Learn the game, but play it your way.
masterful moves
Charleston, SC | Wednesday, February 24th - Sunday, March 1st, 2026
At Masterful Moves, we’ll connect that same Charleston intentionality to your career. When you sharpen your ability to think strategically, you stop reacting and start directing your next chapter.
What to Expect
This is not another conference where you take notes you’ll never look at again. Masterful Moves is an intimate, experiential, laptop-down retreat. Over four days, you’ll step into a rhythm of learning, reflecting, connecting, and simply being present.
The Mornings
☀️ Dedicated to immersive workshops that sharpen your strategic thinking and give you practical tools to apply to your own career.
The Afternoons
⛅️ Afternoons are left open for rest, reflection, and exploring Charleston at your own pace with our custom travel guide.
The Evenings
🌙 Evenings bring us back together for unforgettable dinners and cultural experiences that make Charleston come alive.
A peek at how this came to life at past retreats
RETREAT DAILY FLOW
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Check in at the Palmetto Boutique Hotel
Evening walking food tour in Charleston’s historic district to meet the group, taste the city, and set intentions for the days ahead
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Workshop 1: The Opening Gambit: Discover Your Strategic Style — learn chess basics, discover which piece matches your natural decision-making style, and map your first three “gambits” for the next 90 days
Afternoon: Time to explore Charleston, reflect, or relax
Evening: Group dinner
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Workshop 2: Layered Decisions: Build Depth in Every Move — apply the Six Thinking Hats framework to your career decisions, then create your layered strategy blueprint. You’ll also experience indigo dyeing as a tangible metaphor for how layered decisions compound into something lasting.
Afternoon: A magical lunch experience and then a relaxing afternoon to yourself.
Evening: Dinner together + a few surprises.
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Workshop 3: The Endgame Map: Design Your 12-Month Strategy — bring together lessons from chess and the Six Hats to design your 12-month Master Moves Map
Afternoon: Rest, shop, or journal at your own pace with time to integrate and prepare for what’s next
Evening: Closing dinner celebrating your Masterful Moves and the community you’ve built
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Morning closing circle & send-off before departures
Meet Your Hosts
Together, we partner to make sure every retreat element feels intentional, inspiring, and unforgettable for the Pivot Point community.
Brittany Neish
I’m Brittany Neish, Founder of What You Do Matters, a boutique career & leadership development company, and creator of Pivot Point, a professional network for women making bold career and leadership moves.
These retreats are part of Pivot Point, born from my own desire to step away from the noise, learn about myself, and build skills I could carry back into everyday life, all while exploring beautiful places (my favorite hobby!). That blend of growth + travel is at the heart of every retreat I design, giving attendees the space to think differently, connect deeply, and return home ready to make their next masterful moves.
Jessica Melton
I’m Jess Melton, an event designer, community builder, and strategist with a passion for crafting unique and immersive experiences. As both a history and design enthusiast, I’m always looking to weave stories that connect people & places, sparking creativity and conversation.
Our Retreat Location
Charleston in February is extraordinary with mild weather, fewer crowds, and a city that feels both historic and alive. Known for its intentional preservation, artistry, and resilience, Charleston is the perfect setting to sharpen your strategic thinking. Here, every corner reminds you that thoughtful planning creates impact that lasts.
What’s Included
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Three immersive workshops facilitated by your host, Brittany, blending career strategy frameworks with cultural experiences.
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Custom retreat workbook with tools, frameworks, and reflection prompts
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A custom journal for notes, scribbles, and insights.
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A digital Charleston travel guide with unique restaurants, shops, and experiences to enjoy during your afternoon downtime.
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Restful, relaxed afternoons following each workshop to explore Charleston at your own pace or reflect on what we’ve covered.
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All cultural experiences
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All meals: breakfasts, group lunches, and magical evening dinners
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Transportation to all group experiences and workshop locations
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Welcome reception & closing celebration
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Tangible artifacts from experiences
Not Included: Hotel accommodations, Airfare to/from Charleston, Transportation to and from the airport, anything you choose to purchase during your afternoon downtime.
Our Retreat Hotel
We’ve secured a block at the Palmetto Boutique Hotel, a stylish, centrally located property that blends Charleston charm with modern comfort.
The Palmetto prides itself on providing a deeply authentic Charleston experience. Situated in the historic district, within touching distance of the city’s finest restaurants and bars, the boutique hotel is particular to the place in which it lives, even a bit peculiar in the way of all charming Southern eccentrics.
Booking information will be provided after registration. Your room is booked separately, but once you arrive, everything else is taken care of, including meals, workshops, and cultural experiences.
Investment
Retreat Cost: $3,799
Given that we like to keep these as intimate experiences, spaces will be limited.
Deposit to Hold Your Spot: $950 (non-refundable, applied toward total)
Remaining Balance: Split evenly across two payment installments on January 16 and February 20, 2026.
We highly recommend investing in Trip Insurance to protect your trip in case something comes up & you are no longer able to attend.
Please Note:
Airfare, transportation to/from Charleston and the Palmetto Boutique Hotel, and your accommodations costs at the hotel are not included.
Who This Is For
This retreat is open exclusively to Pivot Point members. If you’re not yet a member but want to join us in Charleston, you can become a Pivot Point member and then register for the retreat.
Masterful Moves is for you if:
You’re ready to grow and want a clear strategy for your next career move.
You’re seeking to sharpen your strategic thinking — a skill almost every professional wants but few intentionally practice.
You’re preparing for a promotion, exploring a pivot, or finally ready to build something of your own.
You want to step out of reactive mode and start making thoughtful, intentional, intelligent moves.
You value connection with other women who are also building bold, strategic paths forward.
If you’ve been craving time to step away from the daily grind, focus on your bigger vision, and leave with both clarity and concrete next steps, Charleston is for you.
past retreat testimonials
Charleston Retreat Workshop Details
Across three workshops, you’ll sharpen your strategic thinking by learning to anticipate, evaluate, and design a plan you can put into action. Here’s a taste of what you can expect:
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Every career turning point starts with a move, and the quality of that first move can shape everything that follows. In this session, we’ll use the game of chess as a living framework for how you approach strategy. You’ll discover your natural decision-making style, learn to recognize patterns on the board, and see how the rules of the game mirror the rules of a career played with intention.
You will:
Take a custom assessment that reveals your strategic style and the chess piece that reflects it.
Receive a custom-crafted chess piece tied to your results.
Learn the fundamentals of chess from an expert and translate them into principles you can apply to your career: positioning, anticipating, and choosing moves that build momentum.
Takeaway: A clear picture of your strategic strengths and three concrete “gambits” you’ll put into action in the next 90 days.
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Strategy rarely comes down to one choice; it’s built from layers of decisions that create depth and durability over time. In this session, you’ll step into a framework for thinking more broadly and systematically about your options. Through both structured practice and the art of indigo dyeing, you’ll learn how layers of perspective create stronger outcomes.
You will:
Learn to apply the Six Thinking Hats framework to weigh risks, opportunities, and alternatives in your career.
Experience indigo dyeing as a tangible metaphor for how layered decisions compound into something lasting.
Use the process to work through a real decision you’re facing, such as pursuing a promotion, shifting industries, or launching a new initiative.
Takeaway: A repeatable, layered approach to making career decisions with clarity and confidence.
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The most masterful players never just react, they see the whole board and play several moves ahead. In this session, we’ll bring everything together: your natural strategic style, your layered decision-making, and your long-term vision. You’ll map out your own “board,” identifying where you’re positioned now, what moves are possible, and what sequence will carry you toward your goals.
You will:
Apply endgame strategy to your own career, anticipating trade-offs and preparing for challenges before they arise.
Build your personal chessboard, laying out immediate and future moves.
Create your Master Moves Map, a 12-month strategy that connects today’s actions to your long-term vision.
Takeaway: A concrete, actionable career strategy that turns abstract goals into a mapped sequence of masterful moves.
peek at our previous retreats
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Why This Retreat Matters
This retreat is part of Pivot Point, a professional network for women making bold moves in their careers, leadership, and lives.
Learn more about Pivot Point Membership
These retreats are designed to serve as a reset. An immersive long weekend to cut through the noise and make a true connection to place, people, and yourself. A mix of thoughtful learning experiences, unique cultural exploration based on each city we visit, connection to our community, and time to rest & reflect.
Every retreat focuses on a growth area. In New York, we built confidence. In Miami, we explored identity. In Charleston, we’ll strengthen the muscle of strategic thinking.
At Masterful Moves, you’ll step away from the noise and learn how to:
Think several moves ahead.
Evaluate opportunities with intelligence and clarity.
Build a strategy that connects daily decisions to long-term goals.
And you won’t be doing it alone. You’ll be surrounded by a community of Pivot Point women who, like you, are ready to stop playing small and start playing with intention.