Forgiveness and Faith Fuel Entrepreneurship

Posted on: September 3rd, 2015 by Hayim Herring



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.


Why forgiveness? When you encourage individuals to provide “entrepreneurial” responses to situations, they will err. If your initial response is rebuke for their miscalculations, they will quickly realize that you are risk-averse and return to old patterns. That doesn’t mean that every failed risk should be applauded! There have to be some standards so that being “entrepreneurial” doesn’t become an excuse for carelessness. But well thought-out, novel efforts that don’t work should be forgiven quickly. (And another way to be forgiving is to recognize that if a well-planned risk is failing, let it fail faster so that people around you don’t have to watch an agonizing death!) If you want to create a culture of entrepreneurship, be forgiving, so that people will continue to challenge themselves to get it right the next time.


And faith? I’ve come to understand faith or, in Hebrew, emunah, as knowing that a positive resolution will emerge even if it isn’t immediately self-evident. Having faith that ideas arise from within an intelligent, empathetic and passionate group won’t ever disappoint you. It always works when you genuinely believe that the collective wisdom of a group is pleasantly unpredictable and accurate.


If you’ve ever worked in a congregation, Jewish organization or, in fact, some other nonprofit, you probably know how challenging it can be to become more entrepreneurial and assume greater risk. Who wants to mess with a tradition (read: a familiar routine), even if it isn’t working very well? More to the point for religious organizations, who wants to experiment openly with God’s word, tradition, custom – whatever you choose to call it? Doesn’t that audacity clash with the value of humility in which leaders, especially religious ones, are supposed to be stepped?


And yet… purpose driven communities and enterprises are at their best when they are audaciously entrepreneurial. Betting on a monotheistic God who demanded human dignity and equality, against a Pharaoh backed by a military-idolistic complex was pretty risky. Gambling more Jewish lives after the Holocaust to build a Jewish state looked like an irrational gamble to many, too. And, putting a man on the moon or sequencing the human genome, two risky, enterprises, had plenty of skeptics. Fortunately, legions of audacious entrepreneurs persevered.


Miles Davis, one of last century’s great jazz musicians and trumpet players said, “If you’re not making a mistake, it’s a mistake.” His provocative statement was a call to musical entrepreneurship, and a challenge to the resistance of playing it safe. I’m not sure if he ever heard the sound of a shofar blowing, but it’s meant to have the same effect of awakening us to risk reaching inward together so that we can surpass our potential for excellence.


So, as a leader, how will you let your capacities for forgiveness and faith enable your organization to become more entrepreneurial? What wise risks are you open to having your team take on this coming new year?




©2024 Hayim Herring – Rabbi, Entrepreneur, Consultant
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