Why Do this Crazy Thing?

Alan Gilbert
5 min readMay 25, 2022


Over the past five years I’ve immersed myself more and more into road cycling. It has been a wonderful way to stay fit and sane during COVID and even allowed for safe social interaction. It‘s a natural fit in my home of Columbus, OH with all of the country roads and a strong cycling community, fueled by the annual Pelotonia event. And both my brother and son are equally enthusiastic, culminating in an annual week-long cycling adventure. Last year I rode enough miles — nearly 3,000 — to travel from one end of the country to the other. This year I have decided to literally do just that — to ride from the Oregon coast to the Georgia coast. I also made the (most definitely related) decision to retire after an amazing 40-year career, working with incredible people, building products, organizations, and businesses.

I recently met a friend for coffee and he asked me a simple question, “why are you doing this?” I gave him a simple, superficial answer, “because now I can and it’s something I’ve always wanted to do.” Unsatisfied, he probed deeper. “But why something this… big? This isn’t like running a marathon. It’s months of planning and training — and weeks and weeks of riding a century every day. Is that even possible? Is this why you retired? Or are you doing this because you retired?”

That really got me thinking about what is driving me to do this rather crazy thing. But before I dive in, some basic details on the trip… After considering a number of pre-organized trips, and finding that each of them had one or more major disadvantages, I decided to plan and execute my own 40-day adventure. Which is actually half the fun and one of the reasons I am doing it.

I found an equally passionate and crazy riding partner on an adventure-cycling forum, because having a partner is way more safe and a lot more fun. To keep the load light, the speed fast, and the daily milage high, we are doing what is commonly called “credit card bikepacking,” which takes advantage of hotels and BNBs for sleeping and restaurants and local markets for food. And most importantly, our saintly and amazingly supportive wives have agreed to drive a SAG (support and gear) vehicle, each for half of the trip, to provide food, water, spare parts, tools, emergency services, and moral support.

I also suspect that this trip is a subconscious backlash to COVID, after two years of isolation and working from home. What could be more different from COVID isolation than traveling across the country, one town at a time, and seeing different things and meeting new people every single day? The events of the past two years have caused people, me included, to see the world only through the internet, through politically-motivated media channels and social-media echo chambers. I want to get out and interact directly with other Americans, face to face. I have no doubt that I will meet people with very different views than mine. But I also want to balance these differences with our common ground as human beings and Americans.

There are also lots of other little “whys” for this trip. It will be a good forcing function for me, at age 59, to be in the best physical condition of my life — an act of defiance against father time. I get to eat whatever I want and as much as I want every day (especially ice cream!) I get to play with maps and GPS toys. I get to buy cool new gear. I get to see new places — beautiful places — and meet new people. I want to use it as a platform to support Pelotonia and their mission to advance cancer research (here is a link to my fundraising page).

And, well, I just really like riding my bike all day. I always have. I love the exploration, challenge, freedom, speed, health benefits, solitude, and camaraderie.

But the most interesting “why” relates to the question my friend asked. Am I doing this trip because I have retired? Or did I retire because I wanted to do this trip? I think it is a bit of both. A deep dive on retirement is a topic for another post. But suffice it to say that after 40 years of working in tech, I concluded that I don’t get the same joy out of my work that I used to. And once I entertained the idea of retiring, it opened the door to take my cycling adventures to the next level. And once that idea took hold, it fueled my enthusiasm for retiring.

But there’s something more primal that is driving me to this personal BHAG (Big Hairy Audacious Goal, a term coined by Jim Collins) and wanting it to be part of what defines me. To be “that guy who rode his bicycle across the country.” To accomplish something that seems impossible. Despite all that I have accomplished and all that I have, there is something still driving me for more. Maybe it is just how I am wired. Maybe it is just part of the human condition. Maybe I am doing this because I have an itch that my career has somehow not scratched. Or… maybe I am doing this because I am afraid to retire so I am jumping immediately to something else to give me purpose and completely consume my time and energy. I will certainly have a lot of time to ponder this “why” question while I am riding, and to figure out what else I want to accomplish and who else I want to be.

So lots of reasons, big and small, why I chose this as my BHAG. No doubt it will be difficult and seemingly impossible at times. I’ll learn about myself, my country, my riding partner, and my marriage. I expect to be humbled by the people I meet and who help me on this journey. I expect to learn about the compromise required for a team to accomplish a really hard goal. I expect to emerge with better perspective on who I am and my place in the world. And I expect to get far more out of it than just being “that guy who rode his bicycle across the country.”



Alan Gilbert

I build teams that build things.