Side Hustle Freelancing

The Power of Starting a Side Hustle (Work Online While Traveling)

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The conventional, old school approach to long term travel is to work a ton, save up as much money as possible, and then get out there for as long as you can sustain it before the money runs out, the dream comes to an end, and you are jarringly brought back into the “real world”. But the new school approach is by starting a side hustle so you can work online while traveling. This way you can harness the power of the internet and modern communication to sustain your travels indefinitely

The Power of Starting a Side Hustle (Work Online While Traveling) freelancing

I used to get flippant comments from friends every once in a while asking when I’m going to return to the real world.

If by the real world, they mean a normal 9-to-5 job with a boss and W-2s, then hopefully never! I’ll hold out for as long as I possibly can!

In the early days, when I was having trouble starting my side hustle, I was able to use some of my clever travel hacks (spending less money, getting free flights, and cheap accommodation) to keep the ship afloat while not demolishing my savings or investments.

The Power of Starting a Side Hustle (Work Online While Traveling) freelancing

Of course, I’ll also just point out that this is still the real world–I’m out here living my day to day life like any other person just traveling a lot more while I do it. There are still good days and bad days.

I’ve got productive days and unproductive days. Sometimes I feel called by the need to roam and be a vagabond and at other times more susceptible to travel fatigue and wanting to stay put in a certain place.

The only big difference is a have chosen a less conventional path–swapping security, comfort, and conformity, for freedom, adventure, and struggle.

Over the years, my side hustles have evolved. One turned into my main business and is the primary way that I get paid to travel the world, while other side hustles have come and gone. Regardless, the one thing they ALL have in common is that I work online while traveling.

I can’t emphasize enough how important it is to start a side hustle, even if you never plan on traveling! Having the ability to earn even a little bit of money away from your typical jobs will open your eyes that you don’t have to be so reliant on them. That you have other options if things go south or you just want to go. 

The Power of Starting a Side Hustle (Work Online While Traveling) freelancing

Ideally, whatever side hustle you start, it is one that isn’t dependent upon your physical presence in a certain geographic region. This allows you to take advantage of geo-arbitrage and other factors where you could potentially relocate to a place with a cheaper cost of living, even if you just want to leave the expensive city you currently live, start doing remote work, and moving somewhere cheaper.

Be sure that you understand the importance of time and how the wage you are earning is impacted by your commute costs (and time) and other incidentals. If you can work online while traveling (or just staying home) you can suddenly keep much more of your money. This means that even if you earn less per hour from home, you may be making more take-home money compared to your old job with a commute. This is pretty common, actually. 

Working Online While Traveling

Let me emphasize: I do work. Sometimes I work a LOT and sometimes not much for weeks on end. I work both as a freelancer on other people’s projects (while still never having to report to an office) as well as on my own projects, which is perhaps the most rewarding thing–to watch things come together, to grow, and evolve.

You can still have that experience as an employee, but it’s definitely a whole different feeling to watch something of your own rise up from nothing.

One of the most amazing things about this whole blogging thing is that people can be reading my content, commenting, and deriving value from things I wrote much earlier, no matter where I am or what I’m doing at that time. I could be sleeping in my hammock, procrastinating, off hiking, traveling, or whatever.

Star Trails How To

I’ve started to make my primary income directly from the blog, but perhaps not that much compared to my old desk job. While you get a business off the ground, you may want to start your side hustle success since it is much easier and much faster to earn money in freelancing. Travel blogging can be a great personal and professional platform for what you hope to do as well as finding new clients or opportunities, but the real money doesn’t come from the blog in the beginning, it comes from other endeavors.

Read More: How to Start a Travel Blog

The power of a side hustle can’t be understated.

There are so many reasons to start building up your side hustle services even if you are gainful employed and not planning to leave the desk life: the knowledge that you don’t need an employer to make ends meet, all the things you learn about working directly with clients in terms of sales, marketing, pitching, etc, and the confidence, knowledge, and experience you will gain from the process.

Start Your Side Hustle Now

I wish I would’ve started my side hustles much earlier on but I had been a hard-working, gainfully employed desk jockey for five years and I didn’t want to start doing MORE work. This was a mistake.

It is better to start whatever it is today, to get something moving in the right direction because these little wins will only lead to bigger wins in the future and there can often be a sharp learning curve.

The Power of Starting a Side Hustle (Work Online While Traveling) freelancing

The internet is an amazing, amazing place, and that are so many different things you can do to start earning a freelancing side hustle on the internet that one can only really dabble in parts of it.

There is niche marketing, consulting, freelance writing (write for Desk to Dirtbag!), web design and services, teaching English, affiliate marketing, copywriting, actual product sales, and so much more. 

Hack the System

The beauty of the internet is also that you don’t have to be an expert in any of this–you can learn virtually anything and can document your learning process through your blog. In a year’s time or less, you will become a relative expert that can help potential clients (business owners or individuals) who don’t know as much about whatever it is you are offering.

The best course of action would be to launch this process prior to departing on your career break or a big trip, to position yourself in a way that you can continue to work online while traveling and sustain a part-time job while on the road. You might be tempted to hold off starting until you start your trip, but it can often be a tough go trying to dive into something like freelancing and a new type of work while the excitement of travel is just beginning.

The Power of Starting a Side Hustle (Work Online While Traveling) freelancing

Don’t just focus on just the savings and expenses on your trip, but think about the income portion as well. You’ll be rewarded with a longer trip to say nothing of the new skills and abilities that you can garner in the process.

This will also make the transition back to the working world much less intimidating (if you do decide to go back to the traditional 9-5) as you will have demonstrable new skills, a portfolio, and things to add to your resume (while helping you stay afloat in your future job search).

Read Next: How to Travel and Make Money: Stretch Your Savings

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The Power of Starting a Side Hustle (Work Online While Traveling) freelancing


Head Writer and Adventurer at Desk to Dirtbag
Ryan is an author, adventurer, perpetual wanderer, and self-proclaimed dirtbag (but that might not mean what you think). Originally from Seattle, he headed to Washington D.C. where he spent five years working for Congress before heeding the call of the wild. He set out truck camping to road trip across the American West, and then across all of Central America and South America. When he isn't on the move, you can find him living as an expat in Colombia. He is also the author of the best selling book: Big Travel, Small Budget that will help you travel more for less. Follow the adventures on social media or read more.

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