_{Day 100/100 today is the day}

Hey—It's Tim.

This is newsletter #100.

100 days of writing.
100 days of showing up.
100 days of “huh, I think that line could be better.”

And I just want to say thanks.

Thank you for opening these.
Thank you for replying.
Thank you for letting this be part of your inbox each morning.

This daily email started as a challenge.

It became a habit.

Now? It’s a whole creative engine.

“If I wake up today, then I write a newsletter.”

That’s been the rule.

A non-negotiable.

It didn’t matter if I had a cold, a backlog of tasks, or the creativity of a microwave burrito.
If I was alive, I was writing.

At first it was hard.
Now it’s fun.
(Not always. But enough.)

How I made it to 100

People think the hard part is writing.

It’s not.

I found, at least for me, the hard part is choosing what to write.
The blank page doesn’t scare me anymore.
But the blank idea? That’ll ruin your morning.

I knew from my LinkedIn writing day that no idea of what to write about mean no post for the day.

Or at least I’m spending the best part of the morning fighting with what to write, when I should just be writing.

So I planned. I over planned.

I have the next 40-50 newsletters planned out.

Topics.
Headings.
Meme name :D

I agonised hard over this process. Over how to plan out the newsletters. I made 4 systems before I settled on the one I have now. And it ain’t pretty. And that’s ok.

It works. I means I have a thing every morning to write about. And so, I can put what few coffee powered brainwaves I have toward writing.

“Is this actually a Penfriend product?”

Eh, kind of?

Adding newsletter into Penny was always something I wanted to do. But, it turns out, at least from my own experience that’s really fucking hard to do.

Mostly because of how personal a newsletter is.

You let me into your inbox. And that’s not something you’d do to any old AI.

Do I use AI to help me write these? Of course I do. I’ve said so multiple times.

100 newsletters. +1,000 words every day? By myself?
You’re too kind.

What I’ve come to realise, from my own troubles and from talking to a lot of people, is the human part is the most important. We want the speed of AI, without the sacrifice of the human.

And that’s what we’re working on.

That process of extracting the most human experiences, opinions and thoughts out of you. As easily and as frictionless as possible.

And putting that into whatever you want to write.

What we have so far has helped me make these newsletters.
I hope to have it in your hands soon.

The best part?

It wasn’t the likes.
Or the dopamine of deliverability dashboards.
It was this:

Those one-to-one emails from you?
That’s why this feels different.

Real. Intimate.
More coffee chat, less comment thread.

Favourite replies I’ve gotten:

✌️ Tim "What was your favourite middle name?" Hanson
CMO @Penfriend.ai

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

P.S. I will happily ask hard.
Send my newsletter to someone you think should read it.
Screenshot your favourite thing and post about it on LinkedIn and Twitter.
Read it out loud in your daily standups to your marketing team. And then send me a video.

Next big ask is in 100 days. See you there.

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