Becoming Unstuck and Unstoppable.
Welcome To Your Next Chapter.
You are ambitious, high-achieving, and driven—yet something feels off. You’ve built a career, managed life’s responsibilities, and checked off many of the “success” boxes, but deep down, you know there’s more. More fulfillment. More clarity. More alignment between who you are and who you want to become.
Whether you’re navigating a career shift, stepping into leadership, embracing a new life stage, or simply craving a deeper sense of purpose, you’re in the right place. This is where transformation happens.
Here, you’ll find the tools, strategies, and guidance to move from feeling stuck to stepping boldly into your next season—with intention, confidence, and a clear plan of action. Through coaching, workshops, and a supportive community of like-minded women, you’ll rediscover your power, redefine success on your terms, and create a life that feels as good on the inside as it looks on the outside.
You don’t have to figure this out alone. Let’s take action—together.
Welcome to your journey of growth, balance, and purpose.
Meet Clare L. Bailey
Hi, I’m Clare L. Bailey — strategist, intentional living advocate and lifelong dream chaser. For 15 years, I’ve helped ambitious professionals and entrepreneurs move past uncertainty, realign with their purpose, and take bold action toward the life and career they truly desire.
I know what it’s like to hit a pivotal moment—where success on paper doesn’t always translate to fulfillment. After earning my MBA, I launched my corporate career in the U.S., working for Fortune 500 companies like CITGO Petroleum Corporation. Yet, despite financial security and career growth, I felt something was missing. That realization led me to resign from my corporate job in 2012 and embark on a transformative journey to South Africa, where I taught, coached, and facilitated workshops that deepened my passion for social entrepreneurship and business development.
Since then, I’ve trained and coached over 495 individuals across the U.S., South Africa, and the Caribbean, helping them gain clarity, create strategic action plans, and execute with confidence. As the Director of Programmes and Strategic Partnerships for the Richard Branson Centre of Entrepreneurship – Caribbean, I’ve led initiatives impacting 975+ entrepreneurs and businesses, designed and facilitated personal development programs for Virgin Voyages Elevate Series both in the USA and Europe. I have helped to secure US$1.1 million in funding to support the capacity development of Caribbean entrepreneurs.
Whether you're navigating a career shift, stepping into leadership, or craving deeper fulfillment, I’m here to help you move forward—with intention, strategy, and purpose.
If you’re ready to stop feeling stuck and start chasing what truly matters, let’s make it happen—together.
Welcome to your next chapter.
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"It doesn’t matter what you haven’t done before, today is a fresh opportunity to begin again. You are exactly where you need to be, and this is your time to create the life you truly want. Every small step matters because when they compound, they propel you forward, leading to transformation, fulfillment, and the life you deserve."
How can I be of service to you?
1:1 Coaching
A personalized coaching experience designed to help high-achieving women gain clarity, confidence, and strategic direction. Through tailored guidance, accountability, and actionable frameworks, you’ll move from feeling stuck to leading your life with intention and purpose.
Mastermind Group
A supportive, high-impact community where ambitious women connect, learn, and grow together. Through expert-led discussions, shared experiences, and collaborative problem-solving, you’ll gain insights, accountability, and the motivation to take bold, intentional steps forward.
Team Workshops
Interactive and results-driven sessions designed to strengthen leadership, communication, and team synergy. Whether for corporate teams, organizations, or professional groups, these workshops foster trust, collaboration, and strategic growth to drive success without burnout.
Together we can achieve...
Clarity
Fulfillment
Accountability
Strategy
Proactivity
Trust
Real Results. Lasting Impact.
Testimonials
The Dream Chaser
Goal Setting Action Plan
Workbook & Planner
Are you feeling stuck?
Do you have amazing ideas but don’t know where to start?
Do you need a structured plan to guide you toward achieving your goals?
If you answered yes to at least one of these questions, then the Dream Chaser Goal Setting Action Plan Workbook is exactly what you need!
This workbook is designed to help you transform dreams into actionable goals and overcome the obstacles that often stand in the way of success. Achieving your goals requires intentional action, and this book provides the structured framework to turn your ambitions into reality.
What You’ll Get Inside:
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SMART Goal Planning – Set achievable goals with clear deadlines
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Personalized Action Plans – Break down your goals into manageable steps
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Resource List – Access tools to support your success
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Risk Mitigation Strategy – Plan for potential challenges
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12-Month Calendar Planner (January – December) – Stay organized all year
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Monthly & Weekly Action Plans – 52 weeks of guided progress
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Monthly Assessments & 3-Month Check-ins – Track your growth and stay accountable
This workbook is your personal roadmap to success—whether you're pursuing career growth, personal development, or a passion project. Start today and take control of your future!
