This is what I told him:
Cold and Snow=Simple. When it is really cold the key to riding is temperature control. Really cold in the morning and cold at night are easy. Dress so that it is a little chilly when you start the ride and layer. I like to bring some extra base layer clothing in the event stuff doesn't dry and it takes up little space.
Warm/hot weather=easy. Sure really hot can be uncomfortable but you can only take so much off. A long sleeve shirt goes a long way in cool weather.
Cold/wet morning and warm afternoon=not easy. It is really hard to manage temperature with out carrying a bunch of stuff in the evening. Most water proof clothing translates to "water doesn't get in and sweat doesn't get out." This means potential overheating. Breathable and water resistant can mean "wet and cold" if there is too much moisture. Then at the end of the day you have to carry the extra stuff home since it is warmer.
I like to keep is simple, light, and on the bike. I don't like to carry stuff on my back but I will do it if I have too. If I don't want to carry stuff on my back I have to use bigger bags and not my Porcelain Rocket bags. I don't like panniers per se and in the summer it is easy to use bike packing gear like Porcelain Rocket because I carry less running stuff to work.
Tonight rain/snow mix. It is mid-April. I am ready for summer. I need BOB to warm this part of the earth. I have been shamed into riding again thanks to my friend. Tonight I will pack panniers and tomorrow I will sweat on the way home. Sad, I know, but we are ready for summer.
That is all.
