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Learning To Love Risk, As A Lawyer

“Lawyers are risk-averse.” It’s a generality that I’ve heard repeated constantly throughout my career. But as the rare lawyer (yep, that’s me!) attracted to risk — an allegedly rare breed — I’m often puzzled. Law demands creative thinking and innovative solutions — how can you have either of these things without taking risks?

When I hear this generalization, I wonder: Am I not enough of a lawyer? Am I thrill-seeking techie who dresses up in lawyer’s clothing and pretends to be one every day? Or, is your generalization is just that: An inaccurate generalization? In the end, I always conclude the latter. After all, it’s usually easier to conclude that “it’s you, not me” in most situations.

Jokes aside, predicting a personality trait of a group member is a challenging and at best a crude undertaking. Even if your assessment of the group is correct on average, it may or may not be for any one member. And sometimes the standard deviation is so large and there are so many outliers that even talking about averages is meaningless.

Most importantly, just like any group of human beings, individual lawyers don’t fit neatly into a box. Within a group, there are scattered gems of varieties — different personalities, experiences, and talents. Why not enjoy the full spectrum of legal experiences? Why not enjoy the richness of each interaction and get to know each person for who they are, not for who they’re not or for who you expect them to be?

While “lawyers are risk-averse” is and has always been an easy cliché, my experiences in law have also included meeting very interesting people who happen to practice law. After all, as a tech lawyer, I know as well as anyone that the law is a dynamic, constantly evolving body of knowledge — there must be someone embracing change, newness, and risks behind it.


Olga V. Mack is the CEO of Parley Pro, a next-generation contract management company that has pioneered online negotiation technology. Olga embraces legal innovation and had dedicated her career to improving and shaping the future of law. She is convinced that the legal profession will emerge even stronger, more resilient, and more inclusive than before by embracing technology. Olga is also an award-winning general counsel, operations professional, startup advisor, public speaker, adjunct professor, and entrepreneur. Olga founded the Women Serve on Boards movement that advocates for women to participate on corporate boards of Fortune 500 companies. Olga also co-founded SunLaw, an organization dedicated to preparing women in-house attorneys to become general counsels and legal leaders, and WISE to help female law firm partners become rainmakers. She authored Get on Board: Earning Your Ticket to a Corporate Board Seat and Fundamentals of Smart Contract Security. You can email Olga at olga@olgamack.com or follow her on Twitter @olgavmack.