2025 Podcast Recap: Gratitude, Growth & a Misspelled Logo

Hello and welcome back to the Career Flipper Podcast. I'm your host, Jenny Dempsey, and this is a solo episode, so you're getting just me today. This episode is the 2025 Career Flipper recap because we made it. Wow, like, I cannot believe I'm saying this, but Yeah, we're total at 86 episodes with the Career Flipper Podcast. And honestly, I'm a little emotional about it. Yeah, and I'm just recording this straight through like a voice note to a friend. So yeah, thank you for tuning in and listening. And before I get into anything else, yeah, I just I want to lean into the gratitude, like truly from the bottom of my heart. Thank you for listening, for following, for writing in, for sharing your stories, for sending me messages about how an episode hit home or made you think about something, for leaving reviews, for telling your friends about this little show, for following me on Instagram and putting up with my random posts and, um, This podcast really started as something so personal. I mean, almost selfish, really. Like, I just wanted to figure out how to change my own career, how to rebuild a career path when the one I had crumbled. And somehow, through these 86 conversations in the last— well, I guess 2 years since July 2024— I learned that I'm not alone in this, and neither are you. And every single guest that's been on this show has become a mentor to me in some way. And, and I mean every single one of them. And when I started The Career Flipper, I didn't have a plan. I didn't even have a stable job. I was fresh off a layoff, confused, grieving, trying to remember who I was outside of my career title, and doing contract work part-time and flipping furniture and trying not to panic every time someone was like, So what do you do? That was season 1, the In the Thick of It season. But season 2 was different. And season 1 ran in July 2024 to December 2024. And season 2 started in July 20— excuse me, January 2025. I can get this correct. I'm not going to edit this out. January 2025., and, um, is now wrapping up here, uh, in November 2025. And yeah, it was different. Um, and I had a full-time job again. I started it in January 2025, and I— it was a referral from a really good friend of mine, uh, who also works there. And honestly, I was, I was scared. I was resistant, like deeply resistant. I didn't know if I could trust corporate again. After what happened before. I didn't know if I could realign myself with, with the way that corporate works now that I've tapped into this entrepreneurial spirit. And I didn't know if I'd lose myself again in work and it would become my identity and I'd just lose everything that I had learned. I took the job. I needed the stability. I'm grateful, uh, you know, and I decided to really Reframe this, you know, reframe it as the investor in my dreams and trying to, you know, be back in an office and show up and, and just realize I'm focusing on my core values, connecting to great people on my team, being creative, showing up as my authentic goofy self, um, you know, focusing on what matters to me, staying consistent, being a team player, all these things. Um, you know, uh, because it matters to me. And here I was, I'm doing this full-time job, I'm furniture flipping every single Sunday for about 8 to 10 hours, um, and then hosting this podcast, basically doing it kind of like on my lunch break, um, from the day job, um, as well as doing it like after hours. So, um, and then also, you know, gotta throw this in the mix here because I gotta keep it real, but still grieving my dad who died in March 2022. And I feel like I talk about it a lot, but the actual grieving of it, I, I don't know if I really worked through it or worked through what he said to me on his deathbed of, "I wish I wouldn't have worked so much, Jen." And, you know, I'm still figuring out who the heck I'm becoming. You know, and somehow— I know this might sound a little cheesy, but this flipping community kept me going. You all made it feel less lonely. And through these conversations, man, I have learned so much. It has continued to light my— like, light my flame to keep going and leaning into the things that the matter to me. Like, let's start, you know, with Matthew Smith. I'm gonna, I'm gonna go back on some episodes here, so, so come with me. Matthew Smith kicked off season 2. He got laid off and then became a bartender in the Caribbean. Like, he was working in advertising and marketing in New York City, and then lots of things happened. You got to go back and listen to the episode. Um, and, and literally that layoff led him to serving drinks on a beach. And what I love about his story is that it cracked open this belief that layoffs are not the end, you know, they're really the beginning of the most unexpected adventure. And, you know, his story reminded me that a door closing can actually be like a flight boarding to somewhere tropical and beautiful. And then there were Elise Rowan and Kelly Williams, two friends who started the S'mores Cart in, in California. And their story, like messy. It's hilarious. There's burned marshmallows, uh, burnt, shattered glass. Um, go back and listen to that episode, it's a good one. But the joy they found in doing something together and saying yes to an idea, into not pushing away their entrepreneurial spirit, was contagious. They reminded me that you don't have to know everything before you start. You can learn. It might be really messy, but you can learn while you're doing it, and you can, you can laugh along the way. And then Ryan Kelly, uh, you know, he had a successful tech career in UX design and he became a furniture maker. Uh, you already know, you know, like, he's proof that your passions aren't random. They're clues. And his story kind of felt like a mirror for me— this creativity, this craftsmanship and courage all rolled into one from, from a friend that I, I knew in person and I you know, reconnected as they are transforming their career into something completely different. And I love the chat with Katie Asmus. She's a somatic psychologist, and it really— like, our conversation blew my mind with her insights about how our bodies kind of hold the truth of change. Like, that makes sense. It's like she said something, you know, like, your body knows when it's time to move on even before your mind does. Like, that hit me hard because I think for so many of us, we feel it before we can explain it. I know, like, I feel it. I know. I mean, look, my day job, I'm so grateful for it, and the people are amazing, and the company, you know, there's so many good things. But when I sit in the office under the fluorescent lights, I don't, I don't necessarily feel completely aligned. But I feel that my mind is like, okay, you know, you work through it, you just gotta, you do it. Like, but my mind, like, like, I, I feel it. And so I think really leaning into that sometimes and understanding that it's okay to feel these ways before we can explain that is important. And then Julie Hanel, like, she's flipped her career so many times. Um, you got to go back, like, her episode, she was a model and then she worked in tech and she also, um, brought people together with sustainable clothing and then she used her career coach. She has a podcast. I mean, she's done so many things, and she's a reminder that it's completely okay to reinvent yourself over and over. You don't have to have one defining chapter. You can have a whole frickin' bookshelf. And also, speaking of bookshelf, Carol Pearson left corporate marketing and started her own independent publishing company. I love how she talked about stepping into the role of essentially being like a midwife for other people's ideas, guiding them to create something that they've dreamed about for years. And it made me realize that sometimes your career flip is about helping others and lifting other people up and amplifying other people's voices. And then there's Michael Mattson, a fellow customer experience soul that I know from the industry. He used to be a mail carrier before he got into customer experience, and What I love is how his story shows that the heart of any career, especially in service industries, is human connection. And he didn't just pivot careers, he evolved what connection means to him. Or when I totally fangirled with Tanya Cassidy, um, she is a fellow furniture flipper that I found on Instagram and learned from, admire all of her flips, get a lot of inspiration from. And she's a middle school teacher by day and a furniture restoration wizard by night. She's a— she's about to retire and she's going to be doing this full time. And, you know, she's building something she loves. She loves being a teacher, but she also loves sanding, staining, you know. And her joy is just infectious. I don't know how she does it all, but she reminds me that passion multiplies energy in ways logic can't explain. And then there is Case Sandberg. He is a software engineer turned chocolate maker here in San Diego, California. He founded San Diego Chocolate Co. And, you know, he had to flip code into cocoa. And I really wish that I would have thought of that line when the episode first came out. But basically he said something that stuck with me in the episode, like, essentially, I don't want my perfectionism to stop someone from enjoying, like, good chocolate. I mean, he says it way more detailed. You got to go listen to the episode, but I think about that a lot, about how often, like, I personally will hold back from sharing something because I don't think it's good enough. And Kayce reminded me that done, shared, and real is always better than perfect and unfinished, because you can't hold back and deny someone the opportunity to experience it. And there's also Trish Dzinski, who I'm a little obsessed with. Um, she bought a literal château in France um, while she had a full-time job. It was just like on a whim, and then she got laid off, and now she hosts people there. Like, she's an event curator. She makes amazing experiences. And like, what? Like, watching her episodes on Chateau DIY led me to her, and her story feels like a dream, but it's the real dream. The messy, hard stuff that comes with, you know, buying a château. It was from the 1400s. Um, you know, it's proof that sometimes your wildest idea isn't crazy, it is calling you home. And yes, there are dogs in the background, and I'm gonna leave that on. But, um, I also want to talk about Laura Hatcher. Um, she, a U.S. Navy captain turned photographer, um, you know, she's the embodiment of grace and skill. And she found a way to honor her past while creating beauty in her present through something that she loves. And, you know, she started photographing with cars, and then people, and now, you know, people in uniform in the military, helping them tell their stories through images. And it's just such a full circle moment. Also Lisa Chensfeld, who went from being a musicologist to a strategic communications consultant. I mean, Talk about career reinvention. Her journey reminds me that skills are portable. You can pack them up, carry them to a new destination, and they'll still work. Maybe even better, they're reinvented. We also got Beth Kerouan, who started making donuts during her layoff, which somehow tied back to customer experience because she created the stories that made it so. And I just love how she reminds us that play, creativity, and business can all coexist. And you can have a snack at the same time, um, you know. And then, gosh, I feel like— okay, we've got Lori Wallace. She left corporate banking to help others through her own career transitions. She's the one who I met at an event, and she really gave me the word of portfolio career. She defined it, and, and she's just light in human form, and she embodies this heart-led leadership and the power of reinvention through kindness. And Baba Weiss— excuse me, Baiba Weiss, pardon me. Now I'm just rambling, but we all make mistakes. Baiba, I love you. I'm sorry. But Baiba, she and I have been connected from the very start of, at least from my podcast journey. Hers had been ongoing, and she's been doing it for a while with the Career in Technicolor podcast. But she was doing talent acquisition. Now she's teaching tai chi. And her story— I mean, slowing down isn't quitting. Tai Chi teaches us so many things and strengthens us in ways that you will never expect. And she's out there teaching people this. Um, and then I want to lean into Steve Jaffe, who wrote a book about getting laid off, like literally the book, the, um, the Lay —excuse me— The Layoff Journey, and it walks you through the steps of grief post-layoff. Honestly, like, that hit me in my core because it was so honest and relatable, and I was like, I've been there, but I didn't realize I was there until I read it. He doesn't sugarcoat it, you know. Flipping your career isn't glamorous. Getting laid off isn't always, you know, fun employment. It's gritty, it's uncomfortable, it's emotional. There's grief, and he talks about that and he captures that. Go listen to that episode if you haven't. Um, but lastly, we wrap up the entire season with Justin Cohen, who left the film industry to start his own dog walking business, Justin Walks Dogs, in Los Angeles. And you know, it's really kind of this example, this pure example of finding peace and joy, but also like he was burnt out and he knew that what he was doing wasn't exactly what he wanted to do, and he didn't know exactly what that was, so he just started walking dogs really just to pass the time in the meantime till he found something else. And then you realize that he was feeling so much better— mind, body, and spirit. And his daily walks with dogs became his therapy, his business, and his freedom. I mean, if you haven't listened to that last episode, please, please do. He's also got a crazy story in there about rats. But, um, anyways, when I look at this whole season at all these stories, I realized something. Every single career flipper that I have interviewed started with a moment of uncertainty. Every single one of them said, "I don't know," more than once. But they also said, "Yes, I'm gonna try." And I think that's what the career flipper is really about— saying yes to something new even when you don't know, even when it's messy. And speaking of messy, I gotta tell you this story because it just happened recently. It's too real, and you know what, I gotta laugh at it because otherwise I'm gonna have a full-blown meltdown. But right now, while this episode is recording, I'm preparing for my first-ever vendor booth event at the San Diego Home and Garden Show. By the time you're listening to it, it'll be done. Um, so I hope my future self will listen to this and still laugh. But basically, um, you know, the San Diego Home and Garden Show, it's held at the Del Mar Fairgrounds. They reached out to me on social media asking like if I could be— if I would be open to being a part of it and having a booth. And I was so honored. I was like, this is a big deal. I've never done anything like this. Um, why, you know, why not? I don't know, but I'm gonna try, is essentially— I can— I'll try. Let's do it. Um, you know, so I'm representing San Diego Furniture Flipper. Um, and in the meantime, you know, I, I gotta make some, some branding signs and cards and, and maybe some stickers. And so I'm using Canva. I am not a designer by any means as far as like tech stuff. Um, but I got Canva and I was using their AI tool, um, to make me a really nice little logo. And of course it spelled it wrong on the first one, so then I had it redo it and it spelled it right. Um, and I was like, okay, this is beautiful. And, uh, fast forward, you know, I started in advance. I started about probably like a month and a half in advance ordering things because I, you know, I do know working in the tech world, project management, I know you start in stages. I knew I had to phase it out Um, so I'm ordering everything in advance. I'm getting things here, and I'm just kind of putting the boxes away because it's busy working the day job, working the podcast, working furniture, everything else. And like, there's been a lot of events and there's been a lot going on. So I, I made the goal of I'm gonna put everything that I order away into the closet, and then the week prior I'll get everything organized, and then a couple days before we'll do a little more organization, and so on and so on. Well, you know, everything's in, it's printed, I'm feeling good. I spent a couple hundred bucks on everything, a very discount, but I was like, okay, it's there, it's done, I got shirts. Um, you know, I start to open things, I start to look at it. Yeah, well, remember the logo that, that was spelled wrong? Yeah, that's the one I accidentally uploaded to all of these things. The one that was spelled right, yeah, mm-mm, didn't. And, and what's actually spelled wrong is it says San Diego spelled correctly, furniture is spelled F-U-R-N-T-U-R-E, flipper is spelled correct. So San Diego furnitur flipper. Oh my goodness. So I open everything and I'm looking at it and I'm like, oh my gosh. You know what, I'm gonna laugh because this is crazy. I, I— what else can you do? Um, it's such a me moment. It's proof that even with the best intentions and planning, life will still humble you. It's also proof that I was probably doing multiple things at one time. I was probably— I mean, to be honest, listening to a podcast episode to edit it, uh, in the background while typing an email to one of my colleagues at the day job to make sure I get something done. And then hopping back to Canva really quick to get the order going and proof it real quick. So, and then at the same time, there was probably someone at my door, so I went to go open the door. Um, and then I noticed there was probably some dust, a dust bunny, so I grabbed the vacuum to vacuum that. Then I was like, oh, it's time for lunch. You know, these are the things— I'm sure you get it. I know I'm not the only one doing 10,000 million things. I'm not special, I'm not unique. Like, I I'm in it with you. Um, so instead of hiding it, that's why I'm telling you about it, because I want you to feel like, okay, this stuff happens. Um, but I feel like it's very much, uh, a part of the vibe, right? It's part of the story. Because if I learned anything this year, you know, sometimes these mistakes are just second chances in disguise. Like One day maybe I will have a professional branding team making really beautiful things for me and it will be spelled right. I'll be able to, you know, get support and help from people who actually know how to do these things. But for now, this is where we're at. And you know what I will say though, is that I love this. I love this podcast. I love this community. I love flipping furniture. Um, I love, you know, making new friends at my day job. Um, I love contributing to brightening up someone's day, and I love hearing all of your stories. I love knowing that an episode that I share that's not perfect, that I'm literally editing on You know, I know there's a lot of tools out there, but I still use, you know, GarageBand to edit mine. I am using, um, Zoom to record it. You know, like, I'm doing this, um, in a way that isn't super professional, and you still love it. And I love knowing that, and I look forward to next season. You know, I don't really know yet exactly what season 3 of The Career Flipper will look like. It's gonna evolve. It's gonna include new types of flips, new types of stories, um, you know, many new guests and, and all kinds of things. Like, because I— the other thing that I've learned is that career flipping is not just career flipping, it's life. It is all about life flipping, and I'm here for it. And I am so honored that you are too. So if you have ideas or stories that you want to share, you just want to say hi, My email is hello@thecareerflipper.com, but you can also text me 619-354-8116. I hope I don't regret putting that out there, but I would love to connect, um, because this isn't just my story anymore. It's ours. So as I wrap up 2025, here's what I want to leave you with. You're not behind. You're not broken. You're definitely not too late. You're probably doing too much at one time, but that's okay. You'll, you'll find our balance one way or another. You probably have a typo somewhere, and you know, it's gonna look messy. The logo is gonna be spelled wrong, but you're learning, you're trying, you're still showing up, and that's what flipping is all about. So thank you for being here. Thank you for believing in second chances. I am so excited to see you in season 3 coming out in spring 2026. So we'll have a little bit of a time gap, but I am so, so excited to get going on this and bring it to you in the spring. Um, until then, just remember, what's the best that could happen?