The Zen and Stress of Pre-Travel Planning.

Travel Wolves
4 min readAug 3, 2018

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Beginning the adventure at home.

It’s now been a month since my wife, Abby, and I decided that we were going to take the leap and quit our jobs in Chicago and begin our two and a half month journey through Japan and South East Asia. Reading back on our post about deciding to take the leap to this long term travel seems like it was written years ago. Indeed, things like itinerary items and planning seemed so important a month ago. Now the last thing on our minds is itinerary. In fact, what seemed scary back then (the idea of quitting our jobs to begin traveling) seems just matter of fact now and can’t seem to come soon enough.

A month ago I found myself listening to an episode of the Zero to Travel podcast which featured a couple being interviewed before and after a year of travel. In their pre-trip interview the couple talked about their trip preparations which took about a year of saving and preparing to quit their jobs to travel.

“How foolish am I to choose to jump into this travel with such little preparation,” I thought to myself.

However, here we are now 7 weeks away from departure and the date can’t come any faster. At this point in my mind it is impossible for me to fathom how anyone could possibly keep travel plans and preparations quiet without going absolutely mad. Indeed the hardest thing about this trip for me at this point has been patience and mindfulness of our trip ahead. I realize this is especially hard for me as I find myself eager to leave my current job situation for new horizons.

“Quitting, for me, means not giving up, but moving on; changing direction not because something doesn’t agree with you, but because you don’t agree with something.” — Pico Iyer in Rolf Potts’ Vagabonding

This quote stuck out to me while reading a chapter in Rolf Pott’s long-term travel bible and I’ve reflected on it each week since. At this point of my trip preparation I am impatient to move on. I am ready to give up, and I am ready to get on with it already. An attitude that I’m afraid might continue with me on my travel if I’m not careful of it.

Meditating on my trip intentions, I want to make sure I am mindful of my impatience and eagerness both now, on, and after our travels. Of course that is always easier said than done as each day I find myself sitting at my desk and daydreaming of leaving for greener pastures. I admit I’ve done a pretty terrible job of finding patience to help keep myself motivated and pushing toward the goal and that is something that has scared me and given me quite a bit of paranoia.

Life hasn’t made the stress and impatience of planning this trip any easier for me either. Recently a company I really wanted to work for in the past reached out to me and told me they were interested in potentially hiring me. I mentioned the travel to this company early on in the interview process but not really wanting to fully disclose the plan I pitched it as “10 weeks of remote work in Asia”. They were onboard 100%. However, there is only one small issue. At this point in time I feel like working remote on this trip has the potential to ruin the whole significance of the trip for me and my wife.

All of this is rather moot, however, as nothing has been put on paper yet, so I’m not letting myself worry too much about it. Sacrifices have been made and are going to be made. The hard thing for me to grasp, however, is turning this potential vagabonding trip into a digital-nomad trip. Even though both allow us to travel, the two trip types are spiritually world’s apart. One allows for full immersion into exploration into new worlds, while the other keeps a firm foot planted in my old life here in the western world.

Additionally, my wife has made it very clear that she will most likely not be working while on the road, leaving her days open to explore and find that spiritual calling that brought her to travel. I will be honest in that I am jealous that that is no longer my only option. And even though it is not fully an option yet, I find my mind wandering to the possibilities a remote job would bring us. It’s something that has been eating at me the past few weeks. “What if…?”

Ultimately, this has added to my stress level even more. Instead of a defined deadline to quit everything and travel, there is now a big question mark hanging over my head. “What if I get the job? What if I like it and can’t do it from across the globe? Should I even take it?” etc. etc. Luckily I’ve been able to break out of this never-ending loop of thoughts and escape. I breathe, “This is part of the adventure.”

Indeed, in a very cosmic-way I could say “life” has a very funny sense of humor. When we make plans or strive to achieve something it often appears too far, too soon, too hard, too impossible, too something. Nothing ever is on time or in the right order, or even planned for that matter. But isn’t that just the point?

As I stress and drive myself crazy over details of our future, I realize we have begun our journey. This is it. We haven’t even left home and already we are on our adventure. This is where the rubber meets the road. And we’re just beginning.

Previous: Beginning the Leap

Next: Vagabonding to Nomading

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