The Tools  /  Leadership Odyssey
The journey

Leadership Odyssey

The book, and the worldview behind it — a leader's path from forcing the fit to creating it.

the book cover
An image of Leadership Odyssey will live here.
The idea

Leadership isn't a ladder. It's an odyssey.

Most leadership models hand you a destination and a checklist to get there. But real leaders don't climb a straight ladder — they travel. They meet the moments that don't fit, get tested, and grow their range. Leadership Odyssey is the story of that journey, and the worldview underneath the whole Square Peg system: you don't become a better leader by forcing yourself into one shape, but by learning to change the fit.

The arc

From forcing the fit to creating it.

Where most start

Forcing the fit

Leading by pushing harder — on yourself, your people, the plan — and mistaking effort for progress when the shape is wrong.

The turn

Seeing the story

Learning to notice the stories and assumptions driving the room — including your own — and finding the choice that was always there.

Where it leads

Creating the fit

Leading with range: reading the moment, and changing the fit between who your people are and what the situation needs.

Who it's for

For leaders who want to grow their range, not just their title.

Leaders & executives Emerging leaders Coaches Anyone leading through change

Read it on its own, or use it as the through-line for coaching and cohort development — the narrative that connects every tool in the system to a leader's own path.

Where it fits

The story that holds the system together.

If the Lens and the card decks are the instruments, Leadership Odyssey is the map — the worldview that gives them meaning and a leader a path to travel. One language, one idea, running through everything.

See the whole system →

Two ways in

Read the journey, or walk it with us.

The book

Get Leadership Odyssey

The worldview behind Square Peg, in one read — with the stories, the science, and the path from forcing the fit to creating it.

Get the book
With Square Peg

Walk the journey with Neil

Take the Odyssey as coaching or a leadership cohort — the book's path, made personal, with the tools in your hands. Start with a 20-minute call.

Book a call