Have you ever said to yourself,
“If I knew then what I know now,
my life would be so much different.”
I had that exact realization over a decade ago.
And it became the foundation for creating
Stretch to Wynn Success Retreats.
Step Into Your Next Level—It’s Time to Stretch
You’ve checked the boxes. Built the business. Earned the title.
Welcome to Stretch to Wynn—where we go beyond traditional goal-setting and dig deep into the mindset, values, and actions that shape true success.
This isn’t about doing more. It’s about becoming more aligned. More confident. More fulfilled.
From Stuck to Soaring. This retreat is for high achievers ready to stop overthinking and start stretching into their biggest, boldest goals.
Your Next Level Requires a New You. At Stretch to Wynn, you’ll break through mental barriers, gain clarity, and take fearless action.
Success Shouldn’t Feel Like a Struggle. If you’ve been working hard but still feel unfulfilled, it’s time to redefine what success looks like—for YOU.
A Blueprint for Expansion. With my STRETCH Framework, you’ll leave with a game plan for lasting change—mindset shifts, bold strategies, and unstoppable momentum.
Join Us for a Transformational Experience Designed for
High Achievers Who Are Ready to Stretch Beyond Limits
Our Stretch to Wynn Retreats are curated for driven entrepreneurs, leaders, and visionaries who are ready to break through the mindset blocks that are quietly holding them back.
You’ll unplug from the noise, reconnect with your values, and gain the clarity needed to make aligned, bold moves.
This is more than a retreat—it’s a reset.
A reimagining. A recommitment to the life you truly desire.
Let this be the moment you
stop settling and start stretching.
2026 Locations
Monterey, CA
March 16-18, 2026
Registration: $2,500
** Does not include Room:
Room Rate: $285/night plus resort fee
Includes
Workshop Materials
7 Meals
Curated Luxury Experiences
Special Gift Bag
Accra, Ghana
October 11-17, 2026
Registration:
Single Occupancy - $5,000
Double Occupancy - $4,500
Includes:
Hotel for 7-nights
Meals (Only meals not included is on the last day which is a free day with no scheduled activities)
Activities
Ancestral River Tour
Naming Ceremony
Cape Coast Dungeon Tour
Kakum National Park Canopy Tour
Kwame Nkrumah Museum
Shopping at Arts Center & Makola Market
For organizations, executive teams, or private groups seeking a fully customized experience, we offer exclusive retreats tailored to your specific goals, challenges, and vision for success.
This Is Your Time to…
Get out of your own way and overcome the fears, doubts, and habits keeping you stuck.
Redefine success on your terms and create a life that feels as good as it looks.
Elevate your mindset, expand your vision, and take bold, strategic action toward your goals.
Success isn’t just about working harder—it’s about stretching
into who you are truly meant to be. Are you ready?
Testimonials
What they say about us.
Amanda
"This session hit on all the things I need to hear regarding how I am running my life and aspirations and gave insightful tips on staying on track without losing your mind, and (my favorite part) prioritizing goals that actually feed your soul, not just your resume."
Gretchen
" A breath of fresh air. I feel refocused and ready to focus on joy."
Hermence Matsosa
"Right in time presentation!!! Great presentation."
What was your biggest take away?
"Just start Everyone is trying to figure it out and there is support to guide you."
- Anatashia Lewis
How would you describe to someone the benefit of the retreat?
"You will learn so much about yourself and life through this retreat. There's opportunities for you to just be present or either engage in discussion without any judgement."
- Anatashia Lewis
How attendees describe this talk?
"Life changing Intimate Informative Tool-based No judgement. You will feel seen and heard. There is space for you to just Be."
- Anatashia Lewis
Meet Your Host
Deshawn Wynn
For over 15 years, DeShawn Wynn has built and led a thriving business, proving firsthand that entrepreneurial success isn’t just about skill—it’s about resilience, mindset, and the ability to adapt under pressure.
As a trusted leader in the industry, she has spent over 30 years designing transformational experiences that empower professionals and entrepreneurs to stretch beyond their limits and step fully into their potential.
As the founder of Stretch to Wynn Success Retreats, DeShawn curates immersive, high-level experiences designed to help ambitious individuals move beyond hesitation, self-doubt, and burnout—replacing fear with clarity, confidence, and bold action.
Her work has been recognized industry-wide, earning her numerous accolades, including being named among the Top 100 Most Influential People in the Event Industry and receiving the Smart Meetings Magazine 2024 Entrepreneur Award. But DeShawn’s expertise isn’t just built on research—it’s built on real-world experience. Having studied mindset, high performance, and success psychology for over 15 years, she knows that the hardest part of success isn’t external—it’s internal.
Her work is dedicated to helping ambitious individuals redefine success on their own terms, sustain their momentum, and build lives that are not only successful—but deeply fulfilling.
Success Architect
Why you should attend on of our retreats
Exclusive, Transformational Experience – Not just another workshop but a life-changing environment.
Mindset & Strategy Combined – You don’t just want motivation; you want real tools and a plan.
Stretching Beyond Limits – The promise of unlocking your full potential and stepping into a bigger, bolder version of yourself.
Success & Wellness Integration – Learning how to thrive in both business and life without overextending yourself.
Connection with Like-Minded Individuals – A supportive, inspiring community of go-getters who "get it."