The latest episode of Let’s Try This Again features host B. Simone in conversation with comedian and actress Kym Whitley, who offers a wide-ranging discussion centered on personal growth, confidence, and building a sustainable life beyond career achievements. The episode blends humor with practical insight, as Whitley revisits lessons learned across decades in entertainment and shares guidance for navigating relationships, work, and self-development.
Throughout the conversation, Whitley reflects on the value of long-term thinking, what she describes as being young but thinking old. She explains how making decisions with the future in mind shaped her professional relationships and helped her avoid situations that could have complicated her career. The discussion extends into the importance of mentorship, with Whitley emphasizing the role older women and trusted guides play in helping younger creatives make informed choices.
Whitley also addresses emotional discipline, recalling moments when personal news collided with professional obligations, and explains why protecting focus during critical work moments has been essential to her longevity. She highlights the importance of entering spaces with openness and positivity, a practice she says strengthens connections and creates opportunities.
The episode turns toward parenthood as Whitley discusses raising her son and the responsibility of shaping young men to engage respectfully with others. She also speaks candidly about the significance of planning one’s personal life with the same intentionality often reserved for career advancement, noting that timing and preparation matter when it comes to building a family.
Whitley encourages listeners to remain open to possibilities that may not initially appear to fit their expectations, suggesting that long-term compatibility and shared values outweigh surface-level criteria. She expands on the idea of building a life that provides fulfillment outside of work, relationships, community, and personal interests, which she considers essential for sustaining mental and emotional balance in an unpredictable industry.
Financial preparation is another key theme, as Whitley outlines her early approach to saving and how consistent habits contributed to long-term stability. She also recalls the impact of criticism early in her career and how reframing negative feedback helped her maintain focus and resilience.
The conversation concludes with reflections on confidence, intuition, and faith. Whitley acknowledges that self-assurance is an ongoing process and encourages listeners to trust internal guidance when making decisions. She underscores the role her faith has played in navigating disappointments, maintaining perspective, and finding direction throughout her career.
B. Simone frames the episode as one filled with meaningful takeaways, especially around boundaries, friendship, emotional awareness, and the importance of not delaying the work of building a fulfilling life.
