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Serena Williams: A Tennis Lesson on Law Careers

by Shana Simmons

Like millions of other folks, I was saddened when tennis superstar Serena Williams announced her retirement last month in Vogue magazine. Reading her essay, I couldn’t help but to reflect on my own journey; like Serena, I am a professional, a wife and mom, and a Black woman. As someone who’s worked her way up from humble beginnings, I feel deeply connected with Serena’s triumphs, setbacks and hopes, always admiring her brutal authenticity. 

Most recently I’ve been thinking about how Serena’s career trajectory can inspire the next generation of lawyers looking for role models to spur them on to greatness. Here are three qualities that epitomize Serena we can all aspire to confidently own.

Chart Your Own Course 

As Billie Jean King wrote this week, Serena is “The GOAT, the greatest of all time — or at least the greatest of her time.” But in her four decades on the court, Serena’s path hasn’t always been a straight line to the top. She dropped out of the USTA’s Top 100 in 2006. This week she started in her 21st U.S. Open unseeded and ranked 608. No matter what the score on the court, her career is one defined by both an unstoppable drive and the ability to grit through setbacks. 

In our post-pandemic work world, it’s particularly important to understand that absorbing setbacks is not admitting failure. Taking a role with a lesser title or scope, and retreating to acquire more skills is sometimes necessary to move onward and upward. You may think your legal career is going backwards, but in fact you’re making progress – advancing to your own goals. I’ve experienced this myself, going from a lawyer at Cleary Gottlieb, a top tier firm, to a Contracts Manager position at Google. It was a setback for my pride but ultimately well worth it; as I ascended the corporate ladder at Google I gained invaluable experience, adding to the foundation that allows me to be an effective General Counsel. 

Serena Williams Large
Serena Williams at the 2015 Australian Open 2015

Bring Your Authentic Self to Work 

One thing is for sure, Serena and her sister Venus reshaped an entire sport, and the notion of what Black women can accomplish on a largely white playing field. Throughout the peaks and valleys of her career, Serena has remained unflinchingly authentic. She never shied away from being a Black woman. More and more, we are seeing a wide range of professions embrace the idea of bringing one’s authentic self to work — even law! Both individuals and organizations today demonstrate more respect for diversity of thought, and value its impact on the world around us. 

Authenticity has had a personal payoff for me, as well. When I realized I needed to be who I truly am at the table, I began adding exponentially more value to the conversation. This started a virtuous circle; personal confidence fueled my professional confidence, igniting my career.

Become Multi-Dimensional 

The demands of the legal profession often make us feel one-dimensional. Admittedly, earlier in my career it was a badge of honor to exceed my billing hours while relegating personal interests to the sidelines. Serena faced pressure to metaphorically “bill more hours” at unbelievable levels, even as a champion. Serena was at points chastised for not playing enough tennis. She invested time in fashion and business ventures, and having a family. She even won the Australian Open while pregnant. 

At a firm your value as a person is calculated by your billable hours, and it’s easy to let work define your identity. I did. 

I recognized the need for work-life balance while living in London and engaged to an Oakland, California, firefighter. This helped me summon the courage to leave the prestige and professional security of a big firm and relocate to the Golden State. Since then I have dedicated time to raising a family and giving back to my community, such as serving on the Board of the Oakland Zoo and Lawyers for One America. These are inestimable sources of joy to me, yet felt nearly unattainable earlier in my career.

Serena’s multi-dimensionality inspired a new generation of athletes and rewrote the book on accomplishing what you want on your own timeline — a role model for women everywhere. Here's her take on leaving behind tennis, the mainstay of her life trajectory, and embracing business and family life:

I have never liked the word retirement. It doesn’t feel like a modern word to me… Maybe the best word to describe what I’m up to is evolution. I’m here to tell you that I’m evolving away from tennis, toward other things that are important to me. A few years ago I quietly started Serena Ventures, a venture capital firm. Soon after that, I started a family. I want to grow that family.

She Did It and So Can You

Serena has my utmost respect for retiring on her own terms at her time, moving on from the game that’s defined her life to focus more intently on other interests. And the most exciting part is, she’s not finished yet. To my ears her closing words in Vogue speak the loudest: 

To me that’s kind of the essence of being Serena: expecting the best from myself and proving people wrong… My sister Venus once said that when someone out there says you can’t do something, it is because they can’t do it. But I did do it. And so can you.

Thank you, Serena, for being a change agent at the highest level. You inspire me every day!