In a perfect world...
STOP!
There is no such thing as a perfect world... So what's the point of thinking that way?
Here and now. What is. Reality. You have an obligation to start here.
Now don't misunderstand. Leaders can and do strive to improve the status quo. They are not satisfied with leaving things as they are. They would like to see progress toward perfection, so they drive incremental change.
What stalls some leaders out, though, are three nagging little words. Instead of thinking about what's been changed, incrementally, a little bit at a time, these leaders get caught up in the thinking traps of Shoulda, Coulda and Woulda.
Remember Schindler's List? It was the true story of Oskar Schindler, a German factory owner who is credited with saving the lives of more than 1200 Jewish people during the holocaust by employing them as workers in his factories. In the movie, Schindler breaks down and asks "why didn't I do more? I should of... I could have... I would have been able to save more if...."
It's a noble but futile thought process for leaders. We can't go backwards. If we could, we'd probably find legitimate reasons why Schindler shouldn't, couldn't and wouldn't. We'd certainly find evidence that he did so much, as measured by the 1,200 lives he saved. We'd likely conclude that he needed to give himself a little credit for what he accomplished rather than agonizing over what he was unable to do.
We owe ourselves the same. When we beat ourselves up with shoulda, coulda, woulda rhetoric, we hold ourselves back.
Here's a different way of thinking about the work you've done.
First, give yourself credit for the work you've done and the accomplishments you've made. No matter how small, they are victories that count.
Second, if you can't help but wonder what more there may have been to do, redirect that thinking. Turn shoulda into shall, coulda into can and woulda into will. Focus forward on what's next and how your next efforts will build on the successes you've already had.
Finally, extend this same grace and forward focus to others. Don't judge what's already been done for what it may be lacking. Recognize what has been done and encourage others to build from that point forward.
By liberating yourself and others from some unattainable ideal, you and your team will be able to continually move forward. Don't let this thinking trap hold you back.
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