In this episode of In Heels with Keni Silva, Keni sits down with actress and producer Caylee Cowan for an honest conversation about choosing art over expectation — and finding power in the process.

Once on a path toward becoming a doctor, even shadowing physicians at the Mayo Clinic, Caylee made the bold decision to follow her intuition instead. She pivoted into theater and film, launching her on-screen career in 2018 and quickly landing roles in acclaimed projects including Willy’s Wonderland alongside Nicolas Cage, Frank and Penelope, and Divinity, which competed at the Sundance Film Festival.

Caylee opens up about navigating rejection in Hollywood, preparing emotionally for demanding roles, and why acting is a privilege she never takes lightly. She also shares why stepping into producing has become a natural extension of her creative voice and her commitment to deeper, more authentic female storytelling.

This conversation is a reminder that success doesn’t come from following the script handed to you — it comes from trusting yourself enough to write your own.

⭐ Loved This Episode?

If this conversation moved you, challenged you, or gave you a new perspective:

• Tap Follow or Subscribe so you never miss an episode

• Leave a 5-star review — it helps this show reach more women who need these conversations

• Share this episode with someone who needs permission to keep standing

• Follow @KeniSilva_ and @InHeelswithKeniSilva on Instagram

• Watch video clips and full episodes on

• Learn more about Divorce As An Opportunity and Keni’s work at Kenisilva.com

In this episode of In Heels with Keni Silva, Keni is joined by Diana Madison — actress, filmmaker, entrepreneur, and award-winning beauty brand founder — for a powerful conversation about trusting the pivot and building with purpose.

Long before creator culture went mainstream, Diana was one of YouTube’s early pioneers, building a digital media company that amassed billions of views and was later acquired by Radio One / TV One. After 15 years at the forefront of digital storytelling, she reinvented herself again — stepping fully into filmmaking and launching Diana Madison Beauty, a clean skincare line inspired by her personal struggle with eczema and ancestral beauty rituals, now sold at major retailers including Macy’s and Neiman Marcus.

Diana also opens up about her evolution as an actress and director, including her role in The Other Side of Fame and her deeply personal directorial debut, There’s No Place Like Home, a documentary preserving the history of Armenian ethnic cleansing.

This conversation is a masterclass in honoring heritage, embracing reinvention, and building a career rooted in authenticity — proving that true power comes from trusting your voice, even when the path keeps changing.

⭐ Loved This Episode?

If this conversation moved you, challenged you, or gave you a new perspective:

• Tap Follow or Subscribe so you never miss an episode

• Leave a 5-star review — it helps this show reach more women who need these conversations

• Share this episode with someone who needs permission to keep standing

• Follow @KeniSilva_ and @InHeelswithKeniSilva on Instagram

• Watch video clips and full episodes on

• Learn more about Divorce As An Opportunity and Keni’s work at Kenisilva.com

In this powerful episode of In Heels with Keni Silva, Keni sits down with Stacy Phillips, one of the most respected divorce and family law attorneys in the country, for an honest conversation about what divorce really takes — emotionally, mentally, and personally.

With decades of experience guiding families through high-conflict and high-net-worth divorces, Stacy shares what she’s learned beyond the courtroom: why divorce is not just a legal process, but a profound emotional transition. Together, they unpack common misconceptions around divorce, the importance of therapy and support systems, and how women can protect their peace while navigating change.

Stacy also opens up about her groundbreaking 2+1 Intervention Method™, which supports spouses and families impacted by addiction, and reflects on how her own life experiences shaped her mission to empower women through some of life’s most difficult moments.

From co-parenting with intention to reclaiming confidence and control, this conversation is a reminder that divorce can be an ending — and also a powerful beginning. Strength doesn’t always look loud. Sometimes, it shows up quietly… in heels.

⭐ Loved This Episode?

If this conversation moved you, challenged you, or gave you a new perspective:

• Tap Follow or Subscribe so you never miss an episode

• Leave a 5-star review — it helps this show reach more women who need these conversations

• Share this episode with someone who needs permission to keep standing

• Follow @KeniSilva_ and @InHeelswithKeniSilva on Instagram

• Watch video clips and full episodes on

• Learn more about Divorce As An Opportunity and Keni’s work at Kenisilva.com