I usually complain about going to the gym in the cold, but I honestly didn't even feel it so much thanks to the small investment I made into getting some baselayer clothing.

I think people neglect the importance of proper equipment in building disciplines. Just having really solid basics (a good pair of shoes, a nice jacket, a good set of paint brushes or whatever) can really help you making the building of a habit easier. Not to say that special gear or equipment is needed exactly, but having good basics probably is a big help