Here's my fitness story FWIW. From 1992 to 2005 I was an oilfield consultant which meant I would be at a drilling location anywhere from 12 hours to a week at a time, living in my truck and eating a fine diet of microwave popcorn, canned soup, cold pizza, etc. My cholesterol hit 365, my BP was (and still is) 110/70, and my weight had been steady at 185. I got a new job, my first ever office job with normal hours , at the age of 48 so I started going to the gym. Within months my weight hit 210 and has been steady there for 7 years now. I do about 30 minutes of brisk walking on a treadmill or 30 minutes on an elliptical, then I spend about 30 minutes on free weights or different machines, and I do this 4 or 5 days per week. It's almost like an addiction, if I travel and can't workout I get depressed. My original goal was to be healthier at 50 than I was at 40, and I hit that pretty easily. Now at 55 I want to be healthier at 60 than I was at 50 and that will be more elusive. I've cut down on red meat considerably, try to eat one vegetarian meal a week, and I eat out less than once a month on average-I especially try to avoid Chinese buffets.
Running is out of the question for me. Years of skiing at Taos during college left my knees and ankles screwed, and I wear a size 10 shoe with a 4H width, not an easy size to find in normal shoes, forget about trying to find good running shoes.
As for running with headphones, I lost a good friend because she was listening to music and running so she didn't hear the car that ran the stop sign and killed her.