Cocoon Conversations: Host Jenny Dempsey's Career Flip Progress for March 2025
In this episode of the Career Flipper podcast, our host Jenny Dempsey gets real about her journey back to full-time work after being laid off for two years. She opens up about the tough times she faced while applying for over 400 jobs and how each rejection hit hard, making her question her identity, which was so tied to her career. Jenny also talks about her adventures in flipping furniture and podcasting, highlighting how important it is to have the mental space to chase your passions. She sees her new job as a solid base that helps her keep dreaming big. Jenny's message to listeners? Embrace your unique career journey and lean on your community for support when you're going through changes.
Automatically Transcribed With Podsqueeze
Jenny 00:00:02 Hello and welcome to the Career Flipper podcast. I'm your host, Jenny Dempsey, and if you're new here, this is the place where we talk about the absolute roller coaster of career changes. Usually I bring on guests to tell their stories, but once a month I do the solo cocoon episodes where I just talk. No fancy production, no expert advice. It's just me in real time, figuring out my own career flip. Because I don't know. I think that if I'm going to ask guests to be honest about their career flips and get really vulnerable and ask them random questions, I should. I don't know, I feel it's only fair for me to do the same. So welcome to the March Cocoon episode. Here we are. All right, so I'm officially back in a full time job. It's been a couple months now. And I've been. It took me two years after I got laid off to find a full time job again. And to be honest, I wasn't really like after a while.
Jenny 00:01:18 Like, I had applied to 400 jobs, over 400 jobs, and I just, like, wasn't sure that I wanted to go back into corporate life. So I had actually stopped applying toward the end of like, like fall of 2024. I was just like, I think I'm done. I think I'm just like, gonna let that go because I don't want to be back in corporate. I don't trust it. you know, I don't want to be a number again. and I had some very small scale, like, contract roles and the furniture flipping business that I was building, as well as a podcast. and I, you know, in the past, my career path, my career itself was so tied to my identity. So when I was getting these job rejections, it felt so personal. And I think that really just led me into the way of not wanting to go back to corporate because I was just like, whatever, they don't want me. but I really worked through that identity, untying it like I'm not my job.
Jenny 00:02:29 There are a lot of core values. There are a lot of things that I am, but I am not just a corporate job. and then throughout the two years that I was laid off, I just got really resourceful. And if they weren't going to hire me, I'm going to hire myself and did that small scale consulting and really leaned into furniture flipping and kicked off the podcast. And honestly, like, I love the variety, the flexibility that, you know, working for yourself offers. I was definitely working more than I was when I was working any corporate job, but I had this anything as possible mindset. Like I would wake up in the morning and feel like like yeah, anything was possible. I will be honest, I did not love having little to no money in my bank account. I didn't love when a client that I was working with suddenly said, we can't keep you on anymore. that was I mean, the financial part was very difficult and very stressful. Figuring out medical benefits was the same.
Jenny 00:03:43 So this when this job opportunity that I just started back in January landed on my path, I really had to consider a lot of things. and now here I am, you know, two months in and two days a week, I put on pants other than jeans and shoes other than my Nike's. I drive to an actual office. and existed in a space with humans and not just my dog in my remote home office or in the garage. you know, the first couple of weeks, I really felt weird. it's kind of like, I. I doesn't sound so weird, but, like, I had signed up for some experiment to see if, like, this. Like, feral, resourceful raccoon, remote worker, garage workshop person could reenter, like society. But I will say it's getting a little easier. I mean, my coworkers are really good people. there's free organic fruit delivered to the offices on the days that I go in. And, I don't know, it's the little things like that that help.
Jenny 00:05:07 But again, you know, I won't lie, this accepting this job, which I am very grateful for, did come with a lot of emotions. I had really built this like whole new lifestyle around being independent, and I've always been so fiercely independent. But when I really didn't have anything, it just became so much more for me and making my own way and not relying on a 9 to 5 to pay my bills, and instead like seeing a piece of furniture on the curb and thinking that will pay for groceries this week. you know, and so when I accepted this job, my brain really went into this kind of crisis mode. things like, does this mean that I failed, you know, my giving up on my dreams again because I've done things like that in the past, was all of that struggling for nothing? And then, I don't know, somewhere between my morning commute and listening to Mel Robbins podcasts and my third free Banana on Free Fruit Day. I realized the job is not the enemy.
Jenny 00:06:21 It's actually the investor in my dreams. So I get to work with cool people. I get to do work that isn't soul sucking, and I have health insurance. But more importantly, it gives me the mental space to keep building the things that I love. Like this podcast and furniture flipping and all these other really cool things that I am going to build down the road, like writing a book and doing career change coaching and, speaking events and who knows what else. You know, I spent years in the past chasing what I thought was this right kind of success, these, like bigger titles and more money and more responsibility. I, you know, worked in corporate with my regular salary, but I was pulling, you know, 50, 60 hour weeks because I thought I had to I climbed that ladder in the startup tech world and customer experience and customer service. And I mean, there were parts that I really enjoyed, but most of those go back to the people that I worked with. and I also just really overworked myself.
Jenny 00:07:41 I ended up with a lot of exhaustion and anxiety attacks and, I don't know, just like resentment. and this time when I, you know, took on this role, I, I really did the opposite. you know, I took on a job that's actually a lot lower than where. And I say this in quotes where I should be, you know, in my career, where others think I should be. I chose something that wouldn't drain me so I could keep doing the stuff that lights me up. And yeah, there are some people out there that don't get it. They think I'm nuts. I've had more than one person tell me, gosh, with your experience, you could be doing so much more and making so much more and sure, okay. I mean, I have 400 job rejections telling me no, maybe I couldn't, but, you know, at what cost would it have been had I taken on or gotten something like that, like my sanity, my creativity, my ability to get through a day without wanting to scream into a pillow or, I don't know, no.
Jenny 00:08:51 No, thanks. No, I, I learned, you know, when I got laid off and I was literally making $0 a month, and feeling. Which just sounds crazy wealthier than I had ever when I was making, like, my six figures. I'd rather be a little broke and a lot happy Then the other way around. And just. Gosh, I've just been reflecting so much. I try to script these episodes, but it never turns out that way. But I realized that, you know, throughout my career, like, even looking back before I got laid off, I'm just not the type of person to just do one, one job. I've. I've always juggled side things. music. singing. And in guitar. I took I got my health coaching certification, and at one point I was, working a full time job. I was working as a cashier at sprouts part time, and I was health coaching six clients. I have done content writing. I've blogged, and now flipping furniture mentoring.
Jenny 00:10:05 I don't know, I've never been diagnosed with ADHD, but I don't know, maybe I'm just really afraid of being bored or I don't know, but if there's a space in my life, I will fit it in if I want to do it. And so my schedule, like, I'm very adaptable. I can get a little stubborn because I'm very routine oriented, but once I figure out a routine, I really stick to it because I firmly believe in consistency. and so, like, right now, the way things are kind of panning out, you know, in the morning, 30 minutes before work starts, I use this time to, post content on my San Diego furniture flipper, Instagram and TikTok. on my personal LinkedIn, I schedule things as well. and then on my lunch breaks, I'm, you know, interviewing career flippers. I'm also, if I don't have an interview that day, I'm editing episodes. or scheduling it out on my distributor. and then every single Sunday, I am sanding down some kerbside find and turning it into something beautiful and filming content and writing songs about it, and really prepping for the week and getting things staged and ready to share.
Jenny 00:11:29 So, you know, it's it's chaotic. it's it's kind of wacky. it's work. I mean, all of these things are work, but it doesn't feel like work the way work feels like. Work like, does that make sense? I don't know, but it's, I just I guess I just have to put it out there that, like, it takes structure and consistency and just keeping keeping on. even when I feel like, wow, I'm so weird, I am, I don't know, that I don't know what I'm doing, but I can't not do it. Does that make sense? so I guess, you know, if you're listening to this and you're also in the middle of a career flip like, or maybe you're even thinking about one. The things that I'm learning, you know, you don't have to follow anyone else's definition of success. you can take a job for stability. It doesn't have to be, you know, what you're going to do forever. but you can you can take it on.
Jenny 00:12:43 Well, building something else in the background. you don't have to chase money if it cost you your happiness and your, like, your health, you know? Of course, like, we got bills to pay. There are things we need to do. A lot of you listening have families. you know, we got to keep a roof over our head, so there's things that we need money for. but we gotta look at what what we need versus, like, what we really want. Like, I knew, like, back when I, you know, was working full time. Like, I didn't need to go shopping every weekend. I could do without without that. And so, I mean, yeah, there's just little things that we can rethink. and you're not behind in any way. You're exactly where you need to be. And you're not weird. You're not crazy. you know, you might feel lost, or maybe you feel like you got no clue what you're doing. And I am right there with you.
Jenny 00:13:46 And. And the cool part is, like, we don't have to figure this all out alone. I, I thought that I was really on my own island, and it turns out I'm not. And you'll find your people. I found my furniture flipping people. There are hundreds of people that are flipping furniture. woodworking. I will chat with them. I will ask them questions. We'll talk about our dogs. Well, I don't know, talk about challenges we're facing and how a lot of them are also working part time, full time, multiple jobs to make ends meet and work on their passions. And I just I think you'll find your people. and I really hope that this podcast can be a resource for you that, you know, you're not alone in this, and that there's a whole, a whole bunch of others out there trying to figure it out, too. and we all got to lean on each other. Right. So thank you for for being here, for listening to this whole thing.
Jenny 00:14:54 thanks for being part of this wild, messy, confusing, wonderful journey with me. It is just it's so nice to not feel so alone. So, on that note, I hope that you'll subscribe to this podcast. There are new actual career flipper interviews every single Thursday on any podcast platform and I hope that you will listen to them. I hope that you will share them with your friends and your fellow career flippers. So we all know we're not alone, and we all know that someone else is doing something really bold. And if they can do it, you can absolutely do it too. And if you are on LinkedIn, connect with me. Just search Jenny Dempsey. Patrick. Just like Patrick, that's my last name. Dempsey not related that I know of, but, Jenny Dempsey, find me on LinkedIn. Let's connect. You can tell me your career flip story if you want to be on a future episode. I would love that. and then I don't know if you want to. Furniture flipping is something of interest.
Jenny 00:16:08 follow San Diego Furniture Flipper on Instagram and TikTok, and you can see what I am working on. You can also follow the Career Flipper pod on Instagram. We're over there too. I don't know why I said where. It's just me. and all of my wonderful guests. So I guess it is aware. But on that note, thank you for listening to my Unhinge unscripted cocoon episode. I will be back next month with another one just like this to document my career flip journey and just know that you got to keep taking those next steps. Keep going, keep going. You never know where that one little step is going to take you. I always love to say what's the best that could happen? Because seriously, there's a lot of good stuff out there waiting for you. You just got to take that step. Thanks again for listening and I will talk to you soon.