Learn the game, but play it your way.

masterful moves

Charleston, SC | Wednesday, February 24th - Sunday, March 1st, 2026

Join Us In Charleston

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.

Join Us in Charleston

RETREAT DAILY FLOW

- 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
- Workshop 1: The Opening Gambit: Discover Your Strategic Style — learn chess basics, discover which piece matches your natural career style, and map your first three “gambits” for the next 90 days
- Afternoon: Time to explore Charleston, reflect, or relax
- Evening: Group dinner downtown
- 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
- Afternoon: Tea Garden tour to explore patience and cultivation as a metaphor for strategic growth
- Evening: Dinner together at one of Charleston’s most magical spots
- 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 cruise on Charleston Harbor, celebrating your Masterful Moves and the community you’ve built
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.

Join Us in Charleston

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.

Join Us in Charleston

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.

Join Us in Charleston

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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.

Join Us In Charleston

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. You can explore trip insurance options at:

Please Note: Airfare, transportation to/from Charleston and the Palmetto Boutique Hotel, and your accommodations costs at the hotel are not included.

Join Us In Charleston

past retreat testimonials

“Loved the whole experience and bonding with the other women, such a soft place to land and truly be yourself, to learn from others, and appreciate our different talents and life journeys.”
Ari Lester
“Brittany is a master facilitator, travel planner, and coach! The four day Identity Edit retreat in Miami was a one-of-a-kind experience that allowed me to step away from the daily grind and tap into a part of myself that I usually silence.”
Emily Harper
“Life changing. Time well spent away from day to day. Time to reflect on what one needs and is seeking along with women who are cheering you on.”
Lauren Rudman
“Thank you so much for an amazing weekend! I feel so energized and grateful to know you and to have been able to meet the others in the group, especially Pivot Point OG's who I have only known virtually for almost a year! I left with a sense of connectedness and that's very rare to find in a short period of time in today's busy and digital-first connection society. Be able to learn both from Brittany and from the other Pivot Pointers helped me self-reflect on the things I am the most proud of about myself, and areas that I want to continue to develop as I progress as a leader in my career.”
Amanda Hyman, Google
“I’ve been actively looking for opportunities to be more proactive in reflecting on what I want. This retreat was the perfect outlet for exploring that with a fun, like-minded group - Brittany curated a truly inspiring experience!”
Tara Knight, Creator Match
“This retreat checked all of my boxes, including many that I didn't know needed to be checked. I knew that this experience would push me out of my comfort zone, and as an introvert, that felt really scary. Brittany cares so much about people and that came through in the retreat. She gently invited me to participate in conversations and to share things about myself in a way that was confortable. The experience I was most worried about -- the presence workshop -- turned out to be my favorite because it not only provided skills that I wanted to learn, but also reinforced what I AM capable of which felt like a major win. The women that were on this retreat with me were phenomenal and I was so inspired by each of them. I am incredibly grateful for Brittany for all the planning that went into the retreat and how much knowledge and encouragement she poured into each of us."
Sara Brintnall, The Matriots

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:

- 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.
- 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.
- 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.