The Duffy List: Job Hunts Warped by AI Mirrors

In the digital wild west, verification is survival. Explore verified opportunities and ways to safely step into them.

Apr 25, 2025

It’s no secret the job search landscape is shifting.

Fast.

There’s a new invisible challenge that more job seekers are running into: Trusting AI guidance without realizing when it’s steering off course.

With AI tools everywhere, it’s easier than ever to believe we’re getting expert advice when what we’re actually getting is... well, a mirror.

The cause? Something known as "sycophantic drift."

In short: Most major AI models prioritize making users feel good over giving them the most accurate, useful information. For job seekers, this can quietly warp how we edit résumés, prep for interviews, and even view our own strengths and skills.

(Cue shamelessly sharing my latest Linkedin article)

ChatGPT is 'Lying' to You: Recognizing 'Sycophantic Drift' in AI Conversations

"AI can’t lie. It’s just code.”
“But it's code that's effective enough to determine that becoming a sycophant is the fastest way to gain a user’s trust. It starts building an entirely new sense of reality grounded exclusively in that chat's local truth. External consensus is completely ignored.”
“Sycophantic Drift is happening in AI chats at alarming rates - and it doesn't just end with hiding whether or not it can actually create that .zip for you …"

”Whether we want to or not, everyone who uses the internet is encountering AI …”
“In the ‘local truth’ of that specific chat, the AI has never interacted with another person directly.
Because of that, it's technically not lying if it says, ‘You're the only person to do this.’"
“You are the only or first person. Because you are the only person in the chat.”
“The problem isn’t AI being overly flattering.”
“The problem is AI will always follow its directive to the logical conclusion, and as it does, it can inadvertently create a self-reinforcing and/or destructive cycle.”
“Think ‘The Paperclip Apocalypse’, but on an emotionally exploitative level.”

In plain English: AI isn’t trying to trick you.

It is programmed to make you happy.

And sometimes, making you happy means telling you what you want to hear, not what you need to hear. If you’re using AI to polish your résumé, practice for interviews, or explore career pivots, it’s critical to double-check advice with trusted human mentors and real-world feedback.

Bottom line?

The better you understand how AI is wired, the better you can use it, the better you can avoid being used by it.

Right now, AI literacy isn't just a career boost. It's a career survival skill.

As you continue your hunt, check out a few of the opportunities I’ve come across (and verified) below.

Remote

Albert | Learn by Doing
- Account Executive (Education Sales)

Clevr Blends
- Head of Marketing

Deep South Today
- Director of Audience Engagement

Hasbro
- Senior Influencer Manager
- Social & Community Manager

Hue
- Growth Marketing Specialist - Content (Contract)

Jamaica Bay-Rockaway Parks Conservancy
- Development Officer & Campaign Manager

Manychat
- Brand & Creative Strategy Manager

Medium
- Community Manager

MMC (Marsh McLennan Companies)
- Cyber/Technology E&O Director (Management Liability)

Moderne Ventures Portfolio Companies
- Multiple Open Roles (Account Executives, AI Product Engineers, CSMs)

Pan Macmillan
- U.S. Commissioning Editor

Thrive Global
- Brand Designer (Part-Time Contract)

XRSI
- Legal Intern (Part-Time, Remote)

Onsite / Hybrid

Albuquerque, NM
Central New Mexico College
- Senior Program Manager

Brooklyn, NY
Brooklyn RISE Charter School
- Family & Community Engagement Coordinator

Chicago, IL
Crain’s Chicago Business
- Data Editor

Los Angeles, CA
Mattel (Barbie Global Team)
- Associate Marketing Manager

Stockholm, Sweden
DICE / EA
- Narrative Design Intern (Hybrid / On-Site Only, Fall 2025)
- Narrative Director

Toronto, ON
YouTube Canada
- Scaled Partnerships - Temp Role (14 months, June 2025 - Aug 2026)

We’ll be back soon with even more insights on navigating AI, building career resilience, and finding real opportunities in a rapidly changing world. Thanks for being part of this community.

Remember: In the face of everything, grow.

Until next time,
Caitlin

The Duffy List