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Are you a pathological second-guesser?


Let me tell you about my friend, Mark. (Of course, that’s not his real name.) Over the years, Mark has built an impressive, nationally robust corporate practice. Early on, his firm was thrilled to have Mark lead their corporate practice, and he was equally thrilled to practice with his firm, which is a large, multi-office law firm. Mark was a significant rainmaker for the firm, not to mention that the clients he represented spun off a healthy variety of work for others, and he and the firm flourished together and their marriage was strong. His relationships with his clients grew, so naturally so did his practice, not to mention his compensation. Mark had even served in various leadership positions over the years. Like other firms, their growth trajectory continued, and one day, Mark realized that those close trusted relationships within his firm no longer existed. Eventually the firm’s oversight committee (the board) included a group of lawyers that he hardly knew. And the firm’s newly appointed Chair worked in a completely different time zone. Can you see where this is going? And the firm’s board had their priorities, which were based on market studies conducted by an outside consulting firm. Long story short, the firm’s focus was developing and growing in markets and practice specialties other than Mark’s. Mark and I have a great friendship, and it isn’t based on where he practices. Like any good friend, I have patiently spent more than a few hours listening as Mark outlined why he and his practice group are no longer a fit for his law firm. Every couple of months, I receive a call from Mark. This usually occurs after he has made some effort to expand his practice base or broaden a client relationship, and his ideas are not supported. In other words, his ideas are rejected. Initially, he felt discouraged, but slowly his discouragement grew into frustration, and instead of the occasional conflict, it become a monthly, if not weekly battle to try to get the support he felt he needed, and perhaps even felt he deserved. “After all,” Mark explained, “over the years, I’ve made my partners a lot of money during down markets when others practices struggled, but not mine!” Yet Mark continued to stay, always talking himself out of leaving. So here is where we are again. Mark called and wants to grab lunch to talk about transitioning his practice. We’ll meet, and I’ll listen to his latest list of reasons why he should leave. Mark no longer feels frustration, because now his frustration has blossomed into resentment. You’re probably familiar with the story of the Buridan’s ass. It’s a paradox illustration in philosophy in the conception of free will. It refers to a hypothetical situation wherein a donkey that is equally hungry and thirsty is placed precisely midway between a stack of hay and a pail of water. But the donkey is a pathological second-guesser, and therefore is unable to make a decision. So unfortunately, the donkey dies from both starvation and thirst. Thankfully, it’s just an illustration. Back to my friend, Mark, who spends a tremendous amount of time questioning his own decisions, to the point where he resembles the Buridan’s ass. I enjoy Mark’s company, so I don’t consider the time we’ve spent together as wasted. And quite truthfully, his continued flip flopping used to be somewhat entertaining. But because he is also my friend, I can clearly see that Mark has been unhappy and unfulfilled for several years, and now it’s just difficult for me to watch. Mark appreciates my perspective, so I have a role in the play. He expects me not to just sit and listen; he actually wants my feedback. So I ask the same questions: Do you feel supported? Do you feel valued? If you left, would you be missed, or would the firm simply miss your financial contributions? (Hint, the difference matters.) I also ask who knows his clients and market best, and if the firm supports his ideas and vision. I try to avoid the questions regarding trust and loyalty because I know those answers. They would both be negative because he hardly knows the current leadership. Mark has become a gifted leader, yet as I’ve watched him continually feel unsupported, he’s lost some of his edge, not to mention his confidence. He’s a shadow of his former self, the young fiery partner I first met. Rejection has that effect on a person. Clearly, this a problem for Mark. Or is it? (Yes, it is... but wait, maybe not.) What is at the root of the problem? Is Mark risk-averse, or a procrastinator (a lack of self-respect)? Mark’s story has a happy ending, and in case you’re wondering, Mark (again, not his real name) approved this blog. To learn more about the exercises that helped Mark find his courage to make a decision that he didn’t second-guess, contact teamjag@jaglaw.com to talk confidentially with one of our team members.


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