The best content strategy nobody talks about

_{Day 53/100}

Hey - It's Tim.

Most people don’t have a content problem.

They have a life problem. I said it.

They aren’t doing anything interesting enough to write about.

But content marketers?
Entrepreneurs?
Builders?

We are doing cool shit.

We just forget to talk about it.

Guilty as charged.

I moved 4,100 miles around the world.
Sold everything I owned except this laptop.
Came to Canada to build Penfriend.ai from scratch.

That’s cool.

That’s unusual.

That’s a story.

When have I written about it?

Never.

Too busy writing content strategy advice instead of living proof.

Well — not today.

What Counts As A Cool Thing?

Here’s what I think qualifies:

Cool = Specific + Risky + Personal.

If there was a moment where you thought:

“Is this a dumb idea?”

That’s the story.

3 Ways To Find Cool Stories From Your Life

1. Zoom In On The Small Stuff

Big moves get headlines.
Small moves get hearts.

Examples I should’ve written about:

• Selling my desk for $20 to a stranger.

• Running Penfriend demos from cafés with bad Wi-Fi.

• Realising my product screenshots still had "UK Shipping" on them — while in France. (Old product, different times…)

2. Share While You're In It

Best content isn’t reflection.
It’s live reporting.

People don’t want polish.
They want proximity.

3. Turn The Hard Bit Into The Hook

Whatever was painful → That’s the post.

If it sucked for you — it sticks with readers.

How To Turn It Into Content

Simple template:

It’s not copywriting.
It’s diary writing with a point.

Final Thought

You don’t need another content hack.

You need to start mining your own life.

Look at what you’ve built.
Look at what you’ve broken.
Look at what you’ve risked.

Talk about it.

That’s the stuff people remember.

✌️ ✌️ Tim “Still Loading The 'Do Cool Things' Module' Hanson
CMO @Penfriend.ai

P.S. Yes - This Is Our Second Product Update This Week

Turns out when you actually build stuff… you’ve got a lot to talk about.

This week we shipped:

→ A brand new billing page (Tom cooked)
→ Single credit purchases — our most requested feature ever — finally live
→ Offline batch generation — write while you sleep
→ Animated notification bar — small detail, big vibe
→ Mini Echo widget bug fixes — because details matter

All this week.

Second update in 4 days.

Because that’s what we do over here.

We build.
We ship.
We share.

If you want to see what real, working software for content marketers looks like — built by someone who actually uses it...

→ penfriend.ai

See you inside.

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