Common advice given to beginner bike commuters by veterans is, basically, not to bite off more than you can chew. Begin with modest intentions. It is essential to have good experiences to reinforce what you’re trying to do. Each rider needs to establish a basic comfort zone.
The same applies to being active in the winter in general. In winter go out when conditions are reasonably hospitable and stay close to home so you can retreat indoors if you become cold. You must seek positive reinforcement through having good experiences. As your experience increases gradually stay out longer and go further afield. Do not set yourself up for failure by trying to grit your way through unnecessary hardship – it is not a competition.
Trial and error learning is the best (only?) way to approach it. I have a thermometer mounted on the side of the house which I consult before any outing. If you don’t have one consider getting one. It will help reduce the guesswork involved.
The challenge is to keep nudging yourself. If you can comfortably walk one kilometer at minus five with no wind, bundle up a little more when the temperature is minus ten but don’t go so far, turn halfway on your regular route and come back. When you get back to the driveway you can decide to repeat the distance for a full kilometer or retreat to the house to get warm. If it’s windy try the same thing, push yourself a little but bail out before the experience becomes negative. The same goes for distance, work up from one to two to three or more kilometers.
Five kilometers (the Lundy sign) is just about ideal for me/us. It takes an hour or so. An hour of zero cost stress relief and fresh air. A busy day might mean “going to Eldred’s” – our neighbor’s driveway is one kilometer from ours, or another compromise is the Hangar Road, which is about halfway between Eldred’s driveway and the Lundy sign. You can measure distances with your car. It helps if you quantify what you’re doing by keeping track.
I never get bored. Walking the same stretch of road over and over provides familiarity which in turn helps to strengthen the routine.