Leading with a Personal Board of Advisors:
An Empowerment Retreat for Women in Family Enterprise
Join us for an intimate two-day retreat designed for current and emerging women leaders navigating the complexities of family enterprise, multi-generational wealth, complex wealth transfer vehicles.
Set against the stunning backdrop of Garden of the Gods, this retreat creates space for strategic learning, candid dialogue, interdisciplinary problem-solving, and meaningful peer connection among women who understand the unique dynamics of enterprising families.
Through keynote conversations, facilitated workshops, and small-group dialogue participants will deepen their confidence, strengthen their support systems, and gain practical tools for engaging more effectively with advisors, family members, and their own evolving leadership roles.
This year’s retreat explores how women can build a trusted “personal board of advisors,” develop greater clarity and voice in family enterprise systems, and navigate complexity with authenticity, wisdom, and courage.
Registration Details
Dates & Time: October 8th (10a.m.) - 9th (2 p.m.), 2026
Location: Garden of the Gods Resort in Colorado Springs, CO
Investment: $1,450 for program and meals. 15% discount for Bailey Program for Family Enterprise members.
Lodging at Garden of the Gods Resort is an additional cost of $549/night and can be booked here.
Who Should Attend: This is for members of an enterprising family. Whether you are deeply involved in your family business and/ or family office, preparing for future responsibilities, supporting ownership transitions, or simply seeking greater clarity in your rolw in the enterprising family, this retreat offers a welcoming environment for growth, learning, and authentic community.
This intimate retreat is limited to 12 participants, register here and book your room to secure your spot as soon as possible. This is for members of an enterprising family.
Retreat Themes
Creating a Safe Container for Honest Leadership
Our speaker will guide participants through conversations around authentic leadership, psychological safety, strategic communication, and decision-making within complex family systems. Participants will explore how effective leaders balance influence, vulnerability, accountability, and resilience across personal and professional roles.
Understanding the Fundamentals of Stewardship
Interactive sessions will explore the practical foundations many women encounter in family enterprise systems, including estate planning, trusts, insurance, cybersecurity, wealth structures, and advisor relationships—without assumptions, jargon, or judgment.
Building Your Personal Board of Advisors
Participants will reflect on the advisors, experts, mentors, and support systems currently surrounding them—and identify where they may need stronger guidance, advocacy, accountability.
Learning to Navigate Advisor Relationships
Through small-group “speed topic” conversations with trusted experts, attendees will gain practical confidence in asking better questions, understanding key concepts, and engaging more effectively in conversations around wealth, governance, risk, and planning.
Connection Through Shared Experience
Throughout the retreat, women will have opportunities for participants to exchange insights around leadership transitions, family dynamics, generational communication, ownership complexity, identity, and evolving responsibilities within enterprising families.
Building Your Inner Compass
Our closing keynote speaker will explore authenticity, voice, boundaries, and personal alignment.
Retreat Outcomes
Participants will leave with:
- Greater confidence navigating family enterprise conversations and systems
- A clearer understanding of key stewardship and planning concepts
- Practical tools for engaging advisors and asking informed questions
- A personalized framework for their own “board of advisors”
- Stronger connections with peers facing similar opportunities and challenges
- Renewed clarity around their values, voice, and leadership path
- Space to reflect, reconnect, and return home more grounded and supported
Get to Know Your Guides
Judith Pearson
Judith is a seasoned insurance and risk management expert and founder of Precision Brokers LLC. Trust laws and structures are changing, complex, and contradictory, creating fiduciary responsibility and personal liability. Judith educates trustees and other fiduciaries to reduce risk and implements insurance solutions to protect personal wealth and family legacies. Her clients range from individual and professional trustees, trust companies, law firms and CPAs as well as family offices and private trust companies.
Judith’s background includes serving as founder and CEO of Nomadx Solutions, LLC, which provided risk management solutions to fiduciaries. She was also senior executive vice president of AON’s Financial Services Group and its intellectual property division, and held underwriting management positions at AIG and Chubb, where she specialized in intellectual property liability, directors & officers liability, fidelity and similar coverage forms and underwriting for US-based Fortune 500 and equivalent foreign-based corporations.
Margaret Boyle
Margaret brings nearly two decades of wealth management experience advising single-family offices, multi-family offices, and acting as an outsourced family office for ultra-high-net-worth individuals and families. Her career has been defined by a commitment to putting clients first, leading with integrity, and delivering thoughtful, team-based solutions rooted in optimism and long-term trust.
Margaret’s approach to wealth management is grounded in a deep understanding of the complexities families face when managing generational wealth. She thrives in collaborative environments and is passionate about helping clients bring structure and clarity to their financial lives—always through the lens of what matters most to them.