The Compass How are the ten seats filled?
For Year 1, by random lottery — not a selection committee. Every eligible EO Chicago member who enters has the same odds. Lottery entries open September 1, 2026 and close November 1. The draw is on Selection Day — December 1, 2026 — and we notify everyone, drawn or not, the same day, ahead of the program’s March 30, 2027 start.
What does the $1,000 fee cover?
Speaker honorariums for visiting seasoned entrepreneurs, and snacky food during the four Instruction weeks (no alcohol). The fee exists to signal commitment, not to gate.
What if I can’t make every session?
Then this year isn’t your year for the Class — and that’s okay. Attendance at all eight sessions is mandatory and a condition of holding a seat. The format depends on the full cohort being in the room every week, so we ask members to look hard at their calendar before entering. If you can’t commit to all eight weeks, observing is the better fit — you can drop in to Instruction weeks as your schedule allows, and enter again next year.
Is what I share confidential?
Yes. The five-percent conversations that happen in Cohort weeks stay in the room. The cohort agrees to confidentiality at the start of the program. Photos and recordings are not permitted in either Instruction or Cohort weeks.
Why only ten seats?
Depth, safety, and real engagement. Bigger rooms lecture better. Smaller rooms work better. We chose work.
What kind of uncertainty “qualifies”?
If it’s a real, current decision under ambiguity, it belongs in the room. Macro shifts, market or category change, capital decisions, scaling decisions, talent calls, succession, personal leadership questions — any of these. We are less interested in topic and more interested in whether the situation is concrete and active.
I’m not facing a specific decision right now. Can I still attend as Community?
Yes. Community seats are open to EO members and to business owners across Chicagoland. No lottery, no commitment, no fee — just an RSVP. Seating is limited by EO House capacity.
Do I need to be an EO member to observe?
No. Instruction weeks are open to Chicagoland business owners more broadly — we built the Community seats partly as a way for the wider Chicago entrepreneur community to experience what EO is about. The Class itself is for full EO members only.
Why “Compass”?
Because that is what the program gives you: a bearing at the fork in the road. Applied. Intense. Time-bound. On real decisions, with seasoned entrepreneurs who’ve navigated the same terrain. It’s what you do after business school — on the actual work.
How often does the program run?
Once a year. One cohort, ten seats, one theme. That’s the point — quality over quantity, and a number that means something. If you miss Compass 01, Compass 02 will open entries next year.
Will future editions focus on different topics?
Yes. Compass 02 and beyond will pick the theme that matters most to operating members at the time. Compass 01 is Growing Through Uncertainty. The next theme will be announced after the inaugural cohort completes.
Can I sponsor or fund this?
Yes — we welcome the conversation. The program is designed to be cost-neutral, but sponsorship lets us invest more in Speaker travel, room quality, and post-program alumni programming. Write to us.