📉 48% open rate to 19%. A lesson learnt.

_{Day 186/100}

Hey—It's Tim. 

I’ve been writing this thing daily long enough to collect a few scars and a couple of tricks I didn’t expect. Today felt like the right day to confess them.

Nearly at 200 daily newsletters, and before the madness of launch week kicks off, I want to take some time to reflect on what I’ve learnt writing this newsletter.

I write to ship product, not posts

Let’s be honest: I’m writing so you’ll buy Penfriend.

And I wrestle with that.

My instinct is to give it all away and trust the right people to find the right buttons. But when I tie the value of an issue to a feature, clicks jump. Some days that feels gross.

My rule now: teach the principle first, show the product only if it’s the cleanest way to execute the principle.

If the story doesn’t need Penfriend, I don’t force it.
If it does, I owe you the button.

Don’t use this word in your subject line

I average 48% open rate. Which I’m damn proud of. So, to see yesterdays email hit this. I can only see one reason why.

Ooops.
That’s going on the no-no list.

This sh*t is hard

I have absolutely stared at the cursor and thought, “Not today.”

I’ve considered going weekly more times than I’ll admit.

But I said I would do this daily, so I do it daily.

I’ll reassess at one year—maybe shift to 2–3x/week with one deep paid edition.
For now, it’s free and it ships.

The trick that keeps me honest is a 45-minute “stupid pass.” I’m allowed to write the ugly, too-honest draft first. Once it exists, momentum takes over.

Replies are the real KPI

Some days I get 20+ replies and feel invincible.
Other days: three in a row with nothing—same open rate, same CTR, just… silence.

It messes with your head.

I love the replies; they keep me going.
I screenshot every single one and drop them in a folder called “Why I Write.”

Patterns I’ve noticed: a concrete question at the end (“What line helped most?”) beats a vague one by miles; stories about a real failure invite confession; and when I ask for a one-sentence reply, people actually send one sentence.

Do as I say, not as I do

I don’t batch.
I batch the planning, sure.
But I write each issue the day it goes out.

I don’t think that’s the “right” way. I wish I could knock out a week in one sitting, schedule, and disappear. It never feels right for me.

Writing day-of keeps the voice warm and the references alive; it also keeps me slightly terrified, which seems to produce sharper takes.

I’m willing to change my mind - but for now, the habit of publishing daily beats the efficiency of batching. It’s my version of lifting without a spotter: risky, focused.

✌️ Tim "thank you for reading" Hanson
CMO @Penfriend.ai

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

P.S. Send me your favorite emoji.

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