The Job Search Is Rigged Against You | with Jeremy Schifeling

If you're a recent grad staring down a job market that feels like it has the rug pulled out from under it, this episode is exactly what you need. Kevin Cameron sits down with Jeremy Schifeling of The Job Insiders - a former kindergarten teacher turned LinkedIn insider turned career strategist, to talk about what's actually holding the next generation back, and more importantly, what to do about it. From using AI to uncover jobs you didn't know existed, to why reaching out to senior alumni is your biggest untapped advantage, Jeremy brings practical, no-fluff advice for students, recent grads, and the parents trying to help them. He also makes the case for why your first job doesn't have to be your forever job and why that's actually great news. Key Takeaways Use AI to discover job titles that match your strengths and passions — upload your performance reviews and letters of recommendation and ask it what others see in you. Reach out to alumni with curiosity, not a transaction. Ask about their career, not for a job. Don't let a blue chip brand be the goal — small and mid-sized companies build better skills faster. Your first job is a stepping stone, not a life sentence. Notice when work feels like flow — that's your signal. Grad school used to hide from the job market is an expensive mistake. Episode Highlights Jeremy's pivot from kindergarten teacher to LinkedIn and Khan Academy. Why 70% of Gen Z say they want to be influencers — and what that actually reveals. The alumni outreach mistake that kills your chances before you've even started. Why senior leaders get almost no outreach — and why that's your opportunity. The "brand creep" trap: chasing logos over meaning. Why small companies are hiring while big names are laying off. How to do a background check on your future boss using LinkedIn. Timestamps 00:00 — Introduction 00:42 — Meet Jeremy Schifeling and The Job Insiders 03:49 — What grads are feeling right now 04:57 — Using AI to find jobs you didn't know existed 05:33 — A word to the parents 06:51 — What Gen Z actually wants (it's not what you think) 09:48 — Location as a career strategy 12:19 — The cheat sheet for structuring your search 14:30 — The alumni outreach mistake everyone makes 17:05 — Why senior leaders never get messaged (and why you should) 19:17 — Let your kid do the outreach themselves 21:07 — Building confidence through discomfort 21:48 — How The Job Insiders works 23:45 — Your first job is a stepping stone, not forever 25:41 — Should you go to grad school? 27:35 — What to look for in that first role 28:42 — The concept of flow and your career 30:29 — The brand creep trap 32:55 — Small companies vs big names: the truth 35:28 — How to background check your future boss 36:57 — Jeremy's why Connect With Jeremy Website: https://www.thejobinsiders.com/ LinkedIn:   / schifeling   If you found this advice valuable, please hit subscribe, leave us a review. Visit Talent Connect: Website: www.talent-connect.net LinkedIn: Talent-Connect Kevin's LinkedIn: Kevin Cameron PCC Production Credit: Edited and produced by @the32collective_ / https://www.the32collective.co/