... I'm so cool that every time I break out the ouija board, James Dean says "Just Die Already".


Well, I'm not sure if I am talking about the same feelings: when I fail at something, I feel it very keenly. I mean, there are obviously loads of things that I suck at doing, and that's ok: we can't be good at everything. But when I fail at something I should be good at, or something I care greatly about, it stings. I guess it's normal to have some kind of insecurities. But for me it's more a matter of bruised ego than real feelings of inadequacy. My self-doubt is not usually expressed in the form of "maybe I'm not good enough?", but rather "maybe I'm not as good as I thought?". Fact is, usually my reaction is to burn away those doubts and convince myself as hard as I can that "fuck yes! I am as good as I though, dammit! This is just a small road bump". However, in all honesty, the question remains how would I react when I fail at something I care so spectacularly that I couldn't keep pushing it. Will I become wiser and accept my limit? I hope so. But mostly, I hope I will never find out.
If it happens, you'll probably be just fine. In time.
I took a series of hits to my pride towards the end of my first and second years at Oxford. From being used to being considered utterly brilliant at academic stuff, I had to readjust to being considered capable enough, but far from the best. And much later on, in the early years of my career, I had to realise that the system I was working in didn't respect me as much as I felt it should and the system made me do a lot of things I truly resented, felt were unnecessary, if not outright counter-productive. That was another hit to my pride, and my ego.
In hindsight, these knocks were all very useful, letting me shed external validation as a means of ego support, and forcing me to understand what actually made me happy, on a deeper level. Then I could plan and reorientate my life to meet those goals in time, which has been the most useful thing I could possibly have done.
So don't fear it; it might hurt at the time, but you'll appreciate it in the long term.