Come for AI. Leave more Human.

A generative retreat for leaders ready to clarify, create, and carry forward.

Friday, May 30, 2025 · CHIEF Chicago Clubhouse · Fulton Market District

CHIEF Chicago Clubhouse

Nestled in Chicago’s vibrant Fulton Market District, the CHIEF Clubhouse is an intimate, design-forward space that inspires deep conversation, clarity, and creativity.

With natural light, warm textures, and modern furnishings, it's the ideal container for a reflective, high-touch retreat experience.

This event is open to all genders and no CHIEF membership is required.

What to Expect

A day designed to meet you where you are—and take you where you want to go.

We’ll begin with intention-setting and reflection, using AI as a mirror to explore where you are and what’s next. Through visual metaphors and writing prompts, you’ll externalize your vision—even if it’s still taking shape.

Then, we’ll move into deeper creative work: simulating decisions with your inner board of advisors, crafting future narratives, and building your own personalized GPT assistant—one that’s trained to think like you.

Between sessions, expect chef-prepared meals, good conversation, and the kind of clarity that only comes when you finally step off the treadmill.

You’ll leave with real tools, renewed direction, and a signed copy of Temperature: Creativity in the Age of AI.

  • Prompting for Self Discovery

    Metaphors & Moodboards
    Begin the day by exploring your inner landscape. You’ll use AI to generate symbolic imagery that reflects your current path and what’s ready to emerge. Think of it as intention-setting through pixels and poetry.

  • Your Inner Voice, Amplified

    Writing for reflection & expression
    Move from visual to verbal. Through carefully guided prompts, you’ll write with the support of AI—uncovering language that feels precise, personal, and true. Walk away with a mission statement, a letter to your future self, or even a short narrative of what's next.

  • Conversing with Future You

    Decision-making with your inner voices
    Navigate complex decisions by engaging with simulated perspectives. Whether you're at a crossroads or refining a plan, this session helps you clarify tradeoffs, visualize outcomes, and listen to the wisdom you already carry.

  • Design Your Daily Ally

    Build an agent to support you
    Close the day by creating a personalized AI assistant. No code required. You'll train it to align with your tone, needs, and priorities—so it can help you write, plan, reflect, or ideate long after the retreat ends.

Our Menu

Morning Welcome

Fresh pastries & seasonal sips to ease you into the day

Midday Harvest

Mediterranean chicken board, Caprese bites, fig tartlets & vibrant greens

Afternoon Reset

Chocolate chip cookies & botanical mocktails

The Afterglow

  • Clarify it.

    Gain a renewed sense of personal and professional direction through guided AI exercises that reflect your voice, values, and vision.

  • Create It.

    Design a custom GPT assistant—trained on your goals—and generate writing, prompts, and decisions that feel aligned and actionable.

  • Carry It.

    Leave with Certificate in Applied Generative AI from SYNTHETIVITY, and a signed copy of Temperature: Creativity in the Age of AI.

Register Today

What People Are Saying

“Lori, what an eye-opening, inspiring, curiosity-provoking day.   I feel thoroughly engaged and ready to bring AI into my daily routines.”

— Sonya Schroeder

“The day exceeded my expectations, and I left with several great actions to take next. It was a fun, informative and inspiring experience. ”

— Cathy Wolfe

“It was inspiring to see this special group come together curious and ready to explore how AI can empower our work and our leadership — our life.”

— Vic Noble