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How I Became a Digital Nomad

How I Became a Digital Nomad

How I Became a Digital Nomad

My digital nomad story is unusual, as are most. The story to my location independence started more than 10 years ago before the term “digital nomad’ was trending on Instagram, or before there was an Instagram. I was making great money for a 25-year-old as a Technical Recruiter living in San Diego. Life was good except I hated my job, like really hated it. I was working 60+ hours a week, watching the sunset every day over the ocean, while on the 25th floor of my downtown office.

I never really had a plan coming out of college, just to start working so I could pay off student loans. I was fully expecting to hate my career as long as it paid me decent. I graduated with a degree in Economics but came out of college with no real useful skills and I knew it. Uhh, gross, it’s hard to believe this was once my life. My second year as a Tech Recruiter I was making more money than I dreamed of at 25 but knew I couldn’t’ do it much longer as I was miserable and had already given myself carpel tunnel from overwork.

Make Yourself Valuable

I didn’t know what I wanted to do but I knew I needed valuable skills and the ability to work anywhere in the world. As a Tech Recruiter I saw how valuable high level engineers were and how they made their own rules, lived and traveled as they wanted, because they had the skills people needed. I knew I had to develop valuable skills. I decided while still working full time to go to Grad School online for Web Development / Digital Marketing. Working full time and doing Grad school was a crazy experience but I finally had some useful skills that I continue to use every day.

Walk Away Sometimes

The month I made the most money of any in my life I did the best move of my life, I quit. I quit my high paying cushy job for a minimum wage internship type role in web design / marketing. This was my first completely insane and unorthodox life move and I have made dozens since then. These crazy life changes have become part of my personality, ha.

At this internship, I discovered digital marketing and seo from this job and become completely obsessed. I spent every waking moment learning, researching and testing online. I developed my skills rapidly and became an advanced digital marketer. It was much more difficult to find information online about digital marketing back in those days. Nobody was using YouTube and you really had to try to find good information and learn. In 2017, all the information in the world is online and it’s much easier to learn anything you want, quickly.

Bust Your Ass & Follow Your Dreams

I opened my own digital marketing agency on the side but continued to work fulltime. I upgraded jobs a few times and took a senior marketing role with half the year’s experience required. I finally landed a spectacular digital marketing job with great bosses and we all worked remote. I discovered the joys of working from home, skipping traffic to and from the office, and traveling while working. It was obvious that I could do this job from anywhere and I did.

My last year at my job I traveled to 13 countries and spent 45 days abroad. Not bad for someone working full time. I made myself indispensable, always did quality work and continued to learn. After having this dream job and some would say I pulled another crazy move and quit that job as well. I pushed the limits of my remote job and finally decided I wanted to work for myself and become location independent. When you have valuable skills you can start to make your own rules. I was finally achieving my goal from years ago.

Don’t Give Up Because It’s Hard

It was not an easy process, even after I had the skills to work for myself I had quite a few things to figure out. As a 34 year old home owner with a pet, student loan debt and a car I had a lot to figure out. Many people would have given up here and most do. I sold my house, paid off my student loans, found a friend that could use my furniture at his home and another friend to use my car in exchange for watching my beloved Gypsy Cat. I resolved every obstacle in my way.

My last 6 months before becoming nomadic were insane. It takes a lot to sell your home, sell or give away half of your stuff, packing and moving, find health insurance for the road, stocking up on gear I need (and plenty I didn’t), visiting family and friends that I wouldn’t see again for a while, founding an LLC and launching 2 businesses / websites just to name a few.

My end goal was freedom. I wanted freedom from the things I didn’t need, boxes full of stuff I haven’t look at in years, jobs draining me of happiness, location dependence, being an employee and so much more. I probably won’t be full time nomadic forever but my goal is to set myself up to never must become location dependent unless I want to and never to work for anyone ever again.

Travel Hacking + SE Asia Prices = FIRE

I also knew that even though I lived in Denver, Colorado and I wasn’t paying New York or California prices, the cost of living was still quite high and it would be very difficult to survive while transitioning into a full-time entrepreneur. For me, it actually made financial sense to become a location independent entrepreneur, living in affordable locations while my businesses are growing. Combining the affordability of my travel destinations with the fact that I can book flights for pennies on the dollar, stay in free hotels and Airbnb’s and that really opens up your options.

I am a digital nomad and a travel hacker and I feel like I found a massive loophole in lifestyle design that I want to share with as many people as possible. I feel incredibly free and know this is exactly what I am supposed to be doing with my life. I hope my story can inspire you to follow your crazy dreams, bust your ass for massive end rewards and travel hack your way around the world to everywhere you want to go.

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About The Author


Jason is a travel hacker turned full-time digital nomad. He travel hacks his way through the world using millions of points and miles to travel for nearly free. Follow along and learn the secrets to free travel.

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Jason is a travel hacker turned full-time digital nomad. He travel hacks his way through the world using millions of points and miles to travel for nearly free. Follow along and learn the secrets to free travel.

Find out more.