1) Set a crazy goal.
I have heard about setting small attainable goals over and over because you can use one success to build to another. Sometimes, however, you have to do something nutty and way out of your comfort zone. At the end of October, I hadn't run at all in three months and had only run a handful of times in the previous six. Running every day sounded ludicrous, but I needed something that was crazy in relation to my current state. For someone who is already running 5 days per week and has done so for a long time, running every day is not a stretch. For me at the time, it was like jumping into the Tour de France after watching cycling videos on my couch. If you don't succeed, you will have a great story to tell and you can try again. If you do, you have done something that you have never done before.
2) Be resolute.
Running on a treadmill in the basement after 11:00PM sounds ridiculous and obsessive, but I had to do it a number of times to keep the streak going. I know that there are some hardcore types, for whom fitness/running/triathlon/whatever is the focus of their lives, who think working out late at night is essential to wring every last minute out of the day. Speaking personally, I don't, and I don't think I'm alone.
That being said, I had set a goal and was committed enough to tell a number of people what I was doing, which brings me to my next lesson...
3) Make yourself accountable
I normally don't talk about personal stuff with many people, but I decided that I would make a deliberate effort to tell others what I was doing. Being asked at work, "How's the streak going" or "Hey, what day are you on?" was really encouraging, and it made me want to stick to it. After a while, I had so many people asking me that I didn't want to disappoint them.
4) Make it fun.
When training for marathons and other events, I rarely listened to anything when I ran, except for long runs. I made a point of using media more. If you have been following me along, you will have noted binge-watching of old X-Files episodes, watching movies and reading ebooks while on the treadmill. I rediscovered how much I like podcasts and sought out new ones that can be ingested completely during shorter runs. Adding Zombies, Run! has been especially good. I recall reading how one guy elected to run a different route every day during his streak. Any creativity is going to make the streak fun and not monotonous.
5) Be positive.
There is nothing like a crappy attitude to keep you from taking even the smallest steps or knock you off balance. Moving from "I have to do this" to "I want to do this" is not always easy, but when you can do it, it changes everything. I tried to focus on how this next run was going to make something better. For example, "This run will help me lay down a good foundation for races the Summer", or "Getting this run out of the way in the morning will make my whole day better." For me, knowing that I could check the box for another consecutive day was a reward. I tried to focus on the rewards, not the drudgery.