My experience last time wasn't what I had hoped for. I had determined what I was going to fast weeks before the day (alcohol), but after the first week of Lent, I got psyched out and broke the fast. I felt horrible, guilty. What was supposed to be a cleansing turned into a white-knuckle competition of wills: ironically, both mine.
I don't know how it will look this time around. The idea is to relate to Christ on a very small level, meditate on His loss, etc., but I'm afraid that Lent does a number on me psychologically where the experience looks something like this: noble intentions, good start, miserable failure, spend rest of Lent asking for forgiveness.