From politics to nonprofits to executive coach, meet Katie O'Malley

This week, Jenny chats with Katie O’Malley, founder of Encourage Coaching, whose career path took her from the world of politics and nonprofits to coaching individuals from underrepresented communities into leadership roles. Katie’s story is one of heart, grit, and staying deeply connected to her “why.”

Together, they dive into the emotional side of career pivots, what it takes to build a business that actually cares, and how listening, real, intentional listening, can be the most powerful tool for change.

If you’ve ever felt the nudge to do work that feels more meaningful, or if you're building something new and wondering how to stay aligned with your values, this episode will speak right to you.

What We Talk About:

• How Katie’s early work in politics and nonprofits shaped her purpose
• Her bold leap into coaching and why it mattered so much
• Mental health in the workplace (and why we can’t ignore it anymore)
• Building a values-driven coaching business from the ground up
• Why listening is the underrated superpower we all need to practice
• The messy, joyful reality of flipping your career
• Katie’s upcoming TED Talk on the power of listening (happening June 30th in Andover, MA!)

Favorite Quote:

“Listening is more than a soft skill—it’s a radical act of care.”

More from Katie:

• Connect on LinkedIn: https://www.linkedin.com/in/kateomalley/ 
• Find Katie and her work at encouragecoaching.org
• Follow her on Instagram: @encouragecoaching

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Bonus: If you’re in customer experience or building your own business, check out my online courses. Before I started flipping my life and furniture, I led CX teams and created training that’s helped over 12,000 students worldwide. Learn more at thecareerflipper.com/courses.

 

🎵 Music Credits

 

Season 1: Intro & outro music by Audionautix.com

Season 2: Original music by yours truly, Jenny Dempsey, recorded in my home studio

 

And hey, remember my favorite question: What’s the best that could happen? 💫