Cocoon Conversations: My Career Flip Progress for May 2025
In this episode of "Cocoon Conversations" on the Career Flipper podcast, I, Jenny Dempsey, take you along on my career journey.
This year, I’ve committed to opening up about my own career flip, just as I encourage my guests to do. So here we are, in May 2025, and I can hardly believe it’s been four months since I started my current day job. It feels surreal to say that, especially considering I was laid off for two years before this.
During this time, I’ve been balancing my full-time job with furniture restoration on the side, dedicating Sundays to it, and squeezing in podcasting and all the related tasks whenever I can. If that sounds overwhelming, it is! Life can be a juggling act, and I know I’m not alone in feeling this way. Scheduling time with friends often feels like a game of Tetris, as we all navigate our busy lives.
I’ve always been the type of person who thrives on variety. I’m the one multitasking—doing laundry while putting away dishes, preparing to record a podcast, creating social media content for my furniture flipping page, and making sure my dog, Dwight, gets outside for a potty break. My brain has always thrived on this mix of activities, and I’ve been like this for as long as I can remember.
Looking back, I’ve come to realize something significant. For a long time, I believed that work—capital W work—was my identity. I thought it was the only thing I was good at. I didn’t believe in taking vacations; if I did, I’d bring my laptop along and continue working. I even had a panic attack in front of a customer service team I was managing because I was so consumed by my job. I poured everything into my work, only to learn the hard way that companies would replace me in an instant. When I was laid off and struggled to find a new job for two years, I was left questioning my identity. Who was I if I wasn’t working?
I dive into this and more in the episode!
Jenny 00:00:02 Hello and welcome back to another cocoon conversation here at the Career Flipper podcast. These are the episodes that I do on the last Tuesday of every month so far this year, where I share my part of the story, my career, flip my journey because I figure if I'm interviewing people and they're getting vulnerable about their own career flips, it's only fair for me to come on and share mine. So I'm back in your ears. Here we are again. It's May 2025. Whoo! How are you doing? This marks four months for me at my current day job, which, like, that's kind of wild to say out loud because I had been laid off for two years prior to that. So I've been working full time again, doing the furniture restoration on the side. One day a week, about eight hours every Sunday, and then squeezing in this podcast and all the ad mini bits of it somewhere in between. And yeah, if that sounds like a lot, it's because it is. I mean, we all have so much going on in life.
Jenny 00:01:15 I try to schedule something with my girlfriends and it is like a week long adventure, a Tetris game, because everyone is so busy. We're all doing so many things. I know I'm not alone in this. but for me, like when it comes to work and stuff and maybe this resonates with you. I've always been, do ten things at once kind of person. You know, I might be doing the laundry and also putting the dishes away, but also about to record a podcast episode and creating social media content for my furniture flipping wall. Going to paint, a piece of it so it dries. And that's the next step in the process while also making sure the dog, our little pup Dwight, gets out and can go potty. And I don't know all the things. Yeah, I just said potty that a lot of these things are just stream of consciousness while I'm recording, so thanks for hanging in with me. But anyways, my brain has just always thrived on variety. I need variety, I like working on different things, you know, flexing different muscles.
Jenny 00:02:20 And I've been like this forever, even as a kid. and again, maybe this resonates with you. Maybe you're like this too. I'm going to share some examples of of things like back in 2015, I was working a full time customer service customer experience job in the tech startup tech world, and also a part time job at a grocery store. Shout out to sprouts! I was a cashier. and then I was also trying to do health coaching. I had taken a year long course prior to that, and was actually coaching six clients at one time. In addition to that, it didn't really go anywhere. My own personal choice, it didn't really align with my my goals as far as what I wanted to do, but I loved the coaching part, so. And I also I learned so much. I loved creating systems and I loved helping people solve these. I don't know, messy, emotional things and practical ways. You know, not everything can be solved with a green smoothie. But, you know, sometimes it's nice to have a little emotional support as you're sipping it.
Jenny 00:03:28 So, but it goes further back than that. I mean, in college, San Diego State, I was living in the dorms. I had my gateway laptop and an auxiliary mic from, I don't know, like Best Buy or something. I'd be sitting there, between classes, writing songs on my acoustic guitar, recording them on a program on my laptop, in between studying. Probably more songwriting than studying, I'll be honest. I would record them on CDs and then hand them out to friends, and I loved creating my little albums. I'm also taking surfing class because, you know, San Diego. But the point is, I've always had some kind of creative side gig or artistic outlet running alongside whatever my my main thing was, and even going back to like the early 20 tens. I was living in Philly for a couple of years and commuting to New York City for work. Eventually I moved there because yeah, that commute is bonkers. I was taking the bus. but I started playing an open mic night and booking some gigs.
Jenny 00:04:38 I got into this little singer songwriter circuit in the Philly area. shout out to World Cafe Live's open mic night. I played a winery in new Jersey every weekend. Surprisingly, new Jersey has wine, and it's good. I had a set list and everything, and people would dance to my music as I would play and get paid in wine. I'd work my job during the day, ride the bus back home. throw on my clothes, grab my guitar and go head to a gig. And it was a whole era. So looking back, I'm I'm really realizing something kind of big, and this has been on my mind lately, and I think I just have to get it out because it's important for me to share, because for so long and a lot of the conversations that I have with career flippers, I told myself that work, like capital W work, was my identity, that it was the only thing I was good at, that if I wasn't pouring everything into a job, into the company that I was failing, that I wasn't good enough.
Jenny 00:05:52 I didn't believe in taking vacation, and if I did, I had my laptop with me and I'd still be answering questions. I had a panic attack one time in front of a customer service team that I was managing. I just I gave everything to companies that, you know, eventually, I learned would replace me in a heartbeat because I got laid off, and I. I couldn't find a new job for two years, and I was just like, who am I if I'm not working? And it was jarring. It's like looking in a mirror and just you don't recognize the person that is staring back at you. But with a little distance and hopping into a new full time job and having a little more stability, which I'll talk about in a second. But I can see that looking back. I have always been trying to break the idea that work is all I am, Like, maybe I never really fully bought into that narrative, even when I thought I did because I thought I had to.
Jenny 00:06:59 Maybe I was already resisting in quiet ways, like writing songs, or flipping furniture and speaking at customer service conferences and creating courses and running webinars and blogging for customer service life. Or, I don't know, all the little things that I did on the side, even with the health coaching, maybe I've been building this, I don't know, multidimensional life this whole time, and I didn't give myself credit for it because I didn't feel I could. I didn't feel I had permission to say that I was more than just work, because it went against what I saw as a kid with my dad working so hard. What I saw in society with people wanting to climb the corporate ladder, what I thought I had to do To do these things and I don't know. So now you know, I'm here again. I'm doing multiple things and I've got a full time job. I'm flipping furniture on this side. I'm hosting this podcast. And yeah, sometimes it's exhausting. You know, sometimes it creative energy doesn't show up on the day it's scheduled to show up like Sundays, my furniture day.
Jenny 00:08:07 But, you know, creativity doesn't doesn't always have an RSVP. And sometimes that means turning down other things like an invite or event or something fun. Because if I say yes to that, I'm saying no to something else. And I've gotten okay with that. I've gotten really good at checking in with myself. Do I actually want to go out, or am I just afraid of missing out? Am I okay choosing me? Usually I am, but I never thought that I could give myself permission to do these things. So yeah, I don't know. Lately I've been thinking a lot about that, and also what I want from the furniture side of things. I love these furniture rescues, finding this junky stuff in the alley. Like I literally found this funky solid wood corner bookshelf with hairpin legs covered in mud and weeds in the alley down the street from my house the other day. It was so heavy I lifted in my car. There were freaking spiders all over the bottom of it. But I am going to give that a second chance.
Jenny 00:09:14 I love the rescues. I love finding these old crappy things and giving them second life. It's like therapy for me. They're soft with sawdust. But you know, another thing that popped on my radar lately is that someone recently asked me, would you consider doing furniture work that pays more? But, you know, you don't have to do the art and the restoration part of it. It's just literally get some furniture that hasn't been sold and you can sell it for what you want. And I had a visceral reaction, like my stomach churned. I was like, no, no, no, thank you. I don't I don't want that. And that response told me a lot. It told me that this kind of work, this creative spirit work, it feeds that side of myself. It I don't know, it sounds so cheesy, but it scratches some, like, artistic itch in a way that a job never has. But having both is really important to me because, you know, I may not know how to scale my furniture business yet, but I don't need to know that right now.
Jenny 00:10:25 I don't have to have it all figured out. It's working. It's enough. And same with the podcast. We're actually creeping up on the one year mark July 11th. I can't believe it. I never thought I was going to do a podcast, let alone have it running for a year. I actually have some episodes. Oh, I have episodes scheduled all the way into September. and honestly, I'm trying to figure out if I take a little pause in the fall, a little hiatus, and come back in January 2026 with more episodes and more, more fun things ahead with the career flipper? Or do I just keep rolling through like, I don't know yet. I haven't figured it out, but I think the cool part is, is that I finally feel like I can think about this stuff strategically. I've got financial stability from the day job. Thank you. I'm so grateful. The job has structure and some room for variety. I mean, and most importantly, it's not killing my soul so I can actually take a breath and look at things from a bigger picture view instead of constantly putting out fires and running on fumes.
Jenny 00:11:36 I think I just That's why my brain has been going towards all of these random thoughts that I'm sharing with you today. And yeah, I mean, this is all very long, and it's a slightly chaotic way of saying that. I used to think work was all I had, that it defined me, that it was me. It was all I was good at. But when I look back now, when the dust has settled, I think I had it all wrong. I've oh, maybe, maybe I've always been more than my job. And maybe I've always known that. Maybe I've always been building something else, even when I didn't know what it was going to be, because that is just the type of person I am now. I'm giving myself that permission that I hadn't given myself before to keep building it slowly scrapping Rapidly, imperfectly. So if you're still with me. Thank you for riding out that wave of reflection. I mean, if this resonated at all, or I don't know if you have been in a season where you thought you had it all figured out and then realized, oh, wait, maybe I had it backwards.
Jenny 00:13:00 I would really love to hear from you, so please hit follow or subscribe to the Career Flipper podcast on your favorite platform so you don't miss the next episode. And if you have advice or something you learned from your own journey that you think I could use on my journey, please share it. Or just if you have like unhinged stories of you trying to figure stuff out like help me feel less alone. DM me on Instagram at the Career flipper pod Hard is where you can find me. You can message me on LinkedIn, Jenny Dempsey. You can email me. Hello at the career flipper. Com or just go to the career flipper com website and send a message through there. Even if you just want to say hi or tell me you're also running on, I don't know. Scrappy raccoon energy. That's enough. I love hearing from you. And also, I guess this is probably silly, but just because I am curious, you know, if you got feedback on past episodes or maybe you have a favorite one, tell me about it.
Jenny 00:14:11 Or the ad that I have been dropping from my customer service courses. Please be honest. Tell me, is it cool? Is it working? Is it not? Just really helps me make the podcast better as I try to figure this all out? This whole thing only works if it feels like a conversation. I mean, it's me just rambling here in my home office with my dog sleeping on the the bed behind me or his dog bed behind me, and I got plants around. But I want to keep talking and I would love to talk to you. So keep going with those little itty bitty steps, because they're gonna lead you in the direction towards bigger things. It just takes time. Ultimately, I ask, what's the best that could happen? Thanks again for listening, for tuning in, for putting up with me. I'll catch you next time.