10 Kick-Ass Ways to Make Money While You Travel

If it’s your dream to quit your job and travel, or work as you travel as a freelancer, you’re not alone. You’ll be surprised to know the dream is a lot more real that you might think.

The truth is, top college grads are working at Starbucks. Or not working at all. And they have heaps of debt to go with it. On the flipside, people find themselves in jobs they don’t even want because they have to survive. Of course, we all have to survive. But at what cost? I’m not saying to just quit your job and travel the world like a fool. But what I am saying is, there are opportunities and options. And no, I am not telling you to be a blogger. Although, you absolutely can make money blogging (more on that later).


If you’re between the ages of 33-43 you can just take everything you were told you’re supposed to do by Boomer parents and just toss it. We love them but their generation was the last of it’s kind in the free world to survive with a family of 6 on a single income.


We are different.

When it feels like nothing makes sense anymore, this could be your time to take a chance and try something new.

We all seem to be searching for a life with more fluidity, personal meaning and adventure. My generation was on the cusp of what we were traditionally supposed to do and the digital age that opened brand new gilded doors. We tried to fit the old keys in new locks and found out they didn’t open the doors anymore. We were given the internet and it was a total game-changer.

We are getting braver and have less to lose. We are giving up the ideas that have been expected of us and creating our own paths instead. People are downsizing, buying tiny homes. Working where they want to be, instead of allowing work or a job to dictate where they live.

And a lot of people are feeling lost and don’t know where to start. I have read so many life-changing books that have inspired me to just go for it. Before I finally got out of Corporate America for good, I went back and forth from corporate job to freelance. The steady pay was always nice, but feeling trapped indoors, having to play political office games and worrying about my job security was no good for me.

No matter what you do in life, there is always a compromise and something you have to give in exchange for something else. Whatever you decide to give up, though, it has to be OK and worth it to you. For me, my emotional well-being, never taking a vacation or spending time with family or friends was not something I was willing to give up. Any time I doubted myself, I was reminded of the wise words of Leo Buscaglia and gave myself permission to change:

If you don’t like the scene you’re in, if you’re unhappy, if you’re lonely, if you don’t feel that things are happening, change your scene. Paint a new backdrop.

I decided to change my scene. And you can too.

There are tons of solid independent work options out there if you’re willing to do the work, explore, be patient, set yourself up for success and take a chance.

These are my personal favorite work-from-anywhere income opportunities:


If you are tech savvy or creative, there are tons of freelance jobs available through websites with people looking for your expert skills. Try: CrowdSpring, Gumroad, ELance, ODesk/UpWork and Fiverr

The beauty of these sites are, you get to work from wherever you are -whether that’s your own backyard studio, The Bahamas or a flat in France. As long as you have access to wi-fi, of course.

DCF 1.0
My Jamaica trip, 2007 (I worked from home then, selling bridesmaid dresses on eBay that I designed and had made at a factory in China. That year, I had made enough money to pay for two tickets since the guy I was with at the time was a total cheapskate. True story.


If you have a knack for research, thrifting and finding good products and deals, don’t rule out selling on Amazon, Etsy or eBay. I have been selling on eBay since 1999 and over the years, I have made a lot of money from buying and reselling on eBay. Often times, I purchased vintage clothes for $4 and $5 and resold for as much as $50-$100. This is how Sophia Amoruso (aka #GirlBoss) got started and turned her company into the multi-million dollar Nasty Gal empire.

If you are familiar with Gary Vaynerchuk, you know he is always talking up the ability for people to make money on eBay. With the new eBay app, it’s very easy to snap a photo, name your price and voila! It’s listed.


Another good buy and sell app for clothes and accessories is Poshmark. I have been on Poshmark for a month now and the app is super quick, free and easy to use with any smartphone. I don’t have to pay for shipping when an item sells, either. As as super casual user (appx 24 items listed), I have earned about $150 selling my unwanted clothes and shoes. Some ladies claim to have done about $100,000 in sales per year on Poshmark. (If you decide to sign up, use my code: JYUOY and get $5 in your account right off the bat) 😉


Are you crafty? There are other ways to earn money on the go if you don’t want to be stuck at home or a studio, stock inventory, or ship out items. If you have products to sell or you make products (e.g.: your Etsy store), there are fulfillment companies such as Shipwire and Amazon who will warehouse and ship for you. All you have to do is provide the products and market/sell them. You can be anywhere and do this. If you are a graphic artist with a good T-shirt designs, check out Printful. They’ll print and fulfill your orders.


If you have a good vehicle, you can sign up to be an Uber or Lyft driver. Apparently, the average Uber driver in San Francisco makes $20-$30 per hour on normal hours. I am not sure where Uber is going these days, so you might want to research this option. Another driving option is Postmates.com It’s the on-demand delivery from every restaurant & store in your city. Once you sign up for the service, you can work when you want. The website claims delivery drivers can earn appx. $25 per hour + tips. And you have the option to walk, drive, scoot or bike.


If you are a home chef foodie, professional chef or the next Franklin barbecue pitmaster, Check out: EatWith, where you can earn up to $700 for hosting a communal meal. The awesome part is, you can do this anywhere in the world.


If you LOVE travel and Yoga more than anything, check out Trip Tribe, where you can earn money for planning a yoga retreat. Seriously. This is a no-brainer.


If you are good with tools, don’t mind getting your hands a little dirty or running errands, check out TaskRabbit.  

A lot of online freelance jobs can allow you to live anywhere, even overseas.  😀


If you are an animal lover, you can offer your services as a house/pet/dog sitter. One to try is USA-based Rover.com, which offers the option to sign up as a sitter and stay at a home for free while you care for the family pooch.  There is also Trusted House Sitters which is worldwide. You sign up as a sitter and you get to stay at guest homes and watch over their home and care for their furry babies while they’re away. It’s a win-win situation.

The sky’s the limit and the world is your oyster!


If you want to work abroad, get to where you want to be and plug into the expat community. Apply for a working holiday visa or get some freelance work with the above mentioned websites and services. You can also  teach English or be a Nanny abroad.

A working holiday visa is a residence permit allowing travellers to undertake employment (and sometimes study) in the country issuing the visa to supplement their travel funds. … Many are intended for young travellers and, as such, have an age restriction (usually from 18 to 30 or 35) – Wikipedia

Have I given you enough ideas to chew on?? Good!
Now get crackin! ❤

Did you find this article helpful?  Please pass it on so others can be working nomads, too!

4 Books that will motivate you and probably change your life:




2 thoughts on “10 Kick-Ass Ways to Make Money While You Travel

  1. Hmm it seems like your blog ate my first comment (it was extremely long) so I guess I’ll just sum it up what I submitted and say, I’m thoroughly enjoying your blog. I as well am an aspiring blog blogger but I’m still new to the whole thing. Do you have any rediomencatomns for rookie blog writers? I’d certainly appreciate it.


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