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- The Punk PM #19
Hey there, punk!
At the hedgehog lab conference this week, I spoke about something that often gets overlooked when we talk about innovation: the importance of building safe spaces to fail.
Because success rarely shows up on the first try. It usually comes after a string of false starts, near misses, and “not quite” moments. If your team doesn’t feel safe to experiment—or mess things up—they’ll hold back. And that’s when you stop moving forward.
Here’s why it matters.
Quote of the Week 🙊
I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.
— Michael Jordan
Insight 🦉
That Michael Jordan quote has been shared so many times it’s practically a cliché. But like most clichés, there’s a reason it stuck around—it’s true.
In product, failure isn’t something to avoid. It’s something to expect.
Most of the ideas you test won’t work. Even the smartest, most experienced teams get it wrong more often than they get it right. Y Combinator backs some of the best early-stage startups in the world, and even they only see a handful break through.
That doesn’t mean we stop trying—it means we keep going.
As product leaders, our job isn’t to chase perfection. It’s to build an environment where our teams feel safe to take risks, learn quickly, and keep moving. Nothing shuts down innovation faster than fear of failure.
Creativity gets you started—but it’s persistence and resilience that see you through. Testing a hundred ideas to find the one that sticks is always better than sitting on your hands because you’re scared to miss the mark.
The wins will come. But only if you're willing to make space for the misses, too.
Action 🚀
This week, make space for experimentation. Pick one idea your team’s been hesitant to try and run a lightweight test. No overthinking, no over-engineering. Just enough to learn something real.
And if it doesn’t work? Even better. That’s one step closer to something that will.
Inspiration 💡
The Great Cognitive Migration – Gary Grossman unpacks how AI is reshaping the landscape of work and meaning. As machines take over the “thinking” jobs, human strengths like creativity and emotional intelligence become more valuable than ever. The future? Less about competing with AI, more about doubling down on what makes us human. Read more
The Cannae Problem – Joan Westenberg uses a brutal Roman defeat to warn against relying too heavily on what’s worked before. Hannibal exploited their predictability—and it cost them everything. A powerful case for challenging your defaults before they break you. Read more
Why High Performers Make Assertions – Wes Kao explains why suggestions and insights aren’t enough. High performers don’t just share ideas—they take a stand. If you want to lead, make the call and own it. Read more
Signing Off ✍️
If this resonates with you, hit reply and let me know how you’re building a safe space for creativity and innovation 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