All Episodes

April 28, 2025 76 mins

Thinking about quitting a job to start a business but paralyzed by fear and “what ifs”? You're not alone.

In this episode, I sit down with my friend and former nurse-turned-entrepreneur Kelly Endres to talk about what it really looks like to go from employee to entrepreneur—especially when you're walking away from a job that felt like a calling.

Kelly’s story of leaving nursing to work side-by-side with her husband in their insurance agency is deeply honest, relatable, and full of the kind of real-talk we need more of in midlife entrepreneurship. If you're craving more freedom in business, more purpose in your work, and less hustle-for-the-sake-of-hustle, this episode is for you.

We’re pulling back the curtain on the messy middle—the doubt, the money fears, the identity shifts—and how Kelly built a business rooted in service, heart, and unapologetic alignment.

In this episode, we dive into:

  • What no one tells you about quitting a job to start a business—and why Kelly almost didn’t
  • The emotional rollercoaster of going from employee to entrepreneur (especially when the job you’re leaving is one you love)
  • Why women often stay in “safe” careers too long—and how leaving nursing finally gave Kelly the freedom in business she was craving
  • How to work with your spouse without losing your mind—or your boundaries
  • What it really takes to find purpose again after walking away from a helping profession

Let’s chat: Are you thinking about quitting a job to start a business but feeling stuck in fear or guilt? DM me on Instagram @katyripp and tell me: What’s your biggest fear about going from employee to entrepreneur?

I’d love to hear your story.

RESOURCES MENTIONED IN THIS EPISODE:

The Art of Hello

Actually, We Can Community

Female Founders Collective

CONNECT WITH KATY RIPP: 

Website: www.katyripp.com

Instagram: @katyripp

Pinterest: @katyripp

Facebook: @katy.ripp

CONNECT WITH KELLY ENDRES:

Endres Insurance Agency Website

Endres Insurance Agency Facebook

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.