Career Flip Stories

Jenny Dempsey

Aug 293 min

Ep. #9: Kim Masiello, Museum Curator to Teacher

I had the pleasure of catching up with my neighbor and friend, Kim Masiello, about her incredible career journey one sunny afternoon in...

Jenny Dempsey

Aug 203 min

August Bonus Ep. MiLB Pitcher to Country Hip Hop Recording Artist

Ever wonder what it’s like to chase a childhood dream of becoming an MiLB pitcher for the Houston Astros, only to find out it’s just one...

Jenny Dempsey

Aug 153 min

Ep. #7: Tracy Carmen Watkin, Hospitality Manager to Content Manager/Writer

Hey Flippers! Jenny here, and I recently had the absolute pleasure of chatting with my dear friend Tracy Watkin on the podcast. Now,...

Jenny Dempsey

Aug 83 min

Ep. #6: Jeremy Smith, Sea Turtle Marine Biologist to Vintage Reseller

This episode features a conversation with Jeremy Smith, who transitioned from being a sea turtle marine biologist to becoming an...

Jenny Dempsey

Aug 13 min

Ep #5: Roy Atkinson, Professional Musician to IT CEO

As a kid, I dreamed of becoming a singer. Many hair brush microphones later, I took guitar lessons and was in a promotional band for the...

Jenny Dempsey

Jul 253 min

Ep #3: Karli Williamson, Event Marketing Manager to Career Coach

Meet Karli Williamson, a former event marketing manager and consultant turned career coach based in Portland, Oregon. Karli's journey is...

Jenny Dempsey

Jul 184 min

Ep #2: Sally Mildren, Brain Injury Trauma Therapist Therapist to Marketing Agency CEO

Sally and I know each other from the customer experience industry. There's a lot of community building in this world, and CX Accelerator...

Jenny Dempsey

Jul 113 min

Ep #1: Nick Musica, SEO Expert to Animal Psychic Communicator

Nick and I met back in 2015 when I took a new job with a content startup in Encinitas, CA. We bonded over the cushy corporate culture of...