The Oaks Roundtable
Professional Experts Summit
2026 · Three Days · Twenty People
September 20–23, 2026 · Westlake Village, CA
Co-chaired by Jim Cathcart and Michael Graham. A morning at the Reagan Library. An evening on Westlake. The acorn, fully grown.
20
Maximum Seats
3
Full Days
$7,500
Early Enrollment, Through Aug 31
$9,997 from September 1. Lodging and all meals included.
Not a Conference
What Happens at the Summit
The Professional Experts Summit is not a conference. There is no stage. No scroll of speakers. No name badges and networking lunches with people you will never speak to again.
It is twenty people. Three days. Jim Cathcart, the man who has spent fifty years studying what it means to become, sitting at a table with people who are serious about theirs.
“The conversations that change people do not happen in breakout sessions. They happen at dinner, on a walk, in a quiet moment between the agenda and the evening.”
That is what the Summit is built for. Twenty is not a limitation. It is the architecture of real conversation.
The round table. Where the real work happens.
Every handshake means something in this room.
The Details
What to Expect
Westlake Village Inn
Home base for the 2026 Summit. A resort set around the lake, chosen for the kind of quiet that lets real conversations happen between the moments on the agenda.
Maximum 20 Attendees
Every year, Jim holds the line at twenty. Not because he could not fill a larger room, but because he knows what is lost when you do.
Three Full Days
September 20 through 23. Enough time for ideas to settle, for relationships to root, for something real to take hold.
Co-Chaired by Michael Graham
Joining Jim at the helm this year is Michael Graham, CPE, a former Santa Monica police sergeant, movie actor, and Mindset Matters Consulting founder. A peer in the room, not a staffer.
Reagan Presidential Library
One morning is spent at the Reagan Library's Situation Room Executive Experience. Twenty people assigned Cabinet roles, a live crisis-management simulation, and a debrief in the replica press room.
A Day of Wisdom Parlor at Sherwood
An unhurried afternoon of discussion at Sherwood Country Club, the original home of Jim's Sherwood Parlor conversations. Deep topics, quiet setting, peers at the table.
Evening on Westlake
An electric-boat flotilla on Westlake, followed by an evening of music, close conversation, and an up-close magic performance. Built to be remembered.
Westlake Village, California
Location & Experience
Three days spent in rooms that were built for consequential conversation. Each place below opens in its own tab, so you can look and come straight back.
The Ronald Reagan Presidential Library
Situation Room Executive Experience
Private Strategic Discussions
A private room at the Westlake Village Inn
Wisdom Parlor at Sherwood Country Club
An unhurried afternoon at the original Parlor
Westlake Village Inn
Home base for the 2026 Summit
Lakeside Collaboration
An evening on the water
Lodging centered at the Westlake Village Inn & Spa.
The people in the room are the curriculum.
CPE holders at a past Summit dinner.
Who’s Coming?
Twenty People. Serious about Growth.
At the Table in 2026
And others joining them at the roundtable.
At the CPE Dinner
The CPE dinner draws its own table. Deborah Waitley will be there with her son, Denis Waitley’s grandson. Diana Nightingale, Earl Nightingale’s widow, joins by video.
Certified Professional Experts
CPEs who have built real bodies of work and want to continue building alongside peers who understand the standard.
Jim's Closest Peers
Long-time colleagues, collaborators, and friends from across the professional development world. People who have been in the room for decades.
Emerging Professionals
People earlier in their arc who are serious enough to belong in the room. Not beginners. Builders.
Where We Have Gathered
Past Venues
Each year, the setting is chosen deliberately. Not for convenience, but for character. The work is the same. The place becomes part of the memory.
TN
Nashville
Music and meaning in equal measure.
TX
Austin
Where the West begins and the work gets done.
CA
La Jolla
The view that built the industry.
CA
Santa Barbara
Where Jim Jr. runs the Inn. Where the family gathered.
In Their Own Words
Voices from the Summit
Austin
What the Summit feels like
Santa Barbara
What the Summit feels like
Austin Summit
Christina Richter
0:41
Shandra Livingston
2:12
Daniel Pope
4:28
Sue Graham
0:46
Robin Creasman
1:02
Brian Livingston
0:43
Mike Graham
1:27
Linda Bonner
0:32
Santa Barbara Summit
Beth Robins
1:43
Joseph Todd
0:49
Niki McCuistion
1:26
Ken Rochon
0:41
Jason Cathcart
0:25
Brian Livingston
1:12
The Oaks Roundtable
Enrolling Now
September 20–23, 2026 · Westlake Village Inn, CA
Early Enrollment
$7,500
On or before August 31, 2026
Standard Enrollment
$9,997
September 1, 2026 and after
Lodging and All Meals Included
Both tiers. Business casual. Payments available, or pay by credit card.
Twenty seats. When they are gone, they are gone. Only one Summit is held each year. So now is the time.
The Founding Fifty
Become One of the Founding 50
43
CPEs Awarded
7
Remaining
Could you be one of them? Reach out today.
Nurture Your Nature.