When Discipline, Moderation & YOLO Collide

June 28, 2025

9:00am PST/ Noon EST

(90-minutes)

A Mindset Reset for High Achievers Who Want to Win Without Burning Out

You’ve got big goals—but lately, you’re tired. Torn between sticking to the plan, easing up on the pressure, or saying “forget it” and doing something bold.

This workshop is for high-achieving professionals, leaders, and entrepreneurs who are ready to explore what it really means to create a life that’s driven and fulfilling. We’ll break down how to balance the structure of discipline, the sustainability of moderation, and the spark of “YOLO” (You Only Live Once)—without sabotaging your goals or burning yourself out.

Using practical strategies, mindset shifts, and guided reflection, you’ll discover your own sweet spot—the place where you can lead, build, create, and stretch without losing yourself in the process.

In this workshop you will:

  • Uncover how perfectionism and pressure may be hiding behind your discipline

  • Learn how to pace your goals through moderation without losing momentum

  • Reignite your sense of joy and possibility through calculated, purpose-driven risks

  • Identify the belief systems keeping you stuck in cycles of overworking or under-living

  • Create a personalized “Stretch Map” to move forward with clarity, balance, and boldness

Who is this workshop for?

This workshop is designed for:

  • High achievers who are exhausted from hustling in silence

  • Leaders who feel stuck between stability and their next big leap

  • Entrepreneurs who want strategy and soul in their success story

  • Anyone craving more joy, more meaning, and more belief in themselves

Whether you’re in a season of expansion, transition, or soul-searching—this session will give you tools to realign your thinking and stretch into the next version of your success.

DeShawn Wynn – The Success Architect

For over 15 years, DeShawn Wynn has built and led a thriving business, navigating the ever-changing landscape of entrepreneurship with resilience, strategic vision, and an unshakable belief in the power of mindset. As a trusted leader in the industry, she has worked with high-level organizations, top professionals, and ambitious entrepreneurs, proving that success is not just about talent—it’s about the ability to think, adapt, and lead with clarity and confidence.

But DeShawn’s success wasn’t built on external validation—it was built from within. She learned firsthand that the hardest part of being an entrepreneur isn’t the competition or the market—it’s the internal battles: self-doubt, fear, and the mental roadblocks that keep even the most ambitious people stuck. Determined to stay in business and thrive, she committed herself to over 15 years of deep study on mindset, high performance, and transformational success strategies—not just as theory, but as a lived practice that directly fueled her longevity, profitability, and influence.

A Visionary Leader in Personal & Professional Growth

With over 30 years of experience in strategic planning, leadership, and event design, DeShawn has built a reputation for crafting experiences that drive real impact. As the founder of Stretch to Wynn Success Retreats, she creates immersive, high-level experiences that push participants beyond their perceived limits, integrating proven success strategies with mindfulness practices like breathwork, meditation, and sound therapy.

Her expertise has been recognized industry-wide, with prestigious honors including:

  • Smart Meetings Magazine 2024 Entrepreneur Award

  • Top 100 in Events (2024) – Black in Events Network

  • Entrepreneur of the Year (2022) – National Coalition of Black Meeting Professionals

  • Top 100 Most Influential People in the Event Industry (2021 & 2022) – Eventex Awards

Why High Achievers Trust DeShawn Wynn

  • Proven Mental Resilience & Clarity – I’ve faced the self-doubt, imposter syndrome, and fear-based thinking that hold so many high achievers back. I did the deep mindset work to break through those barriers, and now I help others do the same.

  • Fearless Execution – I know what it’s like to hesitate, second-guess, and play small. But I also know what happens when you push past fear and take bold, strategic action—because that’s exactly how I’ve built my success.

  • Sustainable Growth Without Burnout – I refused to believe that success had to come at the cost of exhaustion. Through trial, refinement, and intentional mindset shifts, I’ve created a way to grow, scale, and succeed without constantly hustling to the point of burnout.