Bartender to Jet-Setting Copywriter in 9 months – Colin Pomeroy

Colin Pomeroy was a craft cocktail bartender in Portland, OR before deciding to make the switch to a location independent career in copywriting. A student of Sean Ogle’s Location Rebel program, Colin had been sitting on the course materials for 2 and half years before finally making the commitment to pursue his destiny as a ‘Location Rebel’. In March 2015, he got his first official full-paying freelance writing job and on September 16th 2015, he took a one-way flight to Paris.

After meeting with Colin in Chiang Mai, I asked him if he’d like to share his experience as the second interviewee in this ‘Inspiring Nomads’ Series. Here are his answers:

What made you decide that you wanted to be location independent and how did you make it happen?

Becoming location independent wasn’t easy for me.

I first learned about the concept of location independence when I stumbled upon Sean Ogle’s site, www.location180.com. I remember thinking to myself, “I want to live a life like that guy, that’s inspiring.” So I decided I wanted more freedom in my life and signed up for his online course, Location Rebel.

After I had become a member of his course, and a few emails later, Sean and I figured out that we worked for the same company back in College; we had even carpooled together to one of the weekend company retreats. It was crazy. Even crazier was that he lived in my city!

So I reached out and offered to help him cross off an item on his infamous bucket list in return for meeting for coffee and giving me some advice. Looking back now, Sean would’ve totally met with me and helped me regardless, as he loves helping people go nomadic. But it didn’t hurt having something to offer.

After I had helped him cross off the bucket list item – which was to get a cocktail named after him on a menu – we ended up becoming good friends. But despite his friendship and availability as a mentor, and no matter how hard I tried, I couldn’t seem to make this freelancing thing work…

I was obsessed with doing something I was passionate about, which happened to be editing video trailers. so I decided I wanted to be a professional video editor and work remotely. The problem was it wasn’t a very sustainable model for traveling. After a lot of attempts at making it work, I eventually gave up. I was pretty bummed out and thought maybe location independence just wasn’t for me…

Then I had my location independent awakening

I saw that I had been putting my career first, and it wasn’t getting me anywhere. I had been fixated on WHAT I wanted to do to live my ideal life, and it was an uphill battle. So I switched my priorities, and I chose the kind of lifestyle I wanted to live first, and that’s when things started falling into place. I started being willing to try different things that I might not LOVE to move closer to the life I wanted to live. So I went through the Location Rebel blueprints and chose content writing. It was tough at first but with my new perspective, I was committed to making it work. I found other freelancers in the LR forums and asked them if I could write content for them at highly discounted rates just to get my experience and confidence up. At my pathetic pace and low skill level, I was making around $1/hour writing, but after I got my first PayPal payment of $15 from working in a coffee shop, I knew that I could get better and grow this into something sustainable.

It was after I made my first remote, online dollar that I made a commitment. I gave myself 9 months to learn this stuff part, and then I was going to buy a one-way ticket, start traveling and make it my full-time gig. I began telling people what I was doing and slowing started selling off my belongings to make it more real. The milestone that I set kicked my ass into gear to start getting clients and learning how to get good at writing online.

Eventually, the date came, I sold all my sh*t and haven’t looked back since. There have been tons of struggles along the way, but I learned 100 times faster by making the commitment and figuring it out along the way rather than playing it safe and waiting until I was absolutely, positively skilled enough before I took the plunge.

What are the challenges of working remotely?

Taxes.

Which destinations have you worked remotely from so far and what would you say are some of the drawbacks of living and working in places like these?

I’ve worked remotely from Chiang Mai, Thailand, and Portland Or. I’m about to take off to Saigon in a few days and make my way up the Vietnam coastline. It’ll be the first time I’m officially working while traveling, we’ll see how it goes.

The drawback of living in Chiang Mai is they don’t have New Seasons Markets (which is like Whole Foods but 1,000 x better) and right now it’s over 100 degrees pretty much every day.

Which are your favorites?

Chiang Mai in the winter months, Portland in the summer months. Endless sunshine.

What’s an average day in your life look like?

My average day changes a lot. But currently on a typical day I wakeup around 8 and kick the ladyboy out of my bed from the night before (HA! JK). I get up and follow my morning ritual which is: I brush my teeth, write down 5 things I’m grateful for (part of this new abundance experiment I’m doing) and then have a 10-15 meditation session.

I leave my house and head to one of the cafe’s in town to start planning out my day and what I want to accomplish. Following that, I do a session of Copyhour (handwriting successful ads to get better at copywriting), and start working. I usually do freelance work for the first few hours, and then work on personal projects later on, such as blog posts for my own website, or shooting and editing a video. In the afternoon, I’ll either hit the gym or go to a Muay Thai class.

In the evening, I’ll meet up with friends for dinner and hang out or some nights I just keep working on personal projects. Then I head home, write down what I want to accomplish the following day, read some fiction or personal development material and go to bed.

What advice would you have for others who are looking to live and work anywhere?

I have two pieces of advice.

  1. Choose your lifestyle first, and commit to that before income or type of career. You can always adjust those two later. That was the biggest switch in my way of thinking, and as soon as that changed, all the pieces of the puzzle started fitting. You don’t have to forgo passion, but just recognize you can BE passionate without something to be passionate about. And usually, that will end up attracting the exact stuff you are passionate about.
  2. Be patient with yourself. If you currently have no freelance or location independent skillsets, you’re going to have to practice to get there. When I started content writing, it was a total nightmare at times. I would spend 6 hours writing one blog post that earned me $35. It was completely insane. But I knew every time I did it I could get faster and increase my productivity. It became a personal development journey. I can’t say I ever LOVED content writing, but I love growing and personal development, and since I was motivated by my lifestyle, I didn’t stop when the work got almost too much to bare. The other thing is that I love business, psychology, and personal growth, and I ended up finding work as a copywriter, which I can say that I am much more passionate about than the stuff I was doing before. So even if you don’t like something at first, be patient, do a good job, and opportunities for more fulfilling work will present themselves.

Are you happy with your current lifestyle and would recommend it to others?

Hell yea!

What are your goals now that you have achieved location independence?

I’m currently working on a new goal of switching my perspective to one of abundance. I think it’s not uncommon for people, including myself, to be pre-programmed for a scarcity mindset without even knowing it. Even if people make a ton of money, they can still view the world through a scarcity lens. The goal I’ve accompanied to this is $8K/month in income. I set this as an arbitrary amount, mostly just to have something to measure the experiment with. The experiment is something I’m documenting and showing exactly how I create habits to install this new perspective. And I’m focusing on that first, instead of the goal, and just seeing if and how my income is affected.

To find out more about Colin, check him out at www.colinpomeroy.com and follow his journey on YouTube

Have you been inspired by Colin’s story?
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About the Author

Hi, I'm Chris. I'm a self-taught web developer, YouTuber, Blogger and Digital Nomad.

To find out more about me, check out the 'About page', the 'Hire Me' section of this website or connect on social media

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To read my full story on how I left my corporate career in Accounting to pursue Location Independence, check out my book 'How I Learned to Code'


2 comments

  1. You are inspiring Colin! Enjoy your journeys! :) As I look at and plan my life direction, I will think of you. We’re never too old or too experienced to toss these ideas around and see where they land.

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