Talking Confidence with Holly Caplan

Holly Caplan
  • 5.0 (21)
  • SOCIETY & CULTURE

In this podcast we will be discussing what affects women’s confidence in the workplace. We will cover topics such as imposter syndrome, fear, boundaries, company culture and more. Through this podcast we will address these issues and overcome them together. You can expect to not only hear from me, but from my guests who include corporate executives, entrepreneurs, and business owners!

  1. 07/29/2025

    Injecting Confidence: How Dr. Cheryl Haseeb Inspires Growth in Aesthetics

    Holly sits down with Dr. Cheryl Haseeb, a trailblazing entrepreneur and founder in the world of medical aesthetics and education. Dr. Haseeb shares her journey from small-town Arkansas to leading multiple successful businesses in Houston and beyond, including Pura Medical Aesthetics and the Aesthetic Nation Institute. With honesty and warmth, Dr. Haseeb opens up about the challenges she faced breaking into the aesthetics industry, the importance of empowerment over competition, and why confidence—both in herself and in others—is at the core of everything she does. They explore what it means to find your true purpose, how to combat imposter syndrome, and why lifting others up leads to greater fulfillment. Plus, Dr. Haseeb gives us a sneak peek into her upcoming book "Injecting Success" and her big plans for expanding her training empire to Austin. To find out more and connect with Dr. Haseeb, visit: https://www.thepuralife.com/

    35 min

  2. 06/24/2025

    Understanding the Importance of Self-Worth: Judy Hoberman on Confidence in the Workplace

    In this episode, Holly welcomes Judy Hoberman—author, executive coach, and a true champion for women’s success in the workplace. Holly and Judy share stories of their own winding journeys, from virtual happy hours that brought them together to Judy’s early days selling door-to-door and learning hard-won lessons in resilience. Judy opens up about her transition from a thriving career in sales and corporate leadership to building a business centered on empowering women through coaching, masterminds, and leadership training. The pair dive deep into the challenges women often face with work-life “harmony” versus “balance,” overcoming imposter syndrome, and the real power of celebrating even the small wins. To learn more and connect with Jody, visit: https://sellinginaskirt.com/

    36 min

  3. 06/17/2025

    Guidance, Intuition, and Confidence: The Transformative Role of Tarot

    In this episode, Holly sits down with Grady Smart, a longtime friend, intuitive tarot expert, and criminal defense attorney, to peel back the curtain on their six-year relationship, exploring how their journeys crossed when Holly was at a crossroads in her professional life. Grady shares how he discovered his clairvoyant gifts, what it’s really like to read tarot for clients, and why he believes these readings can give people the confidence to take control of their own destinies. The conversation covers everything from the practical—and sometimes uncanny—ways tarot readings impact day-to-day decisions, to the importance of trusting your intuition, and even what to do when the cards reveal hard-to-hear truths. You’ll also hear Grady’s personal story, from his origins to using tarot as a tool for self-discovery and empowerment. Plus, Grady gifts listeners with practical advice on building confidence and a mantra you can use to transform your mindset, starting today. To find out more or connect with Grady, visit: https://tarotbygrady.com/

    28 min

  4. 06/10/2025

    Making Confidence Accessible Through Fashion, No Matter Your Age or Budget

    In this episode, Holly welcomes Jody Das—a fashion stylist, interior decorator, author, and social media creator with a passion for helping women feel their absolute best. Holly and Jody share honest experiences about how what we wear can shape our self-image, self-esteem, and even our daily outlook. Jody reveals her journey from growing up surrounded by style icons in New York to becoming a sought-after stylist and content creator in South Florida. She opens up about why making styling advice accessible to all women—not just the wealthy—drives her work, and how her book 'Drape Your Shape' came to life. Together, they get real about the challenges women face, especially over 40, from changing body shapes to societal pressures around age-appropriate dressing. Jody and Holly discuss practical tips (including the infamous “menno belly”), the importance of focusing on what you love about yourself, and why confidence is so much more than just what’s on the outside. To find out more and connect with Jody, visit: https://dascaldesigns.com/

    33 min

  5. 05/15/2025

    Boosting Confidence From the Inside Out With Amy Robbins

    In this episode, Holly welcomes Amy Robbins, founder and owner of Youthful Magnolia Med Spa in Fort Worth, Texas to talk about the booming medical aesthetics industry and why it's not just about looking good, but about feeling empowered and confident in your own skin. Holly and Amy get candid about the pressures and motivations behind self-improvement, the ethical side of recommending treatments, and how building ongoing relationships with clients can boost confidence on both sides of the chair. From discussing the top concerns clients bring to med spas, to the unique confidence journeys of both women and men, this episode offers vulnerability, insight, and actionable advice for anyone interested in enhancing their self-assurance—inside and out. To find out more or to connect with Amy, visit: https://www.youthfulmagnolia.com/ or call (682) 261- 7757

    29 min

  6. 04/28/2025

    Redefining Confidence and Embracing Midlife

    In this powerful episode, Holly sits down with midlife transformational coach, author, and speaker Demi Austin-Thomas to dig deep into what impacts women’s confidence as they journey through midlife. Together, they get honest and vulnerable about the realities of aging, caretaking, changing family dynamics, and the emotional weight that comes with trying to balance it all—while still showing up as your best self at work and at home. Holly and Demi share their own stories, including Demi’s raw account of personal struggles with depression and self-worth, and how she learned to shed people-pleasing tendencies and set boundaries in order to reclaim her confidence. They also explore how internalized beliefs from childhood, cultural expectations, and the constant search for validation can chip away at self-esteem—especially for women in their 40s, 50s, and beyond. Get ready for insights on how to break free from self-doubt, nurture your mental health, and rewrite your own narrative. Whether you’re in the thick of midlife changes or just looking for a boost of encouragement, this episode delivers candid conversation, wisdom, and the reminder that embracing imperfection is the ultimate key to confidence. To learn more about Demi Austin-Thomas, visit: https://www.demiaustinthomas.com/

    41 min

  7. 04/28/2025

    Supporting Women’s Confidence in the Workplace

    Welcome back to Talking Confidence with Holly Caplan! After a two-year hiatus, Holly returns to the mic to give us a whole new season of amazing women all learning how to harness the power of confidence in both their personal and work lives. In this episode, Holly sits down with Karen KJ Johnson, Executive Director of Dress for Success Dallas-Fort Worth and founder of The Confident Woman. Together, they explore the power of confidence-building for women in the workplace, the importance of community support, and the transformative impact of organizations like Dress for Success. Holly and KJ get real about the challenges women face—everything from breaking glass ceilings to overcoming inner critics and impostor syndrome. KJ shares her journey from corporate America to entrepreneurship and nonprofit leadership, along with her hands-on approach to helping women stand tall, including her signature “KJ Catwalk.” With plenty of wisdom, laughter, and motivation, this episode is a heartfelt dive into the ways we can all uplift and empower one another. To learn more about Dress for Success, visit: https://dressforsuccess.org/

    43 min

  8. 02/07/2023

    Talking Confidence: Confidence of Young Women in College & High School, Part 2- New Tech High School

    Welcome to part two of this series based on the Confidence of Young Women. In the last episode we talked about college aged women, their confidence, and the challenges they face. In this episode we are going to be having a similar discussion, but this time, with high school women. We are going to discuss how do they manage their confidence, and really, how much has changed over the years, despite women making more and more headway in education and the workplace.   Clarity Empowers is a new community at New Tech high school that is focused on elevating teen girls by teaching them life skills, encouraging leadership, education and most importantly confidence. Clarity, as they call it, was created and is led by teacher and educator Shannon Howard. She will be joining us today with two students of New Tech who are co-founders and key leaders of Clarity Empowers. Vibha R. and Sophia S. Together we are going to talk about what it is like to be in high school today, what challenges women face and how they get through it.

    40 min
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5
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About

In this podcast we will be discussing what affects women’s confidence in the workplace. We will cover topics such as imposter syndrome, fear, boundaries, company culture and more. Through this podcast we will address these issues and overcome them together. You can expect to not only hear from me, but from my guests who include corporate executives, entrepreneurs, and business owners!

Information

  • Creator
    Holly Caplan
  • Years Active
    2021 - 2025
  • Episodes
    34
  • Rating
    Explicit
  • Copyright
    © 2026 Talking Confidence with Holly Caplan Holly Caplan
  • Show Website
    Talking Confidence with Holly Caplan