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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Episode Snapshot
Jackie’s journey from burnout and “doing all the things” to rebuilding life and work around what actually matters
Why 80% of AI projects fail—and what schools and organizations can do differently
The “Disney trash” lesson: stop chasing flashy AI and start with the boring, high-impact problems
Women, confidence, and creating safer spaces to learn and lead with AI
“...our value is in who we are, not in what we do”: using AI to rediscover identity, not erase it
Practical, non-tech-bro ways to play with AI in your daily life (email, trip planning, speaking practice, and more)
Episode Highlights
Jackie’s story of walking away from a job that broke her health and identity and rebuilding life and work from Nashville
Why 2023 felt like a turning point with ChatGPT and how it pulled her from digital marketing into AI adoption and strategy
What “AI adoption” actually means (beyond tools) and why communication, culture, and expectations matter more than features
The harsh reality: most AI projects fail, not because of the tech, but because of people, processes, and misaligned outcomes
The “Disney trash” example: how starting with boring, high-volume, repetitive tasks beats chasing sexy, impossible AI dreams
A compassionate look at why many women hesitate to jump into AI and how community, safety, and “permission to not know” change that
Everyday use cases Jackie loves: practicing presentations with AI video, drafting hard emails, energizing workouts, travel planning, and using voice tools in playful ways
The deeper theme: AI shows us how not-special our tasks are, but it also clarifies how irreplaceable our humanity is
Connect with Jackie Celske
LinkedIn: https://www.linkedin.com/in/jacquelinecelske/
Website – The Prose Co.: https://www.theproseco.com/
Instagram: https://www.instagram.com/theproseco/
Facebook: https://www.facebook.com/theproseco
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Being human is your superpower
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