Remember from the Happy Gilmore movie (if you saw it) where he had a cushion of 4 strokes to win the first match he played? Rather than bear down and get it done with the first one or two tries, he took all 4. I saw the same thing in a actual golf match where all the golfer had to to to win - on 3 holes in a row - was sink the putt. With the kind of a cushion, maybe overconfidence or pressure set in, but he failed to get the job done. Eventually his opponent tied and then went on to beat him.
I think sometimes when we have a comfortable advantage in a selling situation that we tend to back-off a bit and not bear down or focus as much as we might if we were in a "must win" situation.
Having a cushion is like having a mulligan - a do-over if we need it or extra time to get something done - but it isn't always to our best advantage to have a cushion. We need to go all-out everytime like we know how to do, regardless of any apparent advantage that we might have.
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