Why I Quit My Jobs to Travel, Part II

Initially when I was writing my first post about why I quit my jobs to travel I felt like I just had too much to say. Deciding to split it into two seemed like the best idea and I intended to publish the next one a few days later. As I got into it I started to think that it might be best to wait, reflect on the first month, and write about how my perspective has changed.

So I left my jobs, both of them. And the thing about that is I left my jobs. That means I had two reliable streams of income and now I have zero.

Here is a suggestion; have a plan or at least somewhat of a plan. Do not quit your jobs on a whim to travel when you have no money and no place to go. There has to be a finish line.  What I mean is if I were to do what I am doing forever I would run out of money and couldn’t pay for my car insurance, health insurance, AirBnB, food, fuel for my car, etc.  Make sure you have your shit together. I spent the last 3 years pretty much doing nothing but working. Every penny that didn’t go to my bills and obligations went into the piggy bank. I made sure I was not going to be put in a bad spot. I’m also going to California, staying with my brother and his wife, and hopefully going to find a job. That’s the end game. That’s the finish line. Maybe.

I think a lot of people have a very misguided fantastical perception of this dream to quit your job and run away. It’s not like that. I have to be very careful about how much money I’m spending, I slept on my friend Sean’s floor for 4 days straight, I don’t get to shower every day and to tell you the honest truth most of the time I look like I haven’t slept at all in a few days. So even though I’ve had a stiff neck for three weeks, it’s totally worth it.

 I’ll share with you a nice little anecdotal story about my very first day out. Please don’t take this as a “here is why you should do this” kind of a story but it is very real. There’s a pretty cool stretch of road as you get close to the border between New York and Vermont. It extends from Route 47 up to the Lake Champlain Memorial Lighthouse.  There’s a long twisting turning road that runs right through the woods that even in good weather you have to be careful on. When I was passing through it was absolutely down pouring. For a half hour I was driving 5 miles an hour with my flashers on because I couldn’t see a damn thing. Seriously, I was terrified. I’m on this road that I’ve only been on once before, winding through the trees on this narrow road, and it’s raining so hard that I can’t even tell if there’s a car in front of me. I was having all these anxious thoughts about flooding and what to do if I were to get stuck and oh yeah this was my very first day on the road! I had been on the road for probably 3 hours. The trip hadn’t even really started yet and I was about to die.



Then it stopped raining. The 4 pm sun came out just as I was exiting the woods. That twisting turning road ends up as a straight shot across some Vermont farmland and runs right up against Lake Champlain. I so badly wish that I had stopped to take a picture because there’s just no real way to explain how beautiful it was. I turned to my left when the line of trees finally ended and saw the sun peaking out right over the mountains, blanketing the landscape, and causing the rain to evaporate from the road I was on. I opened my car windows and was overwhelmed by the smell of petrichor. Most people think smell is the smell of rain itself but petrichor is actually the smell of dry earth right after it rains. I think it’s one of the most refreshing natural scents there is. It was blissful. I had the biggest grin on my face thinking to myself “This is why.”

It wasn’t just the sun or the scent or the scenery. It was freedom from the mental shackles I’d been chained in. It was the first time in years that I felt like I was moving towards something, even if I wasn’t quite sure where or what to. It was the realization that there is an entire world outside of myself. I had kept myself as a prisoner for so long that I’d forgotten that there still are a million people to meet and a thousand places to visit and just because things were bad absolutely does not mean that things can never get infinitely better. A lot of the best moments that I’ve had in the last month were actually while I was driving. A few times I caught myself just totally cheesing at the fact that this is happening. I can’t believe I’m actually doing this.

Since June 1st I have put almost 3,000 miles on my car, visited 8 states, 14 cities, caught up with friends I haven’t seen in years and got to see how they live their lives. I got to see how their lives have changed, most of the time in positive and unexpected ways, since they left their hometowns. I got to hear about where they’ve gone and how they got there. I’ve been able to see up close structures, buildings, landscapes, and monuments that I have only ever seen in books and on the Internet. I’ve been practicing my photography, which is something I have always loved and appreciated but never really taken a step into. I started using the time I am spending alone to do some attentive reading and a lot of writing. I’ve even started writing at length and sharing it with other people. I’ve reconnected with the people that make me feel truly appreciated and lift me up and with them had so many heavy laughs and enlightening conversations.

Got that Iron Man at a random stop at Dave and Busters in Buffalo

Got that Iron Man at a random stop at Dave and Busters in Buffalo


In Toronto I met a girl outside a comedy club right by the Airbnb I was staying at. The following night after the Blue Jay’s game downtown we crossed paths again and ended up talking all night about 12 Rules for Life, Jordan Peterson, libertarian stuff, and Wegman’s! Last night I had my first Chicago deep dish pizza with a girl I met on national television (more on that later) that I hadn’t seen in 2 years.  I woke up and drank my coffee on the shore of the Atlantic Ocean in two different states. As I’m writing this I am staring straight out at Lake Michigan. You get some really good perspective standing next to something this big.

I made friends with Joe, a taco restaurant owner in Portland, Maine. In Brooklyn I was walking down Knickerbocker Ave and complete at random saw a girl I worked with at Dinosaur BBQ in Syracuse who I have not seen or talked to in probably 6 years. I played a set of music in front of friends that have never seen me perform in the 10 years I’ve known them. I’ve had deeply personal conversations about life that all stemmed from “What made you to do this?” I’ve had people tell me that I’ve inspired them to make changes in their own life. I’ve had more people tell me they are proud of me in the last 2 months than ever before. I have fallen in love with this. It’s been such an incredible, happy, inspiring, and positive time in my life that I can’t even believe it.

I had mentioned before that the Universe is constantly sending signs to us. I was extremely unhappy where I was. I was completely broken. Then everything unfolded in just the right way that allowed me to pursue this dream of mine. My roommate was moving to Connecticut, my lease was up at my apartment, I was quickly being deterred from a job and path that I thought was right for me. I knew it was the right time. I knew if I didn’t seize the moment that it would be harder and harder as time went on.

It only took me 28 years but I am learning, to quote the great Sir Elton John, you can’t stop when your feet say go and you just can’t stay when your heart says no. You’ve got to get up, jump out, and don’t wait when you’ve got to get away. You’ve got to go out and find yours.



Here's a gallery of some of the pictures from the story so far...