To Be or Not To Be?

Here I am again, asking the same old questions. To be fit, or not to be fit, that is the question. You would think the answer would be obvious, but saying and doing are 2 different things.
Status Update:
-So, after my busy May post, I really got out of the groove. I just plain quit working out. I've never been any good at working out in the summer months - too much to do. Life is too busy. I put back on 20 lbs. I kept telling myself - I need to get back to the gym, need to start eating better, but alas, nothing changing.
-My dad came into town to stay. Then he passed away sooner than expected. Big transition there, lots of emotions to deal with. I could write a whole post on how his health affected mine, and how his health was an example to me of what not to do. I don't want to die when I'm 67.
-Work has been busy.
-Side business has been busy.
-School started again. I really did not expect that I would repeat every grade 4X during my adult life. Did I mention I hate homework.
-I'm the fat ref. I wanted to be in better shape for the Fall season, but that obviously didn't happen. So, for the moment, I'm the fat ref. I hate it. I could do so much of a better job if I were just in better shape. Still 2 - 3 weeks left of this season. Not much will change about my physique in that time. The hope is for a better showing next spring.
-Part of my problem is my achilles heel - and I'm not talking donuts. I have a big ol' bone spur on my heel, and it is raising holy heck with my achilles tendon. The pain is such that I'm walking with a slight limp, and I need to get it fixed. I'm going to try an 'in-office' procedure in a few weeks, and see if that helps. If not, then it's foot surgery to remove the spur.

So, why 'to be or not to be'? I have a buddy who is big into weight loss contests, and always organizing them. There was one over the month of August - and I failed miserably at that one. Another one starts tomorrow. It goes for about 5 weeks. It's only $25 to enter. I don't know if I have the umph to enter. Ideally, I should. I need something to get me going. How do you change, when you know what the right thing to do is, but you don't feel like doing it.