Gather Better Showcase

January 21-23, 2026 | Chicago, IL

Our Intent

We are hosting a two-day immersive experience for high-capacity leaders, entrepreneurs, and individuals looking for clarity, momentum, and growth. We believe that thoughtful content and intentional community can create real and lasting transformation. What makes this gathering unique is the precision and purpose behind every detail—an obsessive commitment, shaped by 20 years of experience, to helping people take meaningful action. And we believe that if we gather better, people will walk away connected, equipped, and ready to move forward with courage.

Who is it for?

Individuals Considering a Change

You’re feeling the pull of potential — a shift, a new direction, or an opportunity you don’t want to miss. Whether you're exploring a promotion, a pivot, a side hustle, or a full career transition, this week helps you gain clarity and momentum. If you know something is changing but aren’t sure what comes next, this is for you.

Leaders in an Organization

You lead teams, projects, or culture — formally or informally — and want more clarity, structure, and alignment in your work. This experience gives you practical tools for quarterly planning, strategy, and intentional leadership. It’s for the intrapreneurs, the problem-solvers, and the people others naturally look to for direction.

Register Today

Gathering Professionals

You’re someone who brings people together: hosts, community builders, conveners, and leaders who care deeply about connection. You believe gatherings shape culture, and you want to elevate the way you create meaningful experiences. This week invites you into a community of intentional gatherers who value generosity, humanity, and purpose.

Agenda

WEDNESDAY, JANUARY 21

Location: Chicago, IL

Morning–Afternoon | Arrivals, optional coworking, No formal programming

THURSDAY, JANUARY 22 — Principle Barbers

8:00 AM | Optional Dad Bod Yoga - David Carnes

9:30 AM – 10:15 AM | Welcome and Keynote - Ben Jacobson

The Power of Retreat - by Gather Better

10:15 AM – 10:30 AM | Break

10:30 AM – 11:15 AM | Master of Many Session - David Carnes

Why Generalists are Positioned to Thrive

11:15 AM – 11:30 AM | Break

11:30 AM – 12:15 PM | Session 3

12:15 PM – 1:15 PM

Lunch (with two 5-minute vendor showcases)

1:15 PM – 2:00 PM | Session 4

2:00 PM – 2:15 PM | Break

2:15 PM – 3:00 PM | Session 5

3:00 PM – 3:15 PM | Break

3:15 PM – 4:00 PM | Session 6

4:00 PM – 6:00 PM | Free Time

6:00 PM – 9:00 PM | Gather Better Launch Party (Invite-Only)

FRIDAY, JANUARY 23 — Loft Lucia

9:00 AM – 12:00 PM | Leadership & Quarterly Planning Intensive Workshop

12:00 PM onward | Departures / optional coworking

Agenda: Narrative format

Gather Better Launch Week begins with a soft landing on Wednesday, giving you space to arrive at your own pace, settle in, and ease out of your normal rhythm with optional coworking in the afternoon. On Thursday, you step into a full day of immersive sessions designed to spark clarity, reflection, and momentum as you explore your next chapter, connect with others, and end the evening in celebration at the Gather Better Launch Party. Friday brings everything together with a focused quarterly planning intensive in a bright, energizing space, equipping you with clarity, alignment, and a practical rhythm to carry your momentum into the year ahead.

Speakers