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I have a good friend who detests making plans. Our small circle of colleagues jokingly refers to him as “Houdini,” as he’ll seemingly go to any lengths to get out preparing. When it’s time to detail our yearly group vacation, for example, he’ll come up with the unlikeliest excuses to avoid participating. “I prefer to go with the flow,” is the reliable response.
I’m sure we all have someone in our lives like this — a person who leaves much for the last minute. And I can understand that desire for spontaneity. Back in 2006, when I founded my startup, Jotform, I promised to never get so caught up in strategic planning that I forgot how to live without it. Of course, I was then a newly minted entrepreneur and had many untested ideas about running a business. Now I know better and have grasped that, as leaders, it’s not simply planning that’s key to success, but doing so strategically.