EverMore Edit: The Fool's Journey
- Jun 4
- 4 min read
Dear Readers,
In tarot there’s a card called The Fool. The name alone 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 quickly learned, The Fool isn’t a cautionary tale, it’s someone on the cusp of everything.
The Fool is pure, loose, unlimited potential. If you look deeper into 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.
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 EverMore. The whole day leading up to that 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.
For me, 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.
We recently wrote a guide for EverMore users—Should I Stay or Should I Go, not only because it’s a decision point we’ll all face but also because we noticed that friction has become synonymous with misalignment.
Yet 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?”
I launched into EverMore with unabashed hope, and found that growth takes mistakes, successes, losses, and learnings. 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.”
Even using EverMore is a tad uncomfortable. It requires you to sit with hard questions before it surfaces anything meaningful for your career. While testing our next release, The 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. 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 we hope to do for many with EverMore.
You can’t get there without first being The Fool. So 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 @ EverMore
p.s. My backing soundtrack to this newsletter was Lovefool by The Cardigans, Foolish Games by Jewel, Fools Like Me by Lisa Loeb, and Foolish by Ashanti.
Reflection of the Month
Where are you willing to be The Fool right now?
Fool me, Fool me, Go on and Fool me
The Fool walks off the cliff—trusting the journey before knowing how it ends. EverMore can meet you there, at a new beginning, to help cultivate your magic, but we’re also here for messy middles and unexpected endings.
Speaking of messy middles, we interviewed one user: a director in the middle on how he uses EverMore to balance growth with being a better manager.
To keep us open-hearted to new information, Kelsey and I dove into the trend of building personal curriculums on the Dear EverMore podcast.
Last year, we wrote about artificial authenticity through aesthetics and how AI removes the art of discovery. While reaching for the ready-made is still happening, we’re intrigued by the rise of inconvenience and friction-maxxing.
Finally, consider yourself a little less foolish with our exposé into compensation biases: The Little Lies That Keep Work Unfair. We hope by knowing the system, you can beat or change it.
Manifesting the Magician
This summer, EverMore leaves the nest and makes its way to the Apple App Store.
Beta invites are now closed, and we're hard at work preparing for launch day.
Thank you for being part of the journey—whether you've been exploring EverMore already or cheering us on from the sidelines.
stay Hungry, stay Foolish
We’ll conclude with a quote from Steve Jobs—stay hungry, stay foolish.
He shared as an endcap to his 2005 Stanford Commencement Address as a call to stay ambitious, chase unconventional dreams, and think differently.
It’s just like The Fool to take the risk and walk off the cliff.
For more inspiration, frameworks, and career stories, catch us on Instagram.
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