You Can’t Win If You Don’t Play

A solo traveler setting out on a hike in the hills and mountains
Last Updated: 8/1/20 | August 1st, 2020

Looking back, what I remember the most about cubicle life was the utter boredom. Back before I started traveling, I worked in hospital administration: first in inpatient assistance (I was the guy that greeted patient families when they came onto the units) and then in the administration office of the surgery department.

There were five people in my office, all older than me. I worked for one of the doctors. There often wasn’t much work, so I spent most of my days on MySpace and Friendster (remember those?) or reading the news.

When I came back from my first trip in 2008 and returned to the world of hospital administration, it was the boredom and large amount of downtime that led me to create a travel blog.

Back then, every day felt the same. I felt stale and uninspired. I wasn’t growing.

“What am I doing wrong?” I would wonder. “After all, I work, go to the gym, go out on the weekends, and have good friends and hobbies. Isn’t this the American dream?”

But something was missing. A piece of the puzzle wasn’t there. I felt like the guy from the movie Office Space. My mother used to say it was because I was in a job I didn’t love. Once I found a passion, “work would be more than work.”

It turned out she was right.

But I don’t buy into the idea that “you can find your passion” by sitting down with a pen and paper and thinking, “OK, I’m going to write down my passion and just do that.”

I think you stumble onto it.

You go out and live life and then, one day, realize: “This thing — this thing I’m doing now — is what lights my fire the most.”

Years ago, I knew a girl in Thailand whose uncle fell terribly ill. He was in the hospital in Bangkok, and we were all unsure if he would make it.

My friend, a former marketing manager from NYC, realized while she was caring for her uncle that that was what she was passionate about: caring for people. When her trip was over, instead of going back to her old job, she went to school to become a nurse.

My friend Matt recently got into gardening. He and his wife love growing their own food. With every new season, he finds himself more drawn to farming issues, land use, and gardening, and less interested in his law practice. So much so that, after his wife finishes her doctorate, they are looking for a town for her to teach in where they can buy a farm and he can become a farmer.

The same thing happened to me.

Nomadic Matt overlooking the water and mountains in Patagonia, Chile

When I first started traveling, everyone thought I was crazy for giving up on the American dream. But I had discovered that the American dream didn’t fit in with me. I was a circle trying to fit into a square hole.

While there are many people who are fine with office work from 9 to 5, I am not one of those people.

Once I started traveling, I found out that what I lived for was travel.

It was only when I got out of my comfort zone and started living life that I found out what lit my fire.

After a few years of blogging to earn money for travel, I looked around and said, “Wait.. this is what I like to do? Wow! This is my career!”

I had stumbled on the thing that was my passion.

If you are unhappy or daydream your life away but want amazing things, you have to make a change.

You have to get out there.

You have to push yourself out of your comfort zone, try new things, fail, and figure it out.

You can’t win the game of life if you don’t play it.

Sitting at home watching Netflix isn’t going to change anything. You won’t lose weight if you don’t work out. You won’t meet people if you stay at home. You won’t find your mate if you never go on a date. You’ll never know if you can do more if you don’t push yourself.

You have to show up to the dance, do stuff, have hobbies.

Life happens outside your door. It is something you have to participate in.

The day I quit my job was the day I moved closer to living the life I wanted. When I started my blog, I took another step forward.

Every day I take one more step to my ideal life — from reading 10 minutes longer, to cooking dinner, to signing up for archery classes (the Hunger Games are coming), to learning how to garden, to joining social clubs, to biting the bullet and booking that cheap flight I found.

My life isn’t going to change unless I make it change.

Neither will yours.

A lot can happen when you play the game of life.

But you have to play the game to win.

Even if you don’t “find your passion,” you’ll find yourself. You’ll find new things to be interested in and new hobbies you love.

So stop daydreaming. Go out. Make the changes you want.

Small ripples eventually grow into big waves.

Book Your Trip: Logistical Tips and Tricks

Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

Want to Travel for Free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodation — all without any extra spending. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.

Need Help Finding Activities for Your Trip?
Get Your Guide is a huge online marketplace where you can find cool walking tours, fun excursions, skip-the-line tickets, private guides, and more.

Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.