Cocoon Conversations: My career flip progress for February 2025 and first month back in corporate.
In this episode of the Career Flipper podcast, host Jenny Dempsey shares her personal journey of transitioning back to corporate life after a period of entrepreneurship and creative pursuits. She discusses the emotional challenges of adjusting to a structured work environment, the importance of finding balance between her corporate job and her passion for furniture flipping, and the ongoing struggle with imposter syndrome. Jenny emphasizes the need for self-compassion during times of change and encourages listeners to embrace their messy career journeys.
Jenny Dempsey (00:02.434)
Hey flippers, welcome back to the Career Flipper podcast. This is the second installment of what I'm calling Cocoon Conversations. I'm Jenny Dempsey, a host and fellow career flipper. And basically, if I'm out here asking career flippers from around the world to get all deep and vulnerable about their career journeys, I only felt it fair that I do the same. So each month on the last Tuesday, I'm gonna share my own messy updates because
Spoiler alert, my career is still doing that whole pivoting thing. It's like my job path is that friend who can never decide where to eat for dinner. So yeah, here we are. Still flipping, still podcasting and furniture flipping and now back in corporate life trying to juggle all the things. It's a journey and I am so glad to have you here with
So it's been about a month since I went back to corporate life in a hybrid role. And wow, let's just say what a ride. I feel like I need one of those, I survived my first month back t-shirts. If that is even a t-shirt, I would totally wear it. Cause honestly, the transition was rough at first. Like emotionally and energy wise, I was not okay.
So, okay, let's start with the office part. The company is amazing. The people are ridiculously nice and there are coffee machines and a really fancy water machine. I drink a lot of water. I love having that so close by. So on paper, it's all fantastic. But after two years of working from my garage turned furniture workshop, podcasting in my home office, and basically living in paint stained overalls, stepping
back into a structured environment really felt like I was kind of dropped on another planet. Suddenly I had to remember how to small talk and schedule my day around actual meetings instead of just when Dwight, my rescue pup, needed to go pee. You know, I came home from those first few weeks, just two days in an office, completely wiped.
Jenny Dempsey (02:21.88)
Like someone had pulled my emotional plug out of the wall. And honestly, I think a big part of it was trust. And I'm really thinking back because for two years, I was just trying to find my footing after getting laid off. I built this whole creative, scrappy career path for myself. And I learned to kind of trust my instincts again. But going back to corporate startup, this weird inner dialogue like...
Can I still thrive in this place? Can I be myself? Am I doing enough? Do people like who I am? Do people like me? Then came this other wave of thoughts. Do I still have grit? Am I just having some sort of existential crisis? Like, why is this so hard? It's two days in an office and three days remote. I mean, I'm no stranger to tough situations.
I was frustrated with myself for feeling so out of sorts. It made me question if I was really cut out for this anymore, whether it be corporate life or even entrepreneurial work. But then I realized it wasn't about grit. It was just a big change and I needed to give myself grace to adjust because really that's the thing with change. It shakes everything up, even when it's good change. And so I had to get really structured.
Because getting my footing in this change, just needed something. So that's where Sunday's come in. So I declare Sunday is my official furniture flipping day. I had a heart to heart with my partner and was like, listen, this is sacred time. I need it. And he's like, you got it. So now every Sunday I spend five or six hours getting my hands dirty, flipping curbside fines.
client work and really getting lost in that creative work and it just lights me up. And it's been a bit of a reality check too because I went from spending about 15 to 20 hours a week on furniture projects in addition to kind of like small scale consulting projects, really down to about five hours a week. And that stings a little. Sometimes I walk past my garage and I see pieces waiting to be flipped and I'm like,
Jenny Dempsey (04:44.394)
sorry friends, I'll be back soon, I promise. It looks like they're giving me sad little looks with their chipped paints and wobbly legs, you know, and then there's the Career Flipper podcast and this has really become kind of an after hours, weekend, squeeze it in wherever I can fit it in project and I'm sneaking in editing, you know, a little bit later at night or scheduling interviews on my lunch break and I love it too much to stop and I have received
way too much feedback from others around how it's helping them. And so I have so many goals about furniture flipping and the podcast, you know, speaking at events, writing a book, doing more client projects. I just, I can't give it up. So I had to find time to fit it into my schedule to make sure one, I don't burn out and two, I can still maintain
the energy and attention needed at the day-to-day corporate job. And so I also have to be real with you for a second because there's also been this imposter syndrome creeping in. Because while I'm doing all of these things, and sometimes I'm like, wait a second, who am I to host a podcast about career changes when I'm literally still trying to figure it out myself? And then...
I just have to keep telling myself that's the whole damn point. know, none of us, I'm guessing you listening too, don't have everything figured out. And maybe that's what actually makes these conversations worth having, just because they're real and they're messy, just like life. So if you're in a season where you're also juggling a million things and trying to balance the old version of yourself with the new one and wondering,
how the heck it's all gonna work out. Same, you're not alone. But I think the key is just showing up, even if it's not pretty, to keep doing the things that light you up, even if it's just for a couple hours a week, and give yourself grace for the parts that are not picture perfect. So I'm gonna keep sharing these updates every month, so stay tuned for that, make sure to subscribe, and don't forget, you can also catch...
Jenny Dempsey (07:04.494)
Career Flipper interviews with incredible guests from around the world every single Thursday. So make sure to subscribe for updates. I don't want you to miss any episodes. And if any of this resonates with you, if there's something you're going through and you heard me talk about it on this episode, will you email me and tell me what resonated? Hello at thecareerflipper.com is my email address. It goes right to me. It doesn't go to any...
Support inbox. It's literally just straight to me and I guess I'm curious if doing these types of episodes or even I don't know is it helpful Should I be burying my soul like this or is it just I don't know I would just love to hear your thoughts and if you know someone who's thinking about a Career change or maybe you are also going through one or in the middle of one, you know
The best thing you can do is talk about it. So if you know somebody, share an episode with them. Let them know they're not alone in feeling all the feelings because it's a lot. And if you have your story to share, I am actually still accepting new guests for the podcast. Head over to thecareerflipper.com and you'll find a place right on the top of the website to submit your story. I would love to hear from you. So.
I'm going to stay on this path. I'm going to keep figuring it out. I'm going to keep taking the steps even when I don't necessarily know when it's going. I'm challenging myself. I'm talking about my feelings. I'm not just saying everything's fine. And so honestly, if that resonates with you, if that is something that makes sense for you in your life, I hope you do it too and know that I am right there, right beside you.
So keep taking those steps because the question that I have to ask you is, what's the best that could happen?