How I got started with furniture
My origin story
FURNITURELIFE LESSONSCAREER FLIPS
Jenny Dempsey
1/7/20265 min read


It Started Before the Furniture
If you had met me a few years ago, I would’ve told you exactly who I was.
I worked in the tech startup world. Customer experience. Customer service. That was my lane. I was good at it. I built my entire identity around it.
I taught people how to care about customers. I spoke at conferences with Zendesk, ICMI and SupportDriven for customer service professionals. I ran webinars. I was on podcasts talking about CX. I taught two Udemy classes for beginner customer support agents (that are actually still online). I sat on the board of CX Accelerator, a customer experience organization. I lived and breathed this work.
I worked a lot of hours. Work always came first.
Everything else — music, creativity, reading fiction books (business books only at this time) — lived on a shelf. Sometimes I'd cancel plans with friends to instead work later. I would take trips but I'd work on them, even with unlimited PTO. Work was the priority.
I really believed that this was what I was good for. That this was my contribution. That this was who I was.
And then my dad died.
Losing My Dad
My dad passed away in March of 2022.
He had just come out of an induced coma when he looked at me from his hospital bed and said, softly, “I wish I wouldn’t have worked so much, Jen. I wish I would have spent more time getting to know you.”
It stopped me cold.
My dad was a Bronze Star recipient. A Vietnam veteran. He lived with PTSD that was never diagnosed or talked about. He taught me my work ethic by example. He worked hard. He showed up. He provided.
He also drank and smoked a lot. He made some questionable choices with women. He was complicated. And while I know he did the best he could with what he had, the version of him I knew best was the worker.
As he got older, he’d call and tell me he had about thirty minutes to talk. We’d fill that time talking about houseplants, non-dairy milks, travel, and of course, work.
And then suddenly, he was gone.
I didn’t understand it in that moment, but something had shifted. The ground under me had already started to move.
The Layoff
In November of 2022, I was laid off.
At first, I wasn’t that worried. I had a solid resume. A strong network. A clear specialty. I thought, I’ll find something. I always do.
But weeks turned into months.
I searched LinkedIn obsessively. Job boards. Recruiter calls. Virtual coffee chats. Networking events where everyone pretended not to be scared. I told friends I was “exploring options.” I applied anyway.
I kept track of everything. Spreadsheets. Notes. Dates.
Over two years, I applied to more than 400 jobs.
I was rejected by companies I was overqualified for. Ghosted entirely by others. Auto-rejection emails landed in my inbox within minutes of applying.
In interviews, I was told I was “too niche.” Or “too senior.” Or “not technical enough.” One interviewer laughed and told me I seemed like a “one foot in, one foot out” person because I had interests outside of work.
That one hurt.
Because work had been everything, but something was shifting in my mind around work and I felt so lost and confused.
Who Am I Without This?
At the same time I was job searching, I was grieving my dad. I was turning 40. I was watching the version of myself I’d built for decades stop making sense.
I couldn’t call my dad and ask, “What do I do now that I’ve been laid off?”
I didn’t know who I was without a job title. Without a badge. Without a company to point to.
I felt lost. Untethered. Ashamed, honestly.
And exhausted.
The Table in the Basement
In December 2022, I was at my friend Jordan's house. She has a basement. In the corner was this junky old table she had found in an alley years ago. She’d always said, “One day I’ll do something with it.”
I don’t know why, but something clicked. I had watched every episode of Flea Market Flip. I loved fixer-upper shows. I loved seeing things transformed.
I had just never actually done it myself.
So I dragged that table out of her basement, with her permission of course.
I didn’t have tools. I didn’t know what I was doing. I watched YouTube videos. I scrolled Instagram. I DM’d furniture flippers asking questions. I cornered Home Depot employees in the aisles and asked them what I should buy.
I tried things. I messed up. I figured it out.
When I finished that table, something shifted.
I felt a kind of satisfaction I hadn’t felt in years. Completion. Proof. Like, "oh. I’m still capable."
And it hit me: I gave this table another chance. And in the process, I gave myself one too.
When Furniture Started Showing Up
After that, furniture started appearing everywhere.
It felt ridiculous. Like the universe was testing me.
Pieces on the curb. Friends texting me photos. “Hey, I saw this on the corner of…” People dropping things off. Neighbors asking if I wanted something before it went to the dump.
I said yes.
I worked on pieces in my garage. I learned as I went. I made mistakes. I fixed them. I got better.
I started selling pieces on Facebook Marketplace and OfferUp. Then people started asking me to work on pieces for them.
One day, someone called me an artist.
I remember freezing. An artist? I had never thought of myself that way.
But something about that word stuck.
Healing With My Hands
Working on furniture became a huge part of my healing.
It got me out of my head and off the computer. It gave my nervous system something steady to focus on. I could see progress. I could feel it.
I started documenting everything. Sharing before-and-afters. Writing captions. Talking about what I was learning.
The name San Diego Furniture Flipper came to me in a dream. I woke up and wrote it down.
I leaned into it.
I sang while I worked. Played guitar. Wrote little songs in the garage. Not for content. Not for show. But because it helped me process. Because it brought good energy into the space.
Because it reminded me that I was alive.
Where I Am Now
In January of 2025, I took a full-time corporate job again.
Not because the furniture stopped mattering. But because bills still exist. Rent in San Diego is real. Life costs money.
Furniture flipping wasn’t able to support my life on its own yet. That’s just the truth.
So now I do both.
I work a 9-to-5. And I build this on the side. From my garage. On my terms. Slowly. Honestly. Imperfectly.
This work, the furniture, the writing, the making, it’s not a hobby I’m waiting to outgrow. It’s something I’m building alongside my life as it actually is.
Why I’m Here
This site isn’t about overnight success or quitting your job tomorrow.
It’s about second chances. About rebuilding identity when the one you had falls apart. About creating something with your hands when your head is spinning.
It’s about learning that you are more than what you do for money.
I’m still figuring it out. I’m still building. I’m still making mistakes.
But I know this: nothing is ever too far gone. Not furniture. Not people. Not you.
And that’s what I’m doing here.
If you found this interesting and want to stay in touch, I send a monthly-ish newsletter where I share furniture flips, what I’m learning as I build this alongside a 9-to-5, and a few honest reflections along the way.
You can subscribe using the link below.
