far more appeal to me, than just traveling.

    1. Hey Chas,

      My main goal was to build a lifestyle business that would allow me to fuel my travel passion around the world. I don’t however want to go back to the 9-5 working for someone else route – that’s for sure.

      It’s nice to have that option to combine work with travel, and that’s the appear for me at the moment. 🙂

  13. Hi Sean,

    EXCELLENT post! #2 is gold. We’ve been in Fiji for 4 months and the internet has been great, in the middle of nowhere in Savusavu. In 1 week we’ll go to Bali. Like you we’ve never found a reliable, go to spot. Sanur, Jimbaran, Lodtunduh and Keroutan, and all homes and restaurants in the areas, have been hot and cold. We’re resigned to this and we simply rotate as well between restaurants and other spots.

    Strange, because being full time digital nomads we’ve run into this issue nowhere else on earth, for the entire country/island, and we’ve lived in remote areas of SE Asia, the South Pacific, and in India and Costa Rica, as well. Bali is one of the elite tourist destinations on earth so you’d think they’d have more reliable connects, but oh well. Curious to see how the connection is in 10 days, in the rice fields…but uploading plenty of blog posts now in preparation 😉

    Your blog rocks, and my fiancee Kelli and I have done the same thing. So cool to meet a fellow digital nomad couple who made their dreams come true 🙂

    Tweeting from Savusavu. Thanks Sean!


  14. Whoops, I meant Carlo lol! Great article dude, I need to stop waking up at 3 AM….getting ready for jet lag I suppose 😉

    1. Hey Ryan – thanks for the comment. South East Asia still powers over South America for us. Things just seem a lot easier in Asia – Wifi wise anyways 😉

      Take care and looking forward to following your journey online.

  15. Jon Bowes says:

    Dude. I get this. Especially the internet part.

    I’m in Peru right now, on my first solo trip in the lifestyle I intend to make permanent. My god, a simple 8 minute youtube video has been uploading for 3 hours now, and has an estimated 3 hours left.

    It’s not bad for anything else, reading blogs, uploading pictures, but this video is KILLER. Especially since I plan on Youtube being one of my greater traffic sources.

    Thanks for this post, I appreciate knowing the other challenges I get to face to live this frickin sweet lifestyle.

  16. James says:

    Superb insight Carlo and thanks to Sean for sharing. Just catching up on blog posts from Chiang Mai and there’s no way I would be here if it wasn’t for the community here.

    Struggling with point 5 massively at the moment, but now feeling inspired to refocus.

    Thanks, both of you.

  17. Hi Carlo,

    Your guest post is so in-depth, and it really gives me insights needed.

    As I’m typing this, I’m working in an office.

    Although it’s kinda ok, I’m working on getting to that “I have a couple of online businesses that are sustainable, and I travel the planet” place.

    Just started my website teaching meditation and mindfulness, and started an IG account 2 days back.

    It’s wayyyy more work than I thought when I dreamed this idea up about a year ago, but it’s worth it, especially if I see some of you guys posting and helping guys like us out.


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