The Plan

Shortly after I lost Brynn, I encountered an old Yiddish adage “we plan, and god laughs.” We have ideas, ideals, goals and plans as if life is a linear path, with known stops along the way that has been predetermined for you. Fortunately, and unfortunately, you will eventually be faced with change of plans, detours, or simply getting lost. Some roads have detours ending up on rough patches that take a while to clear through. There are no turnaround points in these stretches; you must simply keep moving forward. Other detours may lead you to beautiful experiences that you wouldn’t have had unless you took them. But sometimes the worst kind of road is the one that remains untaken. These are roads that you come across at specific junctions in life, but the change in direction might be something you’re unwilling to make. You wonder where it will lead you to, but not all roads are meant to be taken. And others, it just takes you many years to make that turn on to them. 

Making the decision to leave my job I had been at for 11 years and go on this adventure is perhaps not a detour, but it’s from all the wanted and unwanted changes in my plans and directions that lead me to this point. Taking this road was going be a significant deviation, but I simply couldn’t stop wondering the places I would go on it.

It all started in April 2022 while searching for a document, I came across a file I had created ten years earlier, outlining a plan for biking from New York City to San Francisco. A smile lit up my face, as I carefully observed the day-to-day biking details, packing list and the plans of turning my road bike with all its racy aggressiveness into a lovely comfortable touring bike. I certainly had the youthful exuberance, arrogance, and let’s be honest, cluelessness shining through the details as I would optimistically get through the 4000+ unsupported miles in 37 days. I laughed at the naïveté, and the lack of planning that was befitting of the seriousness of my commitment to the idea at the time. A decade and a lifetime of lessons later, the experience I started imagining was not just about biking across the country, but to reset and rejuvenate my mind, body and spirit while feeding the curious side of me that traveling always provided. I was finally feeling ready to enter the next chapter that I had been struggling to start writing in, and this would be the perfect starting scene of that chapter. Some might be thinking how does biking across the country rejuvenate? Well, that remains to be seen. But in my experience, it is the most challenging of things I’ve taken on that have left me with the most inspiration and energy.

After coming to terms with my decision, which I am unsure if I really have, I had some planning to do. That planning extended well beyond the logistical details of this undertaking. 

First, I had to answer the question of whether I would be ok leaving my career at Oracle to take on this journey? Over the past 11 years of my time at the company, I had experienced incredible professional and personal growth. I was able to climb the proverbial ladder, and I couldn’t help but develop a self-identity that was based on where I stood on that ladder. I have also developed friendships and working relationships that have been incredibly supportive of me through the good and bad times. In a sense, I had to be ok with saying goodbye to an environment that was like a family. And I would be leaving the safety that comes with family. The safety of knowing I had the support of an environment not just when I provided positive contributions professionally, but also during a time I experienced tremendous lows personally. There are always layers to emotions, and the reality is that fear was a big driver of the oscillating decision. The fear coming from changing the plan; fear of doubting my decision and the unknown of what comes next. Where will I go and what will I do from here on? Fear forces you to face the scariest of all: yourself! The self-doubts, insecurities bubble up to the top as you become your fiercest critic towards the past and that question of “am I good enough to achieve it again?” Leaving my career and the comfort of working in an environment where I felt supported was a heavy decision to say the least, and I think I have not truly experienced the weight of it yet.

However, the past 2 years have been all about change. About discovery and finding a new path. The discovery I had to go through was the person that was left from the trauma I had dealt with. The inspiration and creative streaks I had found through writing was about exploration of emotions, thoughts, and of course snippets of my current state. The heavy feeling was not solely from the decision to leave behind what I knew and felt comfortable with, but the weight I had been carrying because of life.

So, I had to bring some lightness to this heavy feeling. And it started with the bike. I’ve been biking for a long time. And the more you do something, the more investment you give to an area of your life, the more involved it becomes. That means for me, I couldn’t just buy a bike off the shelf. I had to build one that met the standards I have come to expect on something that I will be sitting on for thousands of miles. I also had to reconcile the experience I wanted from this journey that should be a big input into bike decisions. Do I go with a touring bike that provides all the necessary comfort and features you need to load up your entire life and carry along? Slogging through the miles with the comfort of knowing you will be able to survive a nuclear winter with the amount of gear you’re carrying. I see those people from time-to-time while cycling, and it looks painful. Painfully slow. But, I suspect those people might’ve graduated from adventure touring that I am about to embark on to riding towards an unknown destination for an unknown duration. They simple feel most alive pedaling without a plan. That fascinates me, but it may not be me at this point in my life. I wanted to feel agile with where and how I go after being confined in my house and head over these past 3 years. I was already carrying a lot of emotional load going into this journey that if there was a specific theme to this experience, it would be weight reduction – shedding off the emotional weight that was no longer serving me well. And the best way to reduce the load you’re going to be carrying on your biking journey is to start where there is a very low limit to begin with. And that is what I did. I went the complete opposite extreme and bought the most inappropriately aggressive gravel bike frame that was light, fast, and without any of the necessary functions that is needed for touring a country for two months.

Now the new plan was that I am on my way to a credit card tour going from hotel to hotel along the route. One of the important lessons I’ve learned throughout this process is “the plan” is never complete. It’s meant to be adjusted until you’re going along with it, and I suspect it will take a life of its own from here on out.   

As I started building out the bike details, schedules, packing list, I started realizing the new plan was limiting myself on the other end of the spectrum than a bike for the survivalist. I would become a slave to the plan going from point A to point B without much room to deviate when I inevitably encounter a road that looks worth taking or the one I was forced to take, as life presents you with.

It is at that point I came to the conclusion that developing a cross country biking trip plan with the purchase of bike frame was not the best starting point. But I’ve been getting significant enjoyment out of problem solving with the limitations I am having to work with. Traditionally, I’ve always founded it easier to work backwards from what I wanted as the intended outcome. Then identifying the resources and decision that would be needed to get there. But I am not sure there would’ve been any fun in that approach, and frankly I was too deep in to ordering all the necessary parts - it was time to commit and make it work. I had to become a bike real estate agent. Selling to myself the expansive space I had on the bike as it was a blank property that I could build my perfect home for the next couple of months. I may have had a few episodes of buyer’s remorse. Thus, came the incorporation of camping to the plan that included being able to find a camping setup that would be light and compressible enough to fit into a bag that would attach to my handlebar. It’s 5lbs of insurance, and immeasurable in its ability to provide stories to tell.

I was familiar with adding and shedding loads in my life. But the real load I needed to deal with was the one I was carrying personally. Unfortunately, grief becomes a permanent load that you will carry for the rest of your life. You can’t simply shed it. But you work on learning to live with it, eventually leading to growth and wisdom you approach your life because of it. Perhaps, it is why the ride came back into my life when it did… as I started rebalancing my mental and emotional state; as the cliche goes, to bike towards something. This is why I chose the east to west route instead of the preferable west to east because of the prevailing wind direction. But in the end, I simply wanted the road to lead me back home.

The reconciliation of the bike and what I wanted from this experience ultimately changed the schedule, too. I knew the answer to how long will this actually take me would land somewhere between the 37 days in the initial plan and the 90-120 day journeys that I’ve read about. I did not want to rush, but at the same time I felt the need to have a schedule that would keep me moving forward. Babies tend to experience this deep state of joy, because their imagination is working overtime. They’re not burdened by the friction of the world, and they create and live new realities as the world becomes more real for them. Working on the schedule for this trip gave me that deep sense of joy, imagining what I will experience, people I will meet, and some of the lessons I will attach on to.

This is about what is ahead. For a while, I tried hard to hold on to the plan I had. About myself, my life, the places I would be going and how I would be getting there. I’m no longer biking through life on a 15lbs aerodynamic bike and as a moderately tuned athlete on top. I’m carrying 25lbs of additional weight with me that requires adjustment to the way I bike, the way I live. On this road, there is no point B…. just a letterless dot along the way that takes me in a direction. I just have to commit to that direction for the time being. And with that I start pedaling.

As for the plan… there is one. But we shall see.

-Troy

Stats: 38 miles, 1700ft total elevation
Day 0.5: Annapolis - Beltsville, MD (Garmin file)

Customary dipping of rear wheel in Chesapeake Bay to start the Bay-to-Bay ride.