The Leadership Odyssey™
The Leadership Odyssey™
For leaders ready to think clearly, decide confidently, and lead at their next level.
A 6‑day executive experience in Greece, held in small intentional cohorts.
The Leadership Odyssey™
The Leadership Odyssey™
A Strategic Reset for Leaders Who Carry a Lot, and Rarely Pause
This isn’t time away from leadership. It’s where you sharpen how you think, decide, and lead.
The Leadership Odyssey™ is for leaders who recognize themselves here:
✅ making decisions with incomplete information
✅ responsible for people, outcomes, and direction
✅ expected to stay composed, confident, and clear
✅ carrying others forward, while running on empty
✅ navigating transitions or identity‑level shifts
You leave with:
✅ sharper judgment
✅ clear sense of direction,
✅ grounded, commanding presence — not inspiration that fades by Monday.
Six days. A career's worth of clarity.
Now enrolling:
June 27–July 3, 2027 · 5-star resort, Mount Olympus Riviera · Intentionally small cohort
This is where leaders come back to themselves.
Why Leaders Invest in This
Built to strengthen how you think, decide, communicate, and lead under pressure
This goes beyond traditional conferences and forums. It's a structured leadership development experience. For many leaders, it qualifies as professional development their organization will fund.
Through guided peer dialogue, practical frameworks, and applied tools, you
✔ deepen executive judgment
✔ strengthen communication and influence in complex environments
✔ reinforce the clarity and confidence required for expanded leadership responsibility
Bringing a colleague? Teams benefit from shared language, stronger alignment, and better decisions back at work.
A Sponsorship Brief is available upon request, ready to share with your manager or L&D team.
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🎥 Sneak Peek: 3-Minute Resort Overview
A glimpse of the setting that creates space for clarity, reflection, and connection.
Limited early-access pricing available until December 20th. Secure your spot early.
The Leadership Odyssey™ Experience
Where leaders step out of constant motion to reconnect with clarity, judgment, and direction.
Why it matters now
You’ve led through change and carried responsibility with care. Today, leadership demands more than action, it demands judgment. This experience creates the space to step back, think clearly, and recalibrate how you lead and decide.
What it is
A 6-day executive leadership experience designed to strengthen how you think, decide, and lead, grounded in modern insight and the enduring wisdom of Greece.
What it is not
Not a conference. Not a vacation.
A deliberate leadership experience designed to sharpen clarity, presence, and sound judgment so you return focused, grounded, and ready to lead with confidence.
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This isn't a pause. It's where leaders recalibrate.
Strengthen clarity, presence, courage, and judgment to lead with confidence as demands rise.
What's Included
Everything you need for a high-impact leadership experience, curated to support clarity, perspective, and meaningful dialogue.
Leadership Odyssey™ Immersive Experience
Six days of focused leadership sessions designed to strengthen clarity, presence, and confidence. Through practical frameworks, applied exercises, and guided reflection, you deepen self-awareness, strengthen communication, and sharpen how you lead.
Leadership Odyssey™ Growth Companion
Curated set of tools to help you capture insights and turn them into action, including guided exercises, reflection prompts, and practical resources to support continued growth beyond the experience.
Guided Grounding & Renewal Practices
Structured practices designed to restore mental clarity and capacity, from guided reflection and movement to intentional pauses that help you think clearly and lead with focus.
Cultural Discovery Excursions (Family Included!)
Cultural immersion experiences that expand perspective, from ancient sites to local traditions, creating context that deepens reflection and broadens how you think and lead.
Premium Seaside Resort Experience
5-star seaside setting designed to support focus, reflection, and restoration, with premium accommodations, set along the Olympus Riviera.
Community & Connection
Deliberately small cohort of leaders operating at similar levels of responsibility, creating space for meaningful dialogue, shared insight, and lasting professional relationships.
Philoxenia Dinner Celebration (Family Included!)
Private Philoxenia dinner at Dora’s family home, featuring a traditional home-cooked Greek meal prepared by her mother, and a rare opportunity for meaningful connection and conversation.
Seamless travel & logistics throughout, including airport transfers and transportation for local excursions
Additional curated elements that elevate the experience throughout.
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Your 6-Day Leadership Journey
A thoughtfully designed flow of sessions, reflection, and cultural immersion,
creating space leaders rarely give themselves.
Not packed. Not rushed.
Each day is intentionally paced so insight, conversation, and perspective actually land.
Optimized to industry benchmarks for transformational leadership retreats.
Where Leadership Meets Greek Soul
Nested between Mount Olympus and the Aegean Sea, this experience invites you to lead, reflect, and reconnect, with yourself and those who matter most.
Hannah D.
Data Analytics
Shamla N.
Cybersecurity
Josie O.
Data Science
Designed With Intention and Purpose
This is not a bundled vacation package. It’s a deliberately designed leadership experience, combining structured development, cultural immersion, and space to think, reflect, and integrate.
For those who want a detailed view of what’s included:
Every element is designed to strengthen how you think, decide, and lead.
Experiences of this depth and exclusivity are typically priced at $10,000+.
The Leadership Odyssey™ offers a rare combination of executive-level leadership insight and deeply personal, culturally grounded experiences.
What’s Included and How It Adds Up
A clear look at what’s included, and the exceptional value behind every detail.
Every element is intentionally designed to strengthen how you think, decide, and lead.
Experiences of this depth and exclusivity are typically priced at $10,000+.
The Leadership Odyssey™ offers a rare combination of executive-level leadership insight and deeply personal, culturally grounded experiences.
Choose Your Odyssey Experience
Choose the experience that fits how you want to show up and who you want to share it with.
Option a:
Odyssey Leader + Family Companion
Double occupancy • 1 Odyssey Leader + 1 family member
Full Value:..................................................................$7,100
SOAR First-Time Retreat Bonus:..................................− $1,100
Early Access Resort Bonus:........................................− $1,000
Total Savings:............................................................$2,100
Your Early Bird Price Price (leader only):............ $5,000 USD
Add 1 family member:............................................ $850 USD
Your Total Price (leader + 1 family):........................$5,850 USD
Exceptional value at
$2,995 per person
(Optional: Add a 3rd family member for +$650.)
Option B:
Odyssey Leadership Duo ⭐ Most Popular
Double occupancy • 2 Odyssey Leaders
Full Value:...............................................................$10,600
SOAR First-Time Retreat Bonus -leader 1:....................− $1,100
SOAR First-Time Retreat Bonus -leader 2:....................− $1,100
Early Access Resort Bonus:........................................− $1,000
Total Savings:...........................................................$3,400
Your Early Bird Price Price (2 leaders): ................$7,400 USD
Your Total Price (2 leaders):...................................$7,400 USD
Unbeatable value at
$3,700 per person
(Optional: Add a 3rd family member for +$650.)
Option a:
Odyssey Leader + Family Companion
Double occupancy • 1 Odyssey Leader + 1 family member
Full Value:
SOAR First-Time Retreat Bonus:
Early Access Resort Bonus:
Total Savings:
Your Early Bird Price Price
(leader only):.
Add 1 Family Member:
Your Total Price
(leader + 1 family):
$7,100
-$1,100:
-$1,000:
$2,100
$5,000 USD
$850
$5,850 USD
Exceptional value at
$2,995 per person
(Optional: Add a 3rd family member for +$650.)
Option B:
Odyssey Leadership Duo ⭐ Most Popular
Double occupancy • 2 Odyssey Leaders
Full Value:
SOAR First-Time Retreat Bonus:
Early Access Resort Bonus:
Total Savings:
Your Early Bird Price Price
(leader only):.
Add 1 Family Member:
Your Total Price
(leader + 1 family):
$7,100
-$1,100:
-$1,000:
$2,100
$5,000 USD
$850
$5,850 USD
Unbeatable value at
$3,700 per person
(Optional: Add a 3rd family member for +$650.)
💎 Details & Important Notes
All prices in USD. Limited availability; rates and inclusions subject to resort confirmation.
Pricing reflects the 2026 experience and may vary slightly for future offerings.
Early Access bonuses and timing are limited and subject to availability.
Occupancy: Each room accommodates up to 3 guests.
Option A: 1 leader + 1 family guest (spouse, partner, or immediate family). Optional add-ons: +$850 for first guest / +$650 for second (3-person max).
Option B: 2 leaders sharing one room (open to peers, colleagues, friends, or family).
For families of 4 or more, contact Dora directly — a larger room may be available through the resort.
An additional family room (no leader, guest-only access and meals included) may be added for +$4,850. This room qualifies for the applicable Early Access Resort Bonus.
Deposit & Payments:
• A $2,000 non-refundable deposit is required at sign-up.
• Early Access 1 (by Dec 20): $1,000 Bonus. Balance $3,000 due Dec 31 or 2 payments of $1,550 (Dec 31 & Jan 31).
• Early Access 2 (by Jan 31): $500 Bonus. Balance $3,500 due Feb 28 or 2 payments of $1,800 (Feb 28 & Mar 31).
Installment amounts shown apply to Option A (one leader) and do not include optional add-on guests or the Two Leaders rooming option. Listed rates reflect bank transfer pricing. Card payment options are also available.
• Standard Enrollment (after Jan 31): regular pricing; deposit at sign-up and balance due by Mar 31.
Early Access Resort Bonus:
• Early Access 1 (by Dec 20): Choose either $1,000 credit or $700 credit + €200 spending cash provided onsite.
• Early Access 2 (by Jan 31): Choose either $500 credit or $200 credit + €200 spending cash provided onsite.
The euro spending cash is included for convenience and may be used freely for personal expenses.
Cancellations:
• Cancel by Jan 31 for a refund of payments made (minus deposit).
• After Jan 31, all payments are non-refundable.
• A confirmed leader may transfer their spot to another qualified participant upon Dora’s approval (to maintain the experience’s curated circle).
Travel & Insurance:
• Airfare and travel insurance not included.
• Strongly recommend booking flights ≈ 3 months in advance and purchasing comprehensive coverage.
Availability: Live music, venues, and local experiences are subject to confirmation and may vary slightly by schedule or weather.
Spots are intentionally limited to protect the depth of this experience.
Early access pricing and bonuses are released in limited windows.
What Leaders Experience in My Work
Real voices. Real leaders. Each with a unique view of Dora’s work and the change it inspires.
Josie O.
Data Science
“Dora saw strengths in me I couldn’t see in myself.”
▶️ Quick clip: why they trust Dora
Shamla N.
Cybersecurity
“Dora listens deeply and gets you exactly where you want to go.”
▶️ Quick clip: why they trust Dora
Dr. Joe P.
Data & Analytics
“Dora makes the complex feel clear and actionable. A phenomenal coach.”
▶️ Quick clip: why they trust Dora
Josie O.
Data Science
“Dora saw strengths in me I couldn’t see in myself.”
▶️ Quick clip: why they trust Dora
Shamla N.
Cybersecurity
“Dora saw strengths in me I couldn’t see in myself.”
▶️ Quick clip: why they trust Dora
Dr. Joe P.
Data & Analytics
“Dora saw strengths in me I couldn’t see in myself.”
▶️ Quick clip: why they trust Dora
This is the work behind the experience.
The Leadership Odyssey™ brings it to life in an immersive, in-person setting.
A brief, pressure-free conversation to understand your goals and timing.
More Voices. More Wins.
See how coaching with me is helping data & tech leaders unlock clarity, confidence, and momentum.
Lena Z.
Business Analysis & OKRs
Jimmy G.
Data Governance
“Dora is the best person to catapult someone in their career and help them reach their maximum potential, always supporting and providing assistance so that people can get where they want to go.”
Shamla N.
BOD & C-Cuite Executive
"If I were looking for a coach, I would want Dora in my corner, and I suggest you think about how to put her in your ecosystem of advisors, coaches and helpers."
Vladimir S.
IT Service Delivery
"Exceptional leader and coach... Her mentorship was crucial in my earning a promotion ...Dora’s impact extended beyond me... Her ability to foster growth and navigate complex challenges speaks volumes about her capabilities in her area of expertise as a transformational leader."
Suresh T.
Data Engineering
“One of the best leaders I had worked with. Went above and beyond in mentoring and supporting by understanding my strengths, passion and guided me to develop the skills I need to elevate myself. She’s truly wonderful and I cannot thank her enough!”
Dr. Joe P.
Data & Analytics
Feeling inspired by their stories?
If you're ready to rise, this is your moment to take action.
Meet Your Leadership Odyssey™ Guide
A leadership voice shaped by clarity, courage, and connection
Dora Boussias is a trusted global voice at the intersection of data, human-centered AI, and leadership. She helps leaders navigate complexity, sharpen their judgment, and apply practical strategies that drive real results.
After 30 years leading enterprise-scale transformation across industries at global firms like GE, Prudential, and Stryker, Dora now works with leaders to sharpen thinking, strengthen decision-making, and lead with confidence.
Her work helps high-achieving professionals step into leadership and supports senior leaders and executives in strengthening their thinking, decision-making, and leadership presence.
Across her work, one pattern holds: when leaders have the space to think clearly, their decisions improve and their leadership follows.
As the founder of SOAR with Confidence®, Dora brings a practical, grounded approach to leadership development, combining structured frameworks with real-world application to build clarity, strengthen presence, and lead with purpose.
At The Leadership Odyssey™ in Greece, she brings this work to life in an immersive setting, blending leadership development, cultural depth, and authentic connection. It is a rare experience designed not just to learn, but to think, reflect, and lead differently.
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Got Questions? Let’s Clear Things Up!
Still unsure? Read through these common questions to make an informed decision and start your transformation today.
Q1: Who is this experience designed for?
Designed for leaders who are already operating at a high level and feeling it. You're carrying responsibility, making decisions with incomplete information, and expected to project confidence even when things aren't clear. You may be navigating a transition, stepping into greater scope, or simply haven't had uninterrupted space to think while carrying others forward. It's for you if you're ready to lead at your next level with sharper judgment, clearer direction, and a more grounded presence.
Q2: Do I need leadership experience to join?
You don’t need a formal leadership title, but you should be operating at a level where your thinking and decisions matter. The group brings together experienced professionals across data, technology, and related fields, all focused on strengthening their judgment, influence, and impact.
Q3: How do I know if this is the right fit for me?
The best way to know is to talk it through.
In a short conversation, we’ll explore your goals, where you are right now, and whether this experience aligns with what you need next. If it’s the right fit, you’ll know. If it’s not, you’ll still walk away with clarity.
Q4: What can I expect during the experience?
Each day is intentionally designed to balance leadership development, reflection, and meaningful experiences. You’ll engage in focused sessions, guided reflection, and authentic cultural moments, all designed to help you think more clearly, reconnect with what matters, and lead with greater confidence.
Nothing is rushed. The space is designed so insights actually land.
Q5: How much free time will I have?
You’ll have meaningful space to relax, explore, and recharge. The schedule is intentionally designed to include both structured sessions and unhurried time, so you can reflect, reset, and fully experience Greece without feeling rushed.
Q6: What’s included in the experience?
Your registration includes five-star accommodations, immersive leadership sessions, curated excursions, private transportation, and thoughtfully designed group experiences. Daily meals and additional activities are outlined in detail in the full experience breakdown.
Q7: Can I bring a family member or companion?
Yes. You can attend solo or share the experience with a companion. Dedicated options are available for attending with a family member or another professional, with full access to the resort, excursions, and shared experiences.
Q8: When will the experience take place?
The 2027 Leadership Odyssey™ will take place from June 27–July 3, 2027. Participants will receive full itinerary details and travel guidance well in advance to support smooth planning and coordination. The experience is hosted annually.
Q9: Where will the experience take place?
The Leadership Odyssey™ Experience is hosted at the Mediterranean Village Hotel & Spa, a five-star seaside resort in Paralia, Katerini, Greece, at the foothills of Mount Olympus. The setting combines coastal calm with mountain views, creating the ideal environment for clarity, reflection, and connection.
Q10: What if I want to arrive early or extend my stay in Greece?
Yes. You’re welcome to arrive early or stay longer to make the most of your time in Greece. While the experience follows set dates, Dora can share recommendations and trusted contacts to help you plan an extended stay.
Q11: Can my employer sponsor my participation?
Yes. Many participants use professional development or executive education budgets. If helpful, we can provide the Leadership Development Sponsorship Brief, which outlines the outcomes and value to support your approval process.
Q12: What’s the cancellation policy?
Your non-refundable deposit secures your place. If you cancel before the designated cancellation deadline for your cohort, payments beyond the deposit will be refunded. After that, payments are non-refundable. If needed, you may transfer your registration to another qualified participant with approval to maintain the integrity of the group.
Q13: Is this the same material used in Dora’s other programs, such as SOAR with Confidence: Chart, Steer, and Anchor Your Career Success™?
No. The Leadership Odyssey™ Experience is a standalone experience with its own original content, structure, and design. While some core principles may overlap, this is an immersive, in-person experience focused on deep thinking, reflection, and application, supported by the Leadership Odyssey™ Growth Companion.
This might be the reset your leadership actually needs.
A small, highly curated experience designed for clarity, judgment, and meaningful progress.
Let’s determine if this is the right next step for you.
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