Meaningful Lostness

Tree Lost

J.R.R. Tolkien wrote “not all those who wander are lost.”

This great line brings inspiration to countless wanderers trotting across the globe, including many nomadic 20-somethings seeking a poetic justification for meandering about life without a stable career.  No worries, since this includes yours truly…

Look no further — I’ve got you covered! (alright look a bit further; specifically below, where the covering is done).

Not All Those Who Wander Are Lost

Underlying that line are a few assumptions:

  1. That usually those who wander are lost
  2. To wander and to be lost are negative things

Tolkien had a different view, namely that:

3. It is possible to wander and not be lost

(If we digress a bit and play around with the line, then we get “it is possible to not wander and still be lost“, but that’s a whole other discussion.)

This interpretation brings up three questions: What does it mean to wander without being lost? What is wandering? What is lost-ness?

George Meegan took over 2,400 days to walk over 19,000 miles from the southern tip of South America to the northern tip of Alaska; definitely wandering, didn’t seem lost. Paul Salopek is currently on a 21,000 mile walk to retrace the trail of humans migrating out of Africa; definitely wandering, doesn’t seem lost. All these people went on/are still on crazy long walks; definitely wandering, don’t seem lost.


According to, wander means “to ramble without a definite purpose” and “to go aimlessly” and “to extend in an irregular course.” Synonyms include: meander, veer, saunter, stray, and swerve.

Its etymology comes from the same root words as “wend” and “wind”, suggesting everything from “to turn, go”, “to proceed”, “air in natural motion”, and “air that is blown or forced to produce a musical sound”. It reminds me of this Alan Watts video.

The wind twists and turns in tiny movements. These grow large over time and because we don’t notice all the time it took for it to grow, the wind seems to arise spontaneously.

But it isn’t spontaneous, it is an accumulation of all this straying from the “straight and narrow”.

It’s best described in chaos theory and the way it looks at the formation of wondrously complex things like fractals from very simple initial conditions.

The initial conditions of George Meegan in Ushuaia in January of 1977 or someone like Ibn Battuta in Tangier in June of 1325 grew, through countless twists and turns, into wondrously complex 7-year and 30-year journey’s that neither could predict from the first steps. Yet they reflected the first steps — self-similarity.


According to the same source, lost means “no longer possessed or retained” and “having gone astray or missed the way”. Some synonyms include the following: confused, squandered, forfeited, missing, perplexed.

Its etymology comes from a similar root word as “loss” which derives from the Old English “los” meaning “destruction” and the Old Norse “los” meaning “looseness, breaking up.”

Perhaps the lost-ness many seek has more to do with loosening or breaking up “the way” that one has “gone astray” from or “missed” according to common definitions. Who made up “the way”? Why is “the way” the way it is? ….. (let’s not get too wayward now— waaaaaay-t a minute…alright I’m done)

Twisting and turning on and off “the way” is what wandering without being lost is all about. Meaning emerges from the dynamic tension of following a certain structure (“the way”) and allowing for spontaneity (“twisting and turning”).

Structure means feedback from others, grounding practices, goals, hobbies, and states of being that help create maps to guide ones explorations.  Spontaneity means intuition and following the trail of curiosity as it veers this way and that.

So we know what structure means and what spontaneity means, but…

What Does Meaning Mean?

This takes us back to the primordial days when unicellular beings were the shit. Back then the entire landscape of “meaning” was confined to two directions: toward food and away from prey.

Everything else was meaningless. Quite literally, meaning moves you. The evolution of different ways to move (fins, wings, legs etc.) has been critical to the evolution of meaning over time.

Temporarily putting aside the fact that:

1. Untold millions are still forced to live this survival-centric life

2. Untold millions who are not forced still choose (usually very unconsciously; as if unaware there was even a choice) to live this survival-centric life.

In general as evolution chugs along the sense of meaning that in-formed those early movements has expanded through all those twists and turns; quite literally by wandering off “the way”, by being lost.

This is how the landscape of the meaningful starts to transcends fight-or-flight. Abstract motives like “self-knowledge” in the School of Life start to guide movement.


This looseness or breaking up of “the way” brought on by the twists and turns of wind-like wandering leads us to define a goal:

  1. To cultivate Meaningful Lost-ness

And a method for getting there:

   2. Through the art of Purposeful Wandering

This post is about #1, veer on back for a later post dealing with #2.