Uncertainty is the point

Sane guidance for the new year

What’s in for 2026?

I don’t know for you, but for me, it’s not certainty. Not a map.

But a direction.

What’s in is a mindset shift: the belief that things are possible and worth doing—because we don’t know how they’ll unfold.

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I used to think optimism required evidence. A clear trajectory. Some proof that things would work out. I was mostly wrong.

Leonard Cohen knows better

Especially in this 2026 with the how AI world is changing, the most pragmatically optimistic people I know are the ones most comfortable with not knowing. They’ve stopped waiting for certainty and started shipping anyway.

My friend Anatola, in her twenties and impossibly sharp, told me: “Maybe because our generation we are so uncertain and scared about the future, we don’t know how to deal with it, that we have to actively build the future—not trying to control, but to do our part.”

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That’s the paradox I keep returning to: uncertainty and conviction aren’t opposites. They coexist. You can walk between full fear and full aliveness. You can hold both.

In fact, if you aim to do anything worthwhile, you have to hold both. The gift of fear, fully felt in our nervous system, is indeed aliveness.

Do you remember being most alive when you were so scared doing something?

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Why choose uncertainty?

Five years ago, during COVID, I asked the late teacher and elder Joanna Macy—who is now no longer with us—what she thought would happen in the future.

She was in her nineties then, and the most alive human being I know, after a lifetime spent in environmental activism and systems change.

Her answer:

“When my son was about your age, he asked me the same question.
And I laughed: I wish I knew.

Uncertainty is what makes us come alive!”

She wasn’t being glib. She meant it. If you already know what happens, what’s the fun of it all?

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The texture of being alive

During the last few days of 2025, I reread Robert Frost’s famous poem “The Road Not Taken”:

”Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth …

[…]

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.”

It hit me that this poem isn’t really about taking the unconventional path (most people use that to justify their reckless decisions—I certainly did).

It is about something more honest: there is loss in every decision. There is always The Road Not Taken.

Choosing one thing means not choosing everything else.

Opportunity cost isn’t an economics concept. It’s the texture of being alive.

So as we are embracing the enthusiasm of change and new year resolution, remember some old truth.

Change is painful—but staying the same is painful too. The difference is that one kind of pain leads somewhere. The other just accumulates.

Found this sign at a cafe shop in Da Lat, Vietnam in 2018. Wild..

So if pain is inevitable, you might as well choose. You might as well make the trade-off consciously. You might as well feel the weight of the decision and step forward anyway.

That’s not recklessness. That’s the most human thing we can do.

To choose with courage. Leaping into uncertainty with a sense of direction.

Practice Faith

What do we need in order to leap into uncertainty with a sense of direction?

My current answer, using a big word: Faith.

I learned this from the coach Brian Whetten who about the practice of faith not as a belief system or religion but faith in action.

“Leaping & getting caught”—the trust that something will meet you mid-air. But only after you’ve jumped.

The leap comes first. The catching follows.

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The AI direction (and why I’m going all in)

Like many of us, I spend a lot of time thinking and testing this whole genAI thing. Not abstractly—practically. What it means for how we work, create, connect. What it means for what we value.

Zach Kass, former GTM of OpenAI, puts it sharply: “Lead with Optimism—not because a better future is guaranteed, but because optimism is a critical ingredient in building one.”

But he also offers something else as wisdom for this year - and many more to come:

Go Outside. The physical world matters more than anything else. Be in it.

Be Human. As intelligence becomes abundant, human qualities become more valuable.

AI makes human presence more valuable, not less. The scarce thing in an age of abundant intelligence is embodied presence. Human attention. The mess and friction of real relationships.

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What I’m building toward

I’m doubling down on AI this year for my work. Not because it’s certain—nothing is. But because this is where I feel the most aliveness. Where people are building with urgency and hope.

This decision comes from a fair bit of soul-searching & wisdom-seeking. I keep coming back to Peter Drucker’s wisdom, which is an excellent checklist to use in an unprecedented time like this:

“Courage rather than analysis dictates the truly important rules for identifying priorities:

1) pick the future over the past,

2) focus on opportunity rather than problem,

3) choose your own direction rather than jumping on bandwagon

4) aim high, aim to make a difference rather than settling for what’s safe”

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Practically, that means:

Writing down my thinking & experiences using genAI—the practical and the philosophical—and sharing it more widely. Not because I have all the answers. Because the questions matter and I want to think alongside others.

Gathering people for curated, elevated experiences, online & hybrid. Really excited to shape the flagship gathering of my beloved community Sandbox and also host more online gatherings. Something more intimate. More human.

Sourcing, building, and hosting with beloved partner and friends. I don’t want to build alone. The best things I’ve ever made came from collaboration with people I love and trust.

And I’m looking to connect with others choosing the road less traveled. People ready to move with conviction, grace, and speed.

If that’s you, reach out. I’m cooking something to gather people from around the world to join in this journey of The Road Less Traveled, 2026 version.

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Last note

Joanna Macy understood something I’m only now catching up to: we can do something for the world we love.

Not because the outcome is guaranteed.

Because we are eager to find out.

Showing up is how we find out what’s possible.

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Author note: I wrote this with writewithspiral.com, the AI writing-thinking tool from Every.to that I’m a big fan of.