THE INVITATION
Something is calling you
forward.
You’ve built something real. The career, the credentials, the accomplishments—they matter, and you’ve earned them. And yet there's a quiet voice underneath all of it asking: What’s next? Not more of the same. Something richer. Something truer. Something that finally feels like you.
- Where do I want to be braver, in my life and at
work? - What would it look like to lead from who I actually
am—not who I’ve learned to perform? - What would it be like to Dare to Lead my own life?
This week-long immersive retreat answers these calls on two levels.
You'll complete the full 24-hour Dare to Lead™ curriculum — Brené Brown's empirically-based, courage-building program — while living inside a retreat experience intentionally designed to let the work land somewhere lasting.
Seven days in one of the most beautiful places on earth, with a small group of people who are ready to go beneath the surface. Ten people. One facilitator trained directly by Brené Brown.
And the kind of transformation that only happens when the pace is human and the setting is beautiful enough to match the work.
This is a singular offering — one cohort, one week, one beautiful place, once a year.
This is Dare to Lead™ delivered the way it was meant to be experienced: unhurried, embodied, with the Caribbean as your classroom and nowhere you need to be except here.
You leave Dare to Lead™ Trained.
You leave transformed.
This is meant for you if:
You’ve been feeling the pull to live more courageously.
You feel the next chapter of your life emerging and want to give yourself a gorgeous setting to listen, learn, and receive.
You’re craving the beauty of the Caribbean—and the transformation that always unfolds when curious souls gather in sacred space. (Yes, you are one of them.)
You’re ready to be nourished, held, challenged, and restored by Nevis’s natural beauty and island wisdom.
Leadership reality
You Know the Feeling
You lead people, and you feel the cost of doing it from behind armor—the perfectionism, the over-functioning, the inability to let anyone see the full picture.
You’ve read Brené Brown. Maybe you’ve watched every talk, underlined every page. And some part of you knows that reading about courage and practicing it are not the same thing.
You want real conversation with people who don’t need you to perform. You want a week where the pace is slow enough that something can actually shift.
What would it look like to explore who you want to BE instead of what you need to DO?
That whisper you’re hearing right now? It’s telling you the journey has already begun.
Placement is by invitation only
Why Attend a Dare to Lead™ Retreat
Because courage is not a concept—it’s a practice.
You can read about courage, vulnerability, trust, and resilience for years and still find yourself armoring up when it matters most. The retreat format gives you the time, the
space, and the guided practice to move these skills from intellectual understanding into muscle memory. You don’t just learn the four skill sets—you feel them working in real time, with real people, before you go home.
Because the setting changes what’s possible.
A conference room keeps you in performance mode. An island strips it away. When the pace is unhurried, when the beauty of the place mirrors the seriousness of the work, when there’s nowhere to rush off to afterward—you access parts of yourself that a three-day workshop simply cannot reach. The curriculum is the same. What you’re available
for is completely different.
Because transformation happens in relationship.
Ten people. Seven days. Shared learning. By mid-week you’re no longer practicing trust exercises, you’re living them. The cohort becomes a mirror, a testing ground, and eventually a circle of people who know you differently than anyone in your daily life. That kind of connection doesn’t happen in a day.
Because you deserve a week that’s actually about you.
Not about your team’s goals, your organization’s strategy, or anyone else’s development plan. This is a week where the most important question is the one you’ve been carrying quietly: Who am I and what’s next? Everything here, the curriculum, the island, the facilitation, the space, is designed to help you answer that with clarity and creativity.
What is Dare To Lead™?
Dare to Lead™ is an empirically based courage-building program developed by Dr. Brené Brown following two decades of research into courage, vulnerability, shame, and empathy. The program's central finding: courage is not a personality trait. It is a collection of four skill sets that are teachable, measurable, and observable.
More than 150,000 leaders in 45 countries across every sector and industry have completed the program. Participants move from what Brené calls "armored leadership" (leading from self-protection) toward daring leadership (leading with grounded confidence).
The Week
The Curriculumn
Four modules, each building on the last: Rumbling with Vulnerability (the armor you’ve built and the freedom of setting it down), Living into Your Values (the ones that guide you when it’s hard, not just the ones on paper), BRAVING Trust (a precise framework for how trust forms and fractures), and Learning to Rise (the practice of navigating failure with intention rather than reactivity).
The Rythmn
Opportunities for movement (walking, ocean swims, hiking, tennis) before breakfast. Mornings hold the curriculum. Afternoons are yours—walk the grounds, sleep in a hammock, explore the island, join an excursion, continue a conversation that’s been building all week. One full afternoon is a private sailing and snorkeling excursion to a cove accessible only by boat. Evenings bring shared dinners and the unhurried pleasure of being somewhere beautiful with people you’re starting to truly know.
The Integration
By the final day, the four modules come into conversation with each other—and with the question you arrived carrying. You’ll build a personal Rising Strong process, create commitments grounded in your values, and leave with a clarity about what’s next.
The After
A 1:1 virtual coaching session and a group reconnection call ensure that what you discovered on the island stays with you long after you leave.
The 24 hours of Dare to Lead™
curriculum is woven throughout the week.
Nothing is rushed.
The schedule is designed to let the work
breathe—and to let Nevis do what it does best,
provide the perfect balance of tranquility and inspiration.
The Curriculumn
The 24 hours of Dare to Lead™ curriculum is woven throughout the week. Nothing is rushed.
| Saturday | Arrival | Welcome reception and dinner, introductions |
| Sunday | Module 1: Rumbling with Vulnerability | Armor vs. courage; the myths of vulnerability; emotional granularity |
| Monday | Module 2: Living into Our Values | Identifying core values; behaviors vs. aspirations; boundary-setting |
| Tuesday | Module 3: BRAVING Trust | The 7 components of trust and trust inventory. |
| Wednesday | Integration + Excursion | Morning reflection & small groups; afternoon sailing & snorkeling |
| Thursday | Module 4: Learning to Rise | Reckoning with emotion; the stories we make up; rising from failure |
| Friday | Integration, Design & Completion | Action planning; mini-commitments; Closing Celebration; Reflection |
| Saturday | Send-off | Final goodbyes; breakfast together; depart |
The New York Times once called it “the nearest thing to Eden.” Once you arrive, you’ll understand why.
The Hermitage is a small, family-owned boutique inn that has been welcoming guests since 1970, tucked into the hillside of Nevis with open-air porches, swinging hammocks, and a restaurant that turns Caribbean ingredients into something memorable.
Our group has exclusive use of the property for the full week. No other guests. No distractions. Just ten people, one beautiful place, and the kind of privacy that lets real work happen.
Getting There
Fly into St. Kitts (SKB). The Hermitage arranges a taxi to Reggae Beach, then a five-minute water taxi across to Nevis, with another taxi up to the inn. Transfers are included for arrivals before 4pm Saturday and
departures after 12pm the following Saturday.
TESTIMONIALS
“Fabulous experience! Chris is an awesome facilitator and designed high levels of engagement and interaction. It was so helpful to exchange and practice the models we learned. We had plenty of time to dig in. ”
— Monica K.
“I loved having the ability to connect on a personal level. Our shared vulnerability made the constructive feedback and diverse viewpoints so much richer. Chris set expectations but was so kind and curious.”
— Maria D.
“Great content, great energy, great opportunities to connect in small groups. I so appreciated the time and space to disconnect, to reflect, and drill down.”
— Erin D.
What You’ll Carry Home
The transformation here isn’t abstract—it’s something you can hold. You’ll leave with new tools, deep relationships, and a different way of leading. of living.
New Ways Of Seeing
- A practical vocabulary for vulnerability, so you can name what’s happening in any high-stakes moment
- Your two core values translated into specific, observable behaviors
- A completed BRAVING Trust inventory for your most important relationships
- A personal Rising Strong process for navigating failure and disappointment
- Action plans and concrete commitments grounded in your value
People Who Know You Differently
- A circle of fellow leaders who know you beyond your title
- A 1:1 virtual coaching session post-retreat
- A group virtual reconnection session for accountability and continued community
Investment
There is no comparable program. This is the only offering that combines the full Dare to Lead™
certification with a week-long immersive retreat at The Hermitage—and it runs once a year, for a maximum of ten people.
Self-Investment $5,500*
Dare to Lead™ Trained, or
ICF Credentialed (ACC / PCC / MCC)
Corporate-Sponsored $6,650*
Your company covers investment.
Sponsorship letter available on request.
*Optional: Gingerbread Cottage upgrade (Private four-poster bedroom
cottage, sitting room, kitchenette, and personal porch) — + $900
What’s Included
Your investment covers everything (except your airfare to St. Kitts ): the full curriculum and certification, seven nights at The Hermitage, meals, program activities, a sailing excursion, the DTL™ Workbook, all program transportation,
airport transfers, a virtual circle back session, and your post-retreat coaching session.
Payment Plans
- Pay in Full - Due within 14 days of acceptance of your application.
- Two Payments - 50% deposit within 14 days of confirmation; remaining 50% due 90 days before the retreat.
- Three Payments - 33% deposit within 14 days; second 33% due 120 days before; final 34% due 60 days before.
If plans change: full refund 60+ days out, 50% refund 30–59 days, no refund within 30 days. If the 8-person minimum isn’t reached by August 30th, everyone is refunded in full.
A Personal Invitation from Chris
I spent years doing leadership the way I thought I was supposed to—performing competence, managing perceptions, holding everything together so tightly that I forgot there was a person underneath all the holding.
When I trained with Brené Brown in 2019, something shifted. Not because of the content alone—though the research changed the way I understood courage permanently—but because of the experience of being in a room where vulnerability wasn’t a liability. Where I could set down the performance and discover that what was underneath it was stronger than anything I’d been protecting.
More Candor. More presence. More of the leader I’d been circling around for years.
Since then, I’ve facilitated Dare to Lead™ for leaders across industries, and I’ve watched the same thing happen every time: when the pace is right, when the setting matches the seriousness of the work, when you’re surrounded by people willing to go beneath the surface. The curriculum doesn’t just teach you something. It rearranges something.
That’s why I built this retreat. Not another program. A week on an island where the beauty of the place gives permission for the beauty of the work. Where you can learn in the morning, integrate in the afternoon, and let the ocean handle whatever the mind can’t quite reach.
If you’re feeling the pull, let’s talk. That’s all the first step is, a conversation.
-Chris
YOUR FIRST STEP A Space to Be Heard
This retreat runs once a year for a maximum of ten people. Because of the depth of the work and the intimacy of the group, expressing interest does not guarantee a spot—every participant has a brief 1:1 conversation with Chris before a place is confirmed, to ensure the retreat is the right fit for you and for the cohort.
Express interest
By completing our
Application form online.
Have a conversation
A short call to make sure
the retreat is the right fit
—for you and for the
cohort.
Confirm your place
with a deposit.
Payment may be made in full or on a plan.
The retreat requires a minimum of 6 confirmed participants to run. Maximum enrolment is 10. In the event the minimum is not reached, all registered participants receive a full refund.
Registration does not hold your place — your 1:1 with Chris does