5 The Unknowable Path to the Knowable Destination
This chapter is currently in draft form.
In one of my most difficult roles, two and a half years of relentless pressure, I started visualizing my situation as a flat black plane with massive Tetris blocks falling from the sky.
The blocks in that role were organizational, not technical. People who should have left hadn’t. Culture that should have supported the mission actively resisted it. Control and authority were misaligned. The paths I’d been promised were already closed when I arrived; I just couldn’t see it yet.
My job was to navigate across that plane toward objectives I could see clearly. But the blocks kept falling, closing paths I’d been counting on. I’d make progress toward a goal, and a block would land directly in front of me. I’d route around it, find a new path, and another block would fall. Sometimes I’d have to backslide entirely, retreating to find a way around an obstacle that hadn’t existed an hour earlier.
I think I visualized it that way because that was the nature of that role. Almost every path closed at some point. Progress came in fragments: a little forward, stop, reassess, go sideways, sometimes backward. The destination never moved. Only the paths to it.
That’s closer to what leadership actually feels like than any strategic framework will prepare you for. You’re not executing a plan. You’re navigating a field of falling obstacles in real time, constantly recalculating, constantly adjusting, knowing that any path you commit to might close before you reach it.
This chapter is about that reality. Not how to avoid the blocks, because you can’t, but how to keep moving despite them.
5.1 The Inseparable Discipline
Persistence and rerouting are not two skills. They’re one skill with two expressions.
Persistence without rerouting is stubbornness. You bang your head against a door that won’t open while other doors exist. You burn political capital on a blocked path because you committed to it publicly and can’t bear to change. You treat the path as sacred when only the destination is.
Rerouting without persistence is chaos. Every falling block triggers a new direction, sometimes a new destination entirely. Your teams can’t follow because the direction keeps changing. You never build momentum because you’re always starting over. You call it agility. It’s not. It’s drift with extra steps.
The discipline is holding both: committed to the destination, uncommitted to the path.
You persist toward the destination with everything you have. You hold the path loosely, ready to abandon it the moment it closes. The destination is non-negotiable. The path is disposable.
But this only works if the destination is at the right altitude.
5.2 The Altitude of the Destination
The discipline only works if the destination is at the right altitude.
If your destination is “build this system,” every falling block is a crisis. The path and the destination collapse into the same thing. One well-placed block eliminates your destination entirely. There’s nowhere to reroute to.
If your destination is “build an organization that can build systems that accomplish this business objective,” the blocks become terrain. The specific system is a path, not the destination. When that path closes, you find another. The mountain remains visible from anywhere on the plane.
A hill can be blocked entirely by one Tetris block. A mountain can’t.
That’s what makes a destination knowable: not certainty about how you’ll reach it, but visibility from anywhere on the field. The mountain doesn’t move. The paths to it shift constantly. You can see where you’re going even when you can’t see how to get there.
This is what I mean by altitude. First-order destinations are low: ship this feature, hit this deadline, build this system. They leave no room to maneuver. Second-order destinations are higher: create the capability, build the team, establish the conditions. Third-order destinations are strategic: position the organization, build the moat, create the future.
Leadership theorists have mapped similar terrain. Ram Charan and Ian Woodward describe “three altitudes” of leadership thinking: 50,000 feet for strategic vision, 50 feet for tactical execution, 5 feet for self-awareness. They warn against “altitude sickness” when leaders get trapped at any single level (Woodward, 2017). The principle is the same: flexibility across altitudes enables navigation. Rigidity at any one level creates crisis.
The higher the altitude, the more paths exist. The more paths exist, the more blocks you can absorb.
Leaders in constant crisis often aren’t facing more blocks than anyone else. They’ve set their destination too low. Every obstruction feels existential because they’ve left themselves no room to navigate. They’re defending hills, not climbing mountains.
This lens explains one of the two failure modes. Rerouting without persistence isn’t excessive flexibility. It’s an altitude problem. When there’s no mountain, every blocked hill gets abandoned for another hill. The leader pivots constantly because nothing was worth persisting toward in the first place. Every ground-level obstacle triggers a redirect because there’s no fixed point above to navigate toward.
When your technical leader is constantly in crisis, every setback urgent, every obstacle catastrophic, every block requiring your intervention, check their destination altitude.
Ask: What are you actually trying to accomplish? If the answer is specific and immediate (“ship this feature by March”), they’ve set a first-order destination. They have no room to maneuver. Every block that falls near that destination feels like an emergency because it is one.
Push them higher. What capability are you building? What does success look like in a year, not this quarter? A leader operating at second or third order will describe something that survives individual project failures. They’ll have room to reroute.
The leader who can only articulate first-order destinations will burn themselves out navigating blocks that shouldn’t have been crises in the first place.
5.3 Persistence Without Rerouting
This is stubbornness dressed as determination: burning political capital on a path that’s already closed.
The leader commits to a path. They announce it publicly, build plans around it, invest political capital in defending it. Then a block falls.
Instead of rerouting, they escalate. They demand the obstacle be removed. They treat the closed path as a problem to be solved rather than terrain to navigate around. They burn more capital. The block doesn’t move. It was never going to move. But they keep spending anyway.
The error isn’t persistence. The error is failure to recognize—or refusal to accept—that the path is closed. What looks like determination is actually denial. They’re not pushing toward a destination; they’re pushing against a wall, spending credibility on a door that won’t open.
Political capital spent on blocked paths returns nothing. The opportunity cost compounds: every unit of capital burned demanding a block be moved is a unit not spent finding a way around it. The longer you persist on a closed path, the more expensive the eventual reroute becomes.
The remedy isn’t less persistence. It’s learning to read when a path is done. Cut losses. Accept terrain as terrain. The destination doesn’t care which path you take—only that you arrive.
5.4 Rerouting Without Persistence
This is an altitude problem: chaos dressed as responsiveness.
The leader encounters a block and immediately changes direction. New plan. New approach. Sometimes new destination entirely. They call it pivoting. They call it responding to reality. They call it agile.
Their teams experience it as exhaustion. Every week brings a new direction. Momentum never builds because it’s constantly being redirected. People stop investing fully in any initiative because they’ve learned it will change before it completes. The organization develops learned helplessness—why accelerate toward a destination that will move before you arrive? Research on organizational ambidexterity confirms this: leaders must balance exploration (new opportunities, flexibility) with exploitation (persistence, depth), and the failure mode isn’t picking one over the other—it’s failing to hold both simultaneously (Lavie, Stettner and Tushman, 2010).
The error isn’t rerouting. The error is rerouting the destination instead of the path.
When a block falls, the question isn’t “where should we go now?” The question is “what’s another path to where we were already going?” If you’re changing destinations every time a block falls, you didn’t have a destination. You had a vague intention that couldn’t survive contact with reality.
This happens when there’s no mountain—just a series of hills that keep getting abandoned. The leader’s gaze is fixed too low. Every obstacle at ground level triggers a redirect because there’s no fixed point above to navigate toward. They thought they were committed to something, but they’d never raised their eyes high enough to see a destination worth persisting toward.
The remedy isn’t less rerouting. It’s raising your gaze. Find the mountain. Define the destination at sufficient altitude that paths can change while the destination stays fixed. When you’re looking at the peak, the boulders on the ground become terrain to navigate, not crises that demand a new direction.
5.5 The Discipline of Both
How do you actually hold certainty and uncertainty simultaneously?
The destination is knowable. Strategy gives you that. If you’ve done the work, you know where you’re going. The mountain is visible. It doesn’t move.
The path is unknowable. The blocks guarantee that. You can’t plan a route across a field of falling obstacles. You can only navigate it in real time, recalculating constantly, adjusting as blocks fall.
Uncommitted to the path doesn’t mean passive. It means fluid. You’re pushing hard on the current path while holding it loosely. You’re fully engaged in today’s route while ready to abandon it tomorrow. You’re simultaneously all-in and ready to change.
This is not equilibrium. It’s sustained tension. You’re carrying two contradictory commitments at once, and the ground keeps shifting beneath you.
The recalculation happens constantly. Not as a crisis response, but as a background process. Where are the blocks falling? Which paths are closing? Which are opening? What’s the current best route to the mountain? This isn’t emergency thinking. It’s normal thinking. The field is always shifting. Your awareness shifts with it.
The emotional register matters. When a block falls and closes your path, you don’t rage against it. You don’t freeze. You don’t collapse into crisis mode. You note it, feel whatever you feel, and start recalculating. The block is information. It tells you something about the terrain. It doesn’t tell you anything about your destination or your ability to reach it.
This is where the Thermodynamics chapter connects. The frustration you feel when paths aren’t opening is data about navigation. When you’re not seeing movement—when you keep pushing and nothing changes—frustration arises. That frustration isn’t a problem to suppress. It’s a signal to investigate. Is the path still open? Am I spending capital on a door that won’t open? Is this obstacle terrain to navigate around, or a wall I’m refusing to see?
You’re not powering through the frustration. You’re reading it as information about the terrain. The “background process” that tracks which paths are closing isn’t a formal practice—it’s emotional awareness applied to navigation. You learn to feel when a path has gone dead. Not through analysis, but through the particular quality of frustration that comes from pushing against something immovable. That’s different from the frustration of a hard problem that’s slowly yielding. Learn to distinguish them.
This is easier to describe than to do. The blocks feel personal. The closed paths feel like failures. The constant rerouting feels like you’re doing something wrong, like competent leaders would face fewer obstacles, like somewhere executives are running organizations where paths stay open.
They’re not. The blocks fall everywhere. What varies is the relationship to them.
5.6 When the Destination Is You
That two and a half years of pain where this image emerged? I didn’t win there.
The role didn’t work out. I eventually left. By most external measures, it wasn’t a success. But I was persisting toward something, even when I couldn’t articulate it. The destination wasn’t the job. It was who I was becoming.
Sometimes the mountain is further out than you can see.
The blocks in that role forged me. The constant rerouting built a reflex I didn’t have before. The persistence required just to stay in the game, to keep showing up, to keep recalculating, to keep moving despite everything closing around me, that became capability. I left without winning, but I left as someone who could win elsewhere.
This reframes persistence for people in the middle of terrible roles. You’re not failing at persistence because you’re not succeeding. The destination might not be this job. It might be the leader you’re becoming through this job. The path might include leaving. That’s not failure if the mountain is at the right altitude.
Committed to destination, uncommitted to path. The destination might be internal. The path might include roles that don’t work out. Persistence toward capability isn’t the same as persistence toward victory in any particular context.
I didn’t understand this while I was in it. That visualization probably saved my sanity. It externalized the chaos so I didn’t internalize it as failure. Block falls. Path closes. Find another path. Keep going.
Years later, I understood what I’d been persisting toward. The mountain was there the whole time. I just couldn’t see it from where I stood.
If you’re evaluating a leader in the middle of their struggle, or being evaluated yourself, remember this. The forging doesn’t look like winning. It looks like surviving. The mountain only becomes visible after.
5.7 The Connection
This discipline builds on what came before and makes possible what follows.
Political capital is what you spend when you persist on a blocked path, and what you preserve when you reroute wisely. Every hour pushing against an immovable block burns credibility. Every graceful pivot around an obstacle demonstrates judgment. The leaders who go bankrupt often aren’t making bad technical decisions. They’re burning capital on closed paths, or chasing hills because they never found a mountain. Either way, the capital runs out.
The Blub Paradox explains why altitude is so hard to see. A leader operating at first order can’t perceive second-order destinations the same way a Blub programmer can’t perceive Lisp. They’re not being stubborn on purpose. They literally can’t see the mountain—only the hill in front of them. Ronald Heifetz calls this the difference between technical and adaptive challenges: technical problems have known solutions, but adaptive challenges require learning and shifts in perspective (Heifetz, 1994). A leader stuck at first-order destinations is treating adaptive challenges as technical ones—looking for the solution when the real work is learning to see the problem differently. When you watch someone persist on a blocked path long past the point of reason, remember: they may not have the perceptual apparatus to see the alternative. Teaching them to see higher-altitude destinations is translation work, not argument.
The rest of this book will give you lenses for where to reroute, how to protect your team’s momentum when paths change, and how to stay regulated when the blocks keep falling. But lenses are useless if you can’t keep moving long enough to apply them. This is the posture underneath. The willingness to persist despite everything. The fluidity to reroute when paths close. The judgment to know which is which.
This discipline is not optional. Without it, every other lens becomes a liability, another way to see problems you can’t navigate, another framework that breaks on contact with falling blocks. The path is unknowable. That’s not a problem to solve. It’s the operating environment. Your job is to keep moving toward the mountain anyway.
The tell is simple: same destination, different path.
When something blocks your technical leader’s plan, watch what they bring you. The leader with this discipline absorbs the information, acknowledges the path is closed, and presents an alternative route to the same destination. “This approach won’t work because of X. Here’s how we get to the same outcome a different way.”
That’s the behavior you’re looking for. The mountain didn’t move. Only the route changed.
The leader who can do this repeatedly—who can absorb block after block while keeping the destination fixed and the paths fluid—will navigate your organization through obstacles that would break someone less flexible. They won’t need you to remove obstacles. They’ll find their own way around.
Contrast this with the two failure modes: the leader who escalates to you demanding obstacles be removed (burning capital on closed paths), or the leader who pivots to a new destination every quarter (never had a mountain to begin with). The first exhausts your credibility fighting unwinnable fights. The second exhausts their teams chasing moving targets.
The leader worth keeping does neither. They absorb and reroute. The destination stays fixed. Everything else is negotiable.