Hey friends,

A while back, I released an essay called Failing Less, and many of you responded with thoughts, stories, and reflections that pushed the idea further. Thank you. Truly.

If you missed it, you can read it here: Failing Less: On Idealism, Power, and Understanding Human Nature​

And if you’ve already read it, email me what you think, what you’d challenge, what you’d add. It’s through you that my progress is possible. It’s how I fail less.

Since then, the concept of Failing Less has grown. What started as a phrase has become a series—a reef of ideas building on one another, layer by layer.

Which brings me to the latest piece.

Failing Less: The Oyster Reef of Progress

More than a decade ago, I wrote a simple mantra to guide my life:

It’s followed me since. A compass in moments of doubt, tension, and growth.

But over the years, I’ve come to believe that this isn’t just about ideas or intellectual humility—it’s ecological.

In the Chesapeake Bay, once-vast oyster reefs collapsed.
Not because the oysters stopped growing, but because the old shells were taken away, paved into roads, ground down, commodified.

But oysters don’t grow in isolation. One dead shell can host three to four new oysters. The reef only thrives when the dead remain, when failure is not discarded, but layered into the foundation.

And so it is with knowledge.
With culture.
With belief.

Progress isn’t about finding the right idea and standing on it triumphantly.
It’s about learning to fail less.

Each failure—if kept, examined, honored—becomes the bedrock for something new.

But when we rip those shells from the reef, convinced we’ve finally found the right answer, we kill the ecology of inquiry.

Dogma is not a sign of strength. It is a reef with no oysters left.

The best we can do is fail a little less, so others can fail a little less, and together, over time, something vast and alive begins to form.

A reef of insight, seeded not by certainty, but by curiosity and care.

That’s the heart of Ideas Worth Questioning and Failing Less.

Not a platform for answers.
A sanctuary for shells.

I’m Doing This Differently Now

I’ve been writing a lot.
More than I’ve been publishing.
Because I kept waiting for the “right” time to share.
But if I wait until every idea fits neatly into a schedule, most of them will never see the light of day.

So here’s the new rhythm:

• Essays will now be published as soon as they’re finalized, behind the Substack paywall.
• The Monday newsletter will continue as a curated offering of older essays, reflections, and connective threads.
• When an essay appears in the newsletter, it will also become free to read on Substack.

If you’d like to support this work and get early access to everything I write, the best way right now is to become a paid subscriber. It helps me keep going and keep questioning.

Thanks for being part of this.

We rise, together.
—Pete

P.S.​
The very best way you can support me right now? Share this. Seriously.

If you're reading this, you're just a few neurons away from helping me substantially.
Click the forward button.
Send it to 5 or 10 people you think would be interested, challenged, or inspired by this work, or who might help me fail less.

You’re all welcome at the table.
But that share? That earns you a seat at my heart.

👉 winewithpete.me/join — if someone forwarded this to you, you can subscribe here.