27. wayfinding
maps and compasses
“It is not down in any map; true places never are.”
- Herman Melville
Something unexpected waits in between where you are and where you thought you would be. As you make your way, look down at your wayfinder: is it a map, or is it a compass? And is it possible to know?
Maps are fixed and knowable recounts of other lives lived, places gone. Compasses are incremental, uninformed of precedents, not turn-by-turn.
One version of you holds the map (an architect following a blueprint, destination-focused). The other, the compass (a sailor navigating against the wind, direction-focused).
Which life is better lived?
Maps
"He who has a why to live can bear almost any how."
- Friedrich Nietzsche
The why, in this sense, is the map: a vision that imbues purpose and makes each step meaningful.
Maps offer structure, control, predictability, and context. Ambitious goals, broken into manageable steps, measurable progress against a predefined endpoint. Five-year career paths, retirement strategies, relationship milestones.
Maps are teachable systems of record, especially when well-drawn and well-used. There are precedents of people who have followed them and gone to the places they lead before you. There is security and guarantee in that.
Maps minimize uncertainty, offer next steps, and provide a sense of mastery over unpredictability. Linear effort for linear results. Safe transactions.
Certainty is comforting, but it is also constraining. The price paid is unpreparedness for what you do not already know.
The Achilles’ heel is that maps can only be drawn in hindsight. You are headed nowhere new using one.
Compasses
"Life can only be understood backwards; but it must be lived forwards."
- Søren Kierkegaard
What if the best lives aren’t architected but assembled, piece by piece, with each step revealing the next?
Compasses cannot provide turn-by-turn navigation. Instead, they orient you in a direction reliably, unresponsive to variables. No precedents, no context, no accommodations for conditions. The exact route taken in that direction is up to you.
A more interesting reframe on the overdone “embracing uncertainty” could be “trust in emergence”. Writers who begin without knowing what to write or how it will end (me). Careers that unfold through chance encounters and unexpected pivots, when the gameplan (map) implodes (also, me).
Navigating with only the compass requires faith that movement itself will illuminate the path.
Momentum
An adjacent thought: time forces the perception that events occur in linear progression. In some sense, it’s a normalization that makes things make sense, like seeing 4D in 3D. What could in reality be everything, everywhere, all at once feels path-dependent when looking back on the series of events that comprise your life.
A complementary frame to that is the idea of pluripotency, which my friend Nick discusses in better words:
“There's an idea in biology that's useful here: stem cells. Stem cells are pluripotent: a stem cell can turn into a muscle cell, a blood cell, a nerve cell, or any number of different cell types. In other words, stem cells have an infinitude of options for what they could become.”
- Nick Chow
At the very beginning, these infinite paths remain open to you. The second you move in any direction off that tile, you become something but can no longer become anything. Path-dependent, unalterable footprints.
Let me offer a couple of examples:
Momentum becomes destiny. The idea behind path dependency is that once a decision is made, it becomes increasingly difficult to diverge from it. Directional forces are self-reinforcing, and inertia is self-amplifying. Past choices constrain future options
Locking in. Small, sometimes arbitrary choices can lead to massive long-term dependencies. Consider that the QWERTY keyboard layout was arbitrarily chosen for typewriters over a century ago. Switching costs go up, and alternatives go unexplored
Mid-life crises. Career choices made at 22 can define financial and social realities for decades that follow, making reinvention at 40 feel nearly impossible. Early relationships shape emotional patterns and re-surface in your myriad relationships across the entirety of your life. Choices become tracks that your future self can struggle to leave
Some paths compound massively over time, others are not power law games. Some paths have precedents (the map); others are unexplored and incremental (the compass).
While pluripotency is powerful, it is not limitless. Every choice made closes some doors, opens others.
Collecting dots
"You can't connect the dots looking forward; you can only connect them looking backward."
- Steve Jobs
Net new things worth doing happen in ugly, un-straight lines. They emerge from unexpected choices, setbacks, and detours (and sometimes don’t emerge for a long time).
Exploration is inefficient, unpredictable, and inconvenient, but it’s the only way to find that which you didn’t know to look for. What if the most important paths can only be found, not chosen?
I think a lot about the illusion of certainty. You always feel as if the decision you’re making has intent, and well-made plans are coming to be as you imagined them.
Certainty was never the point. The map is comforting because it limits the number of ways you can fail. The compass is terrifying because it suggests an infinite number of ways you can succeed.
Tricking yourself into thinking you are holding the map is useful. Sometimes you need a destination to start moving, or movement to find a destination. It reveals itself only as you move through it and collect dots.
“Always be collecting dots so you can always be connecting dots.”
- Danny Meyer, Setting the Table
One more thing
In better words than mine, related thoughts on using the compass:
“If you cycle through this feedback loop ferociously for ten years, you will end up with a well-designed life. It will not look like you imagined it would. It will have unfolded around you, and you will struggle to wrap your head around how you ended up where you did.”
- Henrik Karlsson
“Life is an endless unfolding, and if we wish it to be, an endless process of self-discovery, an endless and unpredictable dialogue between our own potentialities and the life situations in which we find ourselves. By potentialities I mean not just intellectual gifts but the full range of one's capacities for learning, sensing, wondering, understanding, loving and aspiring.”
- John Gardner
“Is newness essential? I think so. Obviously it's essential in science. If you copied a paper of someone else's and published it as your own, it would seem not merely unimpressive but dishonest. And it's similar in the arts. A copy of a good painting can be a pleasing thing, but it's not impressive in the way the original was. Which in turn implies it's not impressive to make the same thing over and over, however well; you're just copying yourself.”
- Paul Graham
You are tending to something alive, unpredictable, and full of its own will. Set goals, take detours.
