The Career Flipper Podcast

About The Career Flipper Podcast

Thinking about making a career change but have no idea where to start? You’re not alone. Welcome to The Career Flipper, the podcast for anyone wondering, "What else is out there?". I’m Jenny Dempsey—your host and a fellow career flipper. I didn’t plan on changing careers, but after years in customer experience and a surprise layoff, I found myself asking, "How do people actually make big career moves? And more importantly, how do they keep going when it gets messy, overwhelming, and scary?" That curiosity led me to just ask people who have done it. To have real, honest conversations with people from all over the world who’ve made all kinds of career flips. Whether they started over in a new industry, turned a side hustle into a full-time gig, or made a total 180 to do something they actually love, their stories gave me ideas, inspiration, and even a little courage - so I figured they might give that to you too. Be sure to subscribe on your favorite podcast platform for new episodes every Thursday. Got your own flip story? I’d love to hear it! Submit your story for a future episode at https://www.thecareerflipper.com Follow on Instagram: @thecareerflipperpod You don’t have to have it all figured out. Just take that first step. What's the best that could happen?

Publisher

Jenny Dempsey

Category

business

Language

en

Explicit

Yes

First episode

22 May 2024

Latest episode

6 Nov 2025

Latest episodes

4 of 87 episodes have a transcript.

1. 

   6 Nov 2025TRANSCRIPT

   2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo

   The host reflects on the podcast's 2025 journey, highlighting gratitude, growth, and a memorable logo mishap.

2. 

   30 Oct 2025TRANSCRIPT

   From the film industry to professional dog walker, meet Justin Cohen

   Justin Cohen shares his career transition from the film industry to professional dog walking, revealing insights into following your passion in Los Angeles in this interview.

3. 

   23 Oct 2025TRANSCRIPT

   From IT executive to founder & owner of Human Insights Consulting Group, meet Jenn Lorenz

   Jenn Lorenz discusses her transition from IT executive to founder of Human Insights Consulting Group in this interview episode.

Inside a recent episode

2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo

Published 6 Nov 2025 · Transcript excerpt

[…] I'm going to go back on some episodes here. So come with me. Matthew Smith kicked off season two. He got laid off and then became a bartender in the Caribbean. Like, he was working in advertising and marketing in New York City. And then lots of things happened. You got to go back and listen to the episode. And literally that layoff led him to serving drinks on a beach. And what I love about his story is that it cracked open this belief that layoffs are not the end. You know, they're really the beginning of the most unexpected adventure. And, you know, his story reminded me that a door closing can actually be like a flight boarding to somewhere tropical and beautiful. […]

Who has been a guest on The Career Flipper Podcast

Names identified in recent episode analyses. Showing up to five guests.

• Justin Cohen
• Jenn Lorenz
• Lauren Tetenbaum
• Jane Dashevsky
• Manana Jaworska

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

652

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

10 ratings

Spotify

5.0 / 5

17 ratings

Podcast Authority Score: 77 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

87

Social presence

100

YouTube

66

Engagement

51

Contact The Career Flipper Podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about The Career Flipper Podcast