Keep it simple. I used to have the need to change into "jogging clothes". Sweatpants, sweatshirt, headband, music player, etc. Too much work! As I usually jog in the morning, I wear the same clothes I l slept in - it'll get all sweaty so it cannot be any worse. I do have to change the pants to something that have pockets to hold house keys, some money, and a piece of ID. I do have music to listen to along the way but I use my cell phone for that. Just listening via the phone's speaker saves me the time to find a headphone. I jog in the morning before going to work so there is a very small window of opportunity to get ready and be out of the house. The longer I linger in the house the more likelihood I will change my mind. On weekends, when things are less hectic, I do use an iPod with earbuds.
Keep it short, "it" being the distance between your house and the place you want to around. I usually run around some playground/park and usually go to the one that is closest to my house. The sooner you can start the exercise the better.
Keep track of the effort. I use a GoogleDoc spreadsheet, but anything would do, really. Perhaps you are a pen-and-paper person - then just dedicate a notebook, sort like a diary, to record the date you made the run, the distance covered, perhaps location if you want to exercise at different places for changes of scenery. I am sure there are some iPhone apps to help record the info.
Keep track of the kilograms. If your goal is to shred some weight, in the same tracking document, record your weight periodically. It may be disheartening to learn that you only lose 2 kg after 2 months of exercise, but deal with it. No pain no gain, really.
Keep track of the distance. I would love to run around a sports track but there are none around where I live. The typical track length is 1/4 of a mile or 400m. A pedometer is probably the best way to record your effort, but that means one more thing to remember to bring and goes against my idea of keeping things simple. For me, Google Earth works fine. The software is free from Google and is available for both Mac and Windows.
Keep it up! Getting up at 5:30 AM is a big challenge for me but I managed to pull it off most of the times. There was days when I got pulled back by the warm bed and blanket. It really helps to have friends, physical of Facesical (that's another word I conjured up to mean someone you know not in real life but via Facebook only), to encourage you to continue. Share your daily or bi-daily exploits, perhaps even get others to join in your effort.
Good luck with your exercise program! We have only one body to live in, let's take good care of it!