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Guaranteed to Fail at People-Pleasing: A pocket guide to being indispensable, exhausted, and deeply thanked.
Paperback
Series: Guaranteed to Fail
Publisher: Independently Published
Published: Feb 16 2026
Pages: 120
Weight: 0.30
Height: 0.30 Width: 5.50 Depth: 8.50
Language: English
Guaranteed to Fail at People-Pleasing is the pocket-size anti-guide for anyone who's ever said No worries! while quietly becoming worries.
In twelve sharply observed chapters, Doc Disaster takes you on a guided tour of modern niceness as a full-time job: the quick favor that becomes your weekend, the apology spiral that replaces a personality, the availability theater that turns your calendar into a crime scene, and the invisible labor that somehow becomes your brand. You'll meet the workplace characters who don't mean to take advantage-they just love consistency-and the family dynamics that promote you to unpaid emotional operations manager before dessert is served.
This isn't self-help. It's the opposite: a warm, dry, satirical manual for doing the wrong thing flawlessly. Through cringe dialogue, reply-all email catastrophes, chat threads from the pit, and policy theater disguised as teamwork, you'll learn the time-tested methods of saying yes until you disappear-then calling it kindness.
Inside you'll find:
A Boundary Meeting where nobody sets one (but everyone leaves with action items anyway)
A reply-all Quick Favor? thread that metastasizes into a full-blown volunteer position
A dictionary definition of Nice that should come with a warning label
A Choose-Your-Own-Disaster calendar scenario where every option ends in exhaustion
Family dinner emotional labor Olympics, with medals awarded for tone management
Running quietly through it all is a recurring motif-the Calendar Restraining Order Hotline-because if your schedule can't legally stop you, it will at least document the damage.
Beneath the satire is a recognizable truth: people-pleasing isn't a cute quirk. It's a risk-management system-short-term relief traded for long-term self-erasure. The jokes are sharp, but the voice is humane. You'll laugh, wince, and maybe (accidentally) recognize the moment when being nice became your entire operating system.
Perfect for readers who love smart workplace humor, social satire, and books that say the quiet part out loud-without ever turning into a lecture.
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