The 17 Different Ways I Made Money Traveling The World by Rae

A Gut Feeling That I Had To Leave

I started living and working abroad when I was 25 years old because of a gut feeling that I had. Actually, it was more like gut pain. I was two weeks out from finishing my seven-year undergraduate degree when I started to experience a stabbing sensation in my stomach. It was a Wednesday night and I was teaching back to back yoga classes at a busy downtown studio in Toronto, Canada. I chalked up the pain to stress and the dried figs I’d eaten before going into the hot room. I was so fixated on finishing university that I honestly believed I could just go home and sleep it off. When the pain started to get worse around 1am, I biked myself to the hospital hoping it was perhaps gas that could be fixed with a little exercise. As it turned out, my gut was really inflamed and the doctors told me it was severe enough to warrant abdominal surgery. Looking back, I think that the cause of this flare up was probably due to the fact that I was full-time in university, working 60+ hours a week, was in a demanding relationship, and slept no more than four hours a night.

Toronto | Puppet
One of my “soft cyborgs” from art school. They blinked and blushed and responded to touch.

Literally overnight, my entire life changed.

I couldn’t work because the incision points from my surgery needed to heal and my main jam was teaching yoga in a hot room—essentially a bacterial breeding ground. Massage was out of the question as I was forbidden from doing any heavy lifting. Not to mention the fact that I was also too exhausted to do much more than sit on my partner’s couch and play video games. My thesis project—a post-apocalyptic children’s puppet show—never came to life nor did it end up in the graduate exhibition. Instead, I did a PowerPoint of my final work and graduated with none of the glory that I had spent seven years anticipating. I was literally and figuratively gutted.

Toronto | Massage Space
The Thai yoga massage space that I set up in my Chinatown apartment, downtown Toronto.

With all the extra time I suddenly had to think about things, I realized that I no longer wanted to be living the life that I had. Earlier that year, I had signed up for a yoga retreat in Bali as a graduation gift to myself. Having already committed to that, I decided that Bali was as good a place as any to begin my life as a traveler. So, over the next six months, I would break up with my partner, liquidate most of my possessions, and get on a one way flight to the other side of the world.

I told everyone that I was leaving for seven years and, for all intents and purposes, I meant it.

So began my life as a nomad.

Desa Seni where I did my yoga retreat.

All The Different Ways I Made Money, But First Some Chill Time And A Really Long Walk

I spent a month in Bali doing yoga and learning to surf. Then I flew to New Zealand where I walked for three months from the top of the North Island to the bottom on the Te Araroa Trail. I hitchhiked, camped in the bush, lived with farmers and otherwise tramped 20-30km a day with a 30kg pack on my back. When I got tired of walking, I went to the South Island. There, I lived at the Lost Gypsy Gallery where I spent three months running on the beach, surfing in freezing cold water and otherwise hanging out with an eclectic group of artists and musicians. When the gallery closed for the season and temperatures started to drop, I flew to Brisbane, Australia to look for warmer weather and a way to replenish my almost empty bank account.

Views from my time on the Te Araroa Trail and the entrance to the Lost Gypsy Gallery

Becoming A Stripper

When I arrived in Brisbane, I decided that I wasn’t interested in some shitty backpacker job that would barely help me scrape by. I needed to pay off my credit card and wasn’t about to head back to the safety and security of my homeland. I also didn’t know anyone and figured that now would be the perfect time to try something out that I’d never done before.

So I became a stripper. I danced at a club called Love & Rockets and my stage name was Pepper.

In the three months that I worked as an adult entertainer, I learned that not all strip clubs are created equal. Mine had a dress code for both dancers and patrons and an all female management team. Despite the fact that we got fully naked and could do what’s called “open leg work,” there was no mouth contact, kissing or touching of private parts. There were women of every shape and size, and they were all smart and savvy salespeople. I made anywhere from nothing to $800/night cash. And, if I’m being totally honest with you, being a stripper felt a lot like being a yoga teacher—people just wanted to be touched and validated. When I was a yoga teacher, I was a therapist in stretchy pants; when I was a stripper, I was a therapist in lingerie. It’s the same job.

Seven Different Jobs in Australia

Marketing, Massage, and Beekeeping

While I didn’t mind being a stripper, in the end, I quit because going to bed at 5am became too much of a drain. I would work three nights a week and it would take me four days just to feel human again. So, I switched gears and got a job doing marketing for a CrossFit box.

Now, I was getting up at 5am to go train before work. I then opened up my own Thai yoga massage practice in the building, which was an easy thing to get going given the already present clientele. I did this for six months at which point it was time to do farm work so I could get my second year visa. The CrossFit box sold premade paleo meals and it just so happened that they sourced some of their vegetables from an organic farmer who needed an assistant beekeeper. Long story short, I ended up WOOFING for them as a beekeeper for three months. I’d never been stung by a bee until then and, fortunately, I’m not allergic. Which is good because the first time I opened a hive, I was stung ten times!

Remote Travel Work-Oz | Beekeeper
Beekeeping in Northern Queensland near a town called Malaney.

Promotions, Sewing, Yoga, And SuperYachts

After finishing up my beekeeping duties, I moved to Melbourne. There, I did show promotions, worked as a hemmer at Lululemon, sewed costumes for the comedy duo Sammy J & Randy, and taught yoga. At some point, I decided that I wanted to be paid to travel. So I got my sea safety qualifications—called the STCW95—with plans of getting a job on superyachts. Serving the ultrarich on their floating mansions seemed like a good way to go. I also joined a yacht club and started racing on a weekly basis. Always looking to make more money, I lied my way into a serving job at my club—I’d never really worked in hospitality before—and proceeded to break far too many champagne flutes. Despite this, I managed to find work on a small private party boat as a stewardess/deckhand. I even assisted a boat delivery from Australia to New Zealand across the Tasman Sea. It took eight and a half days and I was seasick for the first three. It was still one of the most amazing travel experiences I’ve ever had.

Remote Travel Work-Oz | Yacht Club
Sailing in a weekly race at the Sandringham Yacht Club in Melbourne.

Diving And Cooking In Thailand

Despite my love for Australia, my visa was almost up. So, I decided to go to Thailand and get my PADI Divemaster certification. I went to Koh Tao and spent two months diving twice a day. I’d never been scuba diving before and absolutely loved it. Being underwater was serene. I ended up getting my deep dive, Nitrox and wreck certifications while I was there. I have to say that going inside a submerged shipwreck was one of the highlights of this experience. After I’d finished up all that, I headed to Bangkok to add Thai cooking to my now very eclectic resume. I lived there for a month and studied vegan Thai cuisine. I spent many a meal crying over my creations because the food was so spicy that if I stopped eating it burned even more.

Remote Travel Work-Thailand | Diving
Where I learned to dive on Koh Tao in Thailand.

While in Bangkok, I started to worry about money. I had a computer from my time at the CrossFit box so I thought I’d give online writing a go. I did a bit of research and came across Upwork, an online freelancer marketplace. The interface was user friendly and a quick search showed me there were people looking for content in the health and wellness industry. So, I positioned myself as a yoga expert and picked up a few low paying gigs writing blog posts and website content for businesses that sold wellness products. My first consistent job was writing 10 blog posts a month for a company that sold holistic back pain solutions. I quoted $45 a blog post—mostly out of desperation—and my client said yes.

Remote Travel Work-Thailand | Night Market
A night market in the heart of Bangkok.

Returning To Canada And Writing

I decided to go back home on my way to the Caribbean to find work on a boat. It had been three years since I’d last been in Canada and seen any of my family and friends. I flew into Vancouver because it was the cheapest ticket, and thinking it was only a short term thing. I also had family there so I knew I’d have somewhere to stay when I arrived. What was supposed to be a quick stopover in my homeland turned into a year-long attempt to re-integrate myself into a less nomadic way of living. I also was tired of leaving from visas expiring and all the restrictions on how much I could work. So—after three years of chasing the sun—I spent the Canadian winter teaching yoga and putting more effort into getting online work.

Remote Travel Work-Vancouver | Ocean
The ocean near Kits Beach in Vancouver.

Upwork has a review section—similar to AirBnB—and it didn’t take long for me to get a few good reviews and earn my Top Rated Freelancer badge. Suddenly, I was having people ask me to write for them and I stopped updating my portfolio because potential clients seemed to care more about my reviews than the work I’d done in the past. I quickly learned that as long as I could talk my way into a job and deliver on what I said, my clients cared very little for any formal qualifications or even previous work experience.

At the same time that I was stumbling my way through the process of becoming an online freelancer, I was thinking about how to tie together all the seemly disjointed skills and experiences that I’d accumulated over the past eight years. I thought about writing my version of Eat, Pray, Love—maybe mine would be called Surf, Strip, Sail—but was too anxious about figuring my career out to sit down and write a book. I did, however, enroll in a coaching program in the hopes that coaching might be a viable way to streamline my work experience.

Then I landed my first major copywriting client.

He contacted me through Upwork looking for help with an upcoming product launch. I had no idea what a sales funnel was and, I’ll be honest, I lied and said that I did. I even went so far as to pass someone else’s work off as my own when he asked for some examples of sales pages that I had written. I felt sick afterwards and half hoped he wouldn’t say yes to me. Apparently, karma works differently online because he did end up wanting to work with me and I went from just writing for my main client—emails, sales pages, nurture content, etc.—to doing video editing, graphic design and sound editing as well. My client put me on a monthly retainer of 40 hours a week, which came to $3000 USD a month.

I started making payments towards my debt and otherwise adulting on a level that felt mostly competent. So I started to look at plane tickets because maybe I hadn’t gotten rid of the travel bug after all. Now, I could travel and work my own hours, and that was something I really wanted to experience. So, when my apartment came down with a bad case of bed bugs and I had to move out suddenly, it only took me a minute to realize that I had no interest in relocating somewhere else in Vancouver. I’d heard amazing things about Costa Rica and decided that I would move to a small surf and yoga town called Nosara.

Remote Travel Work-Vancouver | Nook
My tiny expensive Gastown apartment in Vancouver.

Surfing, Social Media, And Life Coaching In Costa Rica

In Nosara, Costa Rica, you can surf something like 336 days out of the year. Not only that, Nosara has a reputation as a wellness spot where locals go to bed at 8pm most nights. As much as I was looking forward to being a fully location independent traveler, I was also hoping to immerse myself in a community of like-minded individuals. That’s when I met Herbert out surfing who had just opened up a conscious coworking space called TribeWire a few months prior. During our early morning surf sessions, Herbert and I talked about community building and the importance of balancing out income with impact. Before long, I was helping to manage the space in exchange for being able to use it. Herbert, Karina and I started talking about workshops we could offer the community and began to brainstorm how to build a program that would allow people to leave their stressful Western lives to come live the dream here in Costa Rica—or wherever.

Remote Travel Work-CR | TribeWire
TribeWire coworking space.

Speaking of stress, my main copywriting and marketing client was doing my head in. As much as I loved the work that I was creating for him, the disorganization was getting to be too much. I was starting to feel burnt out and resented waking up tired in the morning for my sunrise surf sessions. On top of that, we were talking about his annual product launch and I could feel anxiety rising in my chest when I thought back to how taxing the previous one had been. The stress at work was only highlighted more by the pura vida jungle-ocean vibe that I was surrounded by. So, out of the blue after the same chaos hit, I announced that I would be leaving the team that Friday. I think my client was as surprised as I was. I passed off some remaining design files and took my leave despite having only one coaching client and no other source of income. I also only had $4000 in my bank account.

Remote Travel Work-CR | Orange Sunset
Sunsets never get old in Costa Rica.

I spent almost two months trying to figure out what to do next. While I was determined not to get sucked back into marketing, I panicked, and took on a new social media marketing client. I tried to convince myself that it was my previous client and not marketing itself that was stressful. I was wrong. Turns out, I really just don’t like marketing. So, after two weeks, I had an honest conversation with my client and gave her some references for other marketers she might want to get in touch with. Then, I focused my efforts on getting work ghostwriting books for people. I really love writing and, not long after I changed direction, I landed my first ghostwriting contract. Despite the fact that I’m being underpaid for this initial book, it’s interesting work and I know that it won’t take many projects for me to start making industry rates. I also picked up a few more coaching clients in that time so I can at least cover rent and food for the time being.

Remote Travel Work-CR | Beach
Beaches for days in Costa Rica.

Lessons In Moving Abroad Full Time

I think that the biggest lesson I’ve learned on my way to figuring out how to make money while traveling is that the best way to begin is just to get on a plane and go. I guarantee that after the what-the-hell-did-I-just-do thought passes, you’re going to figure out how to make it work. Your very real need for money and shelter and food will force you to become resourceful and to take risks that you might have otherwise avoided in the comfort of your home country. Not only that, you’ll be able to access a very rare kind of social currency that will make it increasingly easier for you to make money abroad. It takes guts to travel long term and a lot of people respect that, sometimes more than a fancy university degree or relevant work experience.

The truth is, you can spend your whole life planning how to become a money-making nomad. Or, you can get on a plane and trust that you’ll figure it out when you arrive. Because you will.

Okay? Okay. Now go pack your bags.

Views from my home in Costa Rica. It’s a seven minute walk to the beach and has a backyard pool. Just sayin’.

Instagram: @raekess

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Website: www.raekess.com

Email: rae@raekess.com

My Upwork profile: https://www.upwork.com/o/profiles/users/_~01dcf0b1b354e468c5/

 

6 Comments

  1. The honesty you share is what I loved most about this blog. Some people will make it sound so easy, but you definitely showed the lengths you took to make it work! Thank you for sharing! Amazing story, and what an amazing adventure!

  2. I love this! What a vast variety of jobs. I’m just imagining how long your resume would be if you put one together! haha. I also love the honesty about stripping.

  3. Your honesty is so refreshing. From the stripping to the lying. I love every single part of it. THANK YOU!

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