20 Pound/$500 Challenge

Update: I won!

20lbs in 55 days

That includes losing two weeks to travel (one week of eating out, and another spent to undo the damage). In the end, it got very close, but I had some events coming up (read, free food) that I didn’t want to miss out on, so I used all my willpower to lose the last few pounds – and I did it!

The true challenge will be maintenance from here on out. But first, lunch.


I made a bet with a friend: Whoever loses 20 pounds first gets $500 from the other.

For me, losing 20 would put me at 10 below my driver’s license weight – which was accurate when I got it at 16—10 years ago. So that’s the big challenge for me, I don’t know when I was last at that weight, so it’s lower than I’ve ever been as an adult. On the other hand just about 2 years ago I put my mind to it and lost almost 50 pounds (though I’ve gained a little back…) so I at least have some experience.

Challenge Accepted.

For my own sake, I’m going to commit myself to a few rules. I don’t usually like “rules” or going on “diets” because they both tend to be unmaintainable. But for the sake of this bet, I’m okay with that. I’ll make some big, hopefully short-term, sacrifices to win, then relax back into good habits. Head on to page 2 if you want to see some of those, but I mostly added them for my own reference. I’m thinking I’ll also make a desktop wallpaper for myself…

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