Chills, Grit, and Going Onward: Deborah Riley Draper at AdClub Boston

I’m still buzzing from yesterday’s The Ad Club Boston Women’s Leadership Forum. The day was full of dynamic women, bold ideas, and fearless leadership—but the moment that truly floored me, that left me sitting there with literal chills, was listening to Deborah Riley Draper.

I can’t stop thinking about her. I was in awe. From her early days in advertising—grinding it out as a junior AD—to walking into rooms with Mick Jagger and Wes Walker as a documentary filmmaker, Deborah’s journey is the stuff of inspiration. But it’s not just the résumé. It’s the grit. It’s the way she owns her story, rewrites the rules, and lifts others while doing it.

Deborah started her career pitching brands and selling ideas to clients, and now she’s pitching bigger stories—the kind that move culture. She’s directed documentaries like Olympic Pride, American Prejudice and The Legacy of Black Wall Street, and she talked about how every single step in advertising laid the groundwork for her storytelling superpower. The pitches, the pressure, the partnerships—all of it was training for something bigger.

What got me? When she said she made her first film while still working full time, using nights, weekends, and vacation days. That hit hard. I’ve been there. Juggling ambition and exhaustion, dreaming big and wondering if I’m allowed to take up that much space. Deborah did it anyway. She submitted her first film to Cannes despite being told to “try a smaller festival.” Spoiler: she didn’t get the official selection… but she still got in. Because she asked. Because she showed up. Because she didn’t shrink.

I saw so much of myself in her story. The moments of doubt. The quiet bravery. The hustle that isn’t about burnout but about forward motion. “Onward,” as she said, again and again. That word is going to stay with me.

Deborah also dropped her “Top 5 Flexes,” which, let me tell you, should be printed and framed:

1. The Heart of Listening – because trust and empathy are where the best stories start.
2. Fortune Favors the Brave – especially when you’re the only woman in the room.
3. Everything Comes to Those Who Hustle While They Wait – shout out to ROH (return on hustle).
4. Be Accountable – own the wins, the fails, and the wild vegan-breakfast-commercial moments.
5. Know Your Story – and never, ever give anyone else the pen.

I laughed, I got teary, and I left feeling fired up. Deborah is the kind of woman who shows you what’s possible—and reminds you that you already have what it takes. I can’t wait to learn more about her work, her films, and her journey. She is pure inspiration, and following her path feels like following a beam of light.

Here’s to moving onward.

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