Host Jenny Dempsey shares insights from her own career flip
In this episode of "Cocoon Conversations," host Jenny Dempsey gets real about the emotional rollercoaster of juggling her career and furniture-flipping side hustle. She spills on burnout, imposter syndrome, and the chaos of pricing her art (“Am I worth it?!”). Jenny shares her messy, vulnerable moments—singing to her furniture, doubting herself, and still showing up. She reminds us that spirals aren’t failures, but part of the process, and that confidence is more like a flickering patio light than a spotlight. It’s raw, relatable, and a little unhinged—in the best way.
Jenny 00:00:02 Hey friends, welcome back to another cocoon conversation episode here on the Career Flipper if you're new. Hi, I'm Jenny Dempsey, your host, and this is a little corner of the podcast where I get extra real and reflective. Cocoon episodes are monthly solo check ins. Kind of like I'm sending you a voice memo and I share behind the scenes stuff. What I'm learning through my own career flip, what I'm struggling with, celebrating or spiraling about. It's raw, it's chatty, and it's a part of how I stay grounded in this journey. So thanks for being here with me. Make sure to follow and like the podcast so you can stay up to date on these episodes, as well as episodes where I interview career flippers from around the world. Every single week. We got to keep building this real and perfect Ever evolving flipping community together. So let's get into it, shall we? Because this month's been well, it's been kind of weird, like, I guess I could just say like a cocktail of emotions.
Jenny 00:01:19 Not like a good cocktail. I mean, it's not a bad one, but it's just it doesn't taste the way you want it to. Like, something just is off. It's kind of a mix of like self-doubt, a splash of burnout, a shot of imposter syndrome, and like, a weird lemon twist of am I just actually losing my mind? Garnished with hope and maybe a fun little umbrella, but okay, I, I guess I want to talk a little bit about the spiral, because maybe you've been there too. Maybe there's that moment where you just slip, like one day you're like, I got this. I'm juggling all the things. I got my full time job, I got my, you know, side gigs that I'm trying to figure out, and I am doing it all while still showing up as a great friend, a great girlfriend, a great dog mom. I'm, you know, making sure I'm still washing the dishes and putting things away. I am going to hot yoga class.
Jenny 00:02:22 I, I'm doing all the things. I'm being a nice person in the world. the next moment you're wondering if I don't know, for me, in this case, selling my restored furniture for basically like five bucks an hour is my subconscious way of confirming my deepest fear that maybe, maybe I'm not cut out for this. Yeah, that's for me. And so, yeah, maybe you've had these types of moments too. And you're putting in the time, the effort, the love. And then when it's time to show it to the world, something in you shrinks. Like, who do I think I am for charging more for this? Or is anyone even going to care? And it's been showing up in these like in these sneaky ways, like, okay, I'll spend hours fixing up a curbside furniture rescue. I will put so much time into sanding, priming it, choosing the perfect paint color, and then when it comes time to sell it, I just kind of panic. I price it low, like really low.
Jenny 00:03:36 Like, this won't even cover supplies, but maybe someone will like me low and and I know it's not what I'm doing it for, but that stuff sneaks in and, you know, it happens when I'm tired. It happens when maybe, you know, I need more protein. Maybe I just need to go walk barefoot on some grass. I don't know what. Maybe I need to reach out to a friend and and, like, just have a grounding conversation and get out of my head, And I don't know, you might have been there too. Scrolling past everyone else's highlight reels, thinking. Oh yeah, they got it all figured out. And I'm just, I don't know, I'm just winging it. But the can of paint and a lot of feelings. But here's the thing I'm noticing when I recollect myself, I get back into a place where I can think a little bit more clearly. And I really know, you know, I know this. It's hard in the moment, but I know this.
Jenny 00:04:44 The spiral isn't always a breakdown. Sometimes it's, it's like a processing portal. It's like, like a weird washing machine cycle where you come out cleaner, but also like, a little dizzy because you've been spinning around and you got one sock missing and you just don't know where it went because it was in there when you close the lid. and in the middle of that messy, sudsy spin. I got a message. And I don't know. Not just like a metaphorical one. Like a real one. Like a real one. In my email box from someone inviting me to speak, like to speak at an event and not for free, like for money and not for like pennies. Like for for money, like like it's happening. And I'll share more about the actual event later when I can talk about it. But the big part is this the universe dropped me a little breadcrumb when I was spiraling, and I picked it up, even though I still felt like, I don't know, like a soggy grilled cheese of a human, I picked it up.
Jenny 00:06:01 And I'm learning again. Forever. Always learning that confidence is not a light switch for everybody. It's for me, like more like a flickering string of patio lights that sometimes needs to be unplugged and then plugged back in, and then you plug it in and there's still one bulb out. You gotta figure out, okay, where do I get that exact bulb? You know, or I'm learning that selling art. And yes, I'm calling my furniture flipping art because it is. but selling it is deeply vulnerable work. It's saying I see potential in something I made and hoping that someone else does, too. And not not doing it because someone else doesn't. Not everyone will. And that's okay. And also that your worth is not tied to a number on a price tag or a like count, or I don't know whether someone goes to on your Facebook Marketplace listing. I mean, how many times has that happened? And also, singing helps. Music helps. For real? I mean, this is a bit of a side note, but I've been singing more and more in my workshop lately.
Jenny 00:07:18 I, I write little songs about the furniture pieces that I'm working on. I, I think of them while I'm sanding. I am painting and they pop in my head. I, I've always loved writing little cheesy, corny lyrics and strumming my guitar and singing along to make up make up a little song. And I know that music is so healing. And you know, on these pieces of furniture, there's the broken drawer that won't slide. There's the cracks on these pieces that were who knows what these pieces of furniture have been through. And the dresser that I found next to the dumpster really needs to be repainted, because it has just water stains all over the top. You know, these are the pieces that I almost give up on, and I sing to them. And again, I go back to this healing thing. There's something so healing about singing. When you feeling feel lost or just music in general. It's like, I don't know. Like, it just makes my soul happy. So I write these songs and I post them on my Instagram over at San Diego Furniture Flipper or my little TikTok.
Jenny 00:08:30 And they're cheesy. But when I'm in that moment and I'm writing that, and I'm singing that in my garage, in my overalls, covered in paint and sawdust, and I'm sure my neighbors nearby can hear it, and they're like closing their windows because they're like, here we go again. it's really meaningful to me. And I just. I'm gonna sing with the spiral. I'm not going to try to avoid it because I think I look dumb or I sound dumb. I really am sitting with it in that moment. I'm singing, I'm sanding. I'm reminding myself that progress looks weird. It's uneven, it's not always cute, and neither am I when I'm. Especially when I'm covered in sawdust, wearing a paint smeared tank top and crying out while building this piece of furniture. It deserves a second chance. But maybe I'll sing on a future episode too. I've been working on a song, like a full song, so I don't know, maybe. Stay tuned next month. We'll see. But despite that, my friends, this is also the magic.
Jenny 00:09:52 At least I see it as magic. And I'm not trying to tie this up with a neat little bow because I don't know. I don't think that the unspooling, the thing spiraling is done. I know it's ongoing for me, for you, and we have so much to learn throughout the entire spinny, spinny cycle. So if you're also in a spiral, or maybe you're dancing near one, or maybe you've literally are climbing out of one. I just want to say I hey, hey, I see you. You're not alone in it. We are allowed to wobble. We're allowed to be unsure and still keep going. So here's to being weird. Here's to singing in the mess. Here's to charging more for what we create. Even if it makes our stomachs flip to remembering that value doesn't always mean viral, and to letting our furniture or art, whatever it is you're creating and our hearts have a second or third or fourth or 11th chance. So thanks for being here. Thanks for being in the spiral with me.
Jenny 00:11:16 But before you go, if this resonated with you because yeah, I'm kind of seeking some validation Can you follow or like the podcast on your favorite platform so you really never miss one of my rambling voice notes to you here. and you never miss one of these amazing career flipper interviews, because these people are getting so vulnerable and sharing their stories and showing you that it is possible. These are real people. They're they're out there doing the thing. It's possible. So please, like, follow the podcast. And if you have an extra second, leave a review. Like it really, really helps because it gets it out there to more career flippers or people thinking about it. So and just know that if you ever want to share your story on a future episode, or I don't know if you ever just want to like, talk about what I'm sharing here and tell me. Tell me your story and how you're handling your spiral, and how you hype yourself back up when your confidence is playing a little game of hide and seek.
Jenny 00:12:33 Well, I'd love to hear it. You can email me. Hello at the Career Flipper. Com you can just drop into my DMs on LinkedIn, on Instagram, Facebook, whatever. Tell me tell me all the things because I want to have conversations about this. I'd really love to hear it. I don't just say that if you know me, you know I love to hear this and I could talk about this all day. So please let's talk. Have a really great month. Keep on spiraling. Keep on flipping. I'll talk to you soon.