Choose Roads by First Choosing a Destination
Created at: September 27, 2025
If you don't know where you are going, any road will get you there. — Lewis Carroll
The Cheshire Cat’s Quiet Logic
Lewis Carroll’s famous idea is a polished paraphrase of a scene in Alice’s Adventures in Wonderland (1865), where the Cheshire Cat tells Alice that which way she ought to go “depends a good deal on where you want to get to.” The lesson is deceptively simple: direction only acquires meaning in relation to a destination. Without a chosen end, every path is equivalently suitable—and equivalently pointless. Thus, the quip is less whimsy than a gentle theorem about navigation: aim clarifies route.
Why Ends Precede Means
From this premise, we move to a classic insight: purposes determine processes. Aristotle’s Nicomachean Ethics posits telos—an end or aim—as the organizing principle of action; things are understood by what they are for. Likewise, Seneca’s maritime maxim captures it pithily: “If one does not know to which port one is sailing, no wind is favorable” (Letters to Lucilius, c. 65 CE). In other words, even abundant resources—time, talent, tailwinds—merely accelerate drift if the destination remains undefined.
The Cost of Drifting Decisions
Consequently, when goals are vague, choices default to convenience, habit, or the loudest demand. Opportunity costs pile up invisibly, and effort turns into motion without progress. Peter Drucker’s distinction reminds us why this hurts: “Efficiency is doing things right; effectiveness is doing the right things” (The Effective Executive, 1967). Teams that chase metrics without purpose risk Goodhart’s Law: “When a measure becomes a target, it ceases to be a good measure” (Goodhart, 1975). One startup I advised shipped weekly features yet stalled user retention—until it defined a clear retention outcome, after which the roadmap finally converged on what mattered.
When Wandering Is Wise
Even so, not knowing can be productive—if framed as exploration rather than drift. James March’s classic distinction between exploration and exploitation (Organization Science, 1991) shows that deliberate wandering discovers options and knowledge impossible to plan upfront. Thoreau’s Walden (1854) romanticizes such meandering as a way to truly see. Yet effective exploration still benefits from a provisional compass: learn-what questions, time-boxed trials, and criteria for switching from roaming to focus. Thus, curiosity stays adventurous without becoming aimless.
From Aim to Action: Practical Wayfinding
Accordingly, translate destinations into navigable cues. OKRs—Objectives and Key Results—anchor intent to evidence (Andy Grove, High Output Management, 1983; popularized by John Doerr, 2018). Backcasting begins with the desired end-state and reasons backward to today (John B. Robinson, 1990). A premortem imagines failure in advance to surface risks (Gary Klein, 2007). Combine these with a simple decision filter: if a task does not move us toward the objective—or teach us something necessary to get there—we pause or prune. One product team adopted this stack and cut its backlog by 40%, yet shipped more value by saying a principled no.
Choosing Not Just Direction, but Values
Finally, where we go matters as much as getting there efficiently. North Star metrics should embed guardrails—fairness, safety, and long-term trust—so that the route chosen does not harm those along the way. In ethics, Beauchamp and Childress’s Principles of Biomedical Ethics (1979) exemplify such constraints: beneficence and nonmaleficence guide action beyond mere success. Likewise in business, stakeholder-minded goals prevent “growth at any cost” detours that erode reputation. Purpose, then, is destination plus values—so the road we take leads to somewhere worth arriving.