Wooditch, Fail More

Bill Wooditch, the founder and CEO of The Wooditch Group, a risk-management and corporate insurance firm, takes on what has become a staple of commencement speeches in the last few years: failure. In Fail More: Embrace, Learn, and Adapt to Failure as a Way to Success (McGraw-Hill, 2019) Wooditch covers well-trodden ground, but he does so in a commonsensical, straightforward way.

For instance, he discusses one manifestation of fear: procrastination. “It’s the salesperson who, instead of making cold calls, creates files, rearranges the office space daily, takes an hour in the break room before, during, and after lunch, and then performs like a dilettante, not a professional. … Hours go by; momentum is lost. And as the hours sweep by, so goes the day, the month, and the year.”

Failure can be constructive, leaving clues and tools a person can use to forge success. “Failure is simply a small price you must pay to satisfy the burning desire of what you must have.”

Wooditch learned in spades about failure in his first job in sales at Liberty Mutual. He made a commitment to himself to make more cold calls than anyone else in the office—350 to 400 calls a day. And he was failing upward of 315 times a day, or 1,575 times per workweek. But he persisted, recognizing that “the only way to move through pain is to partner with it.” He had to habituate himself to rejection and failure if he was ever going to improve.

Although Wooditch draws on his own experiences both as a salesman and as a CEO, he also shares examples from the careers of people like Jack Ma, Gary Cohn, Mark Cuban, David Neeleman, and Steve Harvey. Fail More isn’t going to win kudos from the academic community, but it has enough nuggets of wisdom to be a worthwhile quick read.