A Crash Course in Confidence

By Nina Kaufman, Esq.

As a child, I was painfully shy. And old habits die hard. Fast forward 25 years — I’m not long out of law school, and newly minted as a business owner, having started my own law practice. I had to exert authority in my firm and exude authority to clients and others. But I still felt naïve and vulnerable. I needed a crash course in becoming self-confident – or, at least, in looking the part.

I found mine in performing stand-up comedy.

Stand-up comedy is like Extreme Public Speaking. It’s not for everyone. Despite my experience giving speeches, teaching classes, leading workshops, and running meetings, comedy calls on a whole different set of skills and resources than those I typically use. It takes a certain intensity (insanity) to pursue it. But it’s not just a bizarre hobby; stand-up comedy has strengthened my business skills. Here’s how:


  1. “Riffing”. Preparation is always crucial. But comedy, like business, can’t always be scripted. Your ability to win over an audience, whether of merry-makers or venture capitalists, often hinges on your ability to think on your feet. How well do you handle the curve-ball from the bank loan officer? The heckler at the back of the comedy club? The hypothetical during a job interview? Training your mind to be creative in the spur of the moment takes discipline and practice – but it can be done. Many of the most successful arguments I’ve made in court have come during a riff.
  2. “Teflon” skin. Comedy is an exercise in irony: when you desperately need audience validation (their laughter), you don’t get it. And when you don’t try so hard, you get it – in droves. When you don’t fear others’ dissatisfaction, you exude calm and confidence — even in the face of total disaster, such as in the excruciating silence that follows a flat joke. Or when, during the major business presentation that requires audience participation, the attendees are all dozing after lunch. The key is to cultivate a sense of detachment, so that the outcome doesn’t affect your sense of self. With that detached attitude – not worrying about whether my colleagues liked me – I was once able to vigorously oppose an ill-conceived proposal by a popular Board president . . . and ultimately sway the Board away from it.
  3. Timing. Step on the all-important pause before delivering a punch line, and you ruin your joke. Fail to pause after you’ve delivered the punch line, to let the audience laugh (or not), and you show that you are nervously awaiting their mirth. When your pacing flows smoothly, both in comedy and in business, you reveal your confidence in what you’ve said. Timing is also important in the sense of “keeping to time”. Often in comedy, you’re limited to a 5-minute routine. Exceed the limit, and you’re history. The same applies in business and in normal conversation. Hog the time, fail to listen, and you will not be appreciated. As a result, you learn to wring the most you can from however little time you have. As Franklin Delano Roosevelt said, “Be brief; be clear; be seated”.
  4. Keeping it tight. Words count. Comedy forces you to focus on your speech, as “filler” words cost you time and dull the impact of your punch line. You learn very quickly to cut the fat, choose the right word, and eliminate the crutches or “fillers”, such as “uh”, “er”, “I mean”, “I’m like” “and”, “so”, and “ya know”. Clarity is key – in all messages. Plus, you gain listeners’ attention and respect through the substance of what you say. I once attended a securities litigation seminar given by a trial lawyer. He “ummed” over 160 times in a 15-minute presentation (a rate of more than 10 “ums” per minute), which was distracting. All I could think about was, “Is he this bad when appearing before the SEC?” He got my attention, but for all the wrong reasons. And I can’t remember anything he said.
  5. Perspective. Few situations are so dire that some humor can’t be wrung from it. Having a mindset of “would this make a good comedy routine?” I stay focused on the silver lining (the zippy one-liner) instead of the cloud (the situation that inspired it). No presentation is so abysmal, no client so difficult, no judge so appalling, that it can’t serve as grist for the comedy mill. When an adversary’s bombastic approach whips me into a screaming frenzy, my business partner suggests, “Put him in your next comedy act!” If living well is the best revenge, mocking someone in stand-up is second best. Finally, a humor-seeking disposition has a positive effect on others, too. Customers, colleagues, and friends generally prefer to be with those who laugh instead of kvetch.

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