I think I'm a control-freak. Anything that I can plan and meticulously arrange, I almost always will. I'll stress out trying to get presentations complete and just perfect (perfection is unattainable, though). I'll spend hours searching for just the right image, asset, brush, idea, phrase, "ism", etc... to present an idea and in all of this preparation, I lose a lot.
If I over-prepare I lose the freedom of creativity. The off-the-cuff spontaneity that will generate the best moments. Those moments of creative insight or creative brilliance will never be allowed to happen. Instead I seem to prefer operating in a comfort zone, knowing that the presentation will be just good enough to run smoothly.
Of course "just good enough" means it'll be vanilla and boring, but it'll go off without a hitch. I must force myself to fly free, risk crashing if I fly too close to the sun, but the reward may be an experience for the ages, something that changes me and the audience, something that stands the test of time or sets a new trend. Safe doesn't do that.
Be bold, take the risk, reap the reward or fail gloriously while trying. –This must be my new mantra for my own good and for the people who consume the content I create.