Telos and the Long Game - Part II
“Hope is not a prediction of the future.
It is a declaration of what is possible.”
- Howard Thurman
On Orientation
A meditation on remaining aligned in the midst of time, pressure, and change
In every long game, there comes a moment when the path blurs.
Not because we’ve failed, or lost heart, but because the clarity we once held begins to soften. The lines between what we hoped for and what is possible become harder to trace. Time stretches. Circumstances shift. The noise of competing aims grows louder. And somewhere along the way, we begin to wonder: Am I still moving in the direction that matters?
This is the moment when orientation becomes everything.
Orientation is not belief. It is not a plan. It is not the strength of our will or the sharpness of our strategy. It is quieter than that. More human. To be oriented is to be in relation to time, to truth, to purpose. It is a way of being in the world that allows us to sense, however faintly, when we are aligned with something that matters, and when we are not.
It is not always visible. Others may not see it. We may not even be able to name it ourselves in the moment. But we feel it in the slight hesitation before action, in the subtle ache of dissonance, in the peace that returns when we choose rightly, even at cost.
In the context of the long game, orientation is how we hold to telos without needing to grip it tightly. It’s how we move when the map fades, but the compass still works. It is the quiet fidelity that endures beyond motivation or mood.
But orientation can be lost. And more often than not, it is lost subtly.
We don’t wake up one day having abandoned our purpose. We drift incrementally, understandably, even justifiably.
We don’t wake up one day having abandoned our purpose. We drift incrementally, understandably, even justifiably. We say yes to what seems necessary, then to what seems efficient, then to what seems expected. And before long, we find ourselves moving swiftly… but unsure toward what.
This is why orientation must be tended. Not enforced. Not dramatized. Tended like a fire that can go out not from storm, but from neglect.
Some find their orientation alone in silence, in prayer, in the long walk with no answers. Others find it in community in the questions of those who know how to ask gently but see clearly. For many, it’s both.
But, however it comes, orientation is not a one-time act. It is a rhythm. A returning. A willingness to recalibrate not when the world demands it, but when our own spirit begins to dim under the weight of misalignment.
And so, for those seeking to live wisely in the long game, perhaps the deeper question is not simply: What is your purpose? But: How do you stay oriented to it when no one is watching, when nothing is clear, and when everything around you rewards forgetting?
The long game will ask many things of us. Strategy. Patience. Endurance. But beneath them all, it will ask for this: That we stay close enough to our telos to know when we are drifting.
And that we have the courage and the humility to return.
Because direction is not a given. It is not fixed by declarations.
It is chosen, again and again, in the quiet turn toward what we know, deep down, is still ours to walk.
Begin Where You Are
An invitation to those sensing the call of a different kind of life
No one can give you your telos. It cannot be handed to you, nor justified in someone else’s terms. It can’t be copied from a mentor or borrowed from a movement. Your telos, if it is truly yours, must be heard, received, and chosen.
And yet, for most of us, that choosing doesn’t happen all at once. It happens slowly. In the margins of our lives. In the tension between what we’re doing and what we know we were made for. It emerges not as certainty, but as a kind of restlessness, a discomfort with settling for wins that don’t feel like accomplishment. A quiet ache for something more rooted. More aligned. More true.
This is how the long game begins. Not with a grand declaration, but with a turning. A turning toward purpose. But telos is not enough. It’s one thing to name what you’re for. It’s another to build something that can carry it through time, through pressure, through complexity and change.
Because whatever purpose you hold, it will be tested. Not always by opposition. Often by opportunity. By growth that pulls you off center. By rewards that drift you into someone else’s design. By speed. By exhaustion.
This is why strategy, in the long game, becomes architecture. Quiet, deliberate, relational. It’s about designing a way of living, working, building that can hold your telos not just for now, but for the long stretch ahead. A form of authorship that makes purpose livable.
It might look like:
A partnership that protects your integrity.
A rhythm of rest that preserves your clarity.
A language of agreement that anchors you when the waters rise.
Purpose without structure fades. And structure without purpose becomes machinery.
Not dramatic. But essential. Because purpose without structure fades. And structure without purpose becomes machinery.
Even still, you will forget. You will drift. You will reorient around urgency, around performance, around someone else’s telos that wears like your own. This, too, is part of the long game.
To stay aligned, you will need more than memory. You will need a rhythm of orientation, a way of returning to what matters when the world forgets why you began.
Sometimes, this will look like silence. Other times, it will look like confession. Often, it will look like courage: to say no when everything around you rewards the wrong yes.
Orientation is not heroic. It is human. A posture of listening, again and again, for the voice that called you in the first place. So if you’re here standing quietly at the edge of something you can’t yet name, this is your invitation:
Live with a telos you’ve chosen.
Not a slogan. Not a task. But a purpose you’ve seen and are willing to serve.Build what can hold it.
Not alone. Not all at once. But with care, with others, with a different kind of intentionality.Stay oriented to it when the path fades.
Because it will. And when it does, what will matter most is not how fast you move, but what you are still facing.
This isn’t a strategy. It’s the beginning of authorship. And it begins exactly where you are.
Deeper Dive: Suggested Reading
James P. Carse, Finite and Infinite Games A Vision of Life as Play and Possibility. Free Press 1986.
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With gratitude and anticipation,
John Henderson
Founder, The Pivot Mind
