25lbs. to join the Air Force

I, too, had to lose 25# to join the navy.
I was 240#, and got down to 215# over a few months.

I was reading about people who successfully engender new habits, and it's important to work up to it, to really make it a priority. Start planning a week ahead, over-indulge in your favorite foods a couple days before so you don't crave them, and might even associate them with negative feelings of being stuffed, and set a date. The whole, "I'll eat right tomorrow, I'll make it to the gym tomorrow..." trivialization of healthy living is a doomed excuse.

Plan it out for a week in advance and make an event of it. Bring your friends on board so they will help you, and not tempt you (please don't invite me to mexican, can we skip pizza at least at first until I have more willpower, can you join me at the gym?). Schedule your time at the gym for when you can make it (morning or evening person?) and try to keep it at a consistent time. Treat it like your job/class and don't miss a day or call in sick. Don't skip a day and tell yourself you'll punish yourself the next day with a double workout: you won't do it, or if you do, you'll overexert yourself and be too sore the next day. Keep it reasonable, make it a routine.

For me, for so many reasons, joining the Navy was more important than anything else: even more than making it to work or doing well in my current classes.

When I first made exercise/ better eating a habit,
I gave myself extra time to sleep at time, I needed it-- going from 0 exercise to 6days/week.
I gave myself time to get to the gym early, time to prepare meals properly, etc.
It's easier now, but still not quite a natural routine.

It sounds like working 50hrs/week PLUS school is already stressful. You can't set yourself up for success by adding a serious diet/exercise program as an addendum to an already booked life.
Simplify things, drop some hours at work, take fewer classes next semester and give yourself time to approach this effort properly. It'll pay off when you're in the airforce, later.
I've tried half-assing diet+exercise before, and got nowhere but discouraged, until I really shoved some other things aside and gave it my all. I was setting myself up for failure the previous times I went to lose weight in years past.

I started on March 1, 2014 and I hit my 25 pound loss on November 11, 2014. I probably could have done it faster, but I don't think there is any deadline for weight loss, as it's pretty unpredictable Anyway, I started out by eating low-carb. That helped me get into a routine of healthier eating. Then I bought a food scale, and my real success came when I accurately logged my food and exercise onto my MFP app on my phone every day. The importance of a food scale cannot be underestimated. It is the only way you know exactly how much you are consuming. And the accountability of logging your intake every day is necessary (or at least it was for me). I also made sure I did cardio and weight resistance training of some kind at least four days a week, but I learned that I could be more flexible about this if I just stayed on track with staying under my calorie goal for the day. I eventually started eating what is probably a normal amount of carbs again, and have been able to continue to lose weight, but I do think it helped that I don't eat dessert as much or drink as much alcohol.

And now I am going to get a little philosophical and introspective. I think that I used to think of food and each meal as an isolated event. But when I started looking at everything I was eating in a week and accounting for indulgences by being more restrictive at the next meal, I found it was easier to enjoy the occasional indulgence and still lose weight. Not sure if that makes sense, I'm still trying to articulate it to myself! For example, I had two pieces of cake today for a co-worker's birthday. Not healthy by any stretch, but now I won't eat dessert for the next several days to "accommodate" this indulgence.

Finally, you asked for a "success" story and how to stay motivated. I was motivated because I am 5'6 and tipped the scale at 178 in February 2014. I weighed almost as much as my husband who is 6'2. My bra straps were digging into my shoulders, and I couldn't fit into any of my clothing. I looked and felt heavy and uncomfortable in my own body. I just got so fed up with myself that I resolved to make a change. At first I felt like I was fumbling in the dark. But then I found MFP. This website helped me in a big way. I found a lot of support on the forums. People are so honest about themselves on here, disclosing their goals, hopes, successes and failures, and are willing to help you if you ask for it (case in point right here!). I really found a community on MFP that helped me when I was feeling tempted to skip a workout or eat a donut. And it was gratifying to log my food and come in under my calorie goal. I stayed motivated because I started seeing small changes right away, and over time I saw bigger changes as I continued to make a consistent effort.

One last thing, I wanted to lose like, 30 pounds in three months. I realized very quickly it wasn't going to happen that fast, and that I needed to be patient and consistent. Well you know what? Eight months and 25 pounds down, who cares that it took me that long (which I actually don't think is that long)!! Point is, I got here eventually and I feel awesome and fit back into all of my clothes! Good luck, you will do it, just get started and stick with it. Feel free to add me and I'll always "like" your status when you complete your diary for the day.