On Thursday this week, I attended the 30th anniversary celebration of a well-known law firm, the specialty of which is akin to my own practice. It was fun to see my peers, but due to pandemic distancing, it was more like getting reacquainted than just hanging out. We caught up with each other’s lives: family, travel, law practices, and more than a little gossip. And in far too many cases, current health challenges were the topic of conversation.
At one point, I greeted the managing member of the firm that hosted the event, and I expressed my gratitude for the successful settlement of a large case in which he had served as the mediator. I told him that his guidance and expertise were exemplary and that it was a case that no one believed could be negotiated and settled. He, in turn, complimented my partner who represented one of the parties and related how helpful he had been.
Then he turned to the small group around him and mentioned to it that his firm had asked me to join it decades ago, and that it was a loss when I had declined. I murmured that it would have been a good fit for me and that it would have been a privilege, but that I knew in my heart that starting my own law practice was beckoning. The truth is that had I joined, I would have loved it and flourished, and I would still be there to this day.
The exchange made me think about life choices, and how we view them through the backward-facing prism of wisdom and decision making and, sometimes, with regret.
Regret is a powerful, all-knowing master, and I learned at its feet. In Daniel Pink’s best-selling book, The Power of Regret, he concludes that a person’s life regrets fall into four major categories: foundational, boldness, moral, and connection. Three of those types of regret give me no pause; I view minor failings in the past like not studying in high school (foundational), flirting with the boyfriend of a good friend (moral), and not staying in touch with relatives for short periods of time (connection) as minor blips on the path to maturity.
But I struggled with boldness in the past – not pulling the trigger on adolescent dreams like trying out for the cheerleading squad or, later, not pursuing a career in veterinary medicine because I was afraid of failing. Oddly enough, with each boldness failure, I become incrementally emboldened, realizing that the consequences of inaction were more painful than missteps.
I studied for and took the Law School Admissions Test, certain that my scores would prevent admittance to law school. I entered law school confident that I would flunk out. I took a part-time job after graduation because although my grades were excellent, I was on law review, and I had interned at a well-known law firm the summer before my final academic year, being obviously pregnant during job interviews apparently was not a draw for potential employers. But I persevered, and I drove my career to a level that would have astonished me had I taken the time to examine it objectively.
But when faced with the prospect of joining a new law firm, I was still afraid: the fear of an uncertain future with a fledging firm eclipsed the trying politics that came with my partnership at a large Seattle one. So, I vacillated and ultimately declined the invitation. There was a voice inside my head that my prospects were headed in a different direction, though the destination – and the route – was hazy.
Some years later, I decided to go out on my own, a decision that terrified me. But starting and growing my practice, through its colicky infancy and prickly adolescence, to financial maturity is one of the most fulfilling and gratifying experiences of my life. There was no better outcome for me: the chance to work and prosper at a company where I got to choose who I worked with, what clients we served, and what culture we embodied was the greatest privilege I could have envisioned.
A choice I made years ago that I feared would linger endlessly, tinged with regret, turned out to be the best possible consequence for me. From this I have learned is that it is not the decisions that you make after all. It is what you make of your decisions.