A location-independent life?

Sydney, Australia

Bondi to Bronte coastal walk - 3-kilometer trail along the cliffs between popular Sydney beaches

In the fall of 2020, I had just retired from a life of hosting auctions and sailing on ships to embark on a new adventure as a remote web designer. I was ecstatic because working remotely meant I could work from anywhere in the country as long as I had reliable wifi and a guaranteed workspace. All I had to do was look up where I wanted to go, find a hotel, and book a flight.

Simple, right?

With renewed vigor, I hopped on Kayak and began searching for flights to Chicago (a city I've wanted to visit for a long time). The trip begins on October 1 and ends on November 31. Select 'Next.' All of the flights available for those dates flooded the screen, and as quickly as they appeared, so did the many doubts and fears.

Will it be safe for me to travel alone, and what if something bad happens to me? How am I going to get around? What happens if I am unable to work?

Despite having dreamed of this moment for years and all of my manifestations of becoming a digital nomad were coming to fruition (slowly but steadily), I struggled to summon the courage to take the first step. I quickly talked myself out of the idea.

No, not this month; you should not go alone because it will be dangerous. You'll be able to visit Chicago next year.

After two months, feelings of regret began to creep in. Regret. It's the worst feeling in the world to know you could have done something but didn't.

Ughhh.

I immediately booked a 2-month stay in a lovely loft in the central loop on Airbnb, followed by non-refundable AA flights.

Live your life with no regrets.

This story goes on and on with details, but the point is that if you want it, you just have to go for it. Just like anything else in life, there will never be a "right time." The right time is now. You will find a way if you want it badly enough, and it's perfectly fine to start small to test the waters. I purposefully chose to visit a location where I knew people who lived there, and my father had also lived in the city in his early twenties and could recommend numerous landmarks and tours. The familiarity of the location by thought alone made the trip less frightening for me, and I would recommend the same approach to new nomads who are trying out this lifestyle. So, what exactly happened? To find out, visit my Chicago blog :)

Baby steps everybody - and maybe we’ll run into each other somewhere sometime.

Author: Leslie Lung