POV: Your blunder gets promoted to ‘master plan’

_{Day 95/100}

Hey—It's Tim. 

Some of the best strategies?

Happy accidents wearing a clever disguise.

I’ve planned campaigns that fizzled.
And I’ve blurted half-baked ideas that turned into revenue fountains.

The pattern: stumble first, strategise later.

Two of recent happy accidents.

You’re literally reading it.

I never planned to send a newsletter every day.
I just knew that if I sent everyone a I’ll do “100 in a row” I’ll do it.
Because public shame is stronger than caffeine.

Day 1 was neat.
By Day 14 my drafts folder looked like a murder scene.
Day 37? People were replying.
Day 62? Someone DM’d, “I read you while microwaving oatmeal - don’t stop.”

Accidental consistency → accidental community → not accidental traffic.
 

EM—DASH…

I rage-posted that the em-dash is the avocado toast of punctuation.
Tiny reach, volcanic comments.

This was after a long day. A looooooooooooong day.

And yet it worked?

And one of my favourite failures

Three-Posts-a-Day Tim

If you go back far enough in my LinkedIn posts, you’ll see at one point I was posting three times a day…

For fours weeks I blasted LinkedIn with morning value, noon dad-jokes, evening “thoughts”.
Seventeen jokes died on impact.
Did I delete them? Only the worst ones.
Fail fast. Just move on. People forget faster.

How to trigger your own “lucky” break

1. Voice-note chaos. Vent into your phone for 90 seconds. No filter.

2. Highlight the spark. One line will make you grin - start there.

3. Ship it ugly. Ugly ships quicker. Quicker learns faster.

4. Watch engagement shape the edit. Comments are free copy chiefs.

How I check to see if it’s a Bob Ross or a tire fire.

Track lopsided numbers. 
Low reach + high engagement = future moat.

Pin the feeling, not the metric. 
Resonance > “performance”.

Write for the lifers. 
I’ve got readers 95/95 opens deep; they’re my board of directors.

Holes I’m thinking of falling into next

• Podcast blooper reels as lead magnets.

• 404 pages that sell features.

• Redacted support chats turned into case studies.

If one explodes, I’ll tell you. If they all flop, I’ll still tell you — because that’s how we trip into the good stuff.

✌️ Tim "The blog post is dead, long live the blog post" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. For those asking, “Tim what are your thoughts on the Google AI Mode thing?”
Tomorrow.
The story about how Google might have finally killed SEO…

Penfriend.ai
Made by content marketers. Used by better ones.