I've been trying to bike to work more. As I was biking in today, I noticed a bit about my process of making a change.
In the process of changing something, you have to take things one day at a time. Think of each day as a chance to test out something.
At the end of the day, think about what worked and what didn't, and see if you can plan ahead to do anything that would address what did not work. Then, set up to make things streamlined for you for the next day.
The idea here is to be choosing things ahead of time for yourself, so that future you can focus on actually implementing the change rather than all the little preconditions that you need to do.
In my case, I already had started leaving shoes at my office. I had gotten some windblocking pants so that I was comfortable with temperatures down to freezing. This morning the temperature was a little below freezing. I did my best to guess what I would need to wear. At the end of my ride, what I discovered is that my feet were too cold, so the next priority to address is how to keep my feet warmer.
When you just go do something, but stay self-aware to evaluate how it went and then make some changes, you can make little changes one step at a time. After a while, you look back and it seems like a much bigger change.