Side Hustle Freelancing

The Power of the Side Hustle and Freelancing

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The conventional approach to long term travel is to work a bunch, save up money, and then go all out 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”.

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

The short answer is I’m going to hold out for as long as I possibly can! Through some of my clever travel hacks (both for spending less money, getting free flights, and free housing) and side hustles, I have been able to keep the ship afloat while not demolishing my savings or investments.

The long answer is that this is still the real world–I’m out here living my day to day life like any other person.

Good days, bad days.

Productive days and unproductive days. Sometimes called by the need to roam and be a vagabond and at other times more susceptible to the calls of domesticity and staying put.

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

Working while on the Road

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. Sleeping in my hammock, procrastinating, off hiking or traveling. Whatever.

I’ve started to make a little side income directly from the blog, but certainly not that much. You can start your side hustle success much easier and much faster by getting started in freelancing. 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, it comes from other endeavors.

* Wish you could travel more and more affordably? Click here to grab my free course and resources that will show you exactly how I've been able to travel for more than four years.


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

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 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, 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 whether 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 big trip, to position yourself in a way that you can sustain a certain amount of part time employment 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 freelancing and a new manner of work while the excitement of the road is just beginning.

Don’t just focus on savings and expenditures 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).

Further Resources:

Read Next: How to Earn Extra Money – 40+ Side Hustles

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The Power of the Side Hustle and Freelancing

Ryan

Author, Writer, and Head Honcho 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 living in his pickup truck to road trip across the American West. Since then he backpacked through Colombia, drove across all of Central America, and also wrote a best selling book: Big Travel, Small Budget. He just finished driving his old truck across all of South America -- support the adventures by visiting the D2D Shop. Follow the adventures on social media or read more about me.

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