How I started The Career Flipper podcast
Honestly, I was just curious and wanted all the secrets from others...
CAREER FLIPS
Jenny Dempsey
1/7/20266 min read


I didn’t set out to start a podcast.
Just like I didn’t set out to start flipping furniture.
Both of those things happened while I was trying to survive a season of my life that felt confusing, uncomfortable, and honestly, kind of embarrassing.
When I was laid off from the tech startup world in November of 2022, I thought it would be temporary. I had spent years building a career in customer experience. I spoke at conferences. I taught classes. I lived on the internet talking about CX. I truly believed that was who I was.
And then suddenly, I wasn’t that person anymore.
If you want the full backstory on how furniture flipping entered my life during that time, I wrote all about it. But the short version is this: while I was applying for hundreds of jobs and hearing “no” over and over again, I started spending my days in the garage instead of on my laptop.
I went from Zoom meetings and Google Docs to respirator masks, sawdust, paint-stained hands, and junky furniture pulled off the side of the road.
And it felt weird.
Feeling Like the Weirdest Person in the Room
I remember going to networking events or meeting up with former colleagues and hearing the same question over and over again:
“So, what have you been up to?”
The honest answer was always awkward.
“The job search sucks. But I’ve been in my garage working on furniture.”
You could feel the pause.
Who does that?
Who goes from tech startups and customer experience strategy to sanding tables and hauling dressers home?
I felt wacky. Unsettled. Like I had fallen off the path and didn’t know how to explain myself anymore. I didn’t even think of what I was doing as a “career change.” It just felt like something I was doing to stay afloat.
And then one day, I got on the phone with my friend Nick Musica.
The Phone Call That Changed Everything
Nick and I used to work together years ago at a tech company. He was the SEO guy. Smart. Analytical. Deep in the digital world.
We hadn’t talked in a while, and when we caught up, he asked how the job search was going. I gave my usual half-answer. Then he said, “Do you want to hear what I’ve been up to?”
Sure.
“I’m doing animal psychic communication readings now.”
I was standing in my garage during that call, fiddling with a piece of furniture, covered in dust, and I just froze.
Animal psychic communication.
I didn’t even fully understand what that meant. But what I did understand was this sudden rush of relief.
If this intelligent guy — someone I knew from my former life — could do something that unconventional maybe I wasn’t as strange as I thought.
Maybe it was okay that my life didn’t make sense anymore.
The Validation I Didn’t Know I Needed
After that call, I posted something tentative on LinkedIn. Nothing polished. Just a question.
Has anyone else done something totally different with their career?
People responded.
Not hundreds. Not thousands. But enough.
Enough to make me realize that people were quietly doing all kinds of things they never talked about publicly. Enough to make me feel less alone.
I started hopping on Zoom calls with people who had made career pivots: some planned, some accidental, some born out of necessity post layoff. And every conversation felt deeply validating.
I wasn’t crazy. I wasn’t broken. I wasn’t failing.
I was just in transition.
The Dream I Couldn’t Shake
Around this time, I started dreaming again. I hadn’t really dreamed much before, but after the layoff, it was constant.
In one dream, I was sitting in a gray-walled recording studio. There was a microphone in front of me. On the wall behind me was a neon sign that read: The Career Flipper.
I woke up like, "what the hell was that?"
I tried to brush it off. But the image wouldn’t leave me. And at the same time, I kept meeting people everywhere, walking my dog, chatting with strangers, running into old colleagues, who had wild, unexpected career stories.
It felt like the universe was tapping me on the shoulder.
So I did what I’ve done my whole life when I don’t know what I’m doing next.
I tried.
Making a Podcast With No Idea What I Was Doing
I had never hosted a podcast. I had no idea how to make one.
I reached out to a few people I knew who had podcasts and asked dumb questions. I Googled things. I watched YouTube videos. I figured it out the same way I figured out furniture flipping, one step at a time.
I asked Nick if he’d be my first guest.
We recorded the conversation on Zoom. I edited it in GarageBand. I researched hosting platforms and distributors. I pieced it together.
I told myself I’d just do eight episodes. That was it. A small project. A creative outlet.
This was May of 2024. I recorded everything in advance. The podcast launched in July 2024.
Eight episodes turned into sixteen. Then more. People started introducing me to other people. I slid into DMs. I followed curiosity.
And something surprising happened.
What the Podcast Did to Me
These conversations lit me up in a way I hadn’t felt in years.
There was this electric feeling, like blood returning to a limb I didn’t realize had gone numb. Talking to people about reinvention, identity, fear, and starting over felt like oxygen.
I was still applying for jobs. Still doing contract work to pay rent. Still sanding furniture in the garage.
But the podcast became this thread of meaning running through all of it.
I started sharing my own story in solo episodes. I even wrote a song and shared that. I let myself be seen in a way I hadn’t before.
The show grew quietly. Organically. No big launch strategy. No flashy marketing. Just real conversations.
Eventually, those eight episodes turned into 87.
People listened from all over the world: the U.S., Spain, France, Australia, and other places too. Sometimes I’d stop and imagine someone walking through a park in Australia, or riding a train in Spain, or grabbing a baguette in France, all listening to these stories.
It still blows my mind.
The Complicated Middle
The podcast wasn’t perfect.
Editing took a lot of time. I cared deeply about keeping the conversations honest and unpolished, which ironically took more work. I wasn’t great at promoting it. I didn’t love being loud on social media.
There are a hundred things I could’ve done differently.
But every guest became a teacher. A mentor. Proof that there are a million ways to build a life.
Where This Fits Now
I never meant for the podcast to become a big thing.
But it became an important thing.
It reminded me that trying, even awkwardly, is better than standing still. That curiosity can be a compass. That identity doesn’t have to be fixed.
The podcast was born from the same place as the furniture flipping: grief, uncertainty, and a quiet refusal to give up on myself.
And even as it evolves, that spirit still lives here.
Where It Landed
In January of 2025, I took on a full-time corporate job again.
It was the right decision. Bills still needed to be paid. Stability mattered. I don’t regret it.
But pretty quickly, I realized something else.
I was working a lot. Between the day job, furniture, and the podcast, I was easily clocking 55, sometimes closer to 60, hours a week. Nights. Weekends. Early mornings. Always squeezing one more thing in.
That wasn’t what I wanted.
The whole point of starting the podcast, and furniture flipping, honestly, was never to work more. It was to feel more like myself again.
And now, I had to ask a hard question.
The podcast had been going for about a year and a half. I had recorded 87 episodes. I had talked to people all over the world. The conversations were meaningful and powerful, but the work behind it was starting to feel heavy.
Editing took time. Scheduling took time. Hosting, producing, posting, it all added up. I was funding it out of my own savings. And as much as I loved it, it started to feel unsustainable.
So I had a decision to make.
Do I keep going exactly as I am?
Or do I let this evolve into something that fits the life I’m actually living now?
I chose evolution.
The podcast didn’t end, it changed shape.
What mattered most to me wasn’t the format. It was the stories. The honesty. The space to talk about reinvention, creativity, grief, identity, and second chances, including my own.
So now, that storytelling lives here.
In writing. In furniture. In sharing what I’m learning as I build this alongside a 9-to-5. In telling stories — mine and others’ — in a way that feels manageable, intentional, and true.
If you’d like to follow along, I send a monthly newsletter where I share reflections like this, updates from the garage, and what I’m learning as I go.
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