How can forgiveness and faith fuel leaders to create a culture of entrepreneurship? In the mysterious way that we stumble upon questions to which we don’t automatically have answers, I fell into this one as I was spiritually prepping for Rosh ha-Shanah and Yom Kippur.

Here’s the relationship between forgiveness, faith and entrepreneurship that I’ve come to realize. The upcoming holidays focus us on repentance. The word “repentance” is shorthand for describing the efforts needed to break unproductive and often safe routines that lock us in place—even when it’s a place that we know we don’t want to be! Familiarity often breeds complacency and enables us to rationalize a status quo that we know is deficient—whether in ourselves or in our communities.

If repentance alerts us to the dangers of routine, entrepreneurship evokes uncertainty. Being entrepreneurial requires embracing agility, variation and unfamiliarity; of learning what happens when we “change it up.” When you welcome uncertainty in, even with thoughtful planning, you’re never quite sure where it will lead. That’s precisely why entrepreneurial leaders must also invite forgiveness and faith into their communities as well. (more…)