Motivation . . .
The first tough part is getting me + my bike out the door. It sure helps me to have a good riding partner, and we agree in advance that we're going to do it. (And choosing favorable days and times for going out).
The second tough part is making it thru the first ten minutes. For me the key is to own and put on more warm clothing than I really need, and carry a large enough backpack so I can take stuff off when I find out I didn't really need it. I don't feel like I have to make a "good guess" about clothing before I start riding.
The third part is feeling confident that I can handle things that might go wrong later in the ride. (Having a riding partner helps). For problems of warmth and wind, extra clothing in my backpack gives me confidence.
Mechanical problems with my bike: I carry more tools and parts than most riders. But the idea of actually needing to use them in 25F degrees cold with a bit of wind blowing does not enhance my confidence or motivation to ride.
So I carry a mobile phone with numbers of three taxi services.
Once I broke a cable on a cold day, and even though I had a spare with me, I did not fix it. I was able to ride as far as a fast-food restaurant, went inside called a taxi and waited inside for it to arrive.Why do I ride outside in the cold?
because . . .
(a) indoor pedaling gets boring for me. (less so for Sharon)
(b) there isn't enough snow for cross-country skiing.
(c) sometimes it turns out to be a fun day of riding.
Other days the riding is not so fun, and then just having got thru it on a cold day is satisfyling.