I was overweight and then obese from age 8-26. I got back to simply being overweight during the time I played football (handegg) in high school. Won't get into my injuries in this thread since it doesn't really fit here but after high school I quickly gained all the weight back and by the time I was in my 20's I was pushing 300lbs. 286 was my heaviest.
My biggest problem was portion sizes and eating or drinking way too much sugar. I mentioned in another thread that I'm honestly surprised I never developed diabetes especially since it's pretty common on both sides of my family. So I basically slashed my caloric intake by half and cut out almost all sugar. I knew if I tried to eliminate it completely I'd fail.
That was also the same thought process I had for everything. I never stopped myself from enjoying the foods I love. I either ate less at one time or created healthier alternatives myself that still captured most of the flavor I was looking for. It also helped that I created a text file that I use to keep track of my calories for the day. I know there's apps that do that stuff but I like doing the math and I've found that sometimes the app doesn't have the correct nutritional info for certain things.
I had also started jogging around 26 which was great. I eventually added more exercises and jogged for longer periods of time over the years. I now exercise six times a week, Saturdays are my only day off. Jog all six days, push-ups/weight training twice a week and crunches twice a week.
Most of the weight came off in the first two years and now I weigh 146 and have kept my weight between 145-150 for the past four years. And before anyone worries that I overdid it.. I'm only 5'9" so it's all good!