Of Bucket Lists and Challenging Goals
Lots of people talk about their bucket list, but how many actually make progress?
Last week I finally crossed an item off my bucket list: bicycling the Erie Canal.
Ever since we’d moved back to Upstate New York ~8 years ago, I’ve wanted to do this…but there was always an “excuse”:
Any time I took a vacation, I wanted it to be with my partner since we both value it so highly.
When I left my first remote job to start my own company, I had to get started right away.
When I closed down my company and joined a startup last year, I was operating from a scarcity mindset after years without serious income.
This time, there was no good excuse, and one day while riding along the canal (we live close to a trailhead), I realized this was the perfect opportunity to make it happen.
So I gave myself permission to just go for it.
There were some “small” issues to solve first, though:
I’d have maybe 5 days to do this, meaning I’d have to average 70+ miles per day.
I’d never done more than 200 miles in a week, and this ride would be nearly 400.
I’d had ankle surgery over the winter and was still working through the final recovery stages.
I didn’t have the right bike setup.
Oh, and I decided to start planning less than 2 weeks from when I’d have to start my ride.
Nothing was certain. But when is it?
Fortunately I work well under pressure, and a mixture of ChatGPT and Gemini really helped to make the planning (where to stay, where to eat, how to dress) a breeze. A local bike shop also came in clutch to get me set up right.
Now the hard part: actually doing it!
About a week later, I set off on a crisp August morning (mid 60s) to make it happen.
Five days, 386 miles, and over 28 hours of riding later, I completed my route, and it was as incredible as I had hoped!
Despite riding consistently for the last 15 years, I learned a lot:
how to manage my physical efforts to avoid cramping (the bane of my existence)
the mental slog of long days was actually much harder than the physical aspect
having a series of really engaging podcasts is a life-saver when riding into headwinds and physical pain
that certain sections of the Erie Canal are gorgeous
that chamois butter would’ve been a good thing to pack…









While I don’t know if I’ll ever do this again (especially not solo), it’s one of the few times in my life where I’ve been proud of what I achieved. It was very uncertain whether I’d make it, but it was worth taking the chance.
It’s great to check an item off my bucket list after nearly a decade of excuses. Here’s to making time for the important things in life!