Failing My Way to Success

Abstract

This chapter on “Failing My Way to Success” offers an “in the trenches” account of social entrepreneurship drawn from the 2015 memoir Failing My Way to Success: Life Lessons of an Entrepreneur. The book chronicles personal and professional disappointments, betrayals, and bankruptcies from which grew the author’s hard-won lessons of failure and the climb back to success. These lessons range from business best-practices to interpersonal skills to philosophical truths, but at their heart lie two ancient principles. The first warns against self-deception, expressed as the axiom “know thyself” and is perhaps the toughest challenge that the beginning entrepreneur faces. The second is the Jewish concept of tikkun olam—“repair of the world”—the belief that we bear responsibility not only for ourselves and our immediate circle but for the world at large. This essay argues that perhaps the most important definition of “success” is the capacity both of means and spirit to fulfill this command.