Lots of great stories and advice here! Everyone is different so we all have different methods to our maddness..
The take away theme though I think is that you need 3 key ingredients.
1. A motivating force to get you started. That could be your own personal will and desire to start, a family member, a race you've signed up for, a story, a goal or some bloke from a reefing forum.
2. Some way to measure your progress.
3. A motivating force to keep you going.
For myself I have run on and off over the past few years but have always lacked one of those ingredients so I frequently fell off the wagon. Last August I started running again because I was traveling so much for work which was very stressful. My fish tank was a zillion miles away so I needed a way to relieve that stress. One day I just decided to put on an old pair of running shoes and started running. I didn't run very far and it wasn't pretty but I wasn't training for anything so that was okay with me. I did this again a few days later and ran a little further. I took my shoes with me on my business trips and started running after work. Still not pretty, lots of huffing and puffing and I think the pedestrians were walking faster than I was running at times.
One day my wife said that I was getting faster. I was surprised because I wasn't tracking my runs so I had no idea. She just noticed that I was getting home sooner. I then decided to install a running app for my iPhone called RunKeeper. High recommend!! It is available for just about any smart phone out there. This was my ingredient number #2 that I was missing previously. I started to track every run and could easily see that I was getting faster and was running further. I still had no real goals set. I wasn't planning on running any races. It was just really cool to race against myself and pat myself on the back. You can see here that as I said, my first few runs were nothing to write home about..
http://runkeeper.com/user/Keener/activity/14376332.
After a while running became a chore and I was starting to lose motivation. Lucky for me that ingredient #3 came at the right time. Some fool on canreef was stalking me and watching my runs and started to run as well. They too tracked their runs with runkeeper and posted them. At first i was like, "okay, cool, he's running too." Then, the next thing I know the bastard goes and runs a half a marathon! That's a heck of a lot further than I have ever run. That motivated me to push my runs a little further.
So now I am stuck in an endless cycle. I go out for a run, feel good about myself only to see that my virtual running buddy has gone and run another half a marthon. Or, I'll be lazy and not run for a week only to see that he's run two half marathonds in that week! WTF?? So, I'll go out and crank out a 10K run in 50 minutes to show him who's BOSS!
To this day I still have no particular goals. I don't plan to race any marathons or half marathons. I just put on my shoes and run against myself, try to better my stats or chase my virtual running buddies. I never pictured myself as a winter runner because I absolutely hate the cold, but hey, if Brett can do it so can I :P