Beginning the leap…

Travel Wolves
8 min readJul 3, 2018

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Taking the leap to 10 weeks of travel in Asia.

Last week feels like an eternity ago. A week ago I was sitting across the table from my wife, Abby, over dinner on a Friday night after work and out of the blue she comes in with, “I just want to take off work and travel for a while.” This wasn’t necessarily a new concept. We had certainly talked about it in the past, but after a rather long week I just wasn’t prepared to have the flexible state of mind where I could fathom us putting our lives on hold to travel. All the normal excuses as to why this just wasn’t going to work flashed through my mind but instead I simply just responded, “Maybe in a year or so. We can save up and just plan for it.” We both agreed and sighed a little because a dream such as taking an extended period off to travel is just one of those dreams that just seem so cripplingly large to comprehend.

The next day on an extended bike ride with Abby the topic came up again. “We really should go next year,” she said. Again, excuses came into my head. Thinking to myself, I made a list. First, we’d need to wait till our lease ended and move all our stuff into storage. Expensive. Next we’d have to board the pets. Really expensive. And lastly, the real scary step was quitting our jobs. I paused on that thought.

I had just had a rather unsavory meeting a few days earlier with my boss in which I realized he and I didn’t see eye to eye. The job was still relatively new and Abby and I had just relocated to Chicago from Los Angeles only 5 months prior. Perhaps I was being naive but at that moment a light bulb went off in my head. Wait a second, if I was going to leave my current job what’s to stop me from taking some time to travel? Nothing.

“We could just go now,” I thought aloud. “Instead of taking a new job we could just use some of our savings and travel. We could leave in a few months and be back to spend time with family for Thanksgiving.”

“But what about the apartment? How do we pay rent? And who is going to take care of the pets?” Abby responded.

Thinking for a minute. We did have a friend who had just moved back to Chicago from Los Angeles shortly after we did who was looking for a lease or an apartment starting September 1st. Maybe she would be interested in helping us out. It was a long shot but if we could do it it would certainly help us keep the place and all the expenses down while we were gone. I mentioned this to Abby and she got excited. Yeah, this might just work. We’re crazy for thinking this way but it might just work.

After sleeping on it Abby and I woke up Sunday and discussed. “How are you feeling?” I asked her.

“I’m uneasy but I think it’s a good idea.” She responded. “Let’s do it.”

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For the next few days, any time Chris and I saw each other we would open with the same question.

As soon as we would wake up, one of us would ask the other, “How are you feeling?”

Some days, I’d be the one to say “You know, I’m really not so sure this is a good idea,” while Chris would be like, “This is a great idea!”

Other days, Chris would say, “I’m scared!” while I’d be the one to say it’s all going to work out in the end.

We read articles on the internet, hoping they would persuade us one way or the other. We talked to a few friends, who ranged from, “Yeah, do it!” to others who were like, “But, why?” We talked to our parents.

It became clear to both of us that no one was going to give us a solid yes or no answer on whether or not this was a good idea. We figured we might as well do it. What could be the worst thing that happens? We end ourselves financially. No big deal right?

Ignoring our fears, we stalked google.com/flights for a solid week, trying to develop an itinerary of where we wanted to go. We immediately landed on the idea of Southeast Asia. We had been pretty far into planning a trip to Vietnam for 2019. We landed on traveling throughout southeast Asia pretty quickly without even discussing it. If we were going to travel for ten weeks, we’d finally have the time to visit Thailand as well. And Laos.

We planned to fly directly to Thailand but quickly realized that most flights had a layover in Tokyo. Chris had been talking about visiting Japan forever. We realized, hey, why not? We have ten weeks. Who says we can’t spend one of those weeks in Japan?

After that, we planned to spend 3 weeks in Thailand traveling south to the beaches and back up north before traveling east to Laos for 2 weeks. Finally, we planned to spend the last 3 weeks of the trip traveling through Vietnam, hopefully via motor bike traveling south ending the trip in Ho Chi Minh City. We gave ourselves an extra week to mess around. I’m a very thorough planner and realized I could build a pretty detailed itinerary right away. I want to challenge myself to be open to recommendations of what to do and where to go along the way.

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Finding the major flights for a 10 week trip is easy. Putting your credit card info in and hitting submit is the hard part. Saturday morning Abby and I found ourselves sitting at the dining room table with the computer re-plugging in flight destinations as we had done almost every day that week. But this time we were going to buy them. And we realized that we would also need to buy our accommodations in Japan.

Japan is expensive, at least compared to most of our southeast Asia trip. And even the most modest rentals there seem to be expensive.

All in all the flights ended up not being super expensive which was a relief. In total our flights from Chicago > Tokyo > Bangkok and Ho Chi Minh > Chicago were under $850 a piece. However, all of this considered we found ourselves freaking out a little before we finally hit the “Purchase” button.

Second thoughts rushed through my head and then before it spiraled into a tizzy of self-doubt, I pressed the button. I looked to Abby and she was smiling. We did it. It’s official. A week ago this was nothing more than a thought in our minds. A week later it’s a very sobering reality. A life-long goal actualized with the press of a button. Are we crazy? Probably. Are we nervous? Of course. But luckily we’re not doing this alone.

I feel very blessed that Abby is 100% behind this in the same insane way I am. We’re doing this together and that’s all that matters. Abby is the perfect yin to my yang and because of it we help keep each other balanced. For instance, as soon as that button was pushed I knew the thoughts flying through my wife’s head, and it pretty much included a rough itinerary to our trip. Where I generally follow my gut and tend to take adventures as they come, Abby is always thinking ahead. It’s a good combination because without each other we would either speed through an adventure or easily miss exciting opportunities. I’ve had the opportunity to travel with Abby now for over 10 years and there is absolutely no one I would rather get lost in Southeast Asia with.

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I’m a pretty meticulous planner. The idea of planning a 10-week trip is a breeze to me. I could be on Google and have every single activity and hostel and bus trip and train ride planned out before we even get there. I’ve challenged myself to not do that, though. So far, all we have is our week in Japan booked and roughly planned thus far. It was the most expensive after all. We were in such a rush to book a place that was affordable that we nearly didn’t realize the rental in central Tokyo we were about to book stated there was no bathroom in the listing, suggesting we walk to the public baths nearby to use the restroom.

“Nope!” I said to Chris, and we immediately scrambled to find something else in our low budget.

It wasn’t that hard however as we found a place in Shinjuku, a very enticing area within Tokyo, but we chose it simply because it’s within walking distance to “the Robot restaurant”. I’ve been interested in going to this place ever since seeing it on an episode of one of Anthony Bourdain’s (R.I.P.) many travel shows. My favorite line from the guidebook our host sent us was this: “The staff care about you during your stay, but he can not speak English.” We feel very assured knowing this.

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It’s very interesting finding yourself suddenly planning a dream trip. Unlike my wife, I found myself at first unsure of what to do. Hell I had always figured that when I finally visited Japan I would just simply know what to do. I didn’t. The only thing in my head was the typical itenerary items that linger in your mind when you think of visiting Japan, Sushi, Ramen, Sake, Temples, and strange robotic dystopian fantasies which live in my fantasy of Tokyo like a comic book painted in my mind.

I knew I wanted to do something traditional while in Tokyo. A sporting event such as baseball or sumo was a fun thought. One quick Google search and Abby is pulling up sumo tournament dates. Apparently they only occur six times throughout the year. Luckily for us our trip coincides with the ending of the tournament in September.

But Japan proves an interesting challenge for us. First off we’re on a strict budget. Second, Abby is vegan. Sure I could indulge in some raw fish and noodle delights but I need to make sure that I’m mindful of her situation especially while in our four days in Tokyo.

Luckily some of the world’s best vegetarian food can be found in Japan’s old capitol of Kyoto which was the second Japanese destination we had in mind. Unlike Abby who likes to actually research things on the internet I learn most of my travel info from travel shows… which as I write this is scary even to myself and probably why I only think about food when planning travel. So considering my rather rudimentary “research” methods I was very happy to learn about the charm and cuisine of Kyoto. Our plan is to get a bullet train there which was to be purchased later. We would get there and spend 4 nights splitting our time in Japan. We rented a room in a very pretty hostel with a quaint little courtyard in a very Japanese style.

With a few clicks of a button, which almost rendered us without a bathroom, we had ourselves some places to sleep in Japan. We not only had the majority of our flights booked but we had some decent accommodations and activities planned.

A week ago this felt so impossible, so complex, and yet here we are. Nearly booked and ready to go. The only issue is, we have to keep a majority of it a secret…for now. Now begins the hard part. Working out the logistics of quitting our jobs, getting healthcare and travel insurance, getting the pets settled, and slowly crossing off the other items on our list before we finally take the final leap. A leap which doesn’t seem as colossal as it did a week ago.

Next: The Zen and Stress of Travel Planning

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