See, if you wing it and succeed - your audience applauds, your jokes land, you come across as articulate and compelling, and people want to connect with you afterward - then you can be relieved and pleasantly surprised. You can even tell yourself "I'm good at winging it."
If you wing it and fail - your jokes bomb, you lose your focus, your ideas aren't organized, the audience is polite but bored - you can always say, "Well, I didn't really prepare. If I had prepared, it would have been SO MUCH better."
Because, OMG, what happens if you prepare and you STILL fail? Then you've wasted your time, right? You feel like, "What's the point? If I prepare, I still suck, so why bother?"
To be blunt, most people's preparation looks an awful lot like winging it, so the minimal level of preparation I frequently see is only slightly an upgrade.
We have so many stories we tell ourselves about ourselves. And so many of our stories are based on creating the hard armor of protection. We (try to) protect ourselves from looking stupid, from looking like we tried too hard, from looking like we might be human. So we hold ourselves back, afraid to take too big of a step or put ourselves too far out in front of the crowd. If no one notices us, we can't get hurt.
But what if you pushed yourself further than ever before? Further than winging it and even further than just "preparing?"
What if you changed your whole mindset about speaking, your whole mindset about the audience, your whole mindset about what you could be offering them if you actually made a sincere effort and committed yourself to excellence, connection, engagement, and transformation?
What if, through "failing" (although there's no such thing in speaking or life - just "learning"), you were able to grow and expand and become a more compelling speaker than you ever imagined? What if you were able to touch your audiences and move them to action in a way that only seems like a fantasy right now?
If you don't care about all of that, then sure, go ahead and keep winging it. Or doing the minimum of preparation. Keep protecting yourself from embarrassment, by all means.
But if you do care about making a difference to your audiences and not just getting your presentations over with, you'll have to push yourself further than you ever have. It's not as easy as winging it, but it's going to be worth it.
Interested? Check out my upcoming retreat in Santa Barbara this March, "Shake Up Your Speaking: Get Real... Get Results." No more business as usual. No more playing it safe. Get real and get results! (Only a couple spots left!)