One year of flipping: Cocoon reflections, career chaos & an original song
Welcome to a special solo episode of The Career Flipper Podcast! It’s the podcastaversary!
One year ago, I hit publish on the very first episode of this show, having no idea what I was doing and definitely not realizing how much it would change my life. What started in the messy aftermath of a 2022 layoff (and 400+ job rejections) became a permission slip to rebuild, to reimagine success, and to start over without a map.
In this episode, I share the behind-the-scenes of how this podcast came to be, how flipping furniture helped me flip my identity, and how conversations with guests like:
Nick Musica, a former SEO guy turned animal psychic
Trish Jasinski, who bought a chateau in the south of France and left corporate to open a retreat space
Cat Cheng, a former music teacher turned Netflix-featured baker (hi, tres leches dreams)
And Case Sandberg, who I met at a farmer’s market and learned had just left his software engineering job to become a chocolate maker
…helped me feel less alone and more alive.
Oh and I’m sharing a piece of my music. I wrote a song called Just Wait, about getting laid off, getting lost, and learning how to come back to yourself.
Skip to 14:28 if you want to jump straight to the song.
Whether you’re in the middle of your own career flip, cocoon season, or identity unraveling, I hope this episode reminds you that you don’t need permission from anyone else to change your life.
You can give it to yourself.
🎧 Listen, share, and leave a review if this one resonates.
Welcome back to the Career Flipper Podcast. I am your host Furniture flipper and career flipper, Jenny Dempsey, and you have found July's Cocoon Conversation episode. This is one of those episodes I do on the last Tuesday of every month. It's just me, no guest, just I'm sitting in my home office actually standing at my desk.
Uh, my pup Dwight is snoring in his dog bed behind me. Um, I do these episodes because throughout the month I am interviewing career flippers from around the world and they are sharing their stories. So I thought it was only fair if I do an episode where I focus on my story because a lot of people ask about it.
So here we are. And this, my friends, is career flipper Month. Well, I guess we're at the end of July, so it's almost over. But July 11th, 2024 was the day that the Career Flipper podcast launched. So we are at the podcast anniversary. It's been one year since I hit publish on the first episode. I mean, what, like, how is that even.
Possible, like the wildest part is this show wasn't even something that I was planning to do. It came out of this like grief, is that even a word? Uh, floaty. Kinda what now? Space I landed in after I got laid off back in 2022. At the time though, I didn't know that the layoff would be one of the best things that ever happened to me.
I just knew that I felt fricking lost. I felt scared, like my whole identity had been yanked away because I'd spent so long in my career being the reliable one. The people pleaser, the overachiever, the one who answered the slack messages after hours and said yes to everything, and then boom, gone. No job, no plan, no paycheck, and I just completely lost my sense of self.
And in the two years that followed, I applied to over 400 jobs. Which sounds crazy. Um, I got ghosted rejected. I mean, I cried on the couch more times than I can count. Uh, and in between all that, I started flipping furniture, like, yeah, literal furniture, stuff that people throw away and put on the curb. Uh, dressers with missing drawers, chairs with scratches and broken legs.
And I don't know, something about sanding down these old layers and painting or wood staining new ones helped me feel like. I was doing that for myself too, and I didn't actually know how to do that at first. I, I taught myself and just did a bunch of researching online and asked a lot of questions to very confused Home Depot and Lowe's employees.
Um. But, uh, ultimately I picked up a few freelance gigs and contract gigs throughout this time too, like some really cool stuff with really kind people. One client even took me to Paris, which still blows my mind, but none of these opportunities like fully paid the bills. So it was like I had all these beautiful puzzle pieces and no idea what picture I was building, and then not like.
I guess metaphorically speaking, I, I found myself kind of like in a cocoon. I wasn't hiding on purpose and I felt like this old version of myself was dissolving and I was rebuilding it and relearning like what success meant and letting go of this ladder, this, this career ladder that I thought I had to climb, but honestly wasn't sure I really wanted to anymore.
And slowly, very slowly. Starting to give myself permission to want something different because that's really what this podcast became for me. A permission slip to try something new, to stop waiting until I felt qualified to have a messy conversation with people around the world who flipped their careers, flipped their lives.
In the coolest, most unexpected ways and all the ups and downs in between to get there. And now one year later, there are over 60 people, 60 guests, 60 mentors. I call them mentors who let me slide into their dms, who agreed to come on my little show, who let me pepper them with tons of questions and get really vulnerable and share.
What they have learned and now it's available for everyone to listen to every week. And it is just, I think I'm still, I, I look back and I'm like, wait, I did that. I didn't even know how to do that. Can I even do that? I didn't think I was good enough to do that. Like, okay. My very first guest, Nick Musa, who I used to work with back in the tech world, and he, he was the SEO guy.
Totally normal day job. He's really good at it. Now. He does animal psychic readings. I mean, I kid you not, he's amazing. He also goes around and speaks about it. That first episode, I listened to that and I'm just like, wow. It cracked me right open to what is possible. Then moving forward into the future, there's Trish Dinky, who I actually saw on a show, Chateau DIY.
She literally bought a chateau in the south of France on a whim, uh, eventually leaving her corporate job and now runs a retreat in event center. I slid into her dms and was like, hi, can I talk to you about this? Fairytale life that you created. Uh, and now I am literally saving up to go out there and visit and stay for real.
It will happen. I will show you pictures. Just wait. Um, or Kat Chang, who I also show I saw on a TV show. She was on the Netflix Blue Ribbon Baking Championship, and the second that I heard her say she used to be a music teacher and now she's a baker, I was like. Yes, that's my girl. Come on the podcast. And now the next time I'm in New York, not sure when that's gonna be, but I dream of trying her tris.
Let's chase cake one day. Oh, and maybe I'm hungry right now, but there's also Kay Sandberg, who I met him at a local San Diego farmer's market while sampling chocolate at his booth and found out that he literally had just left his job as a software engineer to become a full-time chocolate maker. Like, you can't make this stuff up.
The stories find me, I dunno. Or I find them, or, or, or we find each other. But either way, there's, there's 60 stories of all sorts of industries and, and people and career flips of all different shapes and sizes. And, and now this little thing that started out of total, I mean, I'm gonna call it emotional chaos, uh, has turned into something that I could have never imagined.
It's been my anchor, uh, my therapy. As I mentioned, every single one of these guests on the show is a mentor to me, and it's a reminder that second chances aren't just possible. They are powerful and absolutely available, and we have permission to take them. And so I think the thing is also is that if you're listening.
To this, and you're in your own cocoon moment right now. Maybe you're untangling or I don't know, you just got laid off or you wanna change, or you're starting to ask the like big what ifs. Like you're not behind in anything. Age. Age is not gonna get in your way. You're not broken, you're not too late, you're just beginning.
And, and you don't need permission from anyone else to change your life, but sometimes we need to know that it's possible. And I want each and every one of these episodes from these amazing people around the world to be your permission slip. You can give it to yourself. The show gave me this, and I just really hope it gives you that too.
So thank you for every single guest who has been on the show. I for letting me slide into your dms or email you or text you, or you giving me the time to be on, share your wisdom and, and your kindness and your mistakes and, and your vulnerability with me. I, and then let, letting me put it out there into the world where I thought, okay, maybe if one person listens to this and gets something out of it.
And then suddenly there are thousands of people listening to it, like in different countries. There are someone on a train in Barcelona listening to an episode. There's someone walking down the cobblestone streets in Paris listening. Uh, there's someone maybe walking under a tree where there's a koala in Australia.
I hope that's okay to say that. Um, or, or maybe, you know, in different states, in the United States and, and, and all across different places in Europe, like, it, it just, it's, I look at the map and I'm like. I didn't even know this area existed, and then I get messages from people, I read the reviews, and I'm just like, wow, this is impacting people.
So thank you. For listening, for sharing your story, for pressing play, for every single dm, for every review, every rating, every story you've shared with me, what you've learned, what you took away, more of, what you wanna see and hear. You've helped keep me going, like for real. I just, uh, I'm getting a little emotional over here, but, um.
Before I go on this episode, I know this is, this is something a little personal, might be a little different, but music has always been a part of my life. I am, I grew up writing songs, playing guitar when I was a kid, the Fender Guitar Museum in Corona, California. I was a part of their kids rock free program.
I learned how to play guitar there. Lee Zimmer, my guitar teacher, shout out to him. Um. Uh, and John Page, who ran the museum? Um, our little band, the Fender Benders, we would tour around. Um, I'm, I'm thinking back now, but it really inspired me to keep writing songs, to keep playing guitar. I started doing open mic nights.
Gosh, at one point I even had a winery gig when I lived briefly in, on the East coast. Um, they paid me in wine, sometimes cash, but wine, no complaints. Um. But as I got older and work took over, I let it go. I'd go through these cycles where I would dig into music because I mean, I started playing when I was 11 and um, when work got busy, I just let it go.
I didn't think I was good enough. I didn't really have any formal singing lessons, so to say. Um. I, I honestly thought my music didn't count. I thought it was cheesy. Um, I thought, you know, I need to be productive. I need to be making a paycheck. I, I need to be doing things that matter. And me singing my little acoustic guitar songs that I write in my journal, um, you know, who am I?
Who am I to do that? I'm, I'm No Taylor Swift. I'm no Adele. I don't sound like Celine Dion, but, um. I have recorded little albums in the past, and I was always so proud of them. And then I would just kind of shove 'em under the rug. It was even a point where I was singing a little business conference, well, not little, but business conferences, because I was just like, so wanting to bring music into my life, and then I would just be like, um, this is dumb.
What am I doing? I'm so dumb. But I've been singing again more lately, and. A lot of it is with my furniture. If you follow me on Instagram, San Diego Furniture Flipper, uh, a TikTok as well, I sing with my furniture. Yes, that sounds wacky. Uh, but yes, I do it. But this year I also wrote a song, um, it's called Just Wait, like a Full Song, and it's about getting laid off, feeling completely lost, and learning to trust that something new might still bloom.
It's a little vulnerable, and honestly, it just means a lot to me because I'm leaning into music again and I wanna sing it here on this episode for you so you could listen to it. I don't have a Spotify music page or anything like that, so I don't know. I just, I wanna do that. So I'm gonna do that here in a second.
But before I do that, if something's been. Flipping in your world, career, your mindset, your identity, your your holding life. Uh, I'd love to hear about it. Like find me on social media, LinkedIn, Instagram, TikTok, email. Um, send me a message. Send me a voice note. I don't know, is there something that you've been hearing whispering to yourself and you're like, ah, this sounds nuts.
I don't think I could do this. Like, tell me about it. You don't have to know where it's going. You just gotta start. So happy podcast anniversary to you, my career flipper audience, I love you so much. Seriously, if, if we meet in person, when we meet in person, you will get a big, old awkward hug from me or a handshake.
If hugs aren't your thing, I'll respect that. But thank you for being here with me. Let's keep flipping. Let's keep taking the tiny baby steps because honestly, what's the best. That could happen. Okay, let me get my guitar on. 16 years intake startups and customer service win. Got,
I thought my job was all I was good at. So who am I without the work?
I brushed up my LinkedIn in my resume only. I get rejections piling up every day. I wiped my tears and looked at the world through a new lens. Started seeing second chances in places Never been. Because if Weno is a redirection, then if Weno is saying yes, something else. Don't doubt yourself when it feels like all the doors are closing, just wait
because the rat ones are gonna open.
Turns out I.
Even when I don't believe in myself, I don't need a title to know what I'm worth. I build new beginnings from what others leave on the curve.
It messy can be full of. What am I. And how to end up ears, but I keep showing up just a little bit more each day because what's the best that could happen in every step that you take? Because every is a redirection and Aveno is saying yes to something else. Don't doubt yourself when it feels like all the doors closing, just wait
because the rat ones are gone open
and maybe. Then not sticking to the noise. 'cause I'd rather pave my own way. The one that's already been more this path. It's messy and it can be you, but I've learned love. What am I doing? And, and the, I keep showing up. Just a little bit more each day because what's the best that could happen in every step that you take?
Because every no is a redirection. And if now is saying yes, something else. Don't doubt yourself when it feels like all the.
Wait, wait. Every No is a redirection and every no saying yes something.
Don't settle when it feels like all the doors closing. Just wait.
Because we're at.