This is a tough problem. In some ways, we are alike. Things came to me easily in life. I was never an athlete, so it was all academic. However I could get As with less than half the work that others had to do. It sounds like you are that way with wrestling. It is sometimes easy to mistake the ease with which you do something to thinking you are a slacker (just due to not having to expend a bunch of effort). My job comes to me so easily that I feel like I'm taking my company's money and only expending a little effort (when in fact I'm one of their highest producers). I'm lucky that I like what I do and make a very good living doing it.
First things first though. Never, ever do things for other people in an attempt to please them. You mention your mom and Becca. How can you know what they will think until you talk to them? Even if they are against it, this doesn't mean that you have to do what they think. How do you think this person who looks up to you would think if he knew you weren't doing what made you happy? On the other hand, you sound unsure about teaching. At the very least, you might be in love with the idea rather than the reality. You could easily go observe in a school somewhere or talk to some Education professors at Davidson or another school to determine if it might still interest you.
I would suggest two kinds of counseling. First, you need to talk to an academic counselor about your career path. They sometimes have tests that you can take that will help you to determine what kind of career you might best be suited for. Second, you probably need some relationship counseling to help to determine where this need to please comes from. I had the same thing. In my case, it was due to my mom being an alcoholic, and I found out that my need to please came out of trying to be careful around my mother when she was drunk. I am able to say no now to things which is a big improvement.
I would absolutely not get involved with this girl at Davidson until you have taken care of things with Becca (either break it off or commit). This might not happen until you have a better sense of who you are through counseling or self-reflection. It sounds like she is not really emotionally available anyway, so going out with her would be the easy way out.
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