For me it was sitting in traffic watching people on their bikes around me in Toronto. I had biked everywhere as a kid and for me too it was the best way to get around in university, but as an adult I got caught in the rat-race car-commute grind. I'd be driving to get downtown and right near me would be people on their bikes in the summer. At stop lights or whatever I found myself staring at them wishing I was on a bike, remembering how free it felt when I was younger. Took me a few weeks to muster up the courage, and once I did I couldn't believe it took me that long. :). Wouldn't have it any other way now!
bikecommuting
for discussion of all thing commuting by bike
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I've been using my bicycle as my main form of transportation since late 2019, when I had just recently moved into a tiny dorm room and had independence for the first time. I was put off of learning the bus system at the time because uncertainty about employment made me hesitant about even a $2 fare and the routes I would need to take before the 2021 systen redesign were significantly slower than biking. That, along with not really knowing many people at the time (for carpooling), meant I pretty much had to bike everywhere, putting up to 30 miles a day on the bicycle depending on what I was doing. Thankfully, I already had the leg strength from years of purely recreational biking.
Since then, I usually only pick the bicycle for trips of up to about six miles in length (per direction), plus or minus a couple miles depending on how suitable of a route I have for biking. The majority of my trips fall within that range. Anything longer than that or any trip where I need to bring a ton of stuff with me and I'll take a bus, train, or carpool to my destination. The end result is that I went from thinking "I'll get a car once I get situated" to "I don't need to get a car for the forseeable future".