From Possessions to Paradise: How I Sold Everything and Moved to Hawaii 🏝

I was living in a trendy Chicago neighborhood when the first rumors of Covid-19 were being heard like a whisper in the wind. Near the end of my lease, that winter breeze was beginning to make the warm leaves fall from their branches. It was around this time that I had the intention to revisit Hong Kong and traverse the rest of southeast Asia. However, this Coronavirus disease was beginning to sound pretty serious. Word of a worldwide quarantine was being proposed.

So where did this leave me? I would be trapped. Confined inside my home during a harsh winter in the Windy City. It sounded like a recipe for a mental breakdown. Asia travel was abruptly out of the question and “The VID” was spreading like wildfire.

Brainstorming commenced. Where else could I go to escape? The idea of moving to an island surrounded by 2500 miles of water had emerged. The most remote island in the world — Hawaii. Volcanoes, waterfalls, rainbows and other dreaminess. How about it? Let’s give paradise a try.

In the two years leading up to my departure for Hawaii, I was already in pursuit of a minimalist lifestyle. Perhaps I realized this during my discovery of Buddhism and meditation. I was beginning to see the world differently. While living alone in that spacious two bedroom Chicago apartment, I began to sell, donate and discard many of my possessions. I lightened the load of what I owned during those two years. Books, video-games, sport and hobby equipment, art supplies, clothes, furniture, decorations, souvenirs, photography tools and more. Bit by bit, I released it all.

By a stroke of luck, a familiar face on Big Island had an opening of a bedroom in their home. A “two-week” lockdown became one month, then three, actually six, a year and so on. With this daunting situation progressing, the option to escape to Hawaii became very desirable. After some debate, with the looming winter plus covid restrictions in place, it was decided to head approximately 4200 miles west. Off the mainland, out of the tundra and into the tropics. My lease had come to an end and covid was decimating the USA. I purchased a one-way ticket to Kona on Big Island, not knowing how long I would stay. I had no expectations but I traveled with everything I needed to make a life there. My backpack was stacked with tech and film gear, my suitcase with clothes and necessities.

Once I landed, I quickly made friends by the social circle available through my roommate. This connection also led to freelance video-work at the local film theatre. Other friends I found through social media. For an island with only 200,000 people, making friends was surprisingly easy. On that rock in the middle of the ocean, all we had is each other and the generous gifts of the land. It makes for a functional community that relies on one another. Those connections are invaluable.

There are alternative methods of moving to Hawaii. Another common path is work-trade. In this situation for example, a person works on a farm for about five hours a day. In return they receive a roof over their head. On Oahu, getting a job in the service or hotel industry is another typical route. People are coming and going from the islands all the time. Therefor many businesses are in need of the workers. More specialized, one of my friends even got a job flying airplanes for the skydiving drop-zone.

Some people travel to Hawaii and never leave. It’s true that it’s one of the most heavenly places in the world. Often times people go for a week-long vacation, get a taste of paradise and dream of going back. I truly feel blessed as a US citizen have the option of a life there.

The island encouraged me to be even more wild and free. It helped me flourish and know myself deeper. From cliff jumping to snorkeling, hiking through volcanic craters and facing relentless downpours. Listening to the ceaseless lullabies of Coqui frogs. Swimming with dolphins, sharks and friendly turtles. Being swarmed by termites and cockroaches. Admiring daily double rainbows and visiting valleys with wild horses. It really is an invitation into a magical world.

I dwelled in the extraordinary for as long as I could. Forgetting about Covid, immersing myself in the natural elements and freeing my mind. There was no better place to escape the pandemic. Nonetheless, eventually we must wake even from the most pleasant of dreams.

I often hear the question “Why would you ever leave?” and I had asked myself this many times. At the airport on the way home, I heard a woman remark “I can’t believe I’m saying this, but I’m glad we’re heading off the island.” I knew how she felt. Hawaii gifts some of lifes most beautiful treasures. A place unique to any other; sacred, rich and vibrant. Yet there is more on this vast globe to discover. Culture and landscapes, connection and celebration, family and love. Hawaii is a fairyland across the ocean and life is but an endless act of letting go.

By the end of my chapter on Big Island I had a lot more than I brought with me. More experience, respect and knowledge for the magnificence of nature, animals, health, relationships and myself. My possessions didn’t matter. My memories, feelings and connections are what left the Island with me.