Skating Toward Tomorrow: The Strategy of Anticipation
Created at: October 12, 2025
I skate to where the puck is going to be, not where it has been. — Wayne Gretzky
From Reaction to Anticipation
At the outset, Gretzky’s dictum recasts excellence as a function of foresight, not speed. Rather than chasing events, he insists on modeling their trajectory—angle, momentum, friction, and opponent intent—then occupying the future before it arrives. The payoff is positional advantage: early access to space and time that others must spend energy recovering. In effect, he turns the ice into a map of probabilities and moves where the highest-probability payoff will materialize. This shift from reacting to predicting is subtle yet profound, because it privileges orientation—how you make sense of the world—over mere motion. To see how this philosophy works in practice, we can start where it was perfected: on the ice itself.
Gretzky’s Instincts on the Ice
Gretzky learned early from his father, Walter: anticipate the play. He became the NHL’s all-time points leader by mastering off-puck positioning—1,963 career assists at NHL.com attest to his habit of seeing two passes ahead. His famed “office” behind the net exemplified this: he waited where angles converged, reading caroms, defenders’ hips, and goalie sight lines before the puck arrived. Crucially, this was not clairvoyance but practiced pattern recognition, refined over thousands of shifts. By treating the rink as a dynamic system and moving first, he forced others into reaction, creating cascading advantages. Extending this logic beyond sports reveals a broader strategic principle: the edge belongs to those who can model and meet the future, not merely chase the present.
Strategy Under Uncertainty: OODA and Tempo
John Boyd’s OODA loop—Observe, Orient, Decide, Act (1970s)—illuminates the mechanism behind Gretzky’s edge. Orientation, the internal model you bring to observations, determines whether decisions anticipate or lag reality. By improving orientation, you compress the loop, acting before rivals have properly framed what is happening. The result is tempo: you shape the game’s unfolding instead of absorbing it. Just as Gretzky got “inside” opponents’ reactions by arriving early, organizations can gain compounding advantage by updating faster and with fewer cognitive errors. In short, skating to where the puck will be is an orientation upgrade; the decision and action that follow are merely its visible wake.
Innovation and Market Foresight
In business, the same principle separates leaders from laggards. Clayton Christensen’s The Innovator’s Dilemma (1997) shows incumbents obsess over existing customers—the puck that has been—while disruptors skate to emerging jobs-to-be-done. Andy Grove’s Only the Paranoid Survive (1996) calls these shifts “strategic inflection points,” where early positioning defines the next decade. Consider Netflix’s 2007 streaming pivot: bandwidth curves and licensing windows signaled where attention would flow, so the company moved before the market fully arrived. Likewise, Eric von Hippel’s lead-user research (1986) urges listening to edge cases that reveal tomorrow’s mainstream. The connective tissue is foresight operationalized—building capabilities where demand is likely to materialize, not where it is comfortable today.
Forecasting with Data and Bayes
Anticipation thrives on disciplined updating. Bayes (1763) provides the recipe: start with priors, observe signals, and adjust beliefs proportionally to evidence strength. Philip Tetlock’s Superforecasting (2015) confirms that calibration—frequent, transparent updates—beats bravado. Moneyball (Lewis, 2003) offers a sporting analogue: on-base percentage predicted run creation better than tradition, so the A’s drafted for what would matter next, not what had mattered. In practice, this means privileging leading indicators over lagging ones: search trends before sales, engagement depth before revenue, prototype cycle time before market share. Consequently, skating to the future becomes a repeatable process, not an act of genius.
Optionality and Asymmetric Upside
Moreover, anticipation pairs naturally with optionality. As Nassim Nicholas Taleb argues in Antifragile (2012), positioning where the upside is convex—and the downside bounded—turns uncertainty into a tailwind. Small, reversible bets in the direction of likely puck trajectories let you benefit from hits while surviving misses. This portfolio of options mirrors a forward drifting into open ice: you don’t know the exact pass, but you maximize the surface area for good outcomes. Thus, the goal is not perfect prediction; it is advantaged exposure to plausible futures.
Practicing the Skill: Patterns and Drills
Anticipation can be trained. Gary Klein’s recognition-primed decision model (1998) shows experts simulate future states rapidly from cues, then test the first workable plan. In organizations, emulate this by backcasting (“If we’ve succeeded in three years, what was true?”), pre-mortems (Klein, HBR 2007), and live dashboards of leading signals. Establish tripwires—explicit thresholds that trigger movement—and run red-team exercises to stress assumptions. On the ice, the analogue is studying tendencies, angles, and rebound patterns; in product, it’s instrumenting prototypes and shortening feedback loops. With repetition, your orientation gets sharper, and arriving early becomes habit, not hope.
Humility, Error, and Course Correction
Finally, anticipation demands humility. Forecasts are probabilistic, not prophetic; overconfidence can skate you into traps. Eisenhower’s adage—“Plans are worthless, but planning is everything” (1957)—captures the balance: prepare deeply, then adapt quickly. Maintain base rates, publish confidence levels, and run postmortems to recalibrate. By embracing error as information and adjusting faster than rivals, you preserve Gretzky’s essential advantage: being first to useful space. In the end, the lesson is practical and hopeful—move early, learn continuously, and let reality make you wiser with each stride.