How your "worst ever" can make a brilliant email

👉 and it's fun to write too

Today’s email prompt is:

“My WORST [thing] ever”

For example, ones I’ve done before include “My WORST sales meeting ever” and “My worst email EVER”. (I quite like capitalising words in the subject line for emphasis - just as I might say it).

“Worst ever” emails work well because we all seem to have a huge schadenfreude-like curiosity to find out about the big mistakes people made or the tricky situations they’ve run into.

That curiosity guarantees lots of people will want to open any emails with the subject line “My worst [thing] ever” - as long as you don’t overuse it.

And because it’s a mistake you made or situation that they’re likely to have encountered themselves (or will be able to avoid thanks to your advice) it builds a lot of empathy. It shows them you understand their situation, and have “been there and done that”. It also highlights your humanity. You’re not some mythical hero who gets everything right every time. You’re just like them and so you’re someone they can learn from.

The key to this template is to:

• Pick a mistake you made or difficult situation you’ve been in that’s a problem your audience will either have hit themselves or be likely to run into.

• Be brave enough to admit to a real mistake or issue you faced. Not a fake “I was too generous” type “mistake” like someone might talk about in a job interview!

• Include details of what you learned or how you did things better the next time. Partly because this provides your audience with useful information, but also you don’t want to leave them with the impression that you’re no better now than when you made the mistake!

Obviously don’t overuse this template. A “My worst...” email once or twice a year is really interesting. If it’s every week or so it begins to feel like you do nothing but make mistakes.

- Ian

PS If you want more detailed prompts with examples and a writing guide, take a look at my Email Template Packs. The “My worse ever” email features in Template Pack 2 with details on how to write every element of it.

Each pack contains 5 emails with a guide to writing each key section and a full example to learn from. You can find out more details and get a preview here