Living the Question: Why Participation Beats Certainty

There’s a Rilke line I keep coming back to. In Letters to a Young Poet, he writes about the importance of living the questions rather than forcing answers; sitting inside the uncertainty long enough to let life move you through it. It’s one of those ideas that sounds beautiful in theory and is genuinely uncomfortable in practice, because most of us would rather have the answer than live in the not-knowing.

Here’s what I’ve learned: certainty doesn’t come from having it figured out. It comes from doing the thing anyway.

I want to talk about participation. Not the inspirational-poster version where you show up and try your best and everyone learns something meaningful. The real version, which is messier and more instructive and occasionally involves you standing at a podium forty-five minutes late while an event organizer stares daggers into the back of your skull.

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The Keynote

In April, I bombed a keynote.

Not in the graceful way where something doesn’t land quite right, and you adjust on the fly. I mean, I arrived forty-five minutes late because Nashville had apparently decided to become a parking lot that afternoon. I missed the A/V check. The A/V, predictably, did not work. The organizer was pissed. The room was already restless.

And then, because I apparently have a flair for the dramatic, I decided this was the moment to tell one of the most vulnerable stories I have ever told publicly for the first time. I wanted to invite those women deeper into their own experience. I wanted them to feel something real.

They looked up at me like I had eight heads. They wanted to redeem their drink tickets.

For someone who loves communicating to a larger group of women, or anyone really (I do love to talk), it was a complete bust. I left feeling profoundly misunderstood, which, if you know anything about Enneagram Fours, is roughly equivalent to a fate worse than death. We can survive almost anything except not being understood. It’s our particular flavor of catastrophe.

The vulnerability hangover lasted a few days. I booked two emergency sessions with my therapist in the same week. I ate some feelings. I questioned my entire professional trajectory.

And then, when the fog lifted, I started looking for the data.

Failure as Information

An executive coach I worked with years ago introduced me to a concept he calls the failure files. Every month, he assigns his clients to write down at least five failures. Not near-misses or things that didn’t go perfectly—actual failures. Things that didn’t work, fell flat, cost something.

The first time he told me about this, I thought it sounded like a clever reframe for people who needed permission to be human, and it is that. But it’s also something more practical: it’s a data collection system. It’s a way of treating your life like a scientist rather than a judge.

Most of us have this backwards. We think success is the teacher and failure is the punishment. But success mostly confirms what we already know. Failure tells us something new. It shows us where our assumptions were wrong, where our timing was off, where the fit wasn’t right, where we were operating out of hope rather than information.

If you aren’t failing at anything, you probably aren’t putting yourself out there. And if you aren’t putting yourself out there, you are not generating the information you need to build a life that’s actually yours.

Certainty doesn’t come first; participation does. As we show up and do the next thing, we gain clarity, not always certainty. (Sorry to be a buzzkill.)

Living the Question

Back to Rilke. He was writing to a young poet who wanted answers: Am I talented enough? Is this the right path? How do I know? And Rilke essentially said: you don’t. Not yet. Live inside the question. The living itself will eventually deliver you to the answer.

This is not passive advice. Living the question is not the same as waiting. It means taking action in the direction of your desire before you know if it’s going to work. It means getting on stage when you’re forty-five minutes late, and the A/V is broken, and you don’t know if the room is with you. It means telling the vulnerable story even when you’re not sure the audience is ready for it. It means you don’t wait for certainty to grant you permission to participate.

The failure doesn’t mean you were wrong to try. Sometimes it just means the room wanted their drink tickets.

What This Looks Like for Every Type

Here’s the thing about the Enneagram: every type has its own sophisticated and deeply convincing reason to delay participation. Every type has a story it tells itself about why now isn’t the right time, why it needs more information or more preparation, or a slightly better set of circumstances before it can really go for it.

And every type has something specific to lose, or rather, something it fears losing, when it steps into the arena before it’s ready.

Ones wait for conditions that will never fully arrive.

They need the approach to be right before they begin, which means they’re editing the plan instead of executing it. They aren’t afraid of failure so much as they’re afraid of doing it wrong.

Participation for a One means beginning before it’s perfect, and trusting that the refinement can happen in motion.

Twos hold back when they can’t locate an explicit invitation.

They’re generous to a fault, but often only when it’s clearly wanted. Going first, claiming space, offering something that hasn’t been asked for; that’s the stretch.

Participation for a Two means showing up without waiting to be needed.

Threes are often the most visibly active, but they’re also capable of quietly avoiding the things that might actually matter by staying busy with the things they know they can win.

They can succeed their way around the real risk.

Participation for a Three means choosing the opportunity that could genuinely fail over the one that guarantees a good outcome.

Fours will wait until they can show up as the fullest, most authentic version of themselves, which is a beautiful idea that can become a lifelong postponement.

They want the moment to be worthy of them. They want to be understood before they’ve said anything. (I can say this because I am one.)

Participation for a Four means going before the moment feels right, knowing that misunderstanding is survivable.

Fives are gathering information. Indefinitely.

There’s always more to learn, another layer of competence to develop, another corner of the landscape to map before it’s time to move.

Participation for a Five means entering the room while there’s still something they don’t know, which is always.

Sixes are running simulations.

The anxiety isn’t laziness; it’s thoroughness applied to every possible way things could go wrong. They’ve already failed in their minds seventeen times before they’ve started.

Participation for a Six means taking the first step without resolution of the doubt, because the doubt will not resolve in advance.

Sevens can look like the most willing participants because they love possibility, and they move fast.

But they can also skim the surface, pivoting before depth requires something of them.

Participation for a Seven means staying long enough to find out what they’re actually made of.

Eights show up fully, often loudly, and they are not afraid of the fight, but they can be quietly terrified of the kind of vulnerability that participation in deeper relationship or creative exposure requires.

Participation for an Eight means letting people see what it costs them.

Nines are extraordinarily skilled at becoming comfortable with a life that keeps almost happening.

They merge with the inertia of the day. The perpetual next season.

Participation for a Nine means taking up space without waiting for someone else to create the conditions that make it okay.

Every type has a different texture to its avoidance. Every type is also capable of something remarkable when it steps through it.

What the Keynote Actually Taught Me

When I finally got past the vulnerability hangover and started treating April like a case study rather than a verdict, two things came into focus.

The first was alignment. The opportunity wasn’t wrong because I failed it. It was wrong before I walked in the door. It wasn’t my audience, it wasn’t my context, and somewhere underneath my “happy to be here” energy, I probably knew that. I said yes to it the way I used to say yes to a lot of things: gratefully, a little uncritically, out of a generosity I was performing partly for myself.

The second was that I am done with my “oh, I’m just so happy to be here” era. You know this era. It’s when you give your time and your craft and your most vulnerable stories away for free or close to it, because being chosen feels like enough. Because you’re still asking to be let in rather than deciding where you belong. That era served me. I needed it. And now we’re moving right along.

Participation generates information. That information, if you’re willing to look at it honestly, will start to show you the shape of what’s actually yours—what fits, what doesn’t, what you should lean into and what you should release. It builds discernment. Not the defensive kind that keeps you safe and small, but the earned kind that comes from having been out there enough to know the difference.

You don’t get that by watching from the sidelines. You don’t get it by waiting until you’re ready. You get it by getting on the stage when you’re forty-five minutes late, and the A/V doesn’t work, and the room might not be with you.

Sometimes they’re with you. Sometimes they want their drink tickets. Either way, you find out something true.

And I believe that, my friend, is exactly the point.

Love & Gratitude,

Katie