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!

Talking Confidence with Holly Caplan
Claim This Podcastby Holly Caplan
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Podcast Overview
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!
Language
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Publishing Since
12/10/2021
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Recent Episodes

July 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/

June 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/

June 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/
34 total episodes available
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Jody Das
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Frequently asked questions
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- What is Talking Confidence with Holly Caplan?
- How often does this podcast release new episodes?
This podcast updates inactive.
- Where can I listen to this podcast?
This podcast is available on 2 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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