What does it take to craft content for global brands, juggle freelance life on your own terms, and still stay true to your values? In this episode, host Dr. D. sits down with veteran content strategist Chaviva Gordon-Bennett to unpack the curiosity-driven career that’s taken her from newsrooms to Silicon Valley—and everywhere in between.
Key Questions Explored in the Episode
How can relentless curiosity propel a career in content and marketing?
What lessons can remote-first professionals learn about healthy boundaries and meeting overload?
Where does AI fit into a writer’s workflow without sacrificing voice or quality?
How do you rebuild confidence and self-worth after layoffs or career pivots?
In what ways has Chaviva’s Jewish journey shaped her personal and professional choices?
Discussion Points
Curiosity as a Career Engine – asking better questions to open unexpected doors.
Remote Work Realities – balancing flexibility with culture, communication, and family life.
From Employee to Freelancer – navigating layoffs, impostor syndrome, and client boundaries.
AI & Content Creation – treating AI as an intern, not an ATM, to scale strategy.
Identity & Growth – how conversion to Judaism and life in Israel reframed purpose and resilience.
Summary of the Conversation
Chaviva traces nearly two decades of writing, editing, and content strategy, beginning with a journalist’s instinct to “never stop asking why.” She reflects on stints at Bizzabo, SmartBug Media, and EverCommerce; the thrill (and chaos) of agency life; and her shift to freelancing after pandemic-era layoffs. Along the way, she recounts stories—from an FBI encounter linked to an ISIS hit list to juggling motherhood during Zoom marathons—that underline the need for adaptability. The discussion closes with her embrace of Judaism, illustrating how personal identity can fuel professional confidence and clarity.
Chaviva Gordon-Bennett is a writer, editor, and content strategist with 19+ years of experience building brand voices, buyer personas, and messaging frameworks for tech and SaaS companies worldwide. Now a freelance consultant, she helps organizations scale content with a blend of journalistic rigor and AI-driven efficiency.
Stay Curious: Treat every role as a classroom—ask questions that unlock bigger opportunities.
Own Your Worth: Layoffs don’t define you; reframe them as launches into your next chapter.
Set Boundaries in Remote Work: Guard focus time and family priorities to prevent burnout.
Leverage AI Thoughtfully: Use generative tools as junior collaborators, then edit like a pro.
Align Work with Values: Let personal growth and identity inform career choices and resilience.
00:00 Curiosity kicks off the conversation
06:16 College years & the first newsroom gig
16:30 Graduate school and converting to Judaism
22:02 Social-media roles during a move to Israel
27:51 An ISIS hit-list scare & FBI phone call
39:03 Pandemic-era remote work challenges
56:34 Layoffs, self-value, and the freelance leap
01:04:23 AI’s evolving place in content creation
01:23:12 Finding identity and fulfillment through Judaism
Ready to supercharge your own career?
Listen to the full episode now and discover practical insights you can apply today!