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The office for my previous job is 23 miles from home in Foster City, and I would do that a couple of times per week. Return leg would either be riding to the Hillsdale Caltrain station or to the Millbrae BART station if I was feeling frisky. A few rides home after work into the afternoon headwinds made it clear to me that a full round-trip commute was not really for me. ?
When I was living in Britain, I had a commute that was 9 miles each way direct through the city, which I used to do every day, but in the warmer months I would do a much longer (and more hilly) ride in and out, up the coast and down some winding country lanes before hitting the city - about 18 miles each way. Then I'd do around 60 miles on Saturday with the club and sometimes a hefty solo ride on the Sunday (or a race).
I used to treat the longer ride as proper training and really wind it up, and this resulted in the only serious crash I've ever had where coming off a roundabout at around 35mph, I was distracted by a driver who narrowly avoided cutting me off and clipped a curb that was protruding a little further into the road than I expected. I flew over the bars and the bike then flew over me. Somehow I managed an instinctive judo breakfall and only ended up breaking something in my right hand (there was still quite a bit of blood) and totalling my helmet. I was lying in the bus lane for quite a while with drivers doing their best to pretend not to see me so they wouldn't have to stop and help. Eventually a lovely woman did stop, cleaned me up, and got me and the bike to the university. I got changed carefully, taught my morning class, then decided I wasn't feeling too good, went to the hospital and was diagnosed with concussion and told to go home... But most of the time the commute was completely uneventful.