I guess from my own perspective the problem was always just that it was a reflection of how I felt about myself. Like you I worked out to see the change and the difference on the scale or in the mirror. Yet at a certain point those progressions take a long time to keep up. It's easy for the first few months, especially when you start from being very overweight. Like you I started at 250 (280 was my max) and the changes came fast and easy (at least in comparison with the other changes). It was enough to eat sort of clean and see the pounds go away. Then I needed to lift heavy. Then I needed to eat real clean. Then I needed to do more cardio. Then I needed to add supplements. At the end of the day it became a little too much for me to handle. I realized that my life was completely run by my health at the expense of my personal life.
So for the last 2-3 months I've been doing more eating out with friends and drinking some more, but still keeping a regular workout regime. Yes I have put on a little bit of weight, but for the moment that isn't my concern. I've also discovered as well that I absoltuely love to cook so while I still cook healthy I don't count the calories or consider the macros as intensely as in the spring. It lets me cook things that taste great, but are still far healthier than what I would find at a restaurant or in a microwave.
I still have my goals for fitness. Since when I first started working out wanted to do a triathlon. It's the sort of thing that I have just always wanted to do. With my groin and foot problems behind me now I suspect that this spring will be the time to do it, but that's in the spring. For now I am just content with lifting some and actually enjoying my state of fitness. Most of the last month I spent moving people (parents, myself, roommates, girlfriend) into their respective houses/apartments and I've realized just how much better condition I am in than the average person. Yet I also realized that I don't really enjoy it as much as I could. So my goal for the fall is to get back into kayaking regularly. In other words, I want to find ways to live an active lifestyle in addition to living a fit life.
I guess my suggestion is to find balance for your life. Yes it is very hard to bring back some of the old habits of eating not perfectly all the time. Going to a restaurant for me is the equivalent of walking a compulsive gambler down the main strip in Vegas and seeing if he has to walk inside to play a few hands. Eating will always be somewhat of an emotional thing for me (and I suspect you as well), but that doesn't mean we should need to be the completely opposite nutrition guy to be happy with our lives.
As for other things to do. I suggest you try a goal that isn't scale or weight lifting related. For me it is doing a triathlon. To get there you need to be fit, not necessary huge or completely cut. Other options though could be flexibility (certainly something most people have problems with), running a marathon, taking a long hiking trip, taking up rock climbing. You've done an amazing job going from unhealthy and overweight to lean and fit. Take some time and enjoy your health by doing some of the things you couldn't have done previously, it just might be that the most progress to be made isn't physical at this point.
p.s. I apologize if this doesn't answer the initial prompt. I think it does (at least the final few comments you made).
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