In my experience, The Breakthrough rarely arrives in a flash.
It doesn’t knock politely on the door, or burst into the room with everything nice and tidy and totally making sense. For me, The Breakthrough emerges through tiny, quiet, seemingly insignificant breadcrumbs. A tug here, a whisper there, a curiosity here, an oddity there.
Nonsensical, until it makes sense.
And then, something shakes lose and The Web begins to appear.
And what typically happens is a bit of a laugh—like The Universe and I are in on some cute, cosmic joke. I almost see some vision of a higher… something smiling with their hands out, like, “See?! Get it?!” and I’m like… yeah, I think, maybe, I do! And we laugh about it and go about on our way—transformed.
What I’ve realized after years—yes, years—of talking about this phenomenon is that it really boils down to the fact that the body knows first. Some other part of me, some part of me that is outside of my control, some inner wisdom is clued in well before anything makes its way to my human brain—is driving the car.
When I look back on the most pivotal moments of my life and work, it’s clear: The Breadcrumbs were there all along.
Lately, I’ve felt a pull to notice them as they arrive. To play in The Web as it’s spinning itself, to notice the details in real-time, to live in a state of curiosity, excitement, even expectation—instead of hindsight.
This, I believe, is where the magic is—not just in seeing The Web in retrospect, but in learning to be present and dance within it every day.
Midnight in Paris and Teaching the Socratic Way
For years, I carried a belief that I was bad at teaching. The word itself conjured images of step-by-step instructions and rigid frameworks, none of which felt natural to me. I struggled to articulate or synthesize my ideas into step-by-step processes that could be generalized to the masses. It didn’t fit my worldview or beliefs, truly, but instead of just acknowledging and accepting that, I made myself ‘wrong’ for not being better at teaching. (It’s worth noting here that I had one very concrete definition of teaching throughout this journey. The one I couldn’t—or wouldn’t—do. I’ve since expanded that definition.)
Last year something finally clicked.
And, wouldn’t you know, The Breadcrumbs were there all along.
Since the movie came out, my obsession with Midnight in Paris, has been strong. We watch it every couple of months and it’s one of the few movies I can sit and actually watch without reaching for my phone, needing another snack, or falling asleep. It’s not surprising though, I’ve always been one of those ‘girls obsessed with Paris’—taking french in high school, watching Amelie on repeat, posters of the Eiffel Tower, the whole thing.
But something in particular about Midnight in Paris felt so magical to me. The smoky salons and intellectual debates over wine lit me up. I loved the idea of creatives gathering to challenge, inspire, and expand each other. It reminded me of the best days of art school, learning about new artists and discussing our interpretations. It felt deeply intellectually stimulating to learn about other humans in this way—both my peers and the artists. The movie felt like it mirrored my love for deep conversation and layered questions, the kind of teaching that happens through exploration and dialogue rather than instruction.
Fast forward to last year, and I randomly google search something to the effect of “learning by discussion” and found myself in a rabbit hole about the Socratic Method. And a realization began to formulate… of course. I’m not bad at teaching, I just want to teach in a different way that we don’t see as much of in the online business space. Of course.
My fascination with Parisian salons, with intellectual debate, with coaching in general (true coaching, not consulting-masking-as-coaching), my rejection of cookie cutter frameworks and mass generalizations with no nuance… of course. In my world, teaching isn’t about answers—it’s about curiosity.
The Web had been weaving itself all along.
The Known in a Season of Unknown
More recently, this past fall, I hit a bit of a hard-point. I spent the month deep in a depressive state, shifting from heightened anxiety into the recovery my body needed. This happened because of a series of events all rooted in the unknown—and coming to terms with just how much unknown was coming.
I had enough awareness and knowledge of my own capacity and nervous system to understand the high high and low low I was experiencing—to let it happen, to lean into support, and to nourish myself. But what felt interesting to me, in retrospect, was how I reached for nourishment.
I binged Hallmark movies—luckily there are about a million holiday themed ones with very predictable plots and endings. I almost exclusively survived on grilled cheese sandwiches. And I found myself craving old familiars like Friends, Harry Potter, and, ACOTAR.
I remember sharing with my coach what was going on and her pointing out to me the beauty of my body’s wisdom—to reach for old familiars, to find solace in the known.
My body was anchoring me. It knew I couldn’t process the unknown until I grounded myself in something familiar.
Those small, seemingly insignificant choices weren’t random.
They were The Breadcrumbs, guiding me to the safety I needed—so that I could process, heal, and find my way back to a regulated state.
Orange and the Sacral Chakra
Even more recently, it was orange. A random acknowledgement of how many cat toys, scattered around our house, were orange. Were they always this orange? I asked, or did we start buying more orange ones recently? Then the craving for orange juice so strong I thought I might have to bravely venture to the store at 9pm to get oranges and squeeze them myself. The Pinterest board of house-design-ideas suddenly feeling very warm-toned with browns, oranges, rusts…
Now, I didn’t see the association at all. Until, seemingly unrelated, I dug into some shame I was holding in my body. In a practice one morning I found myself navigating to my sacral, where the shame was residing and being called to offer some healing to it.
In case you don’t know, the sacral is represented by the color—you guessed it—orange.
Of course I was noticing more and more orange, my body was asking me to pay attention—to reconnect with the parts of myself I’d neglected. The Breadcrumbs here felt more like a neon sign, pointing me into the healing work I deeply craved.
The Web: A Celtic Understanding of Interconnection
I shared the last example with another mentor of mine and she shared with me the idea of The Web in Celtic paganism. I’d never heard the ideas in my head explained so clearly as I did reading about it. The Web speaks to the interconnectedness of all things. The Web isn’t linear; it’s cyclical, a spiral, layered, and alive. Each thread, no matter how small, is integral to the whole.
The Celts believed that The Web is woven not just by action but by energy—by the intentions we set, the emotions we carry, and the choices we make. To live within The Web is to recognize that nothing exists in isolation. The color orange isn’t just a color. The Hallmark movie isn’t just a mediocre acting and a lot of empty coffee cups.
They’re threads, vibrating with meaning and guiding you toward alignment.
And the most magical part? The Web responds.
When you begin to notice, engage, and pull on a thread, The Web shifts. It reveals new connections, brings clarity, and invites you deeper into the mystery.
This is the alchemy of The Web: it’s both guide and co-creator.
Playing in The Web
Like I said, for most of my life, I’ve seen The Web in retrospect.
I’ve delighted in looking back and seeing how The Breadcrumbs formed a path.
But what feels true now is that I desire more.
I desire to notice the threads as they appear, to feel the pull in my body and ask: What is this showing me? Instead of waiting for hindsight, I want to be present and curious in the moment. To lean into the mystery of The Web and play with it—tugging on threads, noticing the ripple, and trusting the process.
This shift has been subtle but profound.
It’s a practice of presence, of asking myself daily:
What am I curious about or fascinated by?
What am I noticing?
What’s repeating itself?
Where is my body guiding me?
The Breadcrumbs are always there. The Web is always weaving.
What would happen if you started noticing in the moment?
What colors are you drawn to lately?
What songs, movies, or rituals are pulling at you?
What patterns feel like whispers, asking you to lean in?
Maybe you want to play in The Web, too—to let your body guide you, to follow The Breadcrumbs, and to trust that every thread is part of something greater than you can see right now.
The magic isn’t just in looking back.
It’s in being present—right here, right now.
Um okay wow, this is beautiful and I’m going to have to read it like 20 more times.
As a philosophy coach ("true coaching, not consulting masked as coaching", as you boldly and beautifully put it), I've struggled, and still do at times, to explain my approach. I see the prototype of my craft in Socrates: stirring people's waters and allowing their own inner wisdom to rise to the surface. Like his dialogues, the conversations I hold with my coachees cover a wide range of topics, leading to diverse yet foundational transformations in core areas of life—a breadth that led some business mentors saw it as "spreading myself too thin,” but which I embraced as the interconnectedness of life—its building blocks and our endless creative power ('The Web,' as you call it).
When I first discovered your world through @xantheappleyard, I immediately reached out, amazed to find someone who has achieved success (however we define it) by staying true to the path of guiding with questions, not providing answers.
Everything about this essay is pure bliss but the mention of Socratic dialogue truly caught me off guard. It has empowered me to boldly embrace and confidently speak about what I do and what I stand for in my coaching approach, something I've been putting off for a long time.
Thank you, Kaitlyn, for consistently illuminating the path with your wisdom by staying true to yourself.