How I write a daily newsletter in less then one hour per day

_{Day 176/100}

Hey—It's Tim. 

Coffee and a blinking cursor.
That’s how I start most days.

Day 176. People keep asking how I do this every day. Here’s the system. Here’s how I write a daily newsletter.

It all starts with planning

Working out what to write everyday is the hardest thing. So I don’t. I do it all before.

I keep a living calendar of the next ~50 sends - each with a topic, a working header, and a meme middle name.

The middle name matters most.

If it doesn’t make me grin, it doesn’t ship.
That’s my litmus test for energy.

The morning ritual

Before the day takes my soul, I open Obsidian and the team’s “found this” Slack channel.
I skim notes, screenshots, half-ideas.

One coffee,
one problem,
one audience.

No vibes. A decision: what today’s reader needs from me.

The machine behind the curtain

I run a ChatGPT project that’s trained on my greatest hits and a curated swipe file of writers I swear by.

I tweak its rules 2–3x a week because good systems rot when they calcify.

Most mornings I talk with “Penny” (our in-dev assistant) for 10–15 minutes to shake out what I really think.

Then I fire the day’s prompt with my notes pasted under it and let it draft.

Write ugly, publish pretty

The draft is a slab. My job is sculpture.

I’ll play with the intro, cut anything that feels “AI-y”, add any drawings or screenshots to show the idea instead of just telling you about it, and rewrite bits until it feels like me.

The ask isn’t, “Is this perfect?” I’m asking, “Does this sound like me on purpose?”

Why it works

It reduces friction.

Friction is the enemy.

Premade topics remove the “what,” the ritual defines the “when,” the project gives me a fast “first how,” and the edit is where I earn my keep.

Tools accelerate; taste decides.

One hundred and seventy six emails later would suggest it’s working.

The Penfriend twist

Penfriend does the same thing for blog content, just with 100+ inputs instead of my messy brain and a Slack channel.

The premise is the exact same. What is a system I can develop that makes writing easier for other writers?

It assembles the high-signal research, aligns with strategy, and hands you a draft worthy of your taste.

Humans make it great; the system makes it consistent.

Steal the system

• Keep a rolling “50 ideas” doc with a topic, working header.
  

• Build a two-bucket note flow: Notes (raw finds) and Lines (sentences worth stealing… from yourself).
  

• Give your assistant a spine. Three rules to start: “short intros,” “one big idea,” “actionable wrap.”
  

• Talk it out before you type. A 90-second voice memo or a 10-minute chat with your AI is faster than staring.
  

• Edit like a reader: kill the apology lines, cut the throat-clearing, replace claims with examples. Can you replace a whole section with an image? Then do it.
  

• Ship on a timer. You’re not writing The Great Gatsby; you’re delivering today’s value.

See you tomorrow.

✌️ Tim "One does not simple skip the PS" Hanson
CMO @Penfriend.ai

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

P.S. I often write the sign off first. I dunno, it gives me a feeling of things are nearly done, and where the email needs to end up. Helps to define the destination to work out how to get there.

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