Still figuring it out? Same.

Messy middles

I’ve been sitting with the quiet complexity of what it means to be a person who holds a lot.

The one who remembers the appointments, shops for back-to-school supplies, leads the meeting, and tries to hold space for all the things — at work, at home, in community.

And in the middle of all that… there’s a longing to shape what comes next — not just supporting what already exists, but imagining what could be.

Over lunch recently, I found myself naming a tension that I know many of us carry: the push and pull between wanting stability and dreaming of something more. The comfort of knowing what's coming and the call to carve out something uniquely ours.

We talked about what it means to keep showing up even when we don’t have it all figured out. And how maybe that’s the point.

To be human while still figuring it out.
To lead while still learning.
To want more, even without knowing exactly what it looks like yet.

Maybe the most important work isn’t having the answers — it’s creating space where it’s safe to ask the real questions. For yourself. For your team. For your community.

The kind of space where uncertainty isn’t a flaw, but a feature. Where not knowing is the first step toward deeper listening.

Where something new, something needed, can begin to emerge.

Handwritten visual note with abstract purple shapes and the following words in mixed fonts: “Overwhelm. I’m ALMOST there. Permission to step in. You were not given a dream that you do not have the capacity to fulfill.”

A snippet of the graphic recording from the keynote during last year’s International Association of Facilitators Conference of the Americas.

Being human while still figuring it out

This August, our Good Talk community gathered for a conversation on Learning Out Loud: Being Human While Still Figuring It Out.

It wasn’t a big circle, but it was a beautiful one — full of quiet honesty, gentle witnessing, and big belly laughs.

We mapped our stories. We talked about truth, change, and courage. And we laughed. We held space for the messy middle. It reminded me that there’s something tender (and deeply courageous) about saying, “I don’t know yet.”

Not as an excuse or a placeholder, but as an intentional position — an openness to keep learning, keep unlearning, keep showing up with curiosity instead of certainty.

Because the truth is: most of us are still making it up as we go.

We’re navigating careers while caregiving. Building dreams in the margins of full lives. Trying to be present for our communities while tending to our own tired hearts.

And somehow, we expect ourselves to do it all with clarity and confidence — like we’re supposed to already have the answers.

But the messy middle, the part where we’re becoming, isn’t a detour.

It is the work.

I think that naming that complexity out loud is the heart of good facilitation, brave strategic planning, and meaningful community engagement.

When we’re invited to show up without pretending we have it all figured out, we create space for something honest to emerge. We build plans that reflect real conditions, not just ideal ones. We engage communities from a place of humility and openness, not control.

Whether you’re guiding a team, shaping a vision, or sitting in circle with neighbours — holding space for uncertainty is not a liability. It’s a strength.

It’s where trust is built, imagination lives and the spark of something new can take shape.

Conversations in progress

In my latest Substack post, There’s Beauty in the Struggle, I reflect on what it means to stay with the messiness of change — both in facilitation and in life.

It’s about the courage it takes to show up before you have it all figured out. About the kind of leadership that isn’t polished, but present. And about the surprising moments of connection and clarity that can emerge when we’re willing to wade through the middle, instead of rushing to the end.

If you’re someone who’s navigating change, holding space for others, or just trying to stay human in the middle of it all, I hope this one speaks to you.

Read the article here

A close-up of a seated conversation circle, showing five people in casual clothes and sneakers, sharing space in a relaxed, informal setting. Only their lower bodies and hands are visible, emphasizing comfort and presence.

Final Good Talk of 2025!

We have one Good Talk left for 2025, and we’ll be exploring a big juicy question: What keeps you going?

As the season changes, so do our rhythms. November asks something different of us and offers a quiet kind of in-between season, between summer motion and year-end obligations. We’ve planned this Good Talk to give us a soft landing as we near the end of 2025.

It’s coming up soon — November 6 @ 6:30 p.m. We’d love for you to join us!

Let’s pause together. Let’s look back on our year. Let’s remind each other what matters — and name the small, steady things that keep us going. We’ll dig into the rituals, values, and surprising anchors that help keep us connected through seasons of stretch.

Come as you are. Bring your reflections, your questions, your tired hearts. We’ll hold the space together. We can’t wait to see you there.

upcoming Good Talks

Lindsay Humber smiles while holding four mugs, including one that reads “Like a Boss.” She’s wearing glasses and a name tag, standing in a warmly lit room set up for a community event.

Conversation starters

Lately I’ve been returning to the On Being podcast with Krista Tippett. Her conversations make space for the kinds of questions that don’t have easy answers. The ones that linger. That shape how we listen, lead, and live in community.

Whether I’m designing a strategic planning session or facilitating a complex conversation, I find myself returning to this core idea: We don’t need to have it all figured out to move forward. But we do need to be present enough to ask better questions.

Questions that invite reflection, not reaction. That centre people, not problems. That help us imagine not just what we’re doing — but why it matters.

Some questions I’m holding:

What are the stories I’ve outgrown — and what’s waiting to be written next?
What does it mean to be in-progress in a world that keeps asking for more of us?
Where am I being invited to imagine something radically different?

If you’re looking for a thoughtful listen that stretches your thinking and softens your heart, On Being continues to be one of my go-to companions.

And if it sparks something in you, I’d love to hear what you’re imagining these days. Just hit reply.

Four books arranged on a wooden surface: Joyful by Ingrid Fetell Lee, Change by Damon Centola, The Art of Gathering by Priya Parker, and Gamestorming by Dave Gray, Sunni Brown, and James Macanufo — each one a conversation starter in its own right.

A final thought

Some seasons don’t ask for answers. They ask for presence. For reflection. For the willingness to stay in the messy middle, before the clarity comes.

Whether you’re showing up as a person or as part of a team, the work of growing isn’t linear. It’s layered. It takes time. And it’s okay to still be figuring it out as you go.

Around here, we’re building something slow and sturdy.
A space that welcomes nuance.
That sees tenderness as strength.
That believes progress doesn’t have to be perfect to matter.

If you or your organization are learning in real time — you’re not behind. You’re right where you need to be.

Thanks for being in this with us.
~ Lindsay

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