Unemployable

Jillian Di Benedetto
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The podcast for anyone who’s ever had a job, needed a job, quit a job, or just plain hated their job. Hosted by Jillian Di Benedetto, self-proclaimed “most unemployable feral bitch in advertising”, this is where design, strategy, and survival in late-capitalist work culture all smash together in a messy glitter explosion. Expect hot takes on how advertising lost its magic, rants about the Pac-Man ATS eating your resume, pep talks for the job-hunting undead, and conversations with fellow creatives who are clawing their way through the chaos. It’s unhinged. It’s cathartic. It’s painfully relatable. ✨Because if we can’t laugh at work, what’s even the point?✨

Episodes

  1. Julia (Jem) Roberts

    JAN 13

    Julia (Jem) Roberts

    In this episode of Unemployable, I sit down with Jem Roberts, storyteller and astrology enthusiast, for an honest conversation about job searching in a market that feels exhausting, unclear, and deeply broken.We talk about the emotional weight of the hiring process, the power of storytelling, and why clarity is so often missing on both sides. Jem shares how astrology can be a tool for reflection and growth when careers feel stuck or misaligned.At its core, this episode is about naming what isn’t working, remembering we are not the problem, and using our collective voices to push for a better, more human job market. astrology site: https://jpember.my.canva.site/astrology substack: https://jpember.substack.com/ website: https://jpember.my.canva.site/portfolio

    44 min
  2. Ben Levy

    JAN 12

    Ben Levy

    In this episode, Ben and I pull apart the advertising industry with care, curiosity, and a healthy amount of disbelief. We dig into the slow shitification of services, how agencies, platforms, and processes have become bloated, transactional, and increasingly disconnected from actual value. We talk about the changing mindset of entrepreneurs, the rise of independent agencies, and why trust has quietly become one of the most endangered resources in client–agency relationships. From there, we get into the realities of recruiting and interviewing in the creative world: performative interviews, vague expectations, and the exhausting pressure to package yourself as a “perfect fit” instead of a competent human. We unpack leadership gaps, pricing discomfort, and why so many businesses struggle to commit while still demanding full loyalty from creatives. I share the thinking behind Untethered Creative, Ben talks about pricing, confidence, and why clients who don’t trust you shouldn’t hire you. Together, we examine how online discourse, personal branding, and AI are reshaping how creatives are evaluated, often badly. It’s a candid conversation about modern advertising, broken systems, and what it actually takes to show up with clarity and integrity in an industry that keeps confusing polish for substance. Equal parts insightful, unfiltered, and validating for anyone who’s ever worked in advertising and thought, “It didn’t used to be like this… right?” Buy his book here! https://a.co/d/5LDzNVn

    1h 4m
  3. Jessica Layne

    JAN 12

    Jessica Layne

    In this episode, I sit down with Jessica Layne, creative director, intuitive channeler, and full-time chaos conduit, to tear open the job market and read its aura like it owes us money. We dive headfirst into the hellscape of ghostwriting, the spiritual whiplash of being a creative in 2025, and the feral crossroads where intuition meets capitalism. We drag ageism by the ankles, scream about authenticity until our throats hurt, and question whether AI copywriting is genius, demon magic, or both. Jessica spills on her personal symbols, energy rituals, and the sacred chaos that fuels her work, while also blowing up the delusional myths people believe about the copywriting profession. We end by staring directly into the flaming dumpster future of work and declaring loudly, unhingedly, that the only real strategy left is staying violently true to yourself in a job market that would absolutely prefer you didn’t. Tune in. Bring your crystals. And maybe a helmet. Lola Lavish: https://www.facebook.com/thebluedollar Jessica's LinkedIn: https://www.linkedin.com/in/jessica-layne-atx/ Jessica's Portfolio: https://www.resonatewithjessica.com/allthingscopy

    43 min
  4. Rachel Schizas

    JAN 9

    Rachel Schizas

    In this episode of Unemployable, Rachel Schizas and I joyfully spiral into the unhinged circus of job searching, the rejections, the delusion, the unhinged energy of it all. We get into real community support (the kind where your friends shove carbs and compliments at you), networking without crying, and remembering you’re worth more than whatever HR troll sent that “we’re moving forward with other candidates” email from their ergonomic throne. Rachel brings her battle-scarred wisdom, we laugh through the unemployment void, and together we attempt to redefine self-worth beyond job titles, layoffs, and corporate crumbs. Rachel also just launched her exclusive community, Career Accelerator — join here: https://www.skool.com/career-accelerator-community-9855/about Welcome to Unemployable, where your meltdown is marketable, your chaos is the aesthetic, and unemployment is a personality trait we’ve decided to monetize

    33 min
  5. Taylor Schumaker

    09/29/2025

    Taylor Schumaker

    This week, Taylor Schumaker and I unpack the unhinged circus that is the job market, from Stranger Things–level upside-down interviews to falling for glitter-coated scams and why LinkedIn is basically The Sims with resumes.

    34 min
  6. Alex Martinez

    09/22/2025

    Alex Martinez

    Once upon a time, advertising was magic. Now it’s math. So excuse me while I keep choosing glitter over Google Sheets. Tune in as Alex Martinez and I dive into the wild ride of advertising, from its history to whether strategy still holds up today, and wrap it all up with some future-focused insights and a few ✨motivational nuggets✨ to keep you going.

    31 min
  • 6 Episodes

Ratings & Reviews

5
out of 5
5 Ratings

About

The podcast for anyone who’s ever had a job, needed a job, quit a job, or just plain hated their job. Hosted by Jillian Di Benedetto, self-proclaimed “most unemployable feral bitch in advertising”, this is where design, strategy, and survival in late-capitalist work culture all smash together in a messy glitter explosion. Expect hot takes on how advertising lost its magic, rants about the Pac-Man ATS eating your resume, pep talks for the job-hunting undead, and conversations with fellow creatives who are clawing their way through the chaos. It’s unhinged. It’s cathartic. It’s painfully relatable. ✨Because if we can’t laugh at work, what’s even the point?✨

Information

  • Creator
    Jillian Di Benedetto
  • Years Active
    2025 - 2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © 2025 Jillian Di Benedetto
  • Show Website
    Unemployable