One of the surprising things about being over fifty that I didn’t expect when I was in my teens and twenties was that I would continue to figure things out. For some reason I used to imagine that at some point in life, likely one’s 30s or 40s at the latest, you’d figure out all the things you would figure out and then you’d be done and just continue to live by that knowledge. But ha ha ha – it’s nothing like that. I’m still learning, and often re-learning things. This more than anything makes me wish I could live a few hundred years instead of just whatever I’m going to get. If I kept learning for 500 years, I’d have figured out so much, not to mention I’d for sure have a few more languages under my belt.
The latest thing I figured out came to me just last week. Every year many cyclists participate in the Rapha Festive 500 challenge. The concept is simple: Get on your bike, indoors or outdoors, and ride at least 500 kilometres between Christmas and New Years Eve. With the weather cold and often snowy I was prepared to spend hours on my bike in Zwift who also has a number of events designed to bring folks together to ride to reach the goal. That sure beats the idea of sitting alone in a room on a bike. And then, on the 18th, despite being vaccinated I got the flu. This one was a pretty rough one – the respiratory effect was not too bad but the fever and exhaustion were so bad that I spent all day and night in bed sleeping and was still so tired. There were loads of repetitive fever dreams including one in which I thought that unless I figured out the proper way to sleep, I would remain tired forever. Fortunately after a few days I did figure out how to sleep properly and started to improve. Still, the improvement was slow. I went back to work one day before the holidays started and it felt like an immense trek even though it was just a 5 minute walk to the station and then a 5 min walk from the bus. So as you might imagine, when the 25th hit, I was in no shape to knock out a big ride. I did give it a try, not intending to ride the whole 500 km but whatever I could do. I joined a huge group ride of over 2000 people who were going to ride 50 km together. After riding a gentle 15 minutes I got off the bike and had a coughing fit. The Festive 500 would not happen in 2025.
This year a new bit of lore entered our family history. In August we had a plan to go visit a nearby city, Hamilton, where Daegan enjoys visiting – it’s got a lot of interesting restaurants, is a bit more of an industrial/post-industrial city that is a bit gritty but also has some interesting culture. And then we all got COVID. Then we made a plan to go again in November, and I had a stomach bug, then we made another plan in December and the flu hit. We are now of the (joking) mind that we will have to sneak up on a trip to Hamilton lest the act of planning for it make one or more of us sick.
These were both hugely disappointing and this last one got me thinking how often a plan is derailed because of one detail that was unexpected. Take my fundraising trip to Montreal. I was trained and nearly ready to ride the 600 km in three days when a combination of bad maintenance and pests of all sorts made us realize that we needed to find a new apartment and move right away. The 200+ km weekend rides ended and at the same time the move also derailed my volunteer work at a downtown breakfast drop-in because now it would be too far away.
This past summer I planned out a week long bike and camping tour with Daegan, booked campsites, got on the bikes and headed out. Our first day was one of the hottest days of 2025 and it showed no signs of letting up. We turned back home after one day.
Sometimes even one goal would get in the way of another. In 2016 I had trained to run my first half marathon. I’d already run that distance and was ready to go. Then my company asked if I could leave for my first trip to India a little early and deliver some training at their Bangalore office – on the day of the half marathon. Jumping at the chance for more time in India with expenses paid I took it – and even booked two half marathons in India: one in Gurgaon and one in Pune. However, what I didn’t plan for was the pollution and my first training run in Delhi was almost impossible.
Some might think I’m either setting unrealistic goals or have really bad luck. I don’t think either is true. There are actually two ways to get success that I’ve been very inconsistent in implementing:
The first is related to our joke that we have to sneak up on our Hamilton trip so we have no time to get sick. One of my favourite trips ever was in late 2016. A couple of days before Christmas, Daegan and I grabbed our passports, hopped in a rental car and drove to Centralia, PA to see a ghost town with a fire burning underneath it, then we visited his birthplace and then went to New York City for a couple of days. (Lucky for me I’d done so much work on remote assignment that I had enough points for free car rental and hotel for the whole trip). It was simple: first we thought it then we did it.
The other method we figured out the following summer. That summer, Daegan and I planned to bike to Montreal again. Again we booked all our stays and had our start day figured out. We took Daegan’s and my bike in the week before to make sure it was ready. Mine was out in a couple of days. His needed parts that wouldn’t arrive for over a week. We couldn’t do our trip as I only had a week off and now half of it would be eaten by waiting for parts. I was really disappointed and then I remembered I still had hotel points and even frequent flyer miles – enough to book Daegan’s flight to NYC free and so I just had to pay for my flight – and that was less than our budget to go to Montreal. This ended up being another excellent trip.
This last one is likely the clue to what I need to do. I need to have a plan B. Make that plan to ride my bike to Halifax, but have a backup goal that is unrelated. If a bike trip needs to have an injury/illness free body, then what’s a goal that I could work on that is more forgiving in that sense, a creative writing goal, a goal in Hindi learning/content production. These should be worked on at the same time so that I’m ready for both and they both matter to me. Worst case, there’s always a reading goal if I’m needing to rest entirely. This almost always would work – the exception would be the first day of my latest illness when I could feel it coming on quickly in the morning and I went from reading a book to listening to energetic music to listening to calm music to finding even that too taxing and going back to bed. But that experience has happened maybe only once every five years.
This solves the issue of having a goal snatched away at the last minute by the unexpected. However, there’s another piece – something I keep having to re-learn: Big projects are great and something I really need, but that is a lot of waiting while putting more and more eggs in a basket to potentially be broken. Put the eggs in the basket, by all means, but cook a few as you go to sustain yourself.
Take my 2024 summer plan to ride to Montreal in three days. This unintentionally met that goal nearly perfectly. The big goal at the end was there, but to get ready for it I had to do a whole lot of riding. Those rides took me to all sorts of places: I stumbled upon an awesome railway museum and rode some antique Toronto streetcars. I saw Ontario’s last remaining wooden covered bridge while doing my longest ride to date: nearly 240 km – almost 150 miles.
My favourite day of all was also a fantastic example of “Type Two Fun” – an addiction of mine. That’s the sort of experience that in the time feels really difficult but after it’s over you think back at what a great time it was. On this day I intended to ride from Toronto, see Lake Ontario and then cross the province to see Lake Erie: two great lakes by bike in one day. The first part of the day was lovely and sunny and, in fact, the first 120 km were sunny and lovely. However, just as I got to the lake, the sky opened up and it was raining sideways like at the end of The Truman Show. I rode out to a lighthouse at the end of a pier and the headwind was incredible. But then just as I got to the end the sun was back out like nothing had happened. Having met the endpoint of my goal, I turned around and headed back the way I came. As I left town I stopped at a giant fish sculpture to grab a photo and noticed the weather was looking really bad. Another line of thunderstorms was coming. I decided to stop at the last business for the next 80 km: a chip truck at a crossroads. I stopped and ordered a big basket of fries and a drink and took shelter under a small tent they’d put over some picnic tables just as the skies opened. And open they did with torrential rain, lightning and thunder. A couple of customers saw me and asked where I’d come from and when they heard “Toronto” they were shocked to find I had 80 km left just to get to the train I would take home. They apologized, saying they’d have given me a ride home if I were nearby but that was too far. I waited and waited but the rain didn’t let up for nearly two hours. Finally, I saw a possible break in the storms on the radar on my phone and soon after, a massive lightning strike hit the river behind me and then everything stopped. I was not only able to make it to the train station before dark, I did so without getting wet. (Well, wet again – I’d finally dried off from my shower at the lighthouse.)
And these are just a few of the great memories of long rides that summer – there were trips to Lake Simcoe with side trips for Italian food, fast rides along the lakeshore in Burlington, more than one trip to Guelph and so many snacks and meals along the way. Viewing this not as a bunch of boxes to tick off in order to be allowed to ride to Montreal and then having that taken away was a mistake I made for a while. Looking back, though, the whole thing was a series of adventures and I had a few less than planned.
And even our summer camping and bicycle tour trip was salvaged by this method. We didn’t ride all over Ontario and camp near lakes and forests. We did, however, go to several art galleries and have another great adventure of a bike ride.
So for 2026, I haven’t a ton of goals just yet, let alone “backup goals” or other projects to work on in parallel. Those will come for sure. But I do know that my one cycling goal for the summer: to ride 300 kilometres in a single day, will result in many adventures on the way there regardless of when and even if I do the final goal.
What goals do you have for the upcoming year?
