My experience in four school districts and having worked with hundreds and hundreds of educators over 22 years tells me that a lot of people don't like to take risks. Perhaps it's the lock-step routine-driven nature of our profession that stymies us. Maybe tenure promotes a level of comfort that few (administrators included) want to relinquish?
Risk-taking breeds an inevitable level of failure. Great risk-taking leaders I have studied and from whom I have drawn inspiration talk about their high failure to success ratio. In other words, with risk has come more failures than successes; the successes have been enormous.
Theodore Roosevelt is one such leader who took risks and reaped the rewards of "jumping" into a bold initiative (who would have thought to take on Vanderbilt, J.P. Morgan and other barons of capital to create sweeping labor rights legislation?).
"And so, the best you can do is to stop, look, and listen - and then jump...and hope [you've] jumped right."
This post is part of the "Leadership Lessons From American Presidents" series.