The Punk PM #23

Hey there, punk!

It’s June already, so this week I’m taking a moment to reflect on what I’ve learned writing this newsletter for five months, and where it might go next. 

If you’ve been reading since the beginning (or even just joined), thank you. It means a lot.

Let’s dig in.

Quote of the Week 🙊

Insight 🦉

It's the first Friday in June, which means it’s already been nearly half a year of writing, sharing, and thinking out loud via The Punk PM.

This isn’t my first newsletter, but it’s the first one that’s stuck this long. So I thought I’d use this week’s issue to reflect on what I’ve learned so far, and where I want to take it next.

It really helps to have a template

Most of my previous attempts fizzled out not because I ran out of things to say, but because I had no idea how to say them. Every week, I’d open a blank doc and wait for inspiration to strike. Most of the time, it didn’t.

This time, I started with structure. Before I wrote a single word, I built a simple template—Quote, Insight, Action, Inspiration. It gave me just enough scaffolding to get going, and turned writing from an open-ended slog into a manageable creative habit.

When the format’s sorted, the friction drops. I’m not starting from zero anymore, I’m just filling in the blanks.

A newsletter is a product

This has been the biggest mindset shift. In the past, I’d sit down each week and try to come up with an idea on the spot. It was high-pressure and low-yield.

Now, I treat The Punk PM like a product. I test ideas in public before I commit to them. Bluesky is my dev environment, LinkedIn is staging, and this newsletter is production. If something lands well on my social channels, I know it’s worth expanding here. If it doesn’t, I move on.

That little pipeline has made everything more sustainable and a lot more fun. Instead of staring at a blank screen, I’m riffing on ideas that already have some momentum.

Private is better than public

From the start, I decided to keep this newsletter invite-only. Not because I want to gatekeep, but because I didn’t want to perform. This isn’t about building a personal brand. It’s about sharing ideas with a thoughtful group of people who might actually find them useful.

That sense of privacy gives me permission to write differently. To go deeper. To be more honest. It feels more like a conversation than a broadcast—and that’s exactly how I want it to feel.

No one’s unsubscribed yet, so hopefully I’m on the right track.

Don’t abdicate creativity and ideation to AI (but definitely use it for editing)

There’s a lot of noise out there about how we should or shouldn’t use AI for writing. My take?

Don’t outsource the hard part.

Coming up with original ideas is your job. But once the thinking’s done, AI can be a brilliant editor. I’ve trained a GPT on my past work, and I use it to help tighten my drafts, clean up phrasing, and spot things I’ve missed. It’s not writing for me—it’s helping me write like me, but better (hopefully).

Back when I was a music journalist, every piece I published went through an editor first. This feels a lot like that (and the em-dashes are all mine—AI isn’t stealing those from me).

Writing is where your thinking compounds

I’ve always believed that if you can’t write it clearly, you don’t understand it properly. That’s why this newsletter has become such a valuable part of my own learning process.

I use tools like Readwise and Drafts to capture interesting ideas and fleeting thoughts. But this is the place where I turn those fragments into something more coherent. It’s where I figure out what I really think about product, leadership, innovation—and where I try to connect the dots.

The Feynman Technique talks about teaching to learn. This newsletter is me trying to do just that.

It’s great to scratch the writing itch

At the end of the day, I’m just enjoying writing again.

From notebooks full of embarrassing teenage lyrics to NME reviews and blog posts, writing’s always been part of who I am. For a while, life got in the way—family, kids, all the good stuff that fills up your time. But The Punk PM has brought that part of me back, and I’m loving it.

If you're enjoying reading it half as much as I enjoy writing it, we're in a good place.

Action 🚀

Five months in, and I’d love your take.

What should The Punk PM look like in the second half of the year? More deep dives? Guest voices? Something completely different?

Hit reply and let me know:

• What’s landed?

• What’s missing?

• What would make this more valuable for you?

I’d love your feedback to help shape what I do with this next.

Inspiration 💡

Some Signs of AI Model Collapse – Steven J. Vaughan-Nichols digs into why AI search tools are getting less reliable. The culprit? AI models feeding on AI-generated content. It’s a cautionary tale for anyone building with (or on top of) LLMs. Garbage in, garbage out. Read more

We Made Top AI Models Compete in a Game of Diplomacy – Alex Duffy chronicles a fascinating experiment where AI agents had to form alliances, deceive rivals, and play politics. The winner? OpenAI’s o3—turns out it’s very good at lying. Raises big questions about how we evaluate and interact with intelligent systems. Read more

Making Progress on Controversial Problems – Ami Vora shares a pragmatic approach to navigating messy, divisive issues at work. No grandstanding, just smart steps for bringing clarity, structure, and momentum to situations that usually stall. Read more

Signing Off ✍️

If you’ve got thoughts on where The Punk PM should go next, I’d love to hear them—hit reply and tell me what you’d like to see more of (or less of). And if you think a friend or teammate would enjoy this newsletter, feel free to forward it on.

Play it your way,

Toby