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Welcome to Engage Your Legacy

Transitions are inevitable—how we navigate them is what defines us. After 25 years of advising individuals, families, executives, and advisors, I’ve seen one truth hold steady: clarity, confidence, and momentum emerge when people align their values, purpose, and actions. That’s the heart of my work.

Through Engage Your Legacy, I help individuals and families of all ages navigate change, define their purpose, and gain the tools to move forward with intention. My Warrior Framework and Warrior Workbook offer a practical, actionable approach to building resilience, strengthening relationships, and creating personal and professional momentum—whether you're facing career shifts, leadership transitions, family business planning, or multigenerational wealth conversations.

I draw on deep expertise across behavioral change, wealth management, family dynamics, and leadership development, along with advanced training in transition planning, exit planning, and coaching. My work is rooted in helping clients ask better questions, access their own wisdom, and build structures that allow them—and those they care about—to thrive.

This is legacy in motion. This is where clarity becomes action.

Black and white portrait of a Ellen Bailey smiling with shoulder-length hair, wearing a dark blazer and earrings, against a plain backdrop.

Meet Ellen

I collaborate with clients of all ages and stages to navigate change, gain clarity, and build momentum in their personal and professional lives. With over 25 years of experience in wealth management, family dynamics, leadership development, and career transitions, I work with individuals, advisors, executives, and families to align purpose, values, and financial decisions. Drawing on that experience, I created the Warrior Framework and Warrior Workbook—practical tools designed to help people move through transitions with more confidence, intentionality, and resilience.

My approach combines deep expertise in behavioral change, life transitions, and family legacy planning with actionable frameworks that help move people forward. I hold credentials including CEPA, CPWA, CeFT, CPRC, RCC, and CIMA, and completed advanced training in family dynamics at the Bowen Center. I bring curiosity, clarity, and contagious energy to my work—helping clients uncover opportunities and create focused, purpose-driven paths forward.

I live in Waccabuc, NY, with my husband and children, and enjoy golf, tennis, paddle, and time on the lake with family and friends.

Who I serve

At Engage Your Legacy, I work with individuals, families, advisors, and organizations navigating transition points where clarity, structure, and forward momentum are needed most.

INDIVIDUALS IN TRANSITION

Career changes, leadership shifts, retirement, or personal reinvention—whether you're just starting out or redefining what comes next, I help you create clarity and build confidence in your path forward.

FAMILIES PLANNING FOR LEGACY

Multigenerational families seeking to align values, communicate openly, and design thoughtful, living legacy plans that reflect both structure and purpose—ensuring their wealth and story serve future generations.

ADVISORS AND PROFESSIONAL TEAMS

Financial advisors and corporate teams looking to develop stronger leadership, client alignment, business growth, or succession strategies—blending human and financial capital to create sustainable success.

BUSINESS OWNERS & ENTREPENEURS

Founders and business leaders preparing for exit, succession, or growth transitions, who want to ensure that their next chapter aligns with both personal purpose and long-term impact.

How I Work

  • Every client, family, and situation is unique—so my approach is always tailored, collaborative, and designed to meet you where you are.

  • We begin by identifying what matters most—your values, purpose, and vision for what comes next. The Warrior Framework simplifies complexity and creates clear, actionable steps to navigate transitions with confidence. Whether you’re facing a career change, business transition, or family legacy conversation, we focus on aligning your personal values, financial decisions, and long-term goals into one cohesive plan.

  • My role is to serve as a partner and sounding board—helping you ask better questions, access your own wisdom, and move forward with clarity and momentum.

The Warrior Framework

This guide is designed to help you develop a career and life rooted in purpose, growth, connection, and stewardship.

IN THIS GUIDE, YOU’LL LEARN HOW TO:

Define success and winning independently, and align your goals with your core values, strengths, and long-term vision.

Silhouette of a person victoriously standing on top of a mountain, with one hand raised and the other planting a flag in the ground.

Navigate inevitable change and challenges while remaining grounded in your strengths and purpose.

A resilient tree that bends when wind hits it, representing authentic adaptability

Make purposeful decisions and maintain daily focus to maintain momentum in your life.

Simple illustration of a bow and arrow pointing upward with intention

Form and sustain high-trust relationships to support happiness and longevity in your life.

Stylized simple icon of people together in a circle

Cultivate optimism to build confidence, motivation, and innovative problem solving.

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Establish routines and practices with a strategic, actionable plan to accomplish your vision of success.

Black and white compass rose with directions North, East, South, and West marked, and detailed arrow points.

Navigate life's challenges with mental toughness, emotional regulation, and perseverance to sustain momentum and joy in your life.

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START YOUR JOURNEY

Let’s Connect.

Whether you're navigating a major transition, seeking clarity in your next chapter, or simply ready to grow with more intention—I’d love to support your journey. Reach out to start the conversation. Let’s explore where you are, where you want to go, and how we can build momentum together.

Black circular logo with a silhouette of a person in yoga warrior pose, surrounded by radiating lines. Around  the circle, text reads: "Authentic Adaptability - Relationships - Realistic Roadmap - Intentionality - Optimism - Resilience - Winning."