Today we’d like to introduce you to Jenny Dempsey
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
My story starts when I got laid off in 2022. I had been working in corporate customer experience/support roles in the startup tech world for over a decade. I applied for new jobs but was hit hard by 403 job rejections—it was tough and made me feel like I wasn’t good enough. It took a toll on my confidence, and honestly, I wasn’t sure what to do next.
One day, a friend of mine mentioned a junky old table she had sitting in her basement. I didn’t know a thing about restoring furniture, but something about that table just grabbed me. I guess I was at a really low point, but I looked at that table and saw potential—like it had a story to tell, or maybe even a second chance to be something beautiful again. So, I took it home, not knowing how to fix it up, but knowing I had to try.
I turned to YouTube, watching videos on how to restore and flip furniture. It was slow at first, and I made some mistakes, but I found myself getting more and more into it. Every time I worked on a piece, I felt a little bit better, a little more in control. It wasn’t just about restoring furniture—it was about restoring myself. Each piece became a symbol of second chances. It was like with every table I refinished, I was healing too.
The more I shared what I was doing, the more junky furniture started showing up—whether it was from friends, curbsides, or just people who were cleaning out their homes. I couldn’t believe how much perfectly good stuff was just being thrown away. It made me realize how many items—and people—get discarded, even though they’ve still got so much life left in them. It became a hobby, and honestly, it gave me something to focus on as I kept applying for jobs and getting rejected over and over.
I eventually turned my new passion into a side gig called San Diego Furniture Flipper to make some extra cash while I was still job hunting and doing some part-time contract work. It wasn’t a grand plan; it was more of a way to keep moving forward, but it ended up changing everything for me. What started as a distraction became my way of proving to myself that I wasn’t broken. I could still create. I could still build something. And somehow, I found joy and fulfillment in this unexpected new path, even when I wasn’t sure what the next step would be.
That little table was the first piece I gave a second chance, and it turns out, it was the beginning of my own second chance too.
But then came the weirdness of it all. Changing careers from tech to furniture restoration didn’t feel like an easy jump. I felt kind of out of place, like who was I to do something so different? So, I posted about it on LinkedIn, asking for feedback and to hear about others’ career changes. Talking to people about their journeys helped me feel less isolated and more inspired.
And that’s when I had a random dream about starting a podcast. I resisted it for a while because I kept asking, “Who am I to start a podcast?” But something in me said, “Why not?” So, after a lot of hesitation, I did it. My goal was just to do 8 episodes of The Career Flipper podcast, but that goal quickly turned into 46 episodes, 2 seasons, and a whole lot of valuable insights from other career flippers in various industries around the world.
It all started from curiosity—curiosity about my own path, curiosity about others’ career changes, and curiosity about what would happen if I just tried. And now, here I am, with a growing community, a side gig that turned into more than I ever imagined, and a podcast that’s changing the way I see career transitions.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It definitely hasn’t been a smooth road! There have been a lot of bumps along the way, and at times, it felt like I was trying to walk uphill that giant hill over on B St. with rollerskates on.
When I first got laid off, the rejections just kept piling up—403 job rejections, to be exact. That really crushed my confidence, and I started to wonder if I was ever going to find a new path. I didn’t know what to do, but furniture restoration wasn’t even on my radar at that point! Then, that old table from my friend caught my eye, and I saw potential in it, even though I had no idea how to restore it. I had to teach myself from scratch, and it was frustrating at times. There were a lot of mistakes made along the way, and there were plenty of moments where I doubted myself, thinking, “What am I doing?”
Turning this hobby into a side gig wasn’t a walk in the park either. Juggling the furniture flipping business while still applying for jobs, doing part-time contract work, and dealing with rejection was exhausting. There were days I felt like I was spinning my wheels and getting nowhere. And, if I’m being honest, making the jump from a career in tech to a creative, hands-on business like furniture restoration felt totally out of left field. I was constantly second-guessing myself, wondering if I was doing the right thing.
Starting a podcast was another hurdle. It felt like such a big leap, and I struggled with that voice in my head saying, “Who am I to do this?” But over time, I realized that even though it wasn’t easy, it was worth pushing through the discomfort. It’s been so rewarding to have people tell me that my podcast is helping them feel seen, heard, and inspired during their own career changes.
So, no—it hasn’t been smooth. But looking back, I wouldn’t change any of it. Each struggle taught me something valuable, and it’s all led me to a place where I’m doing what I love and making a difference in ways I never expected.
Appreciate you sharing that. What else should we know about what you do?
I’m all about giving second chances—not just to people, but to furniture too. My main gig is San Diego Furniture Flipper, where I rescue old, unwanted furniture from being tossed away and restore it to life. I don’t buy pieces—everything I work on has been saved from curbsides, alleys or friends’ garages. I also take on client projects, giving their old furniture a makeover. I specialize in transforming discarded pieces into something beautiful and functional. It’s not just about making things look pretty; it’s about the process of transformation, both for the furniture and for me. Each project has become a way for me to heal and grow after a tough career shift of my own.
What really sets me apart is how I approach the whole process. I didn’t come into furniture restoration with formal training. I learned through trial and error, mostly by watching YouTube videos, asking other furniture flippers, chatting with friends, getting tips from Lowes employees, and even sliding into woodworker DMs with a ton of questions. So, I totally get what it feels like to be learning as you go, and I bring that spirit of resilience and curiosity into my work. It’s not just about restoring furniture; it’s about seeing potential where others might see junk. I’m known for giving each piece a second chance, just like I gave myself one after losing my job and struggling to find a new path.
What I’m most proud of is how far I’ve come—from being stuck and unsure about my next step, to turning furniture flipping into a side gig, all while building *The Career Flipper* podcast. My podcast is a place where I connect with others who’ve made career flips—people from all walks of life sharing their stories. It’s been incredible to watch the podcast grow, and it’s been a way to create a community of people who believe in second chances, both for themselves and their careers.
So, what sets me apart? It’s my blend of creativity, resilience, and the fact that I’m always curious and open to learning. I never buy any furniture; I rescue it. And I want others to see that even if you’re starting from scratch, you can still create something amazing.
Do you any memories from childhood that you can share with us?
I grew up in Norco, CA, which is a mix of country vibes and suburbs. My mom ran an animal rescue right out of our home, and it was pretty much the heart of everything I knew growing up. One of the more unforgettable parts of that was the emus she rescued. These birds were crazy—super strong and could jump really high. One day, they decided to leap over the backyard fence and into our neighbor’s yard, then out of that yard and down the street.
Now, in a town where football ruled and being the “cool kid” was the thing, I was already not fitting in. While everyone else was playing sports, I was riding horses and singing in a band. I was definitely not the popular kid. So when the emus decided to make a run for it down the street, of course, the cool kids from school happened to be out and saw me and my mom chasing after them to wrangle them back home. I remember feeling mortified at the time—like this was the last thing I wanted them to see.
But looking back, it’s one of those memories that makes me smile. It became this funny comment that stuck with me—people would say, “Oh, you’re the girl with the emus!” It was a little embarrassing then, but now, I love how it set me apart. It was such a uniquely wild experience, and it reminds me of how being a little different is part of what makes life interesting. Plus, it always makes for a fun story to tell!
Contact Info:
- Website: https://www.sandiegofurnitureflipper.com
- Instagram: https://www.instagram.com/sandiegofurnitureflipper
- LinkedIn: https://www.linkedin.com/in/jenny-dempsey/
- Youtube: https://www.youtube.com/@thecareerflipperpodcast
- Other: https://www.thecareerflipper.com
Image Credits
The only photo that needs image credit is the first one with me in front of the dresser – credit goes to Danielle Malufau Photography.
