Why avoiding being disappointed may actually result in you being disappointed

While we are excited to leave the law behind, most of us only want to do so if we can guarantee one thing: We leave the law perfectly. We want to make no mistakes. We want to guarantee our path to freedom. We will boldly steer from our current course … as long as we know we’re going in the exactly correct direction. We lawyers play it safe and try to be perfect. In law school, we competed against real smart classmates and faced a steep grading curve and battled to get an OCI interview. For our clients, we regularly advise of worst-case scenarios and assist with risk management and are taught how to identify and avoid issues and concerns. And in our personal lives, we look for job security and dependable career paths and well-respected firms. Many of us are always keeping score and we always want to score high. As such, we attorneys often aren’t inclined to try something new. And to drill into this further, we do not try something new (like leaving the law or trying something new within the law) because we realize that we may not succeed at it. We may not be perfect at it. It may not work. We may fail. We choose to put off networking with other lawyers and non-lawyers because we may flub our words and look stupid. We may not explore how we can leave the law because someone may see us leave the office during the mid day and our managing partner may find out that we are dissatisfied and we may end up losing our job. We don’t take the time to honestly assess our skills and strengths and Unique Genius because we may not like what we see or find out about ourselves. We don’t take the time to start something on the side because we feel it’s doomed to fail anyway. And if we fail at something, we could become greatly disappointed and discouraged and this could prevent us from doing anything else in the future. So we just don’t try. Or just don’t try that hard. But if all we do is try not to fail, we may find ourselves living our life and planning our professional path based on the avoidance of disappointment, and not based on our skills and strengths and Unique Genius. Because inherent in properly leaving the law is following our Unique Genius; and inherent in following our Unique Genius is letting our skills and strengths and enjoyments inform which path and role and job we pursue (and not the other way around); and inherent in letting our skills and strengths and enjoyments inform which role and job we pursue is the need to try things and test things and try things again and learn from things and test things again and run things by other people and fail at things. Ergo, to leave the law, you need to fail. And if we live a life based primarily on trying not to fail, we will likely avoid this disappointment in the short term. We won’t have tried anything new, so our record will not be smirched. No one will have been tempted to laugh at our ideas or doubt us, so our reputation will be intact. We will keep our dependable job, so we will rest easy knowing we have followed the steady and known. But unfortunately, if we live our life in misalignment with our Unique Genius, if we choose roles and paths and titles that do not showcase and optimize and feature our true skills and strengths and confidences and core, we may end up disappointed that we lived a life that was safe, but was not really our own. Take a baby-step. Ask yourself these three questions. Confide in someone you are unhappy as a lawyer. Email me. Comment below. Fail. And fail again. And once more. And you’ll notice a crazy thing: even though you have “failed†(you weren’t smooth in the networking coffee, you were a wallflower at the cocktail party, your friends and family rolled their eyes when you said you were unhappy as an attorney, you can’t yet identify what you are really good at, you admit you have no idea what other non-legal jobs look like, you tried to start a blog, but you quickly ran out of writing ideas, you can’t think of a side consulting gig you’d like to take on, you still feel lost), you are still around. You are still standing. You are smarter. You have tried. You have stories to tell. You have new people to rely on. You have new opportunities. And you may finally realize that the only one keeping score is you.