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Inspiring Conversations with Holly Caplan of Holly Caplan Coaching

Today we’d like to introduce you to Holly Caplan.  

Hi Holly, thanks for joining us today. We’d love for you to start by introducing yourself.
I began my career in sales in the medical device industry in 2001. I quickly began to excel and find my footing in what was considered a male-dominated field. However, as I rose through the management ranks, I was faced with the reality that to continue to excel in the industry I would have to adopt the group values of the “dick clique”, and membership inside the boy’s club would be an uphill battle – ultimately a battle to preserve personal and professional identity. When I had this realization, I began journaling about my experiences, which in 2017 I turned into a book called “Surviving the Dick Clique; A Girl’s Guide to Surviving the Male Dominated Corporate World.” 

Fueled with the passion and knowledge I gained from my many experiences, I decided to open my own coaching business focused on helping other women escape unhealthy work situations and coaching them to build their next chapter and business ventures. I enjoy guiding them into their most confident selves to achieve their dreams. I do this through offering personalized coaching programs and workshops designed to identify where healing is needed, set personal goals, and encourage leadership through purpose. In January 2022 I decided to add another component to my business by hosting my own podcast called, Talking Confidence, in which I interview businesswomen on their own confidence journeys. 

We all face challenges, but looking back would you describe it as a relatively smooth road?
It has been an exciting road, but not a smooth one. While writing my book, my publisher kept asking if I was ready for criticism because she knew the topic and title would be uncomfortable for a percentage of the readers. I had to mentally prepare for that, and the criticism did come. However, the book itself lead to new opportunities that I had not experienced before in my personal life or in Corporate America. These included writing for different business publications, speaking about my book in public, and opening my coaching business. Each one of these experiences brought challenges and discomfort, but most importantly growth. 

Thanks – so what else should our readers know about Holly Caplan Coaching?
I started my coaching business because helping women find the confidence to be successful professionally has always been a passion of mine. I remember wanting to be an advocate for women since the age of 8 years old. I knew at that young age that supporting and elevating women was my purpose. Which is why I do what I do today. I coach women to help them find their confidence, purpose, and professional fulfillment. My personalized coaching programs and workshops are designed to identify where healing is needed, set personal goals, and encourage leadership through purpose. 

What sets me apart from others is that I wrote openly about my experiences in Corporate America on a very relatable and honest level. I wanted to lift the veil on what was happening in corporate, yet was not openly discussed. My goal in writing the book was to evoke emotion and get change in the workplace. 

I’m most proud of my workshop titled SPARK. It focuses on the four areas that affect women the most in the workplace. They are: Imposter Syndrome, Setting Boundaries (or lack thereof), Overcoming Fear, and Narcissists in the Workplace. 

I’d like the readers to know that if they know someone who needs help with personal/professional reinvention that I can help them. My one-on-one coaching programs are focused on confidence, direction, and accountability. I’d also like the readers to know that my workshops can be facilitated the workplace or in community groups. 

If you had to, what characteristic of yours would you give the most credit to?
Boldness. I say this because I took a big risk in writing my book and pushing myself into my own personal and professional reinvention. I’m confident I can help others do the same. 

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Image Credits

Kelly Williams Photography

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