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: https://www.linkedin.com/in/schifeling/
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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/
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