What???
I think the answer to the first question is, "No."
Do you have a winning attitude? A winning attitude is the key to overcoming your doubts, struggles and weaknesses. Winning is not a sometime thing. You don't turn it on and off at a whim. Winning is an all-the-time attitude. You don't win yourself over every once in a while and expect to achieve your more difficult goals, such as weight loss or good mental health.
I think the answer to the first question is, "No."
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Which -- yeah, wanna-be sports coach is about right.
Honestly, i couldn't parse, "You don't win yourself over every once in a while and expect to achieve your more difficult goals." Not only bogus but incoherent.