036: Heather Monahan (Boss in Heels)

Heather Monahan on Innovation City

“Your heart telling you to do something—and you following through—is an act of building your self-confidence.” — Heather Monahan

Welcome to Innovation City—powered by Venture Cafe—where Tyler Kelley and Michael Johnson, Co-Founders of SLAM! Agency, interview innovators, creators, and disruptors to discover how business is changing in the modern world.

Created and produced by SLAM! Agency in conjunction with Venture Cafe St. Louis and Venture Cafe Miami, Innovation City gives you an inside look at how rapidly business and culture are changing thanks to increasing diversity and inclusion, heightened creativity, and a stronger and better-connected business community.

Today’s guest is Heather Monahan, Founder of Boss in Heels. Heather’s first career was a successful 20-year stint in media and sales that ended with a surprise termination. As she wrestled with what to do next, she chose to devote herself completely to helping women take control of their careers, taking Boss in Heels to the next level. Heather is also the author of the best-selling book, Confidence Creator, which she wrote to serve as the resource for other women that she wished she had as a young professional. A Glass Ceiling Award recipient, Heather is also a keynote speaker and social media influencer. Find Heather on all social media platforms at @HeatherMonahan and find Confidence Creator on Amazon.

They discuss:

  • Heather’s path to professional success
  • The strain building her own business put on her work life
  • The challenge of managing her own personal expectations and goals with her relationship with her boss at work
  • Journaling as a way to work through the emotions of getting fired
  • Talking about her termination on social media
  • Asking for help online and receiving 100,000 responses shortly thereafter
  • Writing a book without knowing if she could do it
  • The power of asking for help
  • Heather’s drive to outwork everyone else
  • The process of building Boss in Heels
  • The freedom we have to create ourselves
  • Confidence is learned, not given
  • Learning from a mentor how to look at the bigger picture
  • Firing the villains
  • Learning lessons from her son writing on his basketball shoes
  • The importance of taking baby steps
  • Testing her own confidence
  • The importance of asking for one specific thing:
    • (Asking Maria Menounos for an introduction to Reese Witherspoon, and getting it!)
  • The power of putting things out into the universe
  • Fear is a liar; take it down a few notches and lean in
  • Build success stories, build wins, and record them so you don’t forget
  • Eddie Murphy’s early Letterman interviews; going from very nervous to very confident
  • Successful people’s morning routines
  • Heather says: put yourself first, stay connected with your kids, work out, journal, meditate
  • When faced with a difficult situation — create a 30 day plan, separate yourself from the emotion, and figure out how to manage your problem
  • Manifest your vision to create your future.