Careers Day: Where Brentwood's Future Meets its Past
As winter begins to give way to spring, Brentwood once again welcomed back familiar faces for one of the year’s most anticipated traditions: Careers Day. With alumni and parents returning to campus, classrooms transformed into spaces filled not just with lessons, but with stories, advice, and glimpses into the paths that lie before us, beyond Brentwood.
Designed to bridge the gap between student life and the professional world, Careers Day brought together speakers from a wide range of industries, including law, marketing, engineering, public service, health care, the arts, and economic policy. From corporate lawyer Ian Jonson Privett ‘12 to firefighter and former professional baseball player Derran Watts, students were given the rare opportunity to hear firsthand what life might look like after Brentwood, and the many different directions it can take.
The day began with small-group speaker sessions, where guests spoke candidly about their career journeys, the challenges they faced, and the decisions that shaped their futures. In classrooms across campus, conversations flowed freely as students asked thoughtful questions and explored possibilities they may not have previously considered.
Following the sessions, students gathered in the CIL for the Career Fair, where every speaker was available to connect regardless of which session they had originally attended. The space quickly filled with conversation as students moved from table to table, introducing themselves, asking follow-up questions, and engaging with professionals whose careers had sparked their interest. The informal setting allowed for meaningful one-on-one conversations, giving students the chance to build connections and gain a deeper understanding of different career paths.
For many speakers, returning to Brentwood carried special meaning. “It is a privilege to inspire the next generation,” shared Actor Devon Side Walker ‘15, reflecting on her experience coming back to the place where her own journey began. Her words captured the spirit of the day, as alumni stepped back into the same halls where they once sat, now offering guidance to those following in their footsteps.
In another session, Director of Marketing and Director of Accounts Connor Crabtree ‘16 spoke about the power of communication in his field. “Marketing is a universal language,” he explained, highlighting how creativity and connection play a role in nearly every industry. His message resonated with students curious about careers in business, media, and beyond.
For students, hearing these stories firsthand proved both eye-opening and inspiring. “It was very motivating and encouraging to see people, once in my shoes, achieve such great feats,” said Juan Pablo. “It makes what once felt far away seem possible.”
More than just a series of presentations, Career Day offered something deeper: perspective. It reminded students that while their time at Brentwood is only one chapter, it is a chapter that prepares them for countless others.
A heartfelt thank you goes out to all the alumni, parents, and staff who made Career Day possible. By sharing their experiences, they not only reflected on how far they have come but helped illuminate the path forward for the next generation of Brentwood students. Thanks also to Mrs. Stevens, Ms. Anderton, and Ms. Beausoliel for their Herculean effort in making the event happen.
De manu in manum.
William L, Ellis ‘26