Five Habits of Mind

Standing in front of a blank canvas has taught me everything I need to know about navigating uncertainty and change.

Well, not quite everything, but it makes for a good headline, yes? 

Artistic practice has  given me lived experience in stepping into the unkown and trusting the process. The wisdom traditions have deepened that understanding. 

Through this lived experience, I have come to identify five leadership* habits of mind that are crucial to navigating uncertainty and change. 

*If you’re a human, you’re a leader. Seriously. 

The Five Habits of Mind of Cartographers of the Future


Accompaniment is an embodied metaphor, happening in space and time, placing power dynamics within a spatial framework. An accompanying leader practices active inclusion, not by remaining static in space and time and inviting others into status quo, but by going out in a way that is disruptive to status quo power dynamics. Accompanying leaders move toward the edges, toward others at the edges of power. They move away from the safety and security of the centre, away from their own power and competence. They continually re-centre power at the edges, around conversation and trust. Lastly, as trusting relationships allow, they move through space and time, shoulder to shoulder—an egalitarian disposition—in deep solidarity with those they trust and with whom they converse.


Meaning making leaves behind artifacts—an idea, a system, soup, a painting, a song, a story. We call cohesive collections of artifacts culture. Meaning making is culture making, and culture making is meaning making. Generative leaders perform a kind of cultural photosynthesis, breathing in the unfiltered carbon dioxide of human experience, and breathing out the oxygen of shared meaning. Generative leaders are aware of and actively work toward reversing deficiencies of meaning.


A conversation is, on a foundational level, a co-creative act that makes meaning. Conversational leadership is a special kind of generative leadership. It recognizes the conversational nature of reality. Bravely turning toward and facing our reality puts us in conversation with it. Further, that the people around us are the most important conduits to the reality around us. Conversational leaders show up with a listening disposition, a willingness to listen first and to listen actively, with a mind to co-creating meaning with whoever the leader is in conversation with.


Curious leaders ask good questions rather than have right answers. They understand that answers keep us apart, questions bring us together. They are brave explorers of difference for the sake of mutual learning and the evolution of the community. Curious leaders practice intellectual humility.


Ambidextrous leaders aren't trapped by dualistic thinking. They look out for the both/and perspective. They are concerned with both horizontal development and vertical development. Horizontal (adaptive) development is associated with network leadership capacities. Vertical (technical) development is associated with organizational leadership capacities. An ambidextrous approach strives to integrate both vertical and horizontal development. Potency comes with true ambidexterity, when adaptive capacities meld into organizational contexts and technical capacities empower networks.