When hosting feels hard

This past weekend, we hosted a winter market at the farm.

It began, as most of my ideas do, as a spark - something small and almost laughably simple. A little roadside holiday pop-up, I thought. Maybe a table or two. Holiday cheer, but humble. And then, through conversation and iteration and a feeling deep within me I couldn’t ignore, the spark grew legs. It moved into the barn. It turned into a full-blown market with other local makers and holiday hayrides and warm drinks by the fire.

…and there were so many moments when I wanted to cancel.

The first weekend of December is one of the most crowded for events in the Hudson Valley. We were competing with well-established, beautifully branded holiday markets with marketing teams and big followings. I knew this. Everyone knows this. And still, something in me pressed forward. Not with certainty (let’s be honest), but with a kind of stubborn devotion. I felt compelled to keep going without knowing how many people would show up, or if anyone would show up, or if it would all feel painfully small.

So we cleaned the barn out in freezing temperatures.
We hung lights the night before with numb fingers.
We made a last-minute trip to Lowe’s to buy a high-powered heater - a machine called a Salamander, I learned, which feels appropriately mythic for winter farm life.

The day before the market, the tractor wouldn’t start.

I had pinned my heart on holiday hay rides among our brightly lit maple trees, and without the tractor…well, I wasn’t ready to let go. Our farmer called in a favor to a friend and borrowed a device that warms an engine block. After some tense waiting - and me pacing and breathing and trying not to catastrophize - the tractor finally turned over. A win!

Meanwhile, a handful of friends canceled last minute. My heart pounded in that familiar way it does when my childhood unbelonging wound wakes up. She curls into my palm, whispering: What if no one comes? What if this means something about you? About your lovability?

But I kept going. I kept going because something in me knew I had to.

And in the end, the winter market was pure magic.

People drifted in, bundled and rosy-cheeked. We sold our beef and eggs and honey and tallow balm. We had just picked up our spun wool yarn from the fiber mill the afternoon before that I tied pretty little tags with sheep drawings on them late into the night. Children ran around in the snow and fed cookies to Lupe, our elderly miniature donkey. My daughter set up a little shop in the corner of the barn with salted honey caramels she’d made with her babysitter. She proudly announced that “Everything in my shop is the price of FREE!” And she sold out, proudly beaming.

I watched neighbors who had passed our farm for months finally walk inside the barn. I met new people along our road. A longtime reader drove all the way from New York City with friends just to stop by, meet me, and see the land we are tending here. For an afternoon, our barn pulsed with life, warmth, possibility.

And I felt…proud of myself.
Not in a self-congratulatory way, but in a deeply human way.
The kind of pride that rises when you choose to honor a dream even while your fear is begging you to retreat.

But here’s the part I want to talk about. The part most people don’t speak aloud:

Not just logistically, but emotionally. Spiritually. Somatically.

Hosting, initiating, and bringing people together cracks something open in you. Not because you’re weak, but because community-building is one of the most tender forms of leadership we have.

When you gather people, you are not simply organizing an event.
You are saying:

This matters to me.
I’m putting myself on the line.
I see something possible here.
I want you to come.

And there is nothing casual about that.

Every invitation holds a little of your heart. Every RSVP is a reckoning. Every cancellation touches an old bruise. And every time you press forward anyway - every time you choose creation over self-protection - you stretch your capacity for courage.

I know this intimately. Not because I am fragile, but because the work I do (women’s circles, community gatherings, seasonal rituals) was born from my own wound of unbelonging. Standing at the center of a gathering is a reclamation for me. But it is also a place where old ghosts still rise. Hosting is never neutral.

And for many of us, depending on where we live, the vulnerability is heightened.
If you are new to a place.
If the community around you is closed off or slow to warm.
If the culture is cliquey or fragmented.
If you are different from the status quo.
If you are trying, slowly and steadily, to shift the norms toward connection…

Then gathering becomes even braver.

The people who create community are often the ones who fear rejection the most.
The ones who know the ache of loneliness most personally.
The ones who carry a longing so deep they are willing to risk being hurt to fulfill it.

They gather not because it’s easy for them, but because they know what’s at stake when no one does.

And I want to say this clearly:
It is worth it. You are not silly for trying. Your longing is not naive.
You are doing sacred work.

Our farm’s winter market wasn’t magical because everything went smoothly.
It was magical because we kept going even when it didn’t.
Because the tractor didn’t start and friends canceled and I was scared and the barn was cold and still—still—we created something beautiful.

And that is the invitation I want to leave with you:

And if you are someone who feels called to hold space for others, to create circles or seasonal gatherings or neighborhood rituals - to be the one who steps forward first - then you also deserve support.

You don’t have to do this alone.

Circle Craft is where I gather the gatherers — the women who feel called to bring people together, even when it scares them. It is an 8-week container where your longing to build a circle is met with real support, real skills, and a group of others walking the same path.

Inside Circle Craft, I teach you how to:

• Design a women’s circle that feels grounding and nourishing

• Hold space with steadiness and confidence

• Work with the wobbles - low RSVPs, last-minute cancellations, awkward moments

• Build connection in places where community has grown thin

• Create circles that nourish you as much as they nourish others

This winter will be my last time teaching Circle Craft live before I welcome my second baby, which makes the container feel especially intimate and precious. If your heart whispered yes at any point reading this, I would be honored to welcome you in.

Enrollment is open now.

Curious about leading your own women’s circle in your community? Circle Craft is a winter apprenticeship for women who feel called to gather and lead circles in their communities. You’ll learn the practical skills of facilitation — structure, boundaries, group dynamics, and ritual — while growing the confidence and presence needed to hold a steady, meaningful space. By spring, you’ll be ready to gather your people. We begin January 15th.

Learn more about Circle Craft