Unmasking October & The Wonderland of Identities
October 1, 2025 | Issue #18 |
In this week's edition we’ll unpack:
Wandering Wonderland — Discover what Alice’s curious journey teaches us about masks, identity, and the freedom to grow into ourselves.
The Truth Behind the Mask — Oscar Wilde reminds us that sometimes we reveal more when we hide. How can masks set us free instead of holding us back?
The Halloween Tree — Explore how fear, friendship, and the unknown guide us toward courage, wonder, and a little magic in our lives.
May these words find you well, as we untangle our thoughts and explore new ideas…
“If you don’t know where you are going any road can take you there.”
Unmasking October & The Wonderland of Identities
At some point or another, in our adolescent years, we were bestowed with the option to start picking and choosing things we liked, how we wanted to wear our hair, the clothes we chose, the music we listened to—which then slowly, over time, builds to who we become. So, if you strip those all away, then who are we really?
The Caterpillar and Alice looked at each other for some time in silence: at last the Caterpillar took the hookah out of its mouth, and addressed her in a languid, sleepy voice.
“Who are you?” said the Caterpillar.
As trivial a question as any, if you ask me, and one that can be hard to answer in turn. Most of us are handed masks long before we realize we’re wearing them. Some masks are pressed on us by family, culture, and societal expectations, while others we choose willingly.
An identity that feels safe and secure, or at least presentable to the world. But what happens when we’ve worn a mask for so long that we forget the contours of the face beneath it?
Alice knew this disorientation well—”being so many different sizes in a day is very confusing,” she sighs after nibbling the mushroom, unsure if she’ll grow taller or shrink away.
Identity can feel the same: masks that once seemed useful start to pinch or stretch us into shapes that don’t quite fit. And sometimes, when the day ends, the mask doesn’t fall away easily. It lingers, heavy and close, like a costume still warm from the stage lights.
Just as Alice wanders through Wonderland meeting creatures who are more sure of who she is than she is herself. Sound familiar?
Labels, job titles, hobbies and interests, even personality types—they give us shortcuts, but they can rarely capture the whole of us. We begin to wonder the bigger question:
Are we the sum of the roles we play, or do we exist in the space between the roles and labels?
“I know who I WAS when I got up this morning, but I think I must have been changed several times since then”
In a world that seems to reward certainty and a clear answer to “Who are you?”, maybe the real and truest reply is to simply say, “I don’t fully know yet, and that’s alright.” It could be our truest self is less a fixed mask and more like Alice herself: wandering, questions, stumbling into strange encounters, and growing (sometimes literally, somtimes painfully) along the way.
So perhaps the question isn’t only “Who are you?” but also “Who are you becoming?”
Fun Takeaway: If identity and ‘self’is a story, then we are author, character and reader. And like Alice, the further we go down the rabbit hole, the more we might discover that the masks aren’t cages but merely costumes, meant to be change, shed, or even thrown out when we outgrow them.
Philosophy of the Week:
Oscar Wilde — “Man is least himself when he talks in his own person. Give him a mask, and he will tell you the truth.”
Oscar Wilde, the 19th-century Irish poet and playwright, had a real knack for unmasking society’s pretenses with wit as sharp as a blade. In this quote he suggests that our “real selves” often hide behind the polished versions we show in daily life.
Strangely enough, it’s when we put on a mask that honesty can come out.
Think of Halloween: when the costumes come on, people laugh louder, act bolder, and sometimes reveal sides of themselves they keep tucked away the rest of the year. Wilde’s point is ever so timeless, our disguises don’t just conceal, they liberate.
Behind a mask, we feel free to play, to express, to admit truths we might never say with our bare face showing.
So maybe, this Halloween, the spookiest revelation isn’t the mask we put on—but the parts of ourselves it lets loose.
Day2Day Survival Tip:
Pumpkin Time-Out — Carve out time for you.
Life has a funny way of piling on layers, like old Halloween make-up, stacked and layered on top of your face, until the day feels heavy on our shoulders.
The antidote doesn’t always need to be big or complicated. Sometimes it’s as simple as carving out a small piece of time that’s just for you.
Think of it like carving a pumpkin: you scoop out the mess inside, clear away the clutter, and make space for a little light to shine through.
Try this for the month, set aside even just 10 minutes each day for your own “Pumpkin Time-Out.” It could be as simple as stepping outside with a warm drink, lighting a candle in a dim room, or listening to a favorite song without multitasking.
The point isn’t productivity or self-improvement. It’s to carve space where you can simply breathe, reset, and let your glow return.
Like a jack-o’-lantern on a porch, even a small flicker of light can make the darkness feel less overwhelming.
Words of Wisdom:
Ray Bradbury (1920–2012) was a master storyteller whose works often balanced the line between wonder and dread, reminding us how closely childhood imagination and existential fear can live side by side. The Halloween Tree (1970) a haunting yet beloved tale that explores the origins and different cultures of Halloween, while also being about friendship, mortality, and the way we learn to face the unknown.
Bradbury’s reminder is both chilling as it is comforting: fear is part of being human, but it doesn’t last forever. Even in the shadow of death, there is mystery, beauty, and the promise that one day, all masks fall away.
“Mr. Moundshroud, who are YOU?
And Mr. Moundshroud, way up there on the roof, sent his thoughts back: I think you know, boy, I think you know.
Will we meet again, Mr. Moundshroud?
Many years from now, yes, I’ll come for you.
And a last thought from Tom: O Mr. Moundshroud, will we EVER stop being afraid of nights and death?
And the thought returned: When you reach the stars, boy, yes, and live there forever, all the fears will go, and Death himself will die.
Tom listened, heard, and waved quietly.
Mr. Moundshroud, far off, lifted his hand. Click.
Tom’s front door went shut. His pumpkin-like-a-skull, on the vast Tree, sneezed and went dark.”
As the nights grow longer and the shadows stretch a little bit farther, may you embrace the masks you wear, the stories you carry, and the little sparks of magic that help you along the way. So, light your pumpkins, set out the candy, savior the quiet moments too, and remember: the mysteries that go bump in the night aren’t always to be feared, they’re often the very things that remind us we’re alive.
Thanks for reading and Happy Halloween
Until next time,
Guthrie
Ps. If you see a jack-o’-lantern smiling at you this week, take it as a reminder that even shadows can hold a little magic too.
