Buying a One Way Ticket to Bali

Johnny told me to “just do it”

It was just over one year ago I was sitting at my desk in my Chicago talking to him on the phone. Alternating between glancing at my computer screen and out the window of my top floor apartment, taking in the perfect late summer day.

But Chicago is not California, and every Chicagoan knows the onslaught of winter right around the corner that we endure.

Which played heavily in making this life-altering decision. Just one click of the mouse and it would become a reality.

I had called Johnny for support because he was in the process of uprooting his life in St. Louis en route to Denver for a new experience. He understood what I was going through.

My hand was shaking with nervousness and excitement. I couldn’t believe this was happening.

I was on the checkout page of Singapore Airlines booking a flight. Click…

“Your order is confirmed.”

It’s real. I had just booked a one-way ticket to Bali, Indonesia.

My mind was racing, and I had to rush immediately to the gym, as that is my sanctuary where my worries disappear.

Two years prior, I was living in California.

I had moved out there to launch a business with a few business partners. As much as I loved living in California, I felt a calling after two and a half years to come back to Chicago to be closer to family and friends. Not to say that I never will go back.

But, I woke up one morning with the feeling in my gut to move home. I immediately called my landlord and told him I need to end my lease (it was month-to-month at that point).

Two weeks later, I packed my car and took a 5-day road trip across the country eventually landing in Chicago. And I love this city.

But, now I got another calling in my gut for a new adventure. It wasn’t something I planned out. The feeling was right, so I decided to go all in.

Running a 100% virtual business for the past several years, I would travel on occasion across the states. But, I had never really had a vacation where I actually took time off.

My business is my obsession. I had never thought I needed a vacation from it because it was like I was always on vacation. This would be different.

This would be the beginning of a five-month journey traveling around the world. Fully immersed in the lifestyle I worked so hard to create. Fully immersed in the cultures of the countries visited. Learning to balance my work while still getting out to enjoy the places I travel.

The only thing I planned was to spend the first two weeks completely shut down from my business in an Ayurvedic detox center doing a cleanse.

Many factors came into play in making this decision.

First, I ask myself, “Does this scare the shit out of me?”

The answer was an easy YES.

I didn’t know anyone living in Bali, nor did I know anything about the place.

Why Bali?

When I started my first business in 2007, I saw a picture of Bali. It was tropical and beautiful. Green vegetation and clear waters. I declared that day that I this is the place I wanted to visit most.

After a little research on Google, I found out it’s a place that many people go for healing their mind and body. And I was pushing myself to the limit for a very long time, and I wanted to hit the reset button.

My philosophy on life is always to stay uncomfortable.

When I get comfortable, things grow stagnant. When I am stagnant and feel like I am not growing, I find myself very uneasy. This was about the most extreme thing I could think of doing.

The second thing that came to mind was how cheap the cost of living was in Bali.

Upon returning from my trip, a few friends asked me how I afford to travel for five months. The honest truth was that I was spending LESS traveling, then I was living in Chicago.

People just don’t know how cheap it can be to travel when you look outside staying at expensive hotels and spending loads of cash on tourist stuff. Live like a local.

Where the disconnect is for most people is that they are not location independent. So, they have to trade off their income for travel. I was able to work the whole time I was gone, except when I was getting lost in places with no internet.

With my expenses piling up here in the States, my lease on my car and apartment were ending in the same month. That alone was $2,000 per month in expenses freed up if I didn’t resign.

I didn’t have much of an attachment to my things and figured I could get rid of most of those too.

Third, winter was right around the corner. If you have ever been buried in a snow bank from the city plows and tried digging yourself out at 8am in below zero weather, I feel your pain.

Finally was the need for adventure.

We didn’t travel much growing up. Most of the vacations were camping and road trips as we didn’t have the excess money to spend. The first time I left the country was to Canada on spring break in college, then to Mexico the following spring break.

Lots of drinking. Not much to experience.

My idea of travel was that it was something reserved for the rich or that once per year vacation you could take. This would be my first time leaving North America.

The hardest thing for me to do was asking my parents to look after my dog for five months. After explaining to them why I was doing this, they were very supportive and agreed to look after Cain.

Once that was done, everything else fell into place.

I ended both my leases. The timing between when I bought the ticket and when I would leave was about two months. So, it didn’t give me much time at all. I was in a mad rush to get all loose ends tied up in my business for a two-week sabbatical.

Running around like a crazy man, I was able to sell about half my stuff before my flight. Luckily I had the most amazing assistant in the world who I left with a half full apartment to figure out what to do with. She sold some stuff, gave some away, and put the rest into storage.

With my life packed into one suitcase, I went to Baltimore for a mastermind. Then flew to Los Angeles for about a week to attend a leadership workshop. Then I spent 20+ hours in the air only to land on the other side of the world.

Landing in Bali was a complete culture shock. When the taxi driver took me to the Ayurvedic center, he gave me a big hug and kept thanking me. It was shortly after that I realized I gave him a $50 tip on a $30 cab ride. That made his day.

I can probably write a book about the whole experience, but it was a trip that changed my life.

I spent almost three months in Bali and slow traveled through a total of five countries. There were times that I was scared shitless. Like when I was lost in a small town in Nicaragua. Where faith would only get me to my next destination on a seven-hour bus ride because I didn’t speak any Spanish.

The memories I will have until I die.

Jumping in waterfalls. Driving scooters up a volcano. Tasting kopi-luwak coffee with friends. Rafting in the jungle. Swimming in hot springs. Underwater spearfishing in the ocean. Going to Spanish school in Guatemala. Living in the house with a three generation local family.

There is one thing I’ve always strived for in all my business ventures. It’s the overarching goal of having complete freedom in my life.

Technically, I had the freedom for a long time but was still trapped mentally in my own box. Scared of taking a leap and doing something different. I met so many new friends, and it ended up being the best decision I’ve made in my life.

While I was abroad, I met so many young people and college students just being nomads. Traveling the world without a care in the world. Jumping from hostel to hostel. Eating cheap food. Drinking cheap beer Meeting new people. Creating new experiences. Fully immersed in life.

Getting comfortable being uncomfortable.

Something I wish I did when I was in college.


What I realized is that life is much better outside my comfort zone. The things that scare us are usually the things that free us when we take them head on.

If you are scared of jumping out of a plane, you probably should do it.

If starting a business freaks you out, maybe that is exactly why you should dive in head first.

Life is short, and we can’t go through life having regrets. We can only seize the moment, so when we reflect back on it all, we can say, “Yes, my life was complete.”