Pumpkins, Possibility & the Masks We Wear 🎃

Hello Friends,

October is my favorite month of the year.

There’s something about the cool, crisp air and warm autumn sun, the brilliance of the changing leaves here in New England, and all those traditions that bring me right back to childhood: apple picking, pumpkins, and, of course, Halloween. I love all of it.

And maybe what I love most about Halloween is the invitation to play.

For one night, we can be outrageous, mysterious, powerful, glamorous, ridiculous, or magical. We can step outside the identity we carry through our everyday lives and become someone, or something, completely different. We don't worry quite as much about whether we're too much, too strange, or too visible. We stop confining ourselves to who we think we're supposed to be and, for a little while, play with possibility.

There is something incredibly freeing about that. Which makes me wonder: Why don't we give ourselves that same freedom the rest of the year?

Halloween masks are easy to recognize. The masks we wear every day can be a little harder to see. There’s the professional mask, the I have everything under control mask, the caretaker, the people pleaser, the strong one, the funny one, the successful one, the nothing bothers me mask. Sometimes we've worn a particular version of ourselves for so long that we don't even recognize it as a mask anymore. It simply feels like who we are.

But our masks aren't necessarily bad. Often, they developed for a reason. They helped us belong, succeed, stay safe, or protect parts of ourselves that didn't feel safe enough to be seen. We all have protector parts. The question is whether the mask is still protecting us or whether it has begun to confine us.

And, of course, we're not the only ones wearing masks. We encounter other people's personas every day, which is where discernment becomes so important. Sometimes we're dazzled by the sparkle and shine: charisma, confidence, appearance, status, and all the things that readily catch our attention. Other times, we overlook something beautiful because it doesn't sparkle enough to catch our eye.

The surface doesn't always tell us the whole story.

This is why I believe it’s so important to learn to trust our inner guidance again. There may be times when everything looks right on paper, but something within you quietly whispers, Pay attention. Or you may sense a truth without being able to explain exactly how you know it, one that doesn't fit neatly into the facts you've been given or what your rational mind has concluded.

That doesn't mean abandoning reason or assuming every feeling is fact. It means being willing to listen more deeply, to notice and stay curious, and to look for the thread of truth beneath what is immediately apparent. Sometimes discernment asks us to look beyond the glitter and notice the glow, to see beyond the mask and listen a little more closely to what lies beneath.

And here's something I find especially interesting about Halloween: sometimes putting on a costume gives us permission to reveal something we've been hiding. Maybe we're bolder, more playful, more creative, more mischievous, more powerful, or simply more visible. For one night, the usual rules loosen, and parts of ourselves that we normally keep tucked away are allowed to come out and play.

So perhaps the question isn't simply what mask you are wearing, but who might you allow yourself to be if you stopped making yourself smaller to fit the role you thought you were supposed to play?

This Halloween, I hope you carve the pumpkin. Pick the apples. Eat the candy. Wear the witch's hat, the fairy wings, the vampire cape, whatever makes you smile. Be someone else for an evening if you want to. Play with possibility.

And maybe, somewhere along the way, notice the masks you no longer need to wear. Because sometimes pretending to be someone else gives us just enough freedom to remember who we really are.

Wear the costume. Take off the mask.

Happy Halloween. 🎃

With warmth and gratitude,
Rebecca