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For some reason I get an odd sense of pleasure from failure and sadness (even though I feel bad about it at the same time). I secretly enjoy being a failure and take pleasure from others seeing me in that way.
Sadness is a strong emotion. I've known quite a few people addicted to sadness.
You take pleasure from others seeing you sad/fail because you enjoy their empathy toward you. It fills your need for attention.
Almost everybody wins one, once in a while. I guess that must devastate you.
It's normal for some of us. In my family it's a trait that affects quite a few of us. I've been able to recognize it and work past it. Some members of my family derive more pleasure from people feeling sorry for them because they have it so bad, than they do from just enjoying the good life and the good things they have.
This distortion in their psyche compels them to make mountains out of mole hills, and to magnify every little thing that goes wrong in their life so that they can say "woe is me", and evoke sympathy from others.
It sounds more like you are afraid of succeeding and the responsibilities that come with it than enjoying failure.
You have to actually try to succeed, whereas failure doesn't require any effort.
It's easy to fail, it's hard to succeed.
If you fail on purpose you are hurting only yourself, as I'm sure you know. You might get sympathy from other people but if you fail consistently they will eventually stop giving it.
Maybe it's hard for you to make those decisions? Maybe you're afraid of trying to begin with? In any case, failure is an outcome of certainty so it might feel comfortable, but it's not worth it in the long haul, I promise you.
I'd suggest that you take a good moment of time and think about what you really want in life. No one ever did anything by talking about it, you have to take small steps over and over to get the grand result.
Just try. :]
How about sex? Have you ever been the "victor"? This is actually a good measure of what you think of yourself in regards to accomplishments with the basic urge.
No, not really normal from what I understand. Unless I'm one of the weird ones who want to succeed..