Jenny Dempsey shares her candid career-flipping journey, from customer service to furniture flipping and podcasting, highlighting resilience, creativity, and embracing change.
In this heartfelt Bonus Cocoon episode of The Career Flipper podcast, Jenny Dempsey takes you behind the scenes of her personal career-flipping journey. From 18 years in customer service to unexpected layoffs, she shares how resilience, rejection, and a dash of creativity led her to furniture flipping, podcasting, and rediscovering her purpose.
Jenny reflects on lessons from her past, including the impact of her father’s advice and the challenges of starting over. She opens up about her new job opportunity, the financial ups and downs, and her evolving goals. This episode is a candid reminder that change is messy but worth it, and resilience is the glue that holds it all together.
Tune in for real talk, inspiration, and maybe a few laughs along the way! Don’t forget to subscribe and join the journey.
Jenny Dempsey (00:01.967)
Hey there, career flippers! Your host, Jenny Dempsey here, and welcome to this month's bonus cocoon episode. Basically, your backstage pass into my personal career flipping adventure. These cozy chats drop on the last Tuesday of every month, giving you a peek into the highs, the lows, and all the in-between wiggles of my own career journey. Why? Well, let's face it, if I'm asking other career flippers from around the world to share their stories and get vulnerable every single week,
It's only fair that I spill the beans on mine. So, sound good? Okay, let's dive in. But first, don't forget to smash that subscribe button on your favorite podcast platform so you are updated with new episodes every single week. You don't want to miss one. Okay, let's get real for a second. The only reason that I started the Career Flipper podcast was because I was curious. You know, how do people leave...
a familiar safe job and do something different. How do they get laid off and then start their own business? Or how do they listen to that inner voice and lean into a new industry or role or whatever it is that they may have never even done before? You know, change isn't bad, but dang it, it's messy.
And selfishly, I also wanted to create a resource for myself because I wanted a space to validate these what the heck am I doing moments of my career pivot. I wanted to feel less alone and I felt really alone. And if you've listened to my earlier episodes, you probably picked up on that, but here's the magic. Every single career flipping guest has taught me something profound. These incredible people.
flipping their careers by choice or circumstance have cracked open my perspective on work and life. And I owe them so much gratitude for sharing their journeys. And today I'm going to share a bit of mine and how the things that I've learned from them are filtering into how I navigate my career path. So if you're new here, my career flip in a nutshell, here's the Cliff Notes version.
Jenny Dempsey (02:21.506)
I host this podcast, I produce it, I edit it, I do all the things. And I am also a furniture flipper. But before that, I spent 18 years in customer experience, customer service, leadership roles at tech startups. I loved being a worker bee. I thought that's all I was good at. I worked a lot and I pushed my personal creative hobbies to the side. Music, playing guitar and singing, art.
Crafts, writing. I was taught that just that wasn't important. You work, you make money. And in 2022, six months after my dad passed away and on his deathbed told me, I wish I wouldn't have worked so much, I got laid off. And at first I thought my corporate network and referrals would help me land a new job, but
The tech market with all the layoffs that are happening to so many people around the world. It's a different place to look for a job these days and rejection after rejection came into my email inbox like a tidal wave. It was humbling. I never had an issue getting a job in the past. It was soul crushing. Who am I without work?
It forced me to get scrappy. And I started to pick up some very part-time, small-scale consulting contract gigs. These helped me make sure that I could cover my rent. They kept my skills up to date. I could stay active working. And I met some really cool people through it and had some great experiences. And I also started flipping furniture to make cash on the side.
Yeah, I became that girl, picking up sad broken dressers off the curb and giving them a glow up in my garage. Side note, if you're into that, follow me on Instagram over at San Diego Furniture Flipper. But here's what furniture flipping and contract gigs taught me. You know, rejection doesn't define me. It redirects me. And creativity isn't a side note anymore. It's part of my DNA. And so,
Jenny Dempsey (04:48.098)
There's an update that I want to share with you. Let's go back to December 2024, toward the end of the month. You know, over the last two years, financially, things have kind of been up and down. You know, contract gigs did help, but I was dipping into my savings every month, and I also wasn't able to contribute as much to my household with my partner. And it kind of just made me feel like I was constantly struggling.
Okay, spoiler alert, I wasn't, but try telling my brain that. So job-wise, I knew at this point I didn't want to climb the corporate ladder again. I didn't want any fancy VP or director title. I didn't want a team to manage. I wanted a unicorn role, flexible, remote, low stress, steady paycheck, so I could still do my furniture flips and podcast. I didn't know if it existed though.
but I had to believe it was out there and I was willing to wait, even though I was getting antsy about not having as much money. Then came an unexpected opportunity. My dear, dear friend of 20 years this year mentioned that a junior marketing role opened up at her company. Customer experience expertise, check. Flexible schedule, check. No team to manage, check. Not really much career growth,
check. So I applied, though I knew very well I was overqualified. And that was a phrase that I heard so much over the last two years with every rejection. You're overqualified. But, you know, I at this point have let go of the outcome. And I figured what would happen would happen. I trusted the process. And guess what? I got it.
So who will Office Jenny be? Because this role is hybrid and I have worked in remote roles for the majority of my career, even going back to pre-COVID days. And now I'm stepping into an office setting for the first time in a very long time. So who even is Office Jenny, you know? Will I cry on my first commute home or 50th commute home?
Jenny Dempsey (07:16.59)
Will I make awkward jokes at the coffee machine? Will I struggle with wearing something other than jeans and sneakers? Will I miss the freedom of remote work? Or will I really thrive with human connection again? Will I kind of stop comparing my side gigs to the highlight rails of others on Instagram and actually just enjoy the heck out of it? And will I find peace in knowing now that I have a stable income to fund my dreams?
You know, I guess here's what I know. This job isn't just a paycheck. It's an opportunity to invest in my creative future. Furniture flipping, podcasting, the upgraded version of myself. They're all waiting for me to step up. And it's perfectly okay. In fact, it's perfectly acceptable to take on a role that can offer some financial stability and help achieve my goals, my dreams. It's not silly.
There's no shame in that. There's no shame in moving these dreams to the side because I know they're not going anywhere. They are such a part of me that I can't let them go. And now I might even be able to do a lot more to build them up. So to wrap it all up, to everyone who made it to the end of this ramble, thank you. I mean it. Sharing my journey is vulnerable and messy, but knowing you're here listening makes it all worth it.
So if you're in the thick of your own career flip, let me leave you with this. Change is hard, but you are harder to break. And remember, rejection isn't failure, it's redirection. I start this new job very soon, and I'll have more updates for you next month on how the first month is going. But for now, thanks for hanging in with me on this wild career flipping ride.
Let's keep flipping and rethinking our career paths and not let it consume our minds completely because we have a life to live. So don't forget to hit that subscribe button so you never miss a weekly episode and if something in this episode made you laugh or think or say, don't know, wow, I feel the same way.
Jenny Dempsey (09:43.314)
Leave a review and let me know. Your words mean the world and help others find the show too. So keep going, my friend. What's the best that could happen?