The title should have said ‘shit’, but not sure that would have flown. But it really is epic shit. What is ‘it’?
In May of 2024, while surfing the interwebs looking for a leisurely cycling trip on which my husband and I could embark together — he’s not a cyclist, and I’m a passionate cyclist, I stumbled across something truly epic while on the Trek Travel website. I discovered that Trek offers a Portland to Portland ride. Truthfully, the Canadian in me — even having lived in the US for over 25 years — didn’t know where the ‘other’ Portland was. Portland, Oregon — got it. Another Portland? Okay.
As I dug in further to find out more, I discovered that this was a 3800 mile ride across the northern United States starting ceremoniously by dipping your wheel in the Pacific Ocean and then dipping your wheel in the Atlantic Ocean in Portland, Maine (yes, that’s the ‘other’ Portland) upon completion. Fascinated by this idea, I read through the day by day itinerary and was more and more excited as I read each day. The trip spanned 48 days and 47 nights, and ran between late August and early October. Bikes were provided by Trek and the entire experience had been thought through to the very last detail.
Considering that I was working full-time and had a variety of other commitments, the idea seemed far-fetched and out of reach. Even so, for the next several months, I could not get it out of my head and off my heart. I finally shared the idea with my then fiancee and now husband. He listened carefully and attentively. He asked all the right questions around the feasibility — what about my job? What about him? What about the dog? How much does it cost? All the very same questions I had asked myself. After I’d answered all of them without hesitation… I’d been thinking about the answers to these questions for months already, he shared his support for my doing it as it was something about which I had a clear and decisive passion.
I went back to the website in August of 2024, roughly one year from the start date, to sign up for what would be one of life’s truly great experiences. As I clicked on the registration page, there it was — sold out. My heart sank. A rush of thoughts went through my brain. Why didn’t I speak with my husband sooner? Why did I feel the need to wait? If only…
When I finally stopped beating my head against my desk with regrets on waiting, I saw it — below the ‘sold out’ was a link to join the waitlist. I immediately clicked on the link and provided my information. There, much better. I now have a chance. A modicum of possibility.
Several weeks passed and I hadn’t really thought much of the trip as it was nearly a year out. My phone rang with a call from Wisconsin. I live in Texas and the North American head office of our business was located in Milwaukee. Normally, I don’t answer calls from unknown numbers… that’s another article for another day, but I thought it may be a colleague from the north. It wasn’t. But it was someone from Trek sharing with me that they’d had an abundance of waitlist requests and considered offering a second run of the ride starting a week earlier than the planned ride. They asked if I’d be willing to commit with a nominal deposit which would be refunded if they weren’t able to secure the ride for any reason, but would demonstrate my commitment to riding if they were able to garner interest from enough attendees to plan a second ride. I was definitely interested, but wanted to discuss with my fiance before committing. Within days, I phoned and provided my credit card number for my deposit. My contact advised that if they had enough people interested by the end of September or October they would look to secure the necessary accomodations for the second ride. I waited… somewhat patiently.
Sometime around early October, I received a call from my contact advising that in spite of all efforts, they had not been able to garner the interest of enough individuals to allow for the second ride to be scheduled. Disappointed — and, admittedly, surprised that there weren’t at least another 18 people across this country of 300+ million people silly enough to spend 48 days riding 3800 miles across the country, I informed him that I would still like to be on the waiting list. He was happy to hear that because those of us who had provided a deposit for the possible second ride were given priority status on the waiting list and would be contacted first should potential spots open.
Several weeks went by and did my best to put the ride out of my mind and accept that, if it was in God’s will, I would ride. If not, then something better was planned for me. You see, I don’t believe in accidents. I do believe that everything happens for a reason and that is part of a perfect plan for each of us. We can debate this idea in another article, but this belief is key to how I manage my expectations surrounding opportunities and disappointments presented to me in my life.
It was around this time that I received an email from Trek with a waiver form to execute online. Thrilled that I things had moved relatively quickly and thinking this was it and I was on the ride, I immediately called my contact and asked for more details. My bubble was quickly burst as he shared with me that the waiver form had been an error and he wasn’t sure why I had received it, but there wasn’t yet an open spot on the ride for me. The rollercoaster of emotions continued, and this time we were trending towards the disappointing again.
As one would expect, life happened and continued on while I tucked away this idea of the ride into the back corner of my brain — still keenly aware that it was within the realm of possibility, but that there were a number of obstacles that needed to be overcome to make it happen. The first, of course, was a spot opening up for me. The second — and equally obvious — was this pesky little detail of my job. Equally obvious was a third challenge — I had been married in October and the reality of having a husband to consider was even more prevalent.
Let’s address the third point first. Of course, my now husband and I had already had the conversation in the summer regarding the impact to our lives together with me on a bike for 48 days straight. We’d already agreed that this was something that we would make work. That said, we were now married, and most wouldn’t imagine that one’s idillic first year of marriage would involve spending 48 days of it apart. Thankfully, we’d already been together almost 4 years, so the marriage was sealing our already solidified relationship.
The second point, however, was tricky. How do you up and leave a job for 48 days? I began to consider the idea of investigating taking a leave of absence. As I started this process of understanding how it would work, changes began to take place where I was working. We had leadership changes and a very public announcement regarding cuts in ‘corporate overhead’ — oh, wait, that’s me! These announcements were made on November 1, and I received word of my role being eliminated on November 27 — the day before Thanksgiving day. Over that weekend, I emailed my contact at Trek to let him know that it didn’t look like I had that pesky little job situation to worry about and asked how things were looking on the wait list.
I had to travel to Las Vegas that Sunday to attend the AWS re:Invent conference as I was set to speak at two customer events we were hosting as well as meet with some of our strategic clients. On Tuesday morning, a call came into my phone from Wisconsin. It was my Trek contact advising that my email had been perfectly timed and that there were two spaces available — and, did I want one. YES! It took me roughly a millisecond to respond. I did note that I wanted to discuss with my husband upon returning home the next day to confirm that this was still something we were both comfortable with my doing.
I returned home the next day and spoke with my husband immediately. We discussed the logistics and the details of the trip again. Our decision — yes, our decision — was a resounding ‘Yes’. I contacted Trek and confirmed that I was in making my first deposit towards the trip.
Of course, there were still a few details to work through with my lay-off as there were other ideas that were being proposed — in fact, some the same day I received the call from Trek advising that there were two spots available. After considerable discernment, my choice was to take a ‘gap year’ for myself after going back to work in 2013 as the sole breadwinner for my family and not stopping for the next 11 years.
To have this opportunity to ride across the entire continental United States and experience this amazing journey is a gift beyond measure. For me, the journey has already begun as I started training for the ride in early September making the assumption that a spot would open for me. The training has ramped up in earnest with the confirmation that I will be riding, and I plan to continue to write about my experience preparing for the event as well as our plans for my husband and our dog to follow along.
What has been most apparent to me in the experience thus far is the importance of listening to those things that touch your heart and mind. Once I learned about this trip, I could not stop thinking about it. The thoughts were well beyond my control. Logic suggested that it was nothing more than a lovely dreamy idea — or one that demonstrated a level of insanity — depending on your perspective. Listening to that voice telling me I needed to do this was what made it happen.
Let today be your ‘someday’.
