Deciding to Depart with Samantha Trotter

Connect. Learn. Expand. 🧠⚡

Welcome to The Second Saturday Brain Trust—a monthly morning gathering designed to spark deep conversation, foster community, and introduce you to fascinating ideas right here in Olympia.

Hosted by Bespoke Olympia at the beautiful Harbor House, these sessions bring together local experts, passionate visionaries, and curious minds. We dive into a different topic each month, led by incredible speakers who are living their truth and sharing their expertise. Whether you’re looking to expand your personal growth, learn a new perspective, or simply connect with an incredible community of local neighbors, there is a seat at the table for you.

🧠⚡Session 4: deciding to depart

With Samantha Trotter

Every autumn, the natural world demonstrates a vital survival mechanism: trees cut off nourishment to their leaves so the core organism can survive the winter. Etymologically, to decide shares roots with incision—it means to cut.

Yet when it comes to partnerships—marriages, business alliances, corporate roles, collaborative ventures, or close ties—making that cut often feels paralyzing. Many of us remain caught in prolonged indecision, questioning our own clarity:

• Is this a repairable rut, or have the fundamental agreements expired?
• Am I avoiding necessary boundary work, or am I tolerating the intolerable?
• How do I separate fear of the fallout from the quiet reality that it is time to go?

In this November session of the Second Saturday Brain Trust, Bespoke Olympia founder Samantha Trotter hosts a practical, grounded workshop on navigating departures. Drawing on insights gained from navigating significant career, legal, and relational transitions over the past year, Samantha leads participants through an actionable framework for auditing partnerships and honoring their internal authority.

Session Architecture

• 08:45 AM – 09:00 AM: Doors Open & Check-In
• 09:00 AM – 09:40 AM: Welcome, Community Agreements & The Ecology of Pruning
• 09:40 AM – 10:30 AM: The Diagnostic Matrix: Identifying "Needs a Shift" vs. "Time to Leave"
• 10:30 AM – 10:45 AM: Break
• 10:45 AM – 11:30 AM: Trusting Inner Authority: Quieting External Noise & Naming the Trade-Offs
• 11:30 AM – 12:00 PM: Practical Resourcing: Building Your Emotional & Logistical Runway

Facilitator Bio: Samantha Trotter

Samantha Trotter is an organizational development practitioner, certified change leader, and the founder of Bespoke Olympia. She partners with leaders, groups, and individuals to navigate complex systems, design meaningful change, and reclaim personal sovereignty. Over the past year, Samantha has navigated major personal and professional departures—including stepping out of executive consulting, advocating through legal systems for family care, and dissolving a marriage—deepening her commitment to helping others make clean, aligned choices.

Event Logistics

• Date: Saturday, November 14, 2026
• Time: 9:00 AM – 12:00 PM (Doors open at 8:45 AM)
• Venue: Harbor House, 217 Thurston Ave NW, Olympia, WA 98501
• Supplies: Bring a pen and notebook. Diagnostic frameworks and reflection worksheets will be provided on-site.

What’s Included in Your Ticket:

We believe in creating a beautifully curated, high-value experience for every attendee. Your $55 investment completely covers:

• The Experience: Your reserved seat at the waterfront Harbor House, along with delicious local pastries, fresh morning coffee, and custom workshop materials designed specifically for this session.
• Supporting Local: A portion of every ticket goes directly toward supporting Bespoke Olympia (a homegrown, woman-owned business), allowing us to keep creating intentional spaces for local connection and growth.

Space is intentionally limited to maintain an intimate, conversational atmosphere. Secure your seat at the table today!