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should-i-send-this

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Gut-check a message before you send it — is it going to land the way you intend, or will you regret it in an hour? Use when asked should I send this, is this message okay to send, check this before I hit send, or will I regret this text/email. Produces a read on how the message will actually land for its recipient, the parts that could be misread or that you're sending from emotion, whether now is the right time to send it at all, and a calmer rewrite if needed — catching the hot, snippy, or oversharing message before it does damage you can't undo.

plugins/pm-focus/skills/should-i-send-this/SKILL.md

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Last checked
Nov 9, 2026

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1,539
Repository last updated
Nov 10, 2026
License
MIT

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# Should I Send This

Sent is forever. The angry reply, the 2am overshare, the passive-aggressive "per my last email" — they feel right in the moment and wrong an hour later. This is the pause between writing and sending: it reads how your message will actually land for the person receiving it, flags what's emotion-driven or misreadable, checks whether now is even the right time to send, and offers a calmer version — so you send the message you'd stand behind tomorrow.

## What This Skill Produces

- **The recipient's-eye read** — how the message will likely land for *them*, not how it feels to you
- **The risk flags** — the parts that could be misread, the emotion leaking through, the thing you'll regret, the overshare
- **The timing check** — whether to send now, wait, or not send at all (some messages are better not sent)
- **A calmer rewrite** — if it needs one, a version that gets your point across without the damage
- **The verdict** — send as-is / send the rewrite / wait / don't send

## Required Inputs
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