On Monday, December 2, Upper School students filed into the Assembly Room for the 22nd annual Nicky Chapin Lecture, named after alumna and former faculty member Nicky Stout Chapin ’52. This year’s inspiring speaker, Denise Bailey-Castro, Class of 2005 and former trustee, awaited at the front of room.
The event began with a warm introduction from the Class 12 News President and Mrs. Chapin herself, who shared that Denise is currently the Chief Financial Officer of Westbrook, Inc, Will Smith and Jada Pinkett Smith’s independent film and television studio, overseeing all financial operations. Denise earned her MBA from the MIT Sloan School of Management, MPA from Harvard University's Kennedy School of Government, and B.A. from the University of Pennsylvania.
“It is a true honor to be here,” began Ms. Bailey-Castro, who titled her talk “In Pursuit of Happiness” in honor of the 2006 film The Pursuit of Happyness starring Will Smith.
For those who may not have seen the movie, Ms. Bailey-Castro said, “the important message in the film is that the main character never gives up and it’s full of universal themes that I think everyone can relate to.”
While clarifying that her story is “not as dramatic as the main character in the film,” she said, “I’ve learned a few key lessons in the 19 ½ years since I’ve sat in these very seats at Chapin.”
Number one: Find your “Why” and let that drive you.
Sharing that she has always loved movies, but didn’t, at first, know how to make it a career, Ms. Bailey-Castro only landed her first job in entertainment in 2013. Describing herself as a “non-creative,” she felt nervous about what she might bring to the table. However, during her first few months at Paramount Pictures, Ms. Bailey-Castro created international film strategy, exploring Bollywood in India and Nollywood in Nigeria, and managed analytics of the green-light process. Through this work, she discovered her own professional “Why” – helping creatives to tell untold and important stories.
Number two: Bet on yourself.
After receiving an “amazing offer to become the Brand CFO of BET Media Group (BETMG),” Ms. Bailey-Castro said, “I was terrified that someone would think I was unqualified or had bad ideas.” She remarked that she was “full of doubt” over potential failure, however, believing that “doubt kills more dreams than failure ever will," she took the job and it became a pivotal moment, ending up being the “biggest blessing of her career.”
“Do the things that scare you,” she added. As the Brand CFO, Ms. Bailey-Castro excelled and help grow the company’s portfolio to nearly $1.5B of revenue across cable, streaming, digital and studios. She was instrumental in implementing BETMG’s growth initiatives, structuring landmark, multi-year deals.
Number three: Take care of your whole self.
“I’m a proud Gold,” she said, smiling. As Athletics President and a three-sport athlete at Chapin, and a current competitive powerlifter, Ms. Bailey-Castro noted, “working out and training was at my core…but I lost that when I was in grad school.”
Ms. Bailey-Castro stumbled into powerlifting through an app called Class Pass but stayed in the sport because of the confidence it instilled in her. She found that “focusing on my whole self, including the physical and doing things I loved outside of work,” enables her to be the best, most confident and complete version of herself.
While it was sports for Ms. Bailey-Castro, she underscored that engaging in “whatever sustains and inspires you and sets your heart on fire” is taking care of your whole self. “Honor all of the pieces that are important and bring you joy.”
Number four: Give thanks and give back to help others.
“Wherever you’re going in life, you won’t get there alone,” she stated. “I’m grateful for everyone who spoke to me, taught me, helped me.” Emphasizing that she always wants to “pay it forward,” Ms. Bailey-Castro always seeks opportunities to mentor young people.
Following her passionate speech, the room opened up for Q&A. One Upper School student asked what she considers the most important skill for the workplace.
“Perseverance. Having the fortitude to push through things. And passion. When you truly love what you do, it’s a lot easier.”
When asked for any advice to seniors, Denise shared, “Be fearless. There’s so much out there, so attack every opportunity, listen to your heart and maintain these [Chapin] friendships—they’re extremely special.”
