A friend recently shared an article with me about the concept of “toxic positivity” - the idea that positivity, when taken to an extreme or misapplied, can become harmful or invalidating. As someone deeply fascinated by how the human mind works, I found it refreshing to explore a perspective that challenges mainstream self-help narratives. After all, who among us hasn’t, at some point, reached for that book - the one that promises to fix us, help us lose weight, become a better leader, or finally feel whole?
One of the most impactful books I encountered during my time in startup management was Leading with Questions. The core premise is simple yet profound: asking the right question is half the answer. So, when I asked myself, Why are lawyers so resistant to transformation?, it felt like I had already touched on part of the answer. Still, I wasn’t seeing it clearly. Maybe breaking it down will help - not just to find clarity in the question, but perhaps to understand myself better too.
Let’s start with the lawyer - not as a job title, but as a person. A lawyer isn’t just someone who drafts contracts, argues cases, or navigates regulatory frameworks. Behind every lawyer is a driven, intelligent individual who worked incredibly hard to get where they are. That person is often a former child prodigy of sorts - determined, self-reliant, and unwilling to show weakness. She didn’t arrive at her success by waiting for someone else to lead her; she got there by mastering control, by appearing unshakeable, by telling herself she could not afford vulnerability.
But therein lies the paradox: the very strength that propelled her forward becomes the wall that blocks transformation.
Transformation requires humility. It demands vulnerability. It asks us to let go of the protective layers we’ve built and be willing to question not just what we do, but who we are. That’s not an easy ask - especially in a profession where control, certainty, and authority are currency. But transformation is not weakness; it's the opposite of resistance. It brings liberation, flexibility, and resilience.
In today’s evolving legal landscape, where automation and AI are increasingly handling the rote and the routine, the human lawyer must rise—not as a competitor to machines, but as a complement to them. Empathy, critical judgment, ethical reasoning, emotional intelligence—these are the traits that will set the great lawyers apart. The future belongs not to the unshakeable, but to those who can bend without breaking.