What Was That?
Unforgettable
I wasn’t ready for this trip — in more ways than one.
I’ve traveled regularly on business for over 40 years. The OCD side of me believes that part of being a power-traveler includes packing exactly the right amount of clothes — nothing that takes up extra space in your luggage unnecessarily, and also not leaving anything required at home. From underwear to socks to shirts I find a perverse satisfaction when I pack perfectly.
But I messed up on this trip.
Debbie and I were headed on vacation for a biking trip across two countries in Europe. This was one of Debbie’s “bucket list” items. She’d consistently talked about wanting to do a trip like this since we were first married almost three decades ago. Previously, I had been hesitant.
Don’t get me wrong — I love bicycles. I used to ride my bike a great deal before we had children, and I used a bicycle for transportation throughout junior high school, high school, undergraduate studies, and my graduate work. I also loved riding for exercise. But, I gave it up when we had children as disappearing on a multiple-hour ride became harder to do with little ones.
When it comes to vacations, however, I prefer to lie on a beach and recharge my batteries — not to exercise seven hours a day. For more than four decades I have worked long hours and pushed myself professionally. I prefer taking “vacations” to doing “trips.”
But this travel was different. Last year I dragged Debbie to Africa to watch animals eat other animals, and the year before that I took her to Liverpool so I could sing, “You’ll Never Walk Alone” with 45,000 of my closest friends at a football (soccer) match. I had checked off both of my bucket list items. It was Debbie’s turn.
And I was ready to enjoy this trip and do everything I could to make sure she had the experience she wanted.
But, on the plane to our first stop, I realized I hadn’t packed shorts. Or a pair of flip flops for after the daily rides.
Oops.
I was pretty busy in the month leading up to our trip. Four weeks before departure I was able to get to an athletic store and buy some new cycling gear, but I didn’t have time to cut off the tags until 36 hours before we left. In fact, I taught several classes the day before we departed, and on the morning of our trip I taught for four hours. The latter session required me to race home, quickly change out of my teaching clothes and into travel gear, and then head to the airport to catch our flight.
Only on the airplane did I realize I really wasn’t fully prepared for this excursion as shown by my poor packing skills. Little did I know my not being ready for this sojourn was true in more important ways than simply doing a bad job of not taking the right clothes.
Peering Through the Window
Our cycling group comprised 13 people who hailed from across the United States. There were six people from the Bay Area (including us), a couple from Seattle, several people from Denver, and a couple from Boston. Only two couples knew each other before the trip; everyone else was new to each other.
We met the other participants at a train station where we boarded a bus and drove 90 minutes out of the city into the Spanish countryside. When we arrived at our destination we were dropped off, literally, in a bull-fighting ring and shown our bikes. Individuals introduced themselves as we put on sunscreen and filled up water bottles. After a short 30-minute overview of our equipment and the day’s route, we set off for our first ride: 25 miles through the Spanish foothills outside of Sevilla.
I literally had not been on a bike for 10 years before getting on my equipment in that bull ring (another sign I had not prepared well for this trip).
The good news is that it was literally “riding a bicycle.” The rhythm of the gears, brakes, and road came back quickly as we set out on our journey.
Very soon I noticed that the scenery around us was quite beautiful — hills, valleys, trees, small towns, and limited automotive traffic. Focusing on the bike, staying safe, and keeping up with the group quickly forced everything about my “regular life” out of my brain. At the age of 57, you become infinitely more aware of the potential downside of a bike accident than when you were a teenager or in your twenties.
As we arrived at our first lunch stop, we found ourselves in the middle of some Spanish foothills at a restaurant run by a British brother and sister whose family had emigrated to run a quaint bed-and-breakfast. They served us an amazing meal of fresh meats, fruits, and vegetables as we sat at tables getting to know each other.
Everyone was incredibly friendly. And easy-going. And kind. Individuals shared where they were from, how many trips like this they had been on previously, how long this vacation was going to be for them, etc. Soon people started discussing the ages of their children, and for a few riders, the ages of their grandchildren.
Mid-way through the second day I came to a realization: I was the only person still working full-time. Everyone else was retired. While one rider was still working as a consultant one day a week, she and her husband were off for a month of vacation and were going to visit their daughter in Scandinavia as part of this trip.
Over the next few days I noticed how relaxed everyone was. No one cared about other peoples’ jobs, and no one talked politics. The group simply enjoyed the excursions we took each day and was at ease with the cadence of the rides as the sole focus of our activities.
At various moments people shared what they had done in the past: one had been a fifth-grade teacher, another had worked in the insurance industry, one worked for a government public transportation agency, someone had been a dental hygienist, one had worked on big construction projects, a couple of people had been in sales, etc. There was also genuine interest in the others on the trip — not in peoples’ careers, but who they were, where they had been, and what they were doing. I was asked a lot of questions about the content of my classes and my books, but most questions centered on where I was right now.
It was clear everyone in the group had moved beyond the point in their lives where work provided a current definition of who they are.
One couple was 52 years old. I was the next oldest at 57. Everyone else was between the ages of 60 and 70.
I felt like I was peering through a window into a world that I had never seen before: older people in good health enjoying their lives and being present in the moment of what they were doing. Clearly, the group had achieved a certain level of economic comfort, but no one appeared to be “over-the-top” wealthy, nor did money particularly play a defining role in their lives. There were no discussions about what the next hot thing might be, how messed up geopolitics are, or the ethical and moral implications of AI.
This was simply a group of people living out their later years actively and in good health having left behind the existential stresses of working days.
Of course, there were discussions about health, getting older, the happiness of children, aging parents, etc., but there was no angst to overtake the mind as we passed from Spain into Portugal and rode from mountains to beaches and through numerous small towns.
Tell Me More
By the third day I caught myself asking my new friends questions about their everyday lives.
“What time do you get up in the morning?”
“What time do you go to sleep?”
“What do you do on the average day?”
One person shared that when he stopped working he had to figure out how to “keep his mental edge.” Slowing down was easy, he said, but the fact that he had to put in effort to keep his mind active and current surprised him. Keeping fit physically seemed to be the easy part.
No one in the group talked wistfully about missing work. Or their careers. Or what they did before. They were all simply present in the moment.
Like a Dog That Hears a High-Pitched Whistle
Since getting home from the trip I have shared my observations with several people, and I’ve been asked questions that have felt out of balance:
“Did you feel inspired by this?”
No.
“Was this like a calling to you?”
Not exactly.
“Are you going to go on more trips like this?”
I have no idea.
Right now, I just feel like a dog that hears a high-pitched whistle and seems confused by what it is processing:
“What was that? I had no idea that a chapter of life like that existed. Is that what a life can look like vs. just taking a vacation?”
I like to say that there is no single path in the world — there are eight billion people on the planet and there are many ways to make a living and be a positive contributing member to society. I think this perspective might be why after four decades of work I am currently having more fun doing business outside of Silicon Valley — there are so many interesting people and things happening in other parts of the world. The planet seems increasingly interconnected and part of a greater whole, and getting out of the bubble of tech and a coastal elite (elitist?) American university is extremely mind expanding to see the broad possibilities outside of the San Francisco Bay Area.
But the life possibilities and lessons I learned on this trip were ones I didn’t expect from a bike ride.
How startling it is to be present, not to be chasing anything, and to be living only in the moment. And to see people live a life like that as their main existence…
A friend of ours recently said that right now she is focusing on “being vs. doing” at this stage of her life.
I loved that expression when she said it.
I think I just captured a glimpse of what she meant.




Rob, I really enjoyed your post. As my friends and colleagues cross the 60 threshold, the retirement discussion is a regular topic. My usual response is, "I have a lot of things I want to accomplish when I retire; I just don't know what they are yet." I have been so busy for so many years on the work and family front, it is hard to contemplate a schedule with less work combined with fewer family day-to-day obligations as the kids live on their own.
That said, I have come up with a few guiding principles for myself:
1. I'm never going to retire - I'm just going to modify where I spend my time, focusing on projects that interest me and/or where I can give back a little vs. emphasizing projects that pay well.
2. One can't maintain (let alone build) muscle mass without stressing the muscle. Thus, I need to stay involved in projects that stress my brain and where I have accountability - projects that have problems that need to be solved and where I am responsible for finding a solution.
3. Travel is a great thing to do in retirement, but if we are fortunate enough to live a number of years in retirement, travel will not fill the time, and the older we get, the more we may encounter potential physical and mental obstacles to travel. Thus, we are emphasizing travel now (even if it involves working for four hours the day we leave and returning to a week of catch-up pain). Retirement travel will be a nice addition to our lives but not the intended focus.
I look forward to your next post!
Bob
Rob,
You are about the same age as I was when I decided I needed to reprioritize. I had just earned another master's degree in analytics and AI. I did it so we could be eligible to become a Canadian residents, but I was itching to use the degree. It was such fun and work had always provided validation.
And then Covid hit. I had spent a lot of time across the border from my husband over the previous 2 years, and we still weren't officially in. But at the time, we didn't know if we'd even survive Covid. So I went home. After about a week I realized that even at home, my workaholic tendencies made balance really difficult. So I stopped. Cold turkey. And took the time to enjoy whatever was possible with the man who had been by my side for almost 40 years.
It took me a while to commit to making retirement permanent. But we make our own challenges now. And we did eventually move to Canada and are enjoying life in a friendly multicultural place.
We hope to have you and all of the rest of our GSB friends visit!
Teri