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Writer's pictureJenny Dempsey

Why I'm launching this podcast

Updated: Jun 19

Most people know me as the "customer service gal." For 18 years, I worked in customer service and experience roles with tech startups, climbing from call center front lines to director-level management. I've taught two Udemy for Business beginner customer service training courses, serve on the Board of Directors for CX Accelerator, and have spoken at global conferences like ICMI, Zendesk Relate, and SupportDriven. My career was a major part of my identity.


Then, I got laid off.


Suddenly, job rejections flooded in—hundreds of them—shaking my confidence and making me doubt my entire career. Finding work had always been easy for me, until now.


I'm a creative soul who loves crafting, writing songs, singing, and playing guitar, but I often set these interests aside, believing I wasn't good enough and letting work take priority. Losing my job and struggling to find a new one took a toll on my confidence and mental health.


One day, a friend was getting rid of a beaten-up old table from her basement. Despite its worn look, I saw potential in it. I decided to give it a makeover. I was hooked! After an afternoon nap, I woke up with the idea to check if the name "San Diego Furniture Flipper" was available. It was. I started an Instagram and a website to capture the transformations.


I believe that every piece of old furniture has a story, and I want to preserve those stories for many more years. When I touch a table, I can sense its memories: joyful dinner parties, deep conversations, childhood adventures. Restoring each piece of furniture feels like restoring a part of myself that once felt unwanted. I realized I'm more than just a job title, and I knew I couldn't go back to a 9-5 job again.


Why I Started the Podcast



Throughout this journey, I felt delusional making such a big change from the tech world to being covered in paint and sawdust in my garage. I felt really alone, crazy, and confused. Stories from others who made career flips gave me solace. Knowing I wasn't alone brought me peace. There were more people than I thought with similar stories of career evolution.


One morning, I woke up remembering another dream I had about starting a podcast called "The Career Flipper." I typically don't remember my dreams, so I took this as yet another sign. While there are similar podcasts out there, I found no other podcast with this name, registered the domain, and set out to create a podcast, even though I had actually never done this before and had no idea what I was doing.


I aimed for 8 episodes, knowing about 8 people who had gone through career flips. My interview list soon grew to 18 people, with more waiting. There are so many career evolution stories out there, and I'm honored to share them.


I'm recording episodes virtually and in my home studio, surrounded by houseplants and my rescue doodle pup, Dwight, sleeping on his dog bed. I bought a mic off Amazon, edit using GarageBand and Riverside.fm, and I'm thrilled with my host, Simplecast. It's self-funded for now, until I find amazing sponsors to support the show.


My Podcast Dream


My goal is to create a resource of advice and support for anyone thinking of, going through, or having been through a career flip, to make them feel less alone. I'm learning about the common themes that inspire people to shift careers and keeping track of them for my future book and keynote speeches. I'd love to take this show on the road, doing in-person interviews with live audiences in major cities, at retreats, and workshops.


And if you're reading this, I'm really stoked to have you with me on this journey.

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