Episode 87: Choosing Bravely + Giving Yourself Permission with Heather Vickery


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Heather Vickery is an award-winning entrepreneur, business owner, and transformational life and business coach and works with people to help build an authentic and meaningful life and design their own roadmap for balance and success.  A mother of four, Heather’s world turned upside down after a major life transformation and divorce, and suddenly, she had the freedom to be her most authentic self. She discovered that this same authenticity empowered her with the confidence she needed to repair, rebuild, and reach her life’s vision and goals. Today, Heather leverages her entrepreneurial skills and expertise to coach individuals towards greater personal and professional fulfillment.A strong believer in strengthening her community, Heather also serves as the school board president for The Children’s School and as Vice President on the Board of Directors for the About Face Theatre, Chicago’s premiere LGBTQ theatre. She is obsessed with Hamilton loves to travel.

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  • Heather shares her journey of being an entrepreneur for 23 years, her drive and passion for social justice and her experience of coming out to herself, her then-spouse and her wider friends and family.

  • The opportunities that open when we leave our planned path

  • How planning and systems can be helpful to creatives (despite how much we resist them!) and why multi-tasking is bullshit
  • Working from pain points instead of expectations







When I'm not recording episodes, writing bullshit-free Sunday pep Talks to my wonderful Couragemakers community or working 1:1 with clients, I'm usually covered in paint and thinking of imaginative ways of hide my would-be dog from my landlord. 


I’m Meg and I’m the host of Couragemakers and founder of That Hummingbird Life. I’m an INFJ creative and multipassionate who has a bit of a notebook and post-it note obsession, loves foot-stomping country music and likes her hot chocolate with way too much chocolate.

I started Couragemakers because I wanted to create a platform for passionate and unconventional women to have honest conversations and to share their stories, struggles and dreams. The intention behind this podcast is to inspire and encourage creative and mission-driven women to live a wholehearted life and follow the beat of their drum.



Meg Kissack