Out of the Office: Jennifer Dellapina
On the Art of Holding It Together After Job Loss
Losing a job is rarely just about work. It reshapes identity, finances, health, and the way you move through the world. In this installment of Out of the Office, I spoke with Jennifer Dellapina—a Marina del Rey, California-based advertising executive who, after years at the senior leadership level, found herself suddenly underemployed and navigating a reality she never expected—working a retail job for a fraction of her former salary.
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In this conversation, she speaks candidly about the whiplash of going from executive status to feeling invisible, the financial fear that comes with burning through savings, and the complicated shame and self-doubt that creep in when a career stalls. Despite the frustration and exhaustion, she shares how creativity, human connection, and a stubborn belief that “something good is up ahead” continue to carry her forward.
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Heather: Thanks for talking with me today, Jennifer. To start, can you tell me what you were doing before this period of unemployment?
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Jennifer: Sure. I’m Jennifer Dellapina, although I’ve been called JD through most of my advertising career. I’m not fully unemployed—I’m working a bridge job. But in November of 2022 I was fired from my role as Vice President of Strategy for an ad agency, which is the field I worked in for many years.
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Q: Did you see that coming?
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Jennifer: I saw it coming shortly after I was hired. It was a bad fit right from the beginning.
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Q: Were you given severance, or did you go on unemployment?
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Jennifer: I got a very little bit of severance—one month’s pay. I’ve never drawn unemployment, ever. One reason is I freelanced, and that kept me going. This time, the freelance is okay—it’s not enough by any stretch. But I got a job at a department store. It was an 80% pay cut, and my brain isn’t being engaged the same way. But I’m not unemployed.
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Also, I always felt like I didn’t need it as bad as other people. Which sounds ludicrous, because I know I put that money in. But I didn’t want to take unemployment, so somebody else could use it. So I subsisted on my savings account. When that was empty, I withdrew from my 401(k). I’m still subsisting on that, although it’s getting really, really low again. I don’t know what’s going to happen in the next couple of months.
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Q:What do you do at the store?
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Jennifer: For a while I was a department manager in lingerie. It didn’t pay well, but it wasn’t a lot of stress, and I enjoyed it, and I still was able to freelance in my actual field. Then my store closed. They moved me to another store, but they didn’t have a department manager job, so I’m just a stylist now. It’s fun, but the pay is abysmal.​
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Q: How quickly did you start in retail after losing your job?
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Jennifer: Maybe a week or two. Within two weeks I had interviewed and gotten the job.
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Q: So you’re underemployed. How has that affected your identity?
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Jennifer: Oof. It’s terrible. I feel like I’ve been pushed out. I feel like I’m no longer relevant. I feel very disconnected. I feel unhealthy. I try, but I just feel like I’ve dropped.​
Q: It sounds like this has impacted your life beyond work, too.
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Jennifer: Oh, yeah, but I’m not going to pin it all on my career. I made some bad choices. But my health was probably impacted more than my romantic life or social life. My job caused me so much stress, and my lack of a job has caused me unbelievable stress. I’ve had ulcers, gallstones, and kidney stones. Are they related to stress—who knows?
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Q: What did the first day of unemployment feel like? What was it like waking up and not having to go back to that job?
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Jennifer: I felt super miserable because I had wanted to be a C-suite for a long, long time, and I finally got to that place. I just wanted to be at the executive level. I wanted to be at a decision-making level. And I felt like I had failed. I felt like I wasn’t smart enough. I wasn’t good enough. I didn’t have the business acumen. It wasn’t right.
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But I did feel the relief, too, because I didn’t like being there.
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Q: What’s been the biggest ongoing challenge, day to day?
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Jennifer: I actually wrote a little paragraph about that. I wrote this on a particularly upset day. Let me read it to you:
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The worst part is not that I can’t pay my rent and have to go into my 401(k) just to survive. The worst part is not that I feel like I aged out of being relevant, and no company wants me. The worst part is not that my health has taken a dive. I live with a permanent headache, spent a day in the ER with kidney stones, have high blood pressure for the first time in my life, and I’m itchy, head to toe. That’s a fun one. The worst part is not the feeling of seclusion as work friends slowly fade away. The worst part is not the keen awareness of being undervalued in a job where I’m overqualified. The worst part is that every time there’s a shred of light, I hope that things will get better, they don’t. The ghosting, the rejection emails, the instant AI-generated slamming doors—nothing gets better. The worst part is accepting that this is it. The comfortable home, the travel, the social life, the energy, the passion—they’re gone, and they’re not coming back.
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Now, I wrote that on a particularly upset day. I don’t feel that dire all the time, and I don’t want other people to feel that dire. I think I wrote that on a day where I had had a particularly painful ghosting by a recruiter.
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Heather: How has this changed your relationship with money?
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Jennifer: I almost feel like I have an eating disorder, but it’s financial. There are some days where I am terrified to spend a dollar. My friend will say, “Do you want to go to the theater?” I can’t go. I can’t afford it. And then there are other days when I go, “I do still have a little bit of savings. This dress is 80% off, plus I get a 20% discount. It’s a good investment.” And then I buy a $125 dress.
I don’t know what is going on. My head is very mixed up.
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Also, in my retail job, there are perks that are so unbelievably good. Sometimes I wonder if I’ve not tried hard enough to get another job. I know I didn’t try hard enough the first year because I needed to heal a little bit. I interviewed, but I was like, “It’s fine for me to take this year to enjoy doing something different.”
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Q: Are you still looking in advertising? Have the roles you apply for changed?
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Jennifer: Yeah. In the beginning of my job search, I’d see jobs that paid $25,000 less than I had been making and I’d say, “I can’t do that. It’s too low.” Now I will apply for a job that pays less than half of my former salary. ​ It made me wonder if I was kind of brainwashed to think I needed all this money? Now I believe I could get by on quite a bit less.
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Q: How do you feel AI has impacted your job search?
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Jennifer: It’s negative and it’s positive. The negative is you know AI is sorting these resumes, and if you’re not an exact bullseye candidate, you’re not getting an interview. Which is a real bummer, because there are a lot of things that I know I could do very, very well.​ I’m not just talking about advertising. I’ve applied for administrative assistant roles because it pays better than what I’m making in retail, it could be interesting, and I’m super good at that. I get the rejection email the next day.
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On the positive side, I take a job description, put it in AI, and say, “Here’s my resume—where can I pump this up a little bit?” It’s made many good suggestions. AI picks up on things I might have missed.​ Now I have ten resumes—one for insights, one for strategy, one for digital, one for retail. It’s helped.
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Q: What do you do to prop yourself up and stay hopeful?
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Jennifer: My favorite quote of all time is Carrie Fisher: “Take your broken heart and make it into art.” I’m an actor. I’ve done some acting since this all went down, although there were a lot of times I just do not feel like it. Most recently, I wrote a short play and performed it at a theater festival. At the very end of last year, I got an agent for the first time. I’m psyched. But it’s a double-edged sword. He wants new headshots because mine are old. I can’t afford new headshots. He wants me to go to a class. I can’t afford the class. It’s a double-edged sword: You have time, you don’t have money. You have money, you don’t have time.
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But I don’t want to just say negative things. One of the things that has been cool is working in person again. When I was remote, I was like, “I’m never going back to the office.” But it has been great being out in public. I love talking to people all day, every day.
Working in retail—talking to people about their lives—and working with completely different types of people, I feel like I have a wider grasp of people in America today. It’s been eye-opening and educational and cool.
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Q: Before we wrap, is there any advice you’d want to share?
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Jennifer: I know I’m going to contradict myself. I try not to get my hopes up anymore. I just apply and try not to think about it. Every time I think, “This could change my life,” and then it doesn’t, it’s crushing.
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Having said that, I do think that we have to continue to have hope. The week before Christmas, I had three different job possibilities. One of them could still happen. Three at once felt interesting. I’m wondering if things aren't improving a little.​ I’ve always thought, “Something good is up ahead.” Professional or personal—or both—something cool’s coming. If we didn’t think that, then why would we live? How could you put one foot in front of the other every day? Something good has to be coming.​ I say that knowing my rent is about to go up in April, knowing my parents aren’t doing great, knowing what’s going on in the world. Still, it’s the human condition to believe something good is up ahead. Despite all this, I still am optimistic.
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If you’re inspired to share your own story, I’d love to hear it. You can send me a DM on LinkedIn or reach out here to arrange a time to talk.
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