★ Dear Issy · Advice column ★
Aspiro AI Studio presents
Dear Issy
An entertainment & informational column on AI, work & the human stuff
Entertainment & info only · not legal, medical, HR, or consulting advice
No charge for honest mail · names changed when we run a letter
Welcome to Dear Issy! This is our entertainment and informational advice column about AI, work, and the messy human stuff around both. What's on your mind? You can post with a first name or stay anonymous; either is fine. We choose one Dear Issy to post daily and when we do, we let you know and can tag you if you'd like.
Classified · Reader mail
In this edition · 7 letters
Write to IssyPersonal · Advice wantedNo. 07
2026-04-25
My industry runs on image—and now on AI slop
Clients want AI-generated mood boards overnight. The craft still matters. How do I push back without sounding like a Luddite?
— Modeling in Miami
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Personal · Advice wantedNo. 06
2026-04-22
Sleepless over an AI reorg
Leadership announced an “AI transformation office.” Nobody knows what it does. I’m supposed to report to it. I haven’t slept well in weeks.
— Sleepless in Seattle
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Personal · Advice wantedNo. 05
2026-04-18
I'm tired of being the Copilot champion
I volunteered to pilot Microsoft Copilot. Now I'm the unpaid help desk, trainer, and punchline. How do I step back without looking like I failed?
— Exhausted in Edmonton
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Personal · Advice wantedNo. 04
2026-04-15
A client asked if we use AI agents
RFP wants “autonomous agents.” We mostly use humans and spreadsheets. I don't want to lie. I also don't want to lose the deal.
— Account lead, name withheld
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Personal · Advice wantedNo. 03
2026-04-12
My boss wants AI everywhere
Every slide deck now has to mention AI. Half of it is fluff. How do I push back without sounding like I'm against progress?
— Tired in tech
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Personal · Advice wantedNo. 02
2026-04-10
When the team won't touch AI
Our execs bought licenses. Nobody uses them. What now?
— Skeptical in Scarborough
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Personal · Advice wantedNo. 01
2026-04-08
Should AI write performance reviews?
HR bought a tool that drafts review language from calendar and Slack metadata. Managers love the time savings. I’m not sure I do.
— Anonymous in people ops
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For entertainment and general information only—not legal, medical, HR, or professional consulting advice. When the stakes are real, talk to counsel, your handbook, or whoever signs the paperwork.
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