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Leaving Teaching for a Media Career in Midlife with Tiphany Kane

  1. Leaving Teaching for a Media Career in Midlife with Tiphany Kane Amy Stone 54:48

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In this episode of The Art of Imperfect Adulting, Amy Stone speaks with Tiphany Kane about embracing passion and reinvention in adulthood. Joining the conversation from sunny Southern California, Tiphany shares her journey of escaping a restrictive upbringing, redefining her career path from teacher to media company co-owner, and why true opportunity lies in leaning into your authentic self. Listeners will hear how Tiphany navigated being told she was “too passionate,” faced institutional barriers, and ultimately found empowerment and possibility through podcasting, entrepreneurship, and letting go of sunk costs.

About Tiphany Kane:

Tiphany Kane, M.Ed., is the CEO & co-founder of KaSa Media Productions, Executive Director of Sonic Bloom Podcast Awards, Public Speaker, Award-winning Podcast, Video, & Live Events Producer who brings her passion for the art of the spoken word to people who have a powerful story to tell. She is also a member of the AIVA (Academy of Interactive & Visual Arts) and serves as an AIVA juror. Tiphany is building Just 4 Feet Studio, a 5,500 sq ft state-of-the-art Dolby Atmos recording & post-production studio in Orange County, CA.

Main Topics Covered:

  • Overcoming the limitations of a high-control, patriarchal upbringing and embracing Education and independence
  • Navigating career transitions: from passionate teacher, to frustrated administrator, to dynamic entrepreneur
  • The impact of being labeled “too passionate” in the workplace, and how that informed Tiphany’s decisions and self-worth
  • Addressing inequity in education, especially for gifted and talented programs and underrepresented students
  • The power (and reality) of using podcasting and independent media to reinvent your life and build confidence—not just income
  • Dealing with sunk cost fallacy and fear in career changes—what to let go and how to trust your evolving journey
  • Women’s opportunities and challenges in independent media in the age of AI, gatekeepers, and authenticity
  • The nuanced truth about following your passion, accepting “not a good fit,” and the value of creating your own path

Quote from the Episode:

“This is something I really like about myself. This is something I’d like to lean into more. I am so sick and tired of feeling like I have to hide who I am to show up in a world where I’m showing up in the way they say I should show up. It’s exhausting. And I’m done with it.” — Tiphany Kane

Timestamps:00:00 – Amy welcomes Tiphany 01:13 – Tiphany’s upbringing, expectations as a woman, and experience with high-control religion03:04 – Discovering dinosaurs, geology, and leaving behind misinformation04:34 – Path to teaching: resisting gender expectations, working in sales during 9/11, the pivot06:46 – Loving teaching, working with gifted children, asynchronous development, and personal connections09:51 – Going back to school, financial logistics, pursuing a teaching internship and credentialing hurdles12:14 – Not getting the dream job, learning you can request a debrief, and hearing “too passionate” as feedback13:24 – Processing being “too much” and realizing it was time to make a change20:00 – Designing an exit plan for alignment; accepting when you and a system are not a good fit22:08 – Podcasting as a catalyst for reinvention: what starting a show actually gave Tiphany26:34 – Letting go of sunk cost fallacy, grieving lost paths, and building new ones32:13 – Missing the classroom, but embracing entrepreneurship and the risks involved33:31 – The necessity of independent, authentic media for women in an era of AI and misinformation37:25 – Tiphany’s current business, working with brands like Z Gallerie, and adapting to uncertainty41:32 – Book and podcast recommendations: “When Women Were Dragons” and Pod Save America44:09 – On cold plunges, Health advice, and why universal solutions don’t exist49:06 – Empathy, advice-giving, and supporting people in difficult situations52:04

ABOUT THE SHOW: The Art of Imperfect Adulting elevates the voices of experience by sharing real stories from real people figuring out adult life. Every episode features honest conversations about life’s choices, changes, and challenges—interviews with individuals (not celebrities) who share their personal experiences and insights. Through these authentic stories, listeners find validation, motivation, and inspiration for navigating their own path through modern life. Because there’s a big difference between expert advice and shared experience, and hearing another person’s lived experience helps us feel less alone in our own situations.

CONNECT WITH THE GUEST: https://kasamediapro.com/

TIPHANY’S SHOW: Shut up and Listen to Her https://www.youtube.com/live/e5LeCJT_Ctw?si=j9Dz4G6KevOExw3v

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Here are a few resources that Amy uses to make all this great content. These are affiliate links 🙂

For livestreaming and recording ECamm https://www.ecamm.com/mac/ecammlive/?fp_ref=amy69

Podcast hosting and distribution: Captivate FM https://www.captivate.fm/signup?ref=ntczmwi

Website hosting with Siteground https://www.siteground.com/?referrer_id=9115590

Ai Transcription Tool: Castmagic https://get.castmagic.io/ugrmjjrt8ofj

For Email I recently switched to Beehiiv https://www.beehiiv.com?via=Amy-Stone

before that I used Kit.

Books I like and books written by show guests on Bookshop.org https://bookshop.org/lists/podcast-guest-authors

Amy Stone is a media entrepreneur, storyteller, and founder of The Art of Imperfect Adulting - a growing media platform featuring long-form interviews that explore the messy, non-linear reality of building a life.

Amy is a journalism graduate who started her career as a freelance newspaper photographer. Driven by the desire to be able to pay her bills she took a job in marketing and later client service at a tech startup in the late '90s before building multiple businesses of her own - including an award-winning family portrait studio she ran for 8 years. After closing the studio and moving through fitness and lifestyle coaching, she realized the work that mattered most wasn't offering her own expertise - it was creating a space where real people share real stories about the everyday choices that shape a life.