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Automation Squad
You run thisWritten for ChatGPT or Claude

Write the message I've been putting off for days

Robert MacKelfresh

By Robert MacKelfresh

Founder, Automation Squad

The reason a message sits unsent for four days is almost never that the words are hard — it's that the sender hasn't admitted what they're avoiding. Naming the fear first is what unblocks the draft, and the three-version ending removes the last excuse, which is uncertainty about tone.

The prompt

There's a message I've been avoiding sending. Help me write it.

Who it's to: [WHO THEY ARE TO YOU]
What it's about: [THE SITUATION, INCLUDING THE PART THAT MAKES IT AWKWARD]
What I actually want to happen: [THE OUTCOME]
Why I've been putting it off: [BE HONEST — bad news, my mistake, asking for money, saying no, chasing something]

Before drafting, tell me one thing: what am I actually afraid of here? Name it in a sentence. Most avoided messages are avoided for a reason the sender hasn't said out loud.

Then write it. Rules:
- Lead with the point. The thing I've been avoiding goes in the first two sentences, not paragraph four.
- No cushioning. Cut "I just wanted to", "sorry to bother you", "I hope this finds you well", and every other phrase that exists to soften my own discomfort rather than to help them.
- If I'm in the wrong, say so plainly and once. Repeated apology reads as anxiety, not accountability.
- If I want something, ask for it specifically, with a date.
- Short. Length is a symptom of not having decided what to say.

Then give me:
- A colder version, in case my first instinct is too warm for the situation
- A warmer version, in case it isn't
- The one sentence you'd cut if I made you cut something

Don't tell me it's a difficult situation. I know. That's why I haven't sent it.

Copy it, paste it, run it. Nothing here is gated.

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Written for ChatGPT or Claude as of August 2026. Models change — if this stops working the way it should, that is worth telling us about.