Singing the Song of the Open Road

Singing the Song of the Open Road

When we quit our jobs in 2007 to travel for a couple years, it was fairly simple. Sell the cars, put a few boxes in a friend’s basement, and away we went. Fast forward 15 years to 2022 and that’s just not the case. There’s a career, a dog, a house, a mortgage, insurance, and a perspective benefitting from a decade and a half of additional experience. So while the end result was the same, the path to get there was much different.

When we quit our jobs in 2007 to travel for a couple years, it was fairly simple. Sell the cars, put a few boxes in a friend’s basement, and away we went. Fast forward 15 years to 2022 and that’s just not the case. There’s a career, a dog, a house, a mortgage, insurance, and a perspective benefitting from a decade and a half of additional experience. So while the end result was the same, the path to get there was much different.

The decision is tough to explain, really. There is much more emotion than logic, which, as a former engineer doesn’t sit well. In some ways, it’s ruled by emotion just like the decision to propose to my wife. There was logic, sure, but it was secondary to the emotion, not the driver of the decision. The fact of the matter is that it felt right, and that was it.

Now, I know there are many people out there making hard professional life choices, but who may also be paralyzed for all the reasons that large decisions become overwhelming. So, given one of my StrengthFinder themes is Input, I’m going to break down my thought process with the hope it’ll be helpful to others.

Siddhartha's Art of Motorcycle Maintenance

At the end of the day, a decision needs to be made. Circling around a decision without reaching a conclusion is exhausting both mentally and emotionally. But the larger the decision, the more difficult it is to reach. This is particularly true when talking about “life decisions”.

There’s a bajillion books and coaches to help think through this. But when it comes to getting to a decision, there are two pieces to understand: 1) why are you looking to change and 2) what you are putting at risk.

Answering the “why” gives a clear driver to the decision. It creates focus like a dancer spinning on their toe. Find a point to use as an anchor, don’t lose it, focus on it. This gives a foundational structure to the decision-making process. Without it, the process just falls over.

Breaking down the “risk” gives the ability to make trade-offs, concessions, and compromises. This is essentially like pulling the curtain back on the unknowns and bathing it in as bright a light as possible. It exposes the risks being considered so that they can be addressed independently.

The Why: Travel Deeply

I believe these types of decisions should start with the why. Of course, everyone has their own paths to discovering their why, but it’s usually an affair pretty deep-seated into our psyche. Mine is travel. I’ve loved it from an early age, and the times when I’m not traveling are usually when I’m dreaming about travel.

There’s nothing like hiking a high mountain, summiting the trail to a vista overlook that gives you a sense that you’re a small, small thing in this gigantic world.

There’s nothing like driving through the small towns, remembering that the country is diverse and there are many people who live outside the bubble you normally spend your time in.

There’s nothing like being a traveler in your own town, realizing that the fabric of your town is woven from the intersections of these communities, including all their wonderous diversity.

There’s nothing like leaving the country to strip your assumptions bare about your own homeland, exposing the unique and different paths of people leading their lives.

For me, travel reveals the common threads connecting us all by challenging assumptions we make about our country, our community, and ourselves.

And so, in that vein, the driver of my decision to quit my job was quite clear. First, I want to travel deeply and immersively. Second, I want to find a way to make travel an integrated part of my life, not just a pause from “normal” life.

The Risk: Maslow’s Hierarchy of Needs

Often, a simple concept can often help simply large and unsolvable problems into a pieces that are manageable, and understanding our needs as humans is certainly a large problem. So when I’m trying to think through a large decision like this, I breakdown the risks into different types, and I find Maslow’s Hierarchy of Needs gives a good structure for it.

The idea is from Abraham Maslow’s breakdown of the five tiers of needs we have as humans. The first 2 are defined as “basic needs”: physiological; and safety. The second 2 are “Psychological Needs”: love and belonging needs; and esteem. The last is known as a “self-fulfillment need” and is generally labeled as self-actualization. (Note: there have been many iterations and criticisms of the model which are worth exploring.)

So, when I was thinking through this decision, a big piece was understanding our basic needs: where will we sleep, where will we eat, how can we ensure our physical safety, etc. These are somewhat straightforward logistics, but important to separate from other concerns.

A second set of concern were the needs around the sense of belonging and community. This is a big one, and a lesson we learned from our last travels. In today’s world, connectivity is a blessing, so we thankfully can help maintain our relationships back home. In 2008, that was much less of an option, and a source of much frustration.

The last two of Esteem and Self-Fulfillment are the tougher ones for me. My identify is wrapped up in my career in many ways. I've enjoyed the jobs I had, and they fulfilled both these needs in many ways. So when we were making the decision to embark on this trip, figuring out these needs was critical.

Last time toward the end of our trip, we were stable and living in Argentina in 2010. I started creating concepts for companies and testing out Natural Language Processing python libraries to pursue a few ideas. I was trying to satisfy something that the travel alone couldn’t.

Hard at work at our apartment in Argentina in 2010

So this is where Unanchor comes in. Whether it has the legs to be a successful company or a fun hobby isn’t yet clear, but it has a role to play. And fundamentally, it’s helping fulfill something that was absent in the previous trip. In hindsight, I can identify that gap as both the Esteem and Self-Actualization needs not being met, but at the time it just felt like a driving and stymied urge to build, create, and grow something new. 

The Decision: Launch

Last time, when we returned from our travels in 2010 after 2 ½ years on the road, we re-entered life in the States. It was hard, and some of our decisions came back to bite us, but nothing too crazy. But we said at the time that we wanted to do it again. To give ourselves some accountability, we put a date on it for 10 years from then. There was little more to it other that the this-was-awesome-lets-do-it-again logic.

Then, we talked about this in circles... for years. Was it the right time? What about our careers? What about our financial security? What about our physical safety? So many questions that needed to be answered. But the decision came to a conclusion when we realized our higher-level needs had a real outlet in Unanchor.

This company turned the conversation from running away from careers to running towards a destination. Would we have left if Unanchor wasn’t part of the equation? Probably, but not necessarily in the same way or on the same timeline. It created an opportunity to see if we can make this thing work.

All that’s left is to ride this rollercoaster

So, yeah, we’re here. 15 years after our last Big Trip started, we’re starting our next one. We’re out traveling the world deeply, trying to build this company, all in one go. We can’t see through the end of this tunnel we’re entering, and that’s scary sometimes, but ok.

To be clear, it’s odd to be in a situation where the outcomes are so unknown and unpredictable. But it feels so right, and that’s what this is about in the end. These decisions need to feel good, fulfilling, somehow building towards an end you can’t see but your gut tells you is the right place to be.

I think that’s the best surprise about this whole thing. My engineering brain could rationalize it all. I could think through what it might look like, but I couldn’t predict what it would feel like. And while it’s crazy to say it’s surprising when this was this planned, here we are.

The path feels familiar. The steps feel right. The direction leads where we want to go, and whether we end up at the intended destination is another matter entirely, but wherever the path leads, it’ll be an adventure getting there, for sure.

And regardless of logic, that feels just right.

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