The Fool's Journey
Updated: 10 hours ago
an essay on learning to be a beginner again
There’s a tarot card called The Fool. The name conjures up a cliche dopey-ness, and the image of a figure walking off the cliff really hits it home.
Staring at that card during a tarot reading of my future, I thought — this can’t be good. But I learned, The Fool isn’t a cautionary tale, it’s someone on the cusp of everything.
The Fool is pure, unlimited potential. If you look deeper at the art, there’s a lack of material possessions signifying humility, naivety, and a lack of burdens. The Fool is ready for ego death and to learn what they don’t know.
Even within the deck, The Fool is card zero in the Major Arcana — the set of cards in a tarot deck tied to the archetypes, themes, and qualities we encounter in life. (Literary folks know it as the hero’s journey.)
Being card zero isn’t by chance — it’s a nod to the empty space ahead and the infinite cycles in life. It’s the beginning and the end. We’re in a constant and interconnected state of happening — learning, experience, renewal.
My fool’s journey began with taking the proverbial leap of faith to build my app, EverMore.
The whole day leading up to that tarot reading, my head already swirled with the thought of if I could or even should leave my familiar career.
Rationale never makes choices like that easy — our brains will stall and list all the things we need to have first to avoid the cycle of being the fool.
Despite ideas tugging at my sides, begging me to pursue them, I felt safe in the roles, companies, routines, and identities that were already there.
The Fool had no certainty to offer me.
Staying a Head of People was predictable, logical. So, why did I feel beckoned to leave? It's as if I willed the card to the table, calling — fool me, fool me, go on and fool me.
I recently wrote a guide — Should I Stay or Should I Go, not only because it’s a decision point we’ll all face but also because I noticed that friction has become synonymous with misalignment. Whether that's the friction of staying or going — The Fool walks off the cliff — trusting the journey before knowing how it ends.
No fool’s journey is without friction.
It’s especially tough right now because technology built a world that rewards having all the answers over sitting with questions. It’s so easy to bypass the learning process and pretend.
We’ve made not-knowing feel like a liability when it’s actually a skill.
The best part about being The Fool is the innocent curiosity and license to break convention. With bright-eyes, I get to ask “Why Not?” or “Does it have to be that way?” It’s the optimism after all that propelled me to try.
I launched into EverMore with unabashed hope, and found that growth takes mistakes, successes, losses, and learnings.
It’s also meant an identity collapse; I’m a freshman all over again, no longer an expert, which also means that delicious certainty eludes me.
There are so many times I stare down a decision totally clueless at first. Just the other day, I stared at a Slack thread for what felt like too long only to finally type “I’m fuzzy on what we’re debating.” (I didn’t know.)
And any smidgen of vanity fully dissipated once I realized that nobody was grading me on my previous career anymore. No one feels the need to suck up to or go soft on the first-time founder.
The fool is at day zero.
Even using my own product, EverMore, is a tad uncomfortable. It requires introspection and to sit with hard questions. While testing our next release, Mirror Mirror, I took a little gut punch when reading the themes for what’s holding me back — because spoiler alert, it’s my self-doubt. Most of which is coming from a year as The Fool.
I’ve been teetering on the edge of my capabilities, each time stretching the bounds of what I know before standing on the edge again. At times, that edge can feel embarrassingly public or devastatingly quiet.
There were days I longed for users to tell me anything, even if it was that the product sucked. The silence reverberated and made me feel exposed. Was I failing and flailing in front of everyone I know?
Nobody likes a beginner. Nobody likes being a beginner.
But whether you subscribe to the cult of tarot or not, I think we can learn something from The Fool. Because what’s next in the cycle is card one — The Magician — turning potential into reality and recognizing your power through manifestation, resourcefulness, and creation.
Becoming The Magician means self-mastery — applying the tools, skills, and knowledge you already have to achieve your goals. It’s what I hope to do for many with EverMore.
You can’t get there without first being The Fool.
So where are you willing to be the fool? Much of today’s reality promises the removal of The Fool with instant answers. You never have to not know.
What if the not knowing is worth protecting?
What if the discomfort of learning something new, of not having the answer yet, of being a beginner is the only way to grow?
I don’t have all the answers; after all I’m at the beginning — a fool.
xoxo,
Courtney
p.s. My backing soundtrack was Lovefool by The Cardigans, Foolish Games by Jewel, Fools Like Me by Lisa Loeb, and Foolish by Ashanti.
Originally published in The EverMore Edit about building a brand & app after twenty years securely moored to people & culture for startups.
