Updated: 04/10/19 | April 10, 2019
“I’m going to quit my job when we get back,” I said, turning to my friend Scott.
“Really? I doubt that.”
“No really, I am. I’m going to quit and travel the world,” I said, turning my face back into the warm Thailand sun.
It was 2004, and we were in Ko Samui. We had just visited Chiang Mai, where I had met the five travelers who so inspired me to travel the world.
Their world of no 401(k)s, vacations, and bosses seemed too good to be true and I wanted to be a part of it.
I was determined to be a part of it.
I even started to prepare for it while in Thailand before I had any real idea of what I was going to do.
While on Ko Samui, I bought the Lonely Planet guide to Southeast Asia.
I didn’t even know if I’d go there on my next trip. I didn’t know when my trip would be or for how long or what I wanted to see.
But buying that guide made the whole thing seem more real. It was my commitment to travel. I had the guide; there was no turning back now. The guide symbolized my trip, and for me, it represented what I had to do to make the mental leap.
This book was like an ancient relic that contained hidden knowledge that I, a new initiate, had to decipher. It was my guide into the unknown. How could I stretch my money for a whole year? How could I get by without speaking a word of the language? How could I avoid getting scammed? How could I make my travel as rewarding as I imagined it would be? How could I do it as effortlessly as the new friends I met in Thailand? All of those answers, it seemed to me, were in this book—or at least the clues to the answers were there.
I read every page of the book on the flight home. I highlighted destinations, planned routes, and worked out my trip in my head. I knew everything about Southeast Asia by the time I touched down in Boston.
However, once back home, I came to the realization that I had no idea how to make this happen.
The list of questions seemed endless, and in the days before travel blogs, Twitter, and iPhone apps, the challenge of planning a trip was a lot more daunting than it is today. Outside of a few websites, there just wasn’t as much information on the Internet back then.
It took a lot longer to find and was usually a bit dated.
But the real challenge would be telling people I was leaving and letting them know I meant it. I don’t remember the exact conversation I had with my parents. They always counter my impulsive decisions (of which there are many) with some nervous, “the world is a dangerous place and we worry” parental response.
Over the years I sort of tuned them out. I have my father’s stubborn streak, and once I make a decision, I make it.
For a while, I don’t think they even believed me, and until the day I left, they tried to talk me out of it.
But what I do remember is going into my boss’s office.
It was a few weeks after I had come back from Thailand, and I was getting more and more sure that I was going to do this trip. I knew I had to do this trip. I went into his office and told him we needed to talk.
A bald, heavyset, affable guy with a love for cooking and wine, who always encouraged me to strive for more, I figured he would be the most understanding and encouraging. And I owed it to him to give him plenty of time to find a replacement.
I laid it all out. I told him about how ever since my Costa Rica trip I couldn’t stop thinking about traveling. I told him about meeting my new Canadian and Belgian friends and how I knew from talking with them that I had to travel around the world before I started my career. And I told him that whatever career that might end up being, it wouldn’t be in healthcare.
He leaned back in his large leather chair and gave me a dissatisfied look.
“You’ve only been here eight months, Matt. It’s hard to find a new person, especially someone good. I think there’s a future for you in health care.”
As he spoke, I heard a mix of anger, sadness, and disappointment in his voice. He had taken to being my mentor, giving me more and more important tasks, letting me manage one of the training programs he was responsible for, and coaching me into adulthood. It wasn’t simply that he’d have to go to the effort of replacing me—I really think he believed I had a future there.
“I won’t leave right away,” I replied. “I’ll stay until July, finish my MBA, and then leave for my trip. That will give you six months to find a replacement.”
“I had always seen you as a potential hospital executive or CEO one day.”
It was flattering, if not also totally manipulative. Not a lot of entry-level employees get that sort of vote of confidence from their boss, assuming he really meant it. I choose to think he did. And what did it mean if I was right? A million dollar a year salary. A big office. A staff. Fancy dinners. Attractive things. But would I bet my future happiness that they were really on the table? And would I want to spend the next 25-30 years of my life getting there?
I remembered my elsewhere. And I remembered the guidebook sitting on my desk.
“I appreciate it,” I told him. “But I know this is the right thing for me right now. And the timing is perfect.”
He sat there in silence, his face lost in thought as he processed the information. I grew more nervous as each second on the clocked ticked by.
He rubbed his head and sighed.
“Ok, I’ll talk to the office manager and we’ll start looking for your replacement. I’ll miss you. But if you feel this is right, I think you should do it.”
In a way, it was more than my job I quit that day. I quit my life.
My life had been heading down a road that I realized I wasn’t ready for: marriage, houses, kids, 401(k)s, play dates, college funds — everything you think about when you think about the American Dream.
At 22, I was working 50-60 hours per week, investing in retirement funds, and planning out my next 40 years. I never loved it, but that was just what people did, right?
While there is nothing wrong with that, it wasn’t what I really wanted.
It took a trip to Thailand to make me realize I was unhappy. It showed me that there was more to life than the corporate grind. While that lifestyle is good for lots of people, it wasn’t for me.
The day I left the office was the day I quit a life I had never really liked. I was living to work, not working to live. So when I hopped on the road at 25, I knew I wasn’t ready for that type of life. I’d come back to the “real world” when my trip was over.
Though, as time went on, I realized I could never go back. The divide between that world and mine was too great.
Sometimes decisions we make ripple forward in our lives like giant tsunamis. I thought the day I quit I was just quitting a job. It turned out I was quitting a lifestyle. I quit the American Dream, and in doing so, I found my own and have never looked back.
And they say quitting is for losers.
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 Booking.com 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:
- SafetyWing (best for everyone)
- Insure My Trip (for those 70 and over)
- Medjet (for additional evacuation coverage)
Want to Travel for Free?
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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.