SYS 158: Empowering Women in Business: The Power of Community – Insights from Kolleen Chesley, CEO of LeadHERship Global

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  • SYS 158: Empowering Women in Business: The Power of Community – Insights from Kolleen Chesley, CEO of LeadHERship Global

🎙 Dr. Steve Day interviews Kolleen Chesley, the CEO of LeadHERship Global and founder of Powerful Women of the Gulf Coast. Kolleen shares her personal journey and reveals her deep-rooted passion for supporting women in business.

They discuss the challenges women face in business, including the struggle to quantify their worth and the pressure of societal expectations. She also shares her favourite apps, Harmony and Curable, which have helped her with meditation and overcoming chronic pain.

This episode offers valuable insights into women’s unique experiences and strengths in business.


💡 Kolleen emphasises the importance of community and collaboration in empowering women to achieve success.

💡 Women in business face challenges such as quantifying their worth and dealing with imposter syndrome.

💡 The perception of success on social media can negatively impact women’s confidence.

💡 Successful women prioritise their goals, collaborate with others, take risks, and accept help.

💡 LeadHERship Global provides a network of support and resources for women in business.


09:51 – 💬 “Women struggle in business because we don’t understand how to quantify our worth.”

20:26 – 💬 “Successful women are the women that can collaborate. Collaboration, I think, is having the value of a true partnership and intentional collaborations.”

21:09 – 💬 “Successful women are not afraid to take risks. They’re willing to try something that’s new, and they’re willing to ask for help.”

28:22 – 💬 “If we’re happier as humans, we’re more productive. We’re less stressed. I mean, the world is just a better place if we’re all feeling more valued and feeling supported.”

38:52 – 💬 “Success is conscious competence. Knowing the skills is one thing, but being conscious that you know the skills is a completely different level.”


00:00 Adopted, empowered, supporting women in business.

03:43 Discovering true passion through personal history.

08:19 Connecting with members, discussing struggles during COVID.

12:22 Clients took years to overcome media challenges.

16:25 First radio interview boosted by tiara confidence.

17:28 Flawless radio interview led to Tiara Fridays.

21:45 Relating to shared business challenges and equality.

26:29 UK making progress towards gender equality.

28:28 Self-care is crucial for success in life.

30:59 Respect and support women and men equally.

36:03 Apps Curable and Harmony aid with mental health.

38:45 Success is conscious competence, awareness and skill.






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Steve used to be a slave to his business, but when he moved to Sweden in 2015, he was forced to change how he worked. He switched to running his businesses remotely. After totally nailing this concept, he spent his time helping other small business owners do the same. Steve’s been investing in property since 2002, has a degree in Computing, and worked as a doctor in the NHS before quitting to focus full-time on sharing his systems and outsourcing Methodology with the world. He now lives in Sweden and runs his UK-based businesses remotely with the help of his team of Filipino and UK-based Virtual Assistants.

Most business owners are overwhelmed because they don’t know how to create systems or get the right help.

Our systems and outsourcing Courses and coaching programme will help you automate your business and work effectively with affordable virtual assistants. That way, you will stop feeling overwhelmed and start making more money.


Steve Day

About the Author

Since 2016, Steve has helped hundreds of business owners to systemise their businesses and outsource their work. In doing so, he has helped them regain control of their lives and create the businesses they set out to build.

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