Making Changes #
In early 2025, staring down 45 while overweight and out of shape, I decided I needed to make some changes.
I wasn’t trying to become a cyclist. I wasn’t dreaming about century rides or FTP targets or training plans. Mostly, I just felt increasingly aware that I was headed in the wrong direction physically, and that ignoring it probably wasn’t going to improve with age.
So I started small.
I signed up for OrangeTheory Fitness and started attending classes a few times a week. I immediately liked the structured nature of the workouts. Somebody else had already decided what the session was going to be, which meant I could stop thinking and just execute. More importantly, I could actually see progress happening. Within a few months, I was running faster on the treadmill, recovering more quickly between intervals, and feeling less winded during hard efforts.
That early progress mattered a lot psychologically. Fitness stopped feeling abstract.
Buying a Bike #
A few months later, my older kid needed a bike for a school cycling trip. I didn’t own a bike myself — the one I’d had 20 years earlier had long since been stolen — so I picked up a cheap $200 bike from Craigslist so I could help with practice rides around the neighborhood. I intentionally bought something inexpensive because I didn’t want to become the guy who bought an expensive aspirational bike only to let it collect dust and regret in the garage.
I replaced the tires, tuned it up a little, and figured it was good enough.
At the same time, I had started experimenting with ChatGPT. One of the first things I used it for was helping define a few goals that would justify buying a nicer bike someday:
- ride 1000 miles
- complete the Lake Washington Loop
- reach 2.1 W/kg (2W/kg is often cited as the threshold for an enthusiest)
At the time, all three goals felt improbably far away.
The Lake Washington Loop is roughly a 50-mile ride around Seattle and the east side suburbs, and even thinking about riding that distance sounded vaguely absurd to me. The 1000-mile goal felt similarly unrealistic. And the power-to-weight target — combining both fitness improvements and weight loss into a single metric — seemed more like a conceptual benchmark than something I actually expected to reach quickly.
As I learned more about training and endurance physiology, I started using ChatGPT heavily as a learning tool — not as a replacement for primary sources, but as a way to sharpen my understanding and ask questions interactively. I wanted to understand why certain training approaches worked. If I was going to invest significant time and effort into this, I wanted to understand what adaptations I was actually trying to produce.
By the end of April, I had used ChatGPT to help build my first structured cycling training block. It wasn’t especially complicated:
- one or two interval sessions per week
- one or two bike commutes
- one progressively longer weekend ride
The plan was intentionally modest because I was still figuring out what was realistic and sustainable in my life. The early long rides were only about 60–90 minutes, but over time they slowly stretched toward two-hour and eventually three-hour rides.
Commuting to Work #
About 20 years earlier, I had occasionally bike commuted to work, and I still had the panniers and clip-in shoes sitting around in storage. I looked up the route in Google Maps and saw that the ride was about 35 minutes and almost entirely protected bike lanes or trails. My normal drive was already 15–20 minutes, parking cost $22 a day, and my office had secure bike parking and showers. It felt possible.
I wasn’t especially worried about the ride to work. Seattle’s topography was helping me there. The ride home, however, finished with about a 200-foot hill climb, and I distinctly remember wondering whether I’d actually be able to make it all the way up without stopping.
Looking back at the ride data now, my heart rate spiked to 154 bpm almost immediately on those early climbs. At the time, that felt awful. I remember crawling uphill at around 4 mph in my easiest gear, gasping for air and wondering whether this whole idea had been overly ambitious.
At one point, a group of pedestrians noticed the visible suffering happening on my face and started cheering me on. I understood they were being kind, but I remember feeling deeply conflicted about the whole experience. I didn’t particularly want my commute home to be a spectator sport.
I also remember another cyclist passing me on that same hill. He wasn’t sprinting or showing off. He just looked comfortable. Relaxed. In control. He was climbing steadily at a decent pace while looking completely unbothered by the hill that was currently dismantling me. I remember thinking very clearly: I want to be able to do that.
Learning to Train #
Up until that point, fitness had felt mostly fixed — something people either had or didn’t. But the combination of early progress at OrangeTheory and those first difficult bike commutes started changing my perspective. I wasn’t becoming fit all at once, but I could clearly see movement in the right direction.
One of the first moments where I genuinely thought oh, this is working actually happened on a treadmill before cycling became the centerpiece of the story. One of the OrangeTheory workouts built toward a short sprint interval after progressively increasing incline and speed, and I remember hitting that final 30-second effort and realizing I could actually push hard all the way through it instead of immediately falling apart. That feeling of capability was new.
My resting heart rate in Apple Health started gradually drifting downward. Heart rate recovery improved noticeably too. That one was especially striking because I could feel it physiologically before I fully understood it intellectually. I had spent years being accustomed to my heart rate staying elevated for a long time after hard efforts — even things like climbing multiple flights of stairs — so it felt strange watching it settle back down quickly after harder rides.
I also started learning more about training physiology. Initially, I assumed fitness mostly came from brutal high-intensity workouts, but as I learned more about aerobic training and Zone 2 riding, the whole thing started feeling much more approachable. Long, lower-intensity rides designed to build aerobic capacity and mitochondrial adaptation sounded sustainable in a way that endless maximal suffering did not.
Cycling started turning from “exercise” into something I was actively curious about.
Lake Washington Loop #
The first truly intimidating endurance milestone was the Lake Washington Loop - one of my goals for a new bike.
Initially, I had planned to attempt it later in the summer, but my calendar was starting to fill up with travel and other commitments. I used ChatGPT to help think through whether it was realistic to move the ride earlier. Instead of simply saying “yes” or “no,” it helped me build a progression toward it: a series of increasingly longer weekend rides, including a shorter loop around the north side of Lake Washington as a kind of go/no-go checkpoint before attempting the full loop.
That progression made the whole thing feel much safer and more manageable psychologically. The Loop stopped feeling like a giant leap and started feeling like the next logical step in a sequence.
It also forced me to start thinking more seriously about endurance logistics. Fueling strategy, hydration, electrolyte intake, pacing, water capacity, break timing — all the things that barely matter on shorter rides suddenly became very relevant once I was spending multiple hours on the bike.
I completed the Lake Washington Loop on July 6th, 2025.
The ride was hard. Nearly four and a half hours of moving time felt enormous to me at that point. I got through it, but the last 10–15 miles became a real mental struggle. My body hurt. I was exhausted. By the end, I remember thinking very clearly that there was absolutely no way I could repeat that ride again the next day.
That thought stuck with me because I had already started thinking about Seattle to Portland — a two-day ride with back-to-back century distances. At the time, that seemed completely unimaginable.
Still, the Loop changed something psychologically. A few months earlier, even attempting a 50-mile ride sounded absurd. Now I had done it. Not comfortably, not gracefully, but successfully. The boundary of what felt possible had expanded.
Data and AI #
The data became incredibly useful for reducing uncertainty.
I paced many of my early long rides entirely using heart rate because I didn’t yet own a power meter. I would simply lock into a sustainable heart rate zone and ride at whatever speed that effort allowed.
As rides became longer, I started noticing a recurring pattern: everything felt fine until suddenly, near the end of the ride, things became dramatically harder. That led to a series of conversations with ChatGPT about hydration, fueling, electrolytes, and endurance physiology. I’d share screenshots from rides and use them to reason through what might be happening physiologically.
When I eventually added power data into the mix, concepts like heart-rate decoupling became incredibly useful tools for identifying when something was starting to go sideways physiologically. Over time, the numbers stopped feeling abstract and started feeling practical. Data wasn’t replacing intuition; it was helping sharpen it.
One of the things I appreciated most about using ChatGPT this way was its ability to adapt plans dynamically. Work trips, vacations, fatigue, and life logistics all forced adjustments throughout the year. Instead of treating training plans as rigid documents, I could continuously iterate on them and reason through tradeoffs interactively.
That made structured training feel much more approachable and sustainable.
Building Endurance #
Over the following months, longer rides stopped feeling intimidating in the same way. Three-hour rides became normal. Nutrition and pacing stopped feeling mysterious. The limiting factor gradually shifted from whether I could ride long distances to simply how much time I had available.
By August, I had purchased an indoor trainer and completed my first FTP ramp test. I exceeded the original goal I had set months earlier, reaching roughly 2.3 W/kg. By October, I had crossed 1000 miles.
I also started riding more socially. In the fall of 2025, I began joining group rides with the Cascade Bicycle Club. More recently, I’ve found a regular group of friends to ride with. A year earlier, I don’t think I would have had the confidence to join group rides at all. Now they’ve become one of my favorite ways to explore new roads and spend time with friends.
My original Craigslist bike is still around too. At this point it’s become a bit of a Bike of Theseus — the frame and fork are original, but most of the other components have gradually been replaced or upgraded over time. Ironically, it’s now my commuter bike, and I still ride it multiple days per week.
The Century Ride #
The [century ride I completed on day 363 of this journey wasn’t really an endpoint. It was part of a larger progression toward my current goal: completing Seattle to Portland later this summer.
To prepare for that ride, I’ve been using ChatGPT to help build another progressive endurance block. The progression started with another 50-mile Lake Washington Loop and gradually added roughly 10 miles per week, building toward the century ride. Including STP itself, I currently expect to ride seven centuries this summer.
A year ago, that sentence would have sounded completely absurd to me.
What’s funny is that the century itself didn’t feel dramatic. There was no real doubt in my mind that I would finish it. A year earlier, I absolutely would not have believed I was capable of riding 100 miles confidently and finishing strong. But by the time the century arrived, it no longer felt like some impossible fantasy version of myself. It just felt like the next logical step.
The best part came near the end.
That same hill I had once crawled up at 4 mph with a heart rate pinned in the 150s showed up again around mile 92 of the century route. Except this time, I rode up it at over 8 mph while casually chatting with a friend, averaging a heart rate around 134 bpm. I’m now that guy that I wished I was.
A year earlier, I wasn’t sure I could make it home up that hill. A year later, I rode up it after already completing ninety-two miles. The hill didn’t get easier overnight. It got easier gradually.
The rides felt small at the time, but the months added up faster than I expected. No single workout transformed me. No single ride changed my life. But the accumulation of small, repeatable efforts — combined with systems that made consistency easier — gradually changed what felt normal and possible.
The century was never really the goal. It was just a milestone along the way.