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Molly Fletcher: Being a Woman in a Man's World

A woman standing in front of a sign that says women in leadership.

​The fourth and final day of the 24th annual Women in Leadership (WIL) Institute in Orlando, Fla., ended with the inspiring words of Molly Fletcher. Hailed as the "female Jerry Maguire" by CNN, Fletcher made a name for herself as one of the first female sports agents. During her almost two-decade career as president of CSE (formerly Career Sports & Entertainment), Fletcher negotiated more than $500 million in contracts and represented over 300 of the biggest names in sports. Her five books and ongoing podcast on achieving career success have made her an in-demand speaker across the globe.

At WIL, Fletcher spoke to the ways in which women are called to be bold in their personal and professional lives. Unlike their male colleagues, many women leaders face the unique demands that come with motherhood and being seen as not quite as qualified to be powerhouses in the world of business.

Fletcher's trailblazing career and personal experience of gaining unparalleled success as a woman in the traditionally male domain of professional sports speaks volumes to the value of recognizing and seizing opportunities to be bold—and what can happen when you take a chance.

'I Birdied It'

Fletcher shared personal examples of this boldness and what it can look like for women. She recalled being a first-time mother, rushing to a meeting with an important client and having to pump breast milk and drive at the same time. She also spoke about her experience finding out she was pregnant with twins just a few weeks after the birth of her first child and rushing from her OB-GYN office to a "can't miss" meeting to lock in a deal, calling her parents along the way to inform them they were moving to Atlanta to help out.

A particularly strong flashpoint was the time Fletcher met with the general manager of the Atlanta Braves to negotiate her client's contract, and the manager spoke over her head and directly to her client, as if she wasn't in the room. "At that moment, I was the point person for this contract, and I could see him thinking, 'What is this woman doing in my office?' " Fletcher recalled.

Aware that she was silently being told she did not belong in that traditionally male space, Fletcher's anger boiled inside as she contemplated her next move. "But in that moment of self-doubt, I saw my opportunity to be bold and seize control of the situation," she said.

On the manager's computer screen behind him, Fletcher recognized a screen saver that was a rotating slideshow of the different golf holes from Augusta National. Recognizing a course she had played herself, Fletcher drew the manager's attention to the screen, telling him she particularly recognized hole No. 12 on the green. The manager's face lit up as he told her he played that notoriously difficult hole just a few weeks ago and made par, completing the hole in three strokes. Leaning forward, Fletcher informed him, "I played it last week, and I birdied it" —two strokes.

Fletcher said her boldness was rewarded, as the energy in the room changed abruptly and she earned the respect she deserved. "That manager and I became great friends at that moment, and I negotiated many contracts with him going forward," she said.

"We all have those times of self-doubt, but in those very moments we have an opportunity to change our mindset into clarity and be bold," Fletcher continued, adding that such moments need not be as momentous as her exchange with the Braves manager. "It's not always about achievement. It's about who we become along the way. Complacency is the enemy of boldness. We don't have to accept it when our power is being dismissed."

Harnessing Your Energy

While smart time management is essential in a demanding professional career, Fletcher said, what's even more important is how you manage your energy. "If we don't do that, the world will do it for us," she warned, noting that energy is a finite resource that must be spent carefully.

"Energy is integral to performance. You can't show up in the tough moments if you don't have it," Fletcher said. "There's so much we can't control, but also so much that we can."

Protecting that precious energy, Fletcher concluded, is essential to being able to be bold when a situation calls for it: "The greatest boldness is not only when we help ourselves, but when we help others, the people we serve in our lives. Everyone here has that spark of boldness in them. Now go out and ignite it." 


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