TL;DR: For me, education and observation were the keys to weight loss.
I have often, but not always, been obese. Back in my 20s and early 30s I was heavily involved in MMA, training at least 5-10 hours per week. My diet wasn't anywhere close to perfect but I was able to maintain a reasonable (to me) weight and generally stayed in shape. If I'd known and practiced then what I know and practice now, I think I would have been a ripped monster during those days. Over time I got soft and overweight, then obese. I'd make halfhearted attempts to lose weight and found that NutriSystem worked very well for me. Sure, the quality of the food wasn't that great but it kept the weight off. It was also expensive in the grand scheme of things so I stopped using it and, slowly, the weight returned. In retrospect, although NutriSystem helped me recognize how much I should be eating, it failed to help me recognize what I should be eating. It wasn't until very recently that I learned that lesson well enough to make it part of my life.
I started with a simple goal: I wanted to reduce my processed sugar intake as much as possible for at least two weeks. Obviously this meant things like candy and soda and such, but it also made me focus more attention on the ingredients of packaged foods I was eating. I used an app called "Lose It" to keep track of what I'd eaten and how it affected my calorie intake. Very quickly I discovered that although my portion size was relatively good, the foods I was accustomed to eating — especially those which I had previously considered healthy, or at least not unhealthy — were very high, often tremendously high, in calories. I was determined to stay on track but I also didn't want to throw away food that I had already purchased, so I substantially pared down the portion sizes of what I was eating. This way I got rid of the "bad" food in the house in such a way that didn't put a huge caloric burden on me.
After those two weeks I just...kept going. I expanded my efforts by making strategic substitutions, things that I could swap out with reasonable ease. The first thing on my list was sugar. I substituted Stevia whenever I could and, happily, discovered that I don't suffer from gas after eating it. The things that I added Stevia to, I reduced the sweetener amount by half; a half gallon of lemonade would normally take a cup of sugar/Stevia, so I used half a cup instead. This way I got used to reduced sweetness in things, a way to sort of "reprogram" my taste buds.
About a month into this I finished work on my home gym and started adding some mild exercise to my routine. I alternate between "cardio days" where I mainly focus on my elliptical machine, and "bag days" where I mainly focus on my heavy bag. Stretching and light strength training is added to both days. I hit the home gym as soon as I come home from work, Monday-Friday; I get changed, do my exercise, clean up, then have dinner with my daughter. My only days off are the weekends and whenever my daughter needs to be taken somewhere (Girl Scouts or a doctor appointment, for example)
Other food substitutions were made when I felt I could deal with it. Rice turned into riced cauliflower, for example. Peanut butter (my 100% favorite food of all time) turned into unsweetened peanut powder reconstituted with water and a bit of Stevia for sweetness (and reduced the calories-per-serving from 190 to 50). Breakfast turned from a pretty big bowl of sweetened cereal with 2% milk to more healthy options; banana-strawberry-yogurt smoothies, egg white omelettes, properly portioned cereals with almond milk, granola bars, and things of that nature. When I started craving cake and pastry, I made soft oatmeal bars with a variety of ingredients to mix up the flavors a bit, including things like chocolate chip made with sugar-free chips from my local supermarket, banana, apple cinnamon, and cocoa powder. I started making and collecting low-calorie snacks; strawberries, hard boiled egg whites, and homemade sugar-free beef jerky quickly gained prominence on my list. For the most part I stopped eating out and when the rare occasion happened when I did I chose the lowest-calorie item on the menu and, depending on the count, would sometimes cut my meal in half and bring the rest home for lunch the next day. My pantry is now full of under-100 calorie and often-sugar-free snacks; small granola bars, portioned-out nuts, cereal bars, flavored rice crisps, and more. On the advice of my doctor I added protein shakes. No stranger to protein powders from my MMA days, I found a really awesome sugar-free protein powder and added a post-workout shake to my daily routine, and sometimes I have one for breakfast too.
I shop for groceries differently now. I buy far less processed foods than I used to, and pretty much everything I pick up has its nutrition information examined before I make a decision on whether or not to buy it. Sometimes I pick something up and I'm completely shocked at how many calories are in it, even if I do want to buy it and eat the whole package in one shot. :-)
Right now my weight loss is pretty much stalled at this point. I left "obese" behind several weeks ago but I'm still defined as "overweight" which I'd like to work through. I need to either further reduce my calorie intake (which my doctor doesn't like) or increase my activity level (which my doctor does like). Problem is finding the time for increasing my activity level. I'm writing this after a full day of errands, chores, and "life things" like that. I figure I'm just going to keep doing what I'm doing. If I don't continue to lose weight that's okay; I'm still in a healthier lifestyle than I was before. And if I do continue to lose weight (in a healthy way), so much the better.
Ultimately what helped me was the knowledge of various calorie counts. Things I'd previously considered to be "healthy choices" were, in retrospect, really not. Rice, for example, was a staple food for me but now I know the calorie count is crazy. Once upon a time I would happily eat half a jar of dry roasted peanuts without a second thought. I had no idea that apples were so (comparatively) high in calories. And that was just the tip of the iceberg. On the plus side, I'm able to make reasonable substitutions for many of the foods I'm accustomed to and that's helped quite a bit. The use of various flavorings, extracts, and spices has also helped quite a bit; I rarely feel "deprived" when I'm satisfying a craving.
Thanks for reading this far. I just wanted to share. :-)
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