I spoke with an IT leader in his late 40’s this week. Amidst the news of industry-wide layoffs and economic shifts, we discussed the precariousness of the future. “The problem,” he said, “is that our plans are becoming obsolete.”
He was talking about the five-year plans, the career ladders, the retirement timelines, the structured narratives we build to make sense of the world. But then he added a crucial insight that gets to the heart of the modern leader’s paradox.
“And yet,” he said, “we have more data than ever. We can accurately map out our children’s college years and what it would cost, accounting for inflation. But it is all vague buckets of approximations. We don’t know if those degrees or jobs will exist by the time they get there, or if they would even pick those options.“
This is the central tension of modern leadership:
We have more tools than ever to create maps, but a growing sense that the territory is changing faster than any map can keep up with.
These maps – our strategic plans and project timelines – can be useful tools for creating order from chaos. To operate without any map at all might feel like an abdication of responsibility.
But we also invest so much of our identity in the maps we create because we think of them as safety. We believe in their predictions, their promised destinations because they give us the illusion of a secure and predictable future.
‘Life is what happens when we are busy making other plans’ is a cliche for a reason.
So when the world inevitably deviates from the plan, say the market shifts or a personal crisis strikes, it feels like more than a logistical problem. It feels like a personal betrayal from life.
Our attachment to the plan creates fear and rigidity. We try to force the territory to conform to our plan, or we panic and freeze, unable to act without the certainty the map once provided.
The work of an Awakened Leader is to cultivate a new relationship with uncertainty. It is to shift from operating based on the Map to operating from the GPS.
It is almost like surfing. A surfer does not try to control the ocean. They understand and respect its immense, unpredictable power. The surfer’s confidence is not simply in their ability to predict the next wave, but also in their capacity to ride whatever wave comes.
This requires a unique combination of skill and surrender. It is the ability to be completely present, to maintain balance in a constantly shifting environment, and to adapt your position in a moment’s notice. It is the mastery of dancing with a power that is far greater than your own.
The journey of Awakened leadership is not to create a perfect, unbreakable map to a safe harbor. It is to develop the inner stability and presence to be able to skillfully and even joyfully ride the waves of an unpredictable reality.
To see these ideas intellectually is the first step. To embody them under pressure is the real work.
This is the essence of the work I do with leaders in our 1-on-1 partnership: a confidential space dedicated to moving from insight to lived integration.
Should we begin that conversation?
