“When you work for a large organization, everything is planned out, there's a million committees, a million meetings, things take years sometimes to happen. I knew one of the reasons that I really left was I felt like I had become who they wanted me to be and not who I truly am.”

Welcome back to Startups in Stilettos! In this episode, we dive into the powerful story of Kristen Chimack, a business coach, Hotel Whisperer, and author of "The Cost of Staying." Join us as she shares her journey of deliberate networking, discovering her unique skills, and of course, making the big leap.

Learn how she navigated the fears, built confidence through community, and created a new path filled with purpose. If you're contemplating a career pivot or struggling with the fear of change, this episode offers invaluable insights on listening to your intuition, planning your leap, and stepping into a life you truly love.

Kristen is also part of our Entreprenista Expert Council, where she offers expert advice to help women founders grow and scale their businesses. Kristen also shares how she helped Entreprenista secure the perfect location for Founders Weekend 2026!

What we talked about:

The Cost of Staying [3:00]

How Kristen Prepared to Leave Her Corporate Job [10:25]

Her Hotel Whisperer Expertise [20:25]

Advice for Planning an Event [25:00]

Closing Thoughts [32:00]

Connect with Kristen:

Linkedin

Website

Facebook

The Cost of Staying

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