Several years ago I taught an undergraduate class in business leadership at Queens College. From the beginning I had, what to the students seemed a revolutionary policy: You always got a chance to re-write your essay. If you didn’t like the grade you got the first time, you could incorporate my suggested changes (or not) and re-submit your essay at least once.
The lesson I tried to teach was that doling out Do Overs was a powerful incentive. It mitigated the fear of failing and, more often than not, brought out the best in the kids.
Many walked away with the notion that they, too, when they ran their own companies (and they all thought they would one day), would hand out Do Overs. Fewer of them, though, walked away with the deepest lesson of all: you’ve got the magic wand in your hand right now. Give yourself a Do Over. Let go of the shame, guilt, anger, fear from eating too many Oreos and try again today.
I really love this post by Jerry.
I was listening to the Philosophers note on Learned Optimism a few weeks ago and Brian / Martin Seligman talk about the difference in perspective between an optimist and a pessimist that is very much in line with what Jerry is saying here. Someone with a more pessimistic perspective tends to see things as permanent, especially their own mistakes, while a more optimistic person sees things as temporary. The optimist, they said, truly believes in the do over. It has taken me a long time to finally start believing this.
The reality is this: There are very few things in life where a do over is not possible. So why, sometimes, do we want to torment ourselves by thinking things are permanent? Do you really want to torturet yourself by believing the deal you failed to close was your last shot?
I guess without realizing when it happened, I started giving myself more do overs in the last year, and it’s amazing how different the world looks. It’s so much lighter, I sleep better, and life seems much more playful. When you know you have another chance at something, you’re willing to play. It’s no longer so serious. Why shouldn’t life be more playful?
Life Putting 
A few of the folks who commented on the original post worried that a pre-existing knowledge of the Do Over might discourage people from trying their best. In reading your post, and thinking about it more, I think the problem with that line of thinking is that it assumes a pessimistic attitude about peoples' motivations. Machiavelli essentially taught that it is better to be feared than loved–and so people would be motivated by fear of failing.Plato, in the The Republic, said it was better to be admired than loved–and so people would be motivated by fear of disappointing.In the end, I think the best of all possible motivations is self-love…and the motivation to forgive yourself, drop the rumination, and move on stems from the notion that we all make mistakes. Then the challenging moment we're in right now becomes a great opportunity to learn.
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Yes I saw those comments on your post (you get a ton of great comments bythe way) after I posted this. I think there is a some risk in that ifsomeone knows they have a do over, then perhaps they may not do it “right”the first time. However, as you touched on much more eloquently than I willhere, the risk of not doing at all due to the fear of mistakes is fargreater than the risk of not doing it “right,” the first time. It may bedifferent for everyone, but I know for me the right approach is playful andexperimental, which requires the right to do overs.As you mentioned in your comment, the best of all motivations is self-love. For me the concept of do overs is an important part of that. I've spentway too much time beating myself up about mistakes I've made, things I'vesaid, things I didn't do. I would say that weight, which is cumulative,does far more to prevent my best than the do over policy ever has. For methe do over has lessened that weight of the past, and most importantly makesit possible to detach outcomes and actions from self-love. It's not whatyou do, it's who you are, right?
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Maybe that's really the key here, detachment. Maybe the playfulness for meisn't coming from the idea of do overs, it's coming from the detachment ofmy personal worth to my actions and outcomes. Holy crap is life heavy andscary when your worth is directly related to what you do. Eating 12 oreosis bad and wrong, so you, Jerry, are bad and wrong. I've lived under thisphilosophy before, it sucks. But now in a do over it seems like it's easierto separate the eating of 12 oreos, a mistake, from who you are. So maybe ado over makes detachment from outcomes easier?just thinking out loud here.
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and for the record I don't think eating 12 oreos is bad and wrong. I thinkit's totally understandable…but for the sake of my argument and in thecontext of your diet, it's considered bad and wrong.
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“It's not what you do, it's who you are, right?”That's right…but even more, for reasons to personal to say here, thanks for that reminder.
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Yup. Totally get it.
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