Why Does Standing at a Cross Roads Feel So Full Of Magic, and Yet So Uncertainty?


ahhtherapy ~newsletter ~october 2026

Living Better. Living well. It begins with the exhale ~"Ahh"

“The crossroads is an important place in the training of a warrior. It’s where our solid views begin to dissolve.”
~ Pema Chödrön

The Mystery of Crossroads

Hey there,

I’ve always been fascinated by crossroads. Not the kind that trap us at red lights when we’re already running late, but the mystical old kind, the dreamy and imagined ones that somewhere still exist. The kinds where dirt paths cross in the darkness, and stories are born.

A crossroads is never just a practical intersection. It’s a doorway, a place of possibility, and sometimes a spiritual dare. It’s where boundaries loosen, energy stirs, and choices cannot be ignored.

People have always known this. In ancient times, offerings were left at the crossroads, secret requests were whispered at dusk, and those who guard these liminal places treated with reverence and respect.

Something still gathers in these realms. You can sense it in your body: the held breath, the prickle on your arms, the pull of two directions at once.

The Magic of Making a Choice

Although the liminal space of crossroads may not feel cozy or even reassure us that we're doing the right thing, there is a magic here that is practical, because a crossroads makes choice visible.

Before this juncture, your options can stay abstract, like a cloud or a mist of maybes. At the junction, they become separate strips of ground, pointing toward different paths, and you must lean in toward one.

That’s where this archetype gets its power. A crossroads doesn’t stand for decision because decisions are dramatic. It stands for decision because no one can stay undecided forever.

At first, its meaning begins with potential. The road you haven’t taken can be anything, which is why a crossroads feels generous and threatening all at once. The unchosen path stays spotless in your imagination. It never collects the wrong turns, the bad weather, the dull errands, or the ordinary afternoons that seemingly fill the road you’re actually standing on.

The road you didn’t take is always perfect, because you never had to live through it.

The crossroads is a charged pause, the moment before your future hardens into a story. Right now, a hundred versions of you are still possible…

Where They Hide

Most crossroads don’t announce themselves. They show up as a restlessness you can’t shake, or the sense that the pieces of your life might still function but no longer fill you like they used to.

To the ancient Greeks, this was the goddess Hecate’s territory: the place where three roads meet and a traveler must decide. Today, they tend to appear in three places.

*In the heart. A relationship that is changing shape, a friendship that is fading, or that you’re outgrowing a version of yourself you once knew well.

*In the purpose. The work that once fueled you now drains you, or your goals feel inherited rather than chosen. Whose dreams are you chasing, anyway?

*In the everyday. The third cup of coffee instead of water. The hundredth “I’ll rest later.” Small moments, one persistent question: do you want to keep living like this? (Hecate sees the coffee, and -as you may know-she’s a woman after my own heart.... More on her to come...)

Why We Hold On

We humans are creatures of habit, drawn to what’s predictable, safe, and known. Sometimes we cling to what no longer serves us -perhaps even what hurts us- because the familiar feels better than the unknown.

So we stay a little longer. There’s no shame in that. It’s simply how we’re made.

But when the realization lands, that quiet aha, the door to change opens. Take a moment to notice: when comfort has turned into avoidance.

Familiar isn’t the same as good.

Crossroads and Samhain

Crossroads and Samhain share the symbolism of a threshold: the place where one chapter ends and another begins. Traditionally, Samhain marked the beginning of winter in the Gaelic seasonal calendar, a turning point associated with remembrance and the dying back of nature. A threshold of mystery but also of hardship...

And Halloween? What’s Hiding Beneath the Costume?

You may have never heard of Samhain, but Halloween’s roots reach deep into this ancient Celtic festival. Samhain was a time to honor ancestors and remember those who had passed, when the veil between the spirit world and our own was believed to grow thin, and passable.

As Christianity spread through the Celtic lands, these seasonal traditions gradually mingled with those of All Hallows’ Eve, and the veil-thinning, lantern-lit spirit of the season carried on.

Beneath the costumes and candy, the ancient pause between what was and what will be is still there.

We can think of it as a seasonal crossroads, where we pause between what has been and what is coming. That makes it a meaningful time to reflect on our own transitions.

As the nights lengthen and the world turns inward, Samhain invites us to honor what those chapters have given us before deciding what we wish to carry forward.

It also reminds us that we need not hurry through the space between an ending and a beginning.

Questions to Carry With You When You're at the Crossroads

Where in your life are you trying to make something fit that you may have outgrown?

Which direction is calling you, and which one are you simply used to?

What keeps pulling at you that you keep talking yourself out of?

You need not answer these all at once. Simply notice what rises as you ask. Mull them over and come back to them.

Sometimes the first answer is a surprise, and sometimes it’s a quiet relief. (Occasionally it’s both..and sometimes it’s even a bit rude. That’s usually the telltale sign you’ve been avoiding it.)


Join Me on October 29

On Thursday, October 29, I will host a Samhain Sacred Circle for women, a gathering to honor endings, attend to intuition, and sit with the mysteries of the season.

The evening moves through ceremony, meditation, and movement, into divination and ancestral magic, and closes around the table with a seasonal dinner and a glass of mulled wine or cider.

The circle is held in a private home and limited to 13 guests, so the evening stays intimate. It’s a place to acknowledge uncertainty together, with remembrance, curiosity, and room for whatever is beginning to take shape.

Samhain ~ A Witchy Ouija Circle

📅 October 29, 2026
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⏰ 6:30–9:00 PM
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📍 A welcoming farmhouse in Smithtown near Sweetbriar Nature Center. The exact location will be shared upon registration.


One Last Thing

Sometimes we recognize the crossroads long before we can see what our next step is. That’s not us failing. It’s how most transformations begin: slowly, quietly, in the background, in small moments that look ordinary but are actually the first steps of becoming.

You don’t need the map, and you will never be ready. Stay open and keep listening for the small voice. Feel into the little pulls and watch for the stubborn truths that want to be heard as well.

When it’s our time, the crossroads comes, with or without our permission. So show up, bring your people, and pull up a chair.

With love,
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Shana
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Sea Witch. Energy Weaver. Keeper of the Lineage.

P.S. Want to go deeper? I’ve just opened a space on Substack and I’d love for you to join me for more reflections, questions, and conversations about the mysteries we meet along the way:)

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