The Punk PM #14

Hey there, punk!

I’ve been thinking a lot this week about how much time we spend on estimation.

We act like we can predict how long something will take—but we don’t really know until it’s done.

Sometimes, the best way to find out is to just start.

Here’s why.

Quote of the Week 🙊

Insight 🦉

Estimates are a comfort blanket. They give the illusion of control in a world full of unknowns.

We pour hours into planning sessions, story points, burndown charts—trying to predict how long things will take. But the uncomfortable truth is most estimates in software are just well-dressed guesses.

We don’t do it because it’s accurate. We do it because it makes stakeholders feel better. It mitigates risk on paper, gives someone a number to put in a slide deck, and creates the illusion of certainty in an uncertain game.

But in reality? The best way to know how long something will take… is to start building it.

Instead of chasing false predictions, try this:

• Keep the scope razor-sharp: Small things don’t need estimates—they just need doing. The tighter the focus, the faster you’ll move and the easier it is to course-correct when you learn something new.

• Prioritise accuracy over precision: We often obsess over exact timelines (“Is it 12.5 days or 14?”) when what we really need is a rough sense of size and complexity. Close enough is close enough.

• Zoom out: Use rough, experience-based heuristics instead of pretending you can predict the future. “Last time we did this, it took three weeks.” That’ll do.

Estimates aren’t inherently bad—but they’re not the point. They’re a tool, not the truth.

Progress doesn’t come from guessing harder. It comes from doing smaller, learning faster, and staying flexible enough to adapt when reality (inevitably) punches your plan in the face.

Action 🚀

What’s something your team is estimating right now? What would happen if you just started building the smallest version of it instead?

Inspiration 💡

Three Unconventional Ways to Be a Better PM – Swetha Viswanatha suggests levelling up your product game by thinking way outside the roadmap. Confidence from performance arts. Creativity from non-PM reading. Clarity from visual thinking. It’s not just skills-building—it’s mind-expanding. Read more

Reprogramming Humanity’s Primal Instincts – Scott Belsky explores how AI is hacking our decision-making and what a future “History of Tech” class might say about it. If we’re not careful, we’ll trust the machine more than ourselves. This is a wake-up call to design with agency in mind. Read more

The Death of Product Development (As We Know It) – Julie Zhuo makes the case that AI isn’t just changing how we build—it’s changing who builds, what we build, and why. Smaller teams. Faster cycles. Prototypes powered by prompts. It’s a new era—and PMs need to evolve or be left behind. Read more

Signing Off ✍️

If this resonates with you, hit reply and let me know how you’re revamping your estimation process this week. And if you think a friend or colleague would enjoy The Punk PM, feel free to share it with them!

Play it your way,

Toby