4 Years traveling – turned Musician to Entrepreneur

Musicians are notorious for unique and outrageous fashion, starting trends and being on the cutting edge. I however, was never that guy. For most of my teens and early 20’s I was strictly jeans and a t-shirt guy and fashion didn’t much interest me.

So, some days it still surprises me that I ended up starting a clothing brand. Especially one that specializes in women’s harem pants.

I think I should take a step back…

From 16-24 my only goal in life was to play guitar in rock bands. Part of my drive to be in a band was that I knew I never wanted the 9 to 5 lifestyle, I wanted something different and I wanted to see the world. When my band ended, I was burnt out and ready for something new.

behind the scenes shoot harem pants

   I knew working online was the future.

I had learned to code to build our website, I used social media to grow our following and I had already gone to school to marketing so I knew working online was the future.

I had some friends into affiliate websites and I had started to read about SEO & PPC but like many people it wasn’t until I read the 4-hour work week that it all clicked.

I left my fledgling job in commercial real estate and started working at an online marketing agency focused on SEO. From the beginning, I knew the long-term goal was to start my own projects and travel abroad. I listened to the Tropical MBA religiously and had a photo of Bali as my desktop background.

After two years of honing my SEO chops I made the switch to freelancing fulltime and soon after I booked my first trip to Mexico. Without knowing a single person, I got rid of most of my stuff and headed off to a small surf town outside of Zihuantanejo (where they escape to in Shawshank redemption).

Dirt Biking ryan traveling California

I was offered free stay at a beach hotel in exchange for helping them with their marketing. On paper, it sounded great but they neglected to tell me I’d be staying during rainy season and that the WIFI was terrible on its best days.

It was not the digital nomad dream I had envisioned while pouring through travel & business blogs where all kinds of interesting people were meeting up and talking business & adventure.

The town was mostly abandoned, the dirt roads were falling apart from the daily deluge of rain and I could barely work. Took some surf lessons, eventually met some cool locals in town but overall it was one of loneliest times of my life. In many ways having a difficult first experience as a digital nomad really made me appreciate it once it got better.

And got better it did…

When I was in Mexico I only knew one other digital nomad and he had recently moved to Chiang Mai. After hearing his excitement about the city it was an easy decision to make Thailand my next stop.


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In January 2014, I touched down in Chiang Mai and my journey in Asia began. My first week I met two musicians from the UK and we hit it off and became traveling buddies.

They took me up to PAI, a beautiful town tucked into a valley that has a special place in many people’s hearts. Waterfalls, hot springs, plentiful music and a bustling art scene.

During a chance meeting one night the foundation was laid for One Tribe Apparel. We wanted to take the bohemian fashion popular in Thailand back to the west.

We started with the infamous elephant pants but now we have a diverse array of products including tops, kimono’s, yoga accessories & handmade fringe bags.

I started splitting my time between growing the business & doing my freelance work to pay the bills. All the while I was able to keep traveling and living in new locations.

Rio Carnival ryan traveling

After Thailand, I visited the Philippines & Hong Kong. Later that year I spent the summer in Ireland where I have relatives with a stop in England & Scotland on the way to meet back up with my UK musician friends.

The next year I went back to Thailand then to Saigon in Vietnam, a city I now consider my 2nd home.

At the start of 2017 I ventured to South America for the first time. It started with two friends in Colombia before moving on to visit Macchu Picchu and then Carnival in Brazil to meet up with more friends and have an amazing time.

I’m writing this from Mexico City where some of my best friends I met traveling decided to call home this year.

This summer I’ll head to Budapest and after that who knows…

   The most important thing you can do while traveling is develop a skill set that you can take with you

traveling remote life harempants

The best part is I now have an incredible group of friends following this same path in life and we find ways to meet back up in different places and continue the journey.

When I’m not traveling, or taking a break for a big event like Carnival I work a ton. There are lots of 10 & 12 hour days when you run your own business.

There’s stress, employees counting on you, customer service issues and a million other problems but I wouldn’t change it for the world.

This August I’ll hit four years of this lifestyle and it’s undoubtedly been the best time of my life.

I know it’s hard to hear from the other side but if traveling abroad & working remotely is what you want then be patient. It doesn’t happen for everyone overnight. It took me a few years of preparation until I could make the jump. The most important thing you can do is develop a skill set that you can take with you. There is absolutely nothing wrong with working a regular job while you do that.

Make a plan, set a date and then execute. Hopefully one day I’ll see you out there.

About the Author


Ryan O’Connor is a CoFounder of One Tribe Apparel, traveler, rock n’ roll junkie and in another life used to write about and give talks on SEO. He hopes to be an extra in the final season of Game of Thrones and get killed in a battle. 

Website | Instagram

  • Iram Khanam says:

    What an inspiring travelogue!
    It takes a judicious mind and a cheery spirit to attain success at work while also enriching one’s soul through travel.

  • Devanjali Banerjee says:

    While I was a little skeptical when I clicked on this link- this article is pretty honest about the struggle it takes to attain success. Given I have similar ambitions of combining music with travel, I hope I get to this stage too!

  • visanth says:

    “musician to entrepreneur”, its a big deal brother- congrats
    hope i too be like u

  • Tharikha says:

    A fun, light and inspiring travelogue. Goes to show the power of travel.

  • Coy Venning says:

    I spent a great deal of time to find something as good as this article.

  • Charline says:

    Thanks, it’s very informative