It Depends...
I would suggest that if you are striving to be a great singer, then you must evaluate your voice as if you were "outside" of yourself -- the more awareness the better decisions you can make about improving.
The key (or trick depending on where you are) is to be able to assess yourself from an objective outsider's point of view - accepting what you are and working on a plan for improvement rather than jumping to subjective, emotionally driven conclusions about your voice, appearance, etc...
I've had great success using meditation and some yoga to be able to bring my own emotional responses into check for any situation - especially how I react to what were highly emotional judgements in the past.
That works for putting an objective plan together then it's always nice to be able to tap into the emotional pain side a little in order to keep the motivation up.
Jeff
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