Actress Niecy Nash tells Ashley she knew at a young age that she wanted to be “Black, fabulous and on TV.” She spoke her destiny into being before she even knew what acting was. Growing up, Niecy’s family pushed her to find success in traditional professions like nursing or teaching, but she never gave up on becoming an actress. The tragic loss of her 17-year-old brother the day before she turned 23 helped Niecy realize she could use comedy to spare others the pain she was running from. She says she just had to “trust her gift.” Niecy explains her evolving relationships with herself and those she holds closest strengthens her commitment to never give up on love.  

Actor and activist Kendrick Sampson (Insecure) is learning to dream without limiting himself. Kendrick and Ashley revisit who they were as audacious young adults when they first met at the American Black Film Festival in 2008. The Houston native says growing up he wasn’t taught to embrace his Southern culture, and that having a Black father and white mother often left him feeling like he lived in a ‘gray area.’ However, as an adult, a passion for storytelling and social justice helped him reconnect to his identity and heal. Watching his mother dedicate 37 years to a company that did not appreciate her taught Kendrick the importance of chasing one’s purpose. Now, after seasons of doubt in himself, Kendrick is fully committed to seeing his dreams realized on and off the screen.

Certified sex and relationship expert Shan Boodram has mastered the art of navigating private spaces publicly. The veteran intimacy educator walks Ashley through her humble beginnings on Youtube and gets into the challenges of spreading her powerful message in “an industry of silence.” Shan explains that, for her, conversations on sex and intimacy have always gone far beyond the physical. With over a decade of vlogging experience and nearly a million YouTube subscribers today, Shan now helps others become more competent and confident in the bedroom and beyond.

HBO star Yvonne Orji (Insecure) has decided to retire from perfectionism. In this insightful conversation, the Emmy-nominated actress explains to Ashley how growing personally and professionally required new tools, like welcoming more collaborators into her creative process. Yvonne’s bold faith and relentless pursuit of excellence led to  career highs. But now, instead of striving for a perfect finished product, she’s trusting that others will enjoy seeing her make progress. Yvonne says she is learning to embrace herself unapologetically.

How to Get Away with Murder actress Aja Naomi King is a self-proclaimed eternal optimist. Today, Aja confides in Ashley about how that optimism has sometimes hurt more than it has helped. Aja explains how shedding harmful superstitions and embracing vulnerability helped her receive the support she needed after experiencing two devastating miscarriages. Aja also discusses what both motherhood and her disappointments taught her about idealized expectations, surrender and control. In this engaging conversation, Ashley and Aja also celebrate the community of Black women who have supported their growth and paved the way for them to excel in their craft. 

YouTube star and creative producer Maya Washington, popularly known as ‘Shameless Maya,’ has never said no to a challenge. Maya describes how growing up in Canada offered her a supportive environment of both diversity and exploring the arts. Once Maya moved to New York City, she says she finally found the courage to fully express herself because to make it in NYC, you had to be “shameless.” Maya also talks about the peaks and the valleys of her career, as well as the ups and downs of her romantic life, and how following her heart has led her to live in Sweden. Maya describes the realness of motherhood during a pandemic and how pushing past her fears has allowed her to experience love and success beyond her wildest dreams.

Before landing her dream role as the first Black lesbian superhero in The CW’s Black Lightning, Nafessa Williams prayed for the endurance to persevere in Hollywood. In this enlightening conversation, Ashley and Nafessa discuss taking leaps of faith. In Nafessa’s case, that was trading in the safety of her district-attorney job to pursue acting. Inspired by Sidney Poitier’s famous quote: “The reward is in the journey”… Nafessa now pushes through doubt and fear and embraces her process. Nafessa explains how looking back on God’s resume helps her move forward and how the waiting seasons of her life have made endurance her greatest strength.

With over 40 years in the entertainment industry, Abbott Elementary star Sheryl Lee Ralph has a trove of  both trials and triumphs to her credit. The Tony Award-nominated multi-hyphenate takes Ashley back to the beginning of her career and describes who she was before landing her breakthrough role as Deena Jones in the seminal Broadway musical Dreamgirls. Sheryl underscores key lessons she learned from her parents and mentors, including the power to determine which doors to leave closed. The original Dreamgirl also unpacks the most difficult season of her life: navigating her divorce as a single mother, leaving the hit tv show Moesha and losing herself along the way. Sheryl recalls the encounter that helped her “rise to the occasion of her own life,” and how, just like her character Deena, she owned her inner diva.

Ten years after releasing a concept trailer that would go viral and propel his career, Dear White People creator Justin Simien is learning to take a step back and celebrate his wins. Already close friends, Justin and Ashley reflect on their personal and professional growth since the show ended and revisit the risks that led to their success. The fearless visionary unpacks the pressures of breaking ground as a Black creative and touches on the discipline necessary to create opportunities for himself and the next generation of Black artists. With all his success, Justin says he no longer chases accolades for validation. Instead, he’s committed to resting in the truth that only he “can keep his cup filled.”

Insecure(HBO) &Twenties(BET) actress Christina Elmore has always had a game plan for her career, but now she’s learning how to let the cards fall where they may. Ashley and Christina, who’s also one of her very best friends, dig deep into what it means to let go of unrealistic expectations and allow your most authentic self to emerge. Like most black and brown women, Christina has faced pressure to be everything to everyone throughout her life. As a self-proclaimed planner and overachiever, Christina has found this constant need to over perform and people please damaging. She discloses how she protected her mental health amidst harsh criticism about her body after returning to theInsecureset just six weeks after giving birth. Christina reveals how motherhood and the “fourth trimester” has helped her navigate uncertainty and release the need to control every detail of her life. Christina also opens up about learning to love her postpartum body and embracing where God has her now.