Early 2017
I couldn’t stand my job.
Dreaded Mondays and got (relatively) excited on Fridays.
I was paying $1,375 a month for my share of a tiny 2 bedroom apartment in NYC.
With 15 days of paid time off (PTO) per year, my travel options were limited.
My only relief?
Weekly trips to the bar that never lived up to expectations.
There was the vague promise of a better future. A future where I’d make enough money to afford my own studio apartment in NYC. And maybe an extra 5 days of PTO per year.
I felt like life was slowly being sucked out of me.
Time for a change
I got chewed out by my boss for arriving late to work one day in February 2017.
I emailed him the night before, there was no urgent work, and this was not the norm for me.
Didn’t matter.
Is this my life?
By April 2017, I needed a change. I could start looking for another financial analyst job. Maybe that would help.
No, that wouldn’t do it. I needed something paradigm shifting.
I had an idea.
I could quit my job in June and actually enjoy the summer in New York.
And then, I could… wait for it…
Take a three-month trip to Southeast Asia (SEA) to close the year.
Was it really possible?
It was.
After socking away money every month for the previous couple of years, I had a nice chunk of change in my savings account.
At the same time, I would double down on my basketball card side hustle. Something I actually liked doing and could provide income.
A nice summer
The summer was relaxing.
During the week, I worked on my card business, did solo day trips, and played basketball. I had a lot of alone time, as my friends still had normal jobs. But that was perfectly fine with me.
On weekends, I hung out with my friends.
Barbecues, the beach, and nights out in NYC.
I started feeling excited about life. Really excited.
College was supposed to be the best years of my life.
Supposed to.
Hmm
A trip to the other side of the world
As September approached, I prepared for my big trip. Not going to lie, I was a little nervous. I had barely traveled in my life. Had never left North America. And here I was traveling to the other side of the world.
I booked my first flight – a one-way ticket from New York to Bangkok. Total flight time – 19 hours.
While I planned to return to New York before Christmas, I flew into Asia with nothing booked past that first flight and four days in a Bangkok hotel.
I would wing it from there.
Over the next three months, I spent time in Bangkok, Koh Tao, Chiang Mai, and Ho Chi Minh City.
Most of my time was spent in Bangkok and Ho Chi Minh City – yeah, the beaches and mountains were nice, but the cities had special energy.
I met some amazing people, and started considering the possibilities.
Life on my own terms.
Hmm
Time to come home… at least for a little while
A few weeks before Christmas, I flew back to New York. I wanted to spend Christmas in New York and figured the dream had to end.
I figured I’d get another job.
There was just one problem.
What would I do?
I spent the winter months considering my options. I realized:
- There was no 9-to-5 that excited me.
- I didn’t have the capital to scale my card business to a level that might support me.
- I wanted to build a location-independent income that would cover my expenses, but didn’t know how.
Buoyed by a blind belief in myself and a high risk-tolerance, I came up with a plan to extend my travels and chase my dream of creating location-independent income on my own terms.
A long-term strategy
I would sell my cards and spend my time traveling and networking with successful expats. I hoped to come up with business ideas that could be pursued anywhere in the world with an internet connection.
Selling my card investments would give me enough money to live in Southeast Asia for a few years. More than enough time to carve a new path.
Or so I hoped.
A New Beginning
I traveled through SEA over the next year, building a network, exploring business models, and enjoying life 😉
One business model really stood out – writing.
Let’s take a very quick trip from 2008 through 2015.
I loved writing in high school. But I thought a writing career = financial struggles.
Didn’t want to be broke.
I liked trading stocks – so I decided to major in finance. As an 18 year old, I didn’t realize that successfully trading stocks for a living was as likely as playing in the NBA.
By the time I realized what jobs are available to finance majors, it was too late.
(Or so I thought).
Back to 2018.
I didn’t revisit the idea of a writing career… until I was halfway across the world in SEA in 2018.
I was already a good writer, and had a lot of untapped potential.
In SEA, it seemed like every westerner was doing something different from what they studied.
Sure, billionaire tech founders didn’t have to worry about limitations based on what they studied – or if they graduated.
But us mere mortals? We were supposed to have a specialized formal education if we wanted a job within that specialization.
Supposed to.
But it was clear this wasn’t always the case: I had met guys making good money – in ways unrelated to their college educations. While they were smart, they didn’t have Einstein-level IQs.
I considered the ways businesses are promoted with the written word. There were blog posts, sales letters, white papers, case studies, newsletters, and much more. After doing some research, I realized it was possible for me to make a nice living as a writer.
So, I read every book on commercial writing that I could get my hands on.
And tried to get some writing work.
It was tough in the early days.
I made around $4k in my first year writing. Total.
But I kept at it. Exceeded my income from my financial analyst job in late 2021.
I was enjoying my work… usually 😉
Working on my own terms.
And when it was time for a new challenge in early 2022? I launched a digital marketing agency – which is still going strong.
Final thoughts
This path isn’t for everyone. It takes discipline and tradeoffs. Some people are happy with their 9-to-5 or it’s a necessary sacrifice. And that’s fine.
But this was the right path for me.
And if you’re feeling trapped like I was?
Hope this article gets you thinking of the possibilities.
