I broke my wrist in August 2018 and didn't start biking until next April. It was a very wet winter and cold spring and I was not motivated to start biking. A friend at work had a pace maker installed at that same time and he never really started biking. I have 2500 miles this year, hoping to get to 3000 and if it doesn't rain a lot I'll make it. I biked to work all winter two winters ago. The purchase of Shimano winter cycling shoes made the world of difference keeping my feet warm. Another difference was splurging on a $100 (on sale) Castelli winter jersey. It was warm enough that 80% of the time, it was all I needed for the 22 mile ride to work in the morning (Train most of the way home). Finally, when it got really cold here (sub 40F), fleece lined skull cap under the helmet. That old wive's tale my mother used to tell me really is true: you lose a lot of heat through your head; wear a hat. Rain, however, is showstopper for me :-)