The Leadership Pilgrimage

This is not a retreat, or a training. It’s a transformation.

The pace of change is not slowing down. Teams are navigating uncertainty, burnout, and a growing hunger for meaning. And leaders are asking: Is this still working?

Traditional programs and trainings offer frameworks and tactics to develop skills. They rarely develop the person holding them.

Over the course of a year, a small cohort of leaders move through an intentional sequence of experiences, challenges, and reflection designed to reshape how you see yourself, your work, and the world you're trying to lead.

What the year holds

Individual coaching, guided exercises, and six months of post-program support run throughout. The journey moves in 5 phases:

  • Before you begin: Assessments and reflection tools so you arrive ready and with a foundation of shared honesty.

  • Into the field: Immersive expeditions that reveal who you are when the usual props are removed.

  • The work between: Monthly virtual workshops where individual insight becomes collective practice.

  • Coming together: Integration workshops connecting discovery to how you actually lead, informed by what the cohort is learning together.

  • The culmination: A final expedition to honor how far you’ve traveled, together. And an opportunity to design where you go next.

What you'll carry forward

  • The narratives and beliefs that shape your leadership and clarity on which ones still serve you

  • Resilience and presence to stay grounded under pressure

  • A personal Leadership Manifesto as a living guide

  • Deep relationships with peers who know you, not your title

Who this is for

Senior and emerging leaders navigating complexity, transition, or high-stakes environments who are ready to do the inner work that outer performance demands.

Each cohort is small and intentionally curated. If you're looking for a credential, this isn't it. If you're looking for a genuine shift, you may have found it.

Facilitators and Guides

Kara Pecknold is a designer and sustainability leader with over 25 years of experience guiding global organisations through transformation and systems change. She has worked with Fortune 500 companies, startups and social enterprises by helping leaders translate insight into meaningful action and reshape how their organisations meet complexity. Kara brings analytical rigor and deep human presence to every room she enters.

Carrie Forster is an ICF-certified coach with expertise in team development, neuroscience, systems theory, and grief. She helps leaders close the gap between who they are and how they lead by creating the conditions for change that is not just sustainable, but real.

Together, we have built the Pilgrimage to bridge leadership development and human transformation by holding space for the kind of growth that doesn't happen in a classroom.

Ready to begin?

By providing your details, you agree to be contacted by us. Please note that the submission of this form does not confirm a spot. We will follow up with you directly with more details.