Wayfinder
Uncertainty Coaching
Transform uncertainty from deluge to dance partner.
When you navigate toward clarity, not certainty,
the voyage becomes an adventure.
You're smart. You're self-aware. You've built a career around helping others.
Yet lately, what used to replenish you so you could show up for your people isn’t working anymore. You’re even struggling to help yourself.
That inner voice telling you something's off is very loud.
But when you ask yourself how to fix it?
*crickets*
You’re caught in a storm with no land in sight
At work, you’re talking down your direct report from bursting into the executive suite waving a 12-page manifesto of policy change demands.
Your search history reads like a panic spiral from “how to get dual citizenship” to “how to convince uncle city council was not replaced by aliens”.
You’re real close to getting the world’s worst Think Piece Headline Bingo on a card full of “unprecedented” “loneliness” “enshittification” “polarization” and “chatGPT”.
You’re pondering moving. Quitting. Doing something—anything—to regain a sense of control in a world that just. won’t. stay. still.
These aren’t unfounded worries. But they take you over. They disconnect you from joy. They trap you in an eddy of rumination spirals, second guessing, and analysis paralysis until you’re living only in your head. The wisdom you know your body holds is lost in a fog of fear.
Your mind screams: Figure this out. Right now. Find the answer. Know what comes next.
Instead, let's take a second to look at the big picture.
When staying afloat has become your only goal,
something’s got to change
You want your life back.
You want to mentor your younger colleagues with insight instead of crisis management.
You want the bandwidth to break out the craft supplies and help your kiddo make the best damn cell model 6th grade science has ever seen.
You want to leave your phone in the kitchen and read a real, physical book before bed.
You’re not sure when those rituals slipped away. You just know you want them back, and if you could find the right answers, you might get there.
But what if the problem isn't that you need better answers?
What if the problem is that you're trying to eliminate something that can't—and shouldn't—be eliminated?
Here's what I know to be true: uncertainty isn't going away. The world is going to keep being the hot mess that it is.
But what can change is your relationship to it.
Imagine if uncertainty felt less like an icy bath in January and more like a warm, buoyant sea gently holding you up.
Imagine being able to sit with a question without your nervous system demanding immediate resolution.
Imagine clarity as your North Star instead of certainty—knowing what you're trying to discover rather than trying to predetermine the outcome.
Imagine feeling so centered that the world can be crumbling around you and your spirit remains unshaken. Not because you're pretending everything's fine. But because you've built the inner toolkit to hold complexity without collapsing.
What if you could learn to ride the waves?
Don’t you want to be that kind of badass?!
You don’t have to eliminate uncertainty to get there. Instead, learn to flow with it.
To find comfort in discomfort.
To listen to your body instead of your racing thoughts.
To navigate with a wise council of friends instead of alone.
To access slowness and spaciousness instead of urgency and overwhelm.
You don’t need another productivity hack or framework. You need a way to “live the questions,” as the poet Rilke put it. To let uncertainty wash around you as you sail skillfully toward what matters without drowning in distraction.
Because here's the truth:
Possibility is the twin of uncertainty.
The resourced, abundant, brave twin.
And you can make that expansive twin your guide.
Navigate the choppy seas of uncertainty with Wayfinder Uncertainty Coaching
Enter Wayfinder Uncertainty Coaching. This is an 8-week small-group intensive where curious, capable people shift from bracing against uncertainty to flexing with it.
This program won’t add more lectures or homework to your already-packed life. Instead, it's experiential, embodied, and communal.
We will keep the group small, with a cap of 10 people, so the group can bond and build trust. Because although it may feel like it, you’re not navigating these waters alone. This is a chance to get to know your fellow crew members.
Each session is a playful, experiential journey through an unexpected, supportive modality. We gather for six 90-minute Zoom workshops spread over eight weeks, starting weekly then slowing the pace as we need more integration time.
Important: there's no required homework between sessions. You only commit to the live calls. There are additional resources and readings available to support you when you need them, but the program is designed to make sure you won't be "behind" no matter how you show up.
Real clients, real results
I developed confidence and strategized solutions
“This was a great way to develop confidence, strategize solutions and connect with others… I thought it was beautifully facilitated in a way that helped us to connect with one another.”
Jenn DePrizio, Leadership Coach and Consultant, DePrizio Leadership Group
We shifted from looking backward to looking forward
“Our conversations … shifted from backward looking ‘this isn't working and here are examples of what is going wrong’ to forward looking ‘here are next steps and tangible new approaches to try.’”
Katherine Mitchell, Central Library Visitor Experience Coordinator, Boston Public Library
Meet Your Adventurous Captain
Hi. I'm Rachel, and I’ve been exactly where you are.
I’ve spent a lifetime being many kinds of nerd, diving deep into lots of rabbit holes, and if there’s one thing that has taught me, it’s that there's no single "right" way to dance with uncertainty. Different moments in life call for different moves.
After a 20-year career as an educator in and around art museums including the Guggenheim, the Brooklyn Museum, MoMA, and the Met, I've been riding the waves of solo entrepreneurship since 2021. I guide curious people and their organizations to dance with change and uncertainty.
Colleagues have suggested my title should be Chief Empathy Funkster or Creative Conspirator or even Curator of Prismatic Experience. On my business card, I call myself an educator, adventurer, facilitator, experience builder… and pirate.
Because in the face of imperial, unequal systems, pirates created entirely new ones*. They thought outside the box, and that’s the kind of playful, strategic approach I bring to my work creating training workshops, retreats, and courses that nudge people productively out of their comfort zones to a space where they can learn and grow.
*Seriously. Collective health insurance, equitable income distribution, flattened organizational hierarchies, same-sex marriage. Pirates had versions of ‘em all.
My own uncertainty dance lessons have come from being omnivorously curious. Ask me about the 50+ podcasts I'm subscribed to. Or how the bookshelf by my desk came to include a moose skull, some 19th century French etiquette manuals, and a book called The Ordinary Princess. I’ll happily go deep about art history, bread baking techniques, or jazz dance choreography. Yes, sometimes those dance lessons are literal ones.
I've facilitated workshops across continents and in multiple languages, guiding groups to create interpretive dances based on abstract art and to invent rituals to honor slow change. I build experiences that help people leave having discovered something entirely new.
Wayfinder Uncertainty Coaching is a distillation of those years of exploration into a navigable expedition for people ready to transform their relationship with the unknown.
Words from past clients
Incredible thought leader
“Rachel is an incredible thought leader. She is a joy to work with because she is proactive and patient… She listens and she approaches her work comprehensively. She "knows her stuff" and you walk away from her feeling encouraged and like a weight has been lifted.”
Stacey Shelnut-Hendrick, Deputy Director of Public Engagement and Learning, Chrysler Museum of Art
Finding possibilities on the fly
“You synthesize and find possibilities on the fly, a wondrous thing to watch in action. What a gift to be able to do so, and this is a key skill for any facilitator. One that I believe is rare to find—and trust me, I’ve seen a lot of facilitators in my day. Your generosity is endlessly valuable, and … wields magic.”
Susan Spero, Professor & Chair Emerita, Museum Studies, John F. Kennedy University
Wayfinder Uncertainty Coaching: What’s Included
Your navigation tools for the voyage ahead
The program looks like this:
6 x 90-minute live Zoom sessions over 8 weeks:
All calls will be held from 1-2:30pm ET / 10am-11:30am PT
Encounter the New with Curiosity
January 6, 2026
Reframe Your Story
January 13, 2026
How to Play as a Grown-Up
January 20, 2026
Accept Impermanence
February 3, 2026
Imagine Alternatives
February 17, 2026
Consolidation Session
March 3, 2026
Between sessions, you’ll have access to:
A private digital resource hub
A group chat on Signal for connection and playful prompts
A physical welcome package mailed to your door*
Session recordings (for your privacy, these are available only until the next live call)
*yes, even if you don’t live in the USA. International friends, I’ll make sure you get what you need.
$2,600 (payable in 1 or 2 installments)
Investment:
Words from past clients
Approaching life with a new perspective
“This … gave me the chance to meet new people, think about new questions, be vulnerable and open. I’m leaving our time together thinking about how I can approach life differently, with new perspective.”
Andrea Kovalsky, Director of Institutional Philanthropy, OneTable
Wayfinder Uncertainty Coaching FAQs
-
This program is built around the essential importance of collective, live support.
Please consider joining only if you’re able to attend the majority of the live sessions.
That said, life is complicated, and I realize not everyone will be able to 100% commit to attending all sessions.
Each person may miss up to 2 sessions out of the series.
The sessions will all be recorded and available until the following live session, after which I’ll delete them for your privacy.
-
Then you’ll be able to offer your wisdom to the rest of the group. Each session will include some participatory exercises that I’ll lead, and discussion time for the group to share with each other.
-
Yes! If you sign up within the first 48 hours of the launch window (Dec 11-12), you can use the code WAYearly to get $700 off.
You can also choose to pay in either 1 or 2 monthly installments, to respect your cash flow.
-
Absolutely! It’s a great set of skills to strengthen employee resilience and leadership.
You can download this supporting document to share with your boss, if it will help you make your case.
-
Ask me! I’m hosting an AMA office hour on December 16 at 1pm EST. Come ask your questions!
Of course, you’re also welcome to sign up for a free half-hour call to talk it over with me.
Set Sail
It’s time to hoist the anchor and catch the wind
This program is an investment in your capacity to show up fully for what matters without falling apart.
You’re choosing to build your toolkit now, so you're not white-knuckling your way through the next decade of change.
The uncertainty waves are only growing. You can learn to ride them.
Set your compass. Map your course.
It’s time to direct your own sails!