
Imagine two very bored castaways on a desert island, who have food and shelter but nothing to do. They spend the day throwing coconuts at each other for fun.
One day a crate washes up, with its cargo intact: hundreds of classic paperbacks! Melville, Hugo, Tolkien, the Brontës, and more. The men celebrate, and immediately begin throwing the books at each other. They invent a game like Jenga, but with books instead of wooden blocks.
Life on the island does improve somewhat, with these new forms of throwing and stacking games.
Both men can read well enough, but they regard classics as too boring to bother with, and they’re already bored enough.
A month la…

Imagine two very bored castaways on a desert island, who have food and shelter but nothing to do. They spend the day throwing coconuts at each other for fun.
One day a crate washes up, with its cargo intact: hundreds of classic paperbacks! Melville, Hugo, Tolkien, the Brontës, and more. The men celebrate, and immediately begin throwing the books at each other. They invent a game like Jenga, but with books instead of wooden blocks.
Life on the island does improve somewhat, with these new forms of throwing and stacking games.
Both men can read well enough, but they regard classics as too boring to bother with, and they’re already bored enough.
A month later, the novelty of book-Jenga having worn off, one of the men decides to focus his energies on working through The Lord of the Rings. He has to steel his attention repeatedly to get through the opening section on the domestic life of creatures called “hobbits.”
But by the time Gandalf tells Frodo about the ring, life is never the same for our castaway. He didn’t know that the inky paragraphs inside yellowed books could bring your mind into entirely new worlds, and make you feel things you’ve never felt.
Suspicious of the new arrivals
The other man has by now invented new forms of book-Jenga and coconut-bowling, unaware of this utterly new dimension his friend has discovered. He sees no indication anywhere that a brick of paper can contain something like Middle-Earth. That would be like a coconut containing a rocket to space.
He’s sitting on buried treasure and doesn’t know it.
Worlds you’re meant to walk in
Each of us is both of these castaways.
There are dimensions of experience you know now that you once didn’t, and which remain hidden to others. Maybe you at some point “got” (i.e. entered the world of) distance running, classical music appreciation, or pastry making. Maybe you learned to code, or knit, or meditate, whereas before that thing looked like wizardry to you, and still does to others.
Wizardry from another world
This new world became a part of you, and part of what life even is to you.
Yet at one point that part of you hadn’t been born yet. And it may have remained unborn, if you hadn’t found a way in.
There are still countless realms of experience that remain hidden to you. You may have admired people who play piano smoothly, grow spectacular gardens, or build thriving online communities, and you’ve wanted to do the same. But you still have no idea what it’s like to* inhabit* those abilities, to live inside them and feel the unique sorts of fulfillment they offer.
One of the most life-affirming things a person can do is discover and enter a new world of experience, one that fits their spirit, the way our island-dweller found out how to enter Middle-Earth (and Dune, and Camelot, and the pure heart of Jane Eyre).
Has something to show you you’ll never forget
When you do enter a new world, life really does expand. When you start to “get” photography, for example, you gain a whole new way of looking. The visual world becomes more striking and meaningful, forever. That might sound dramatic but it’s exactly what happens.
You already know where you ought to go
For each of us, there are worlds we know about and we want to enter them.
Some part of you knows you ought to make music, but you’re stuck forever noodling on the guitar and can’t play a whole song. You see others who have entered this world, but you remain outside it.
Ideally, you’d invest your energy in finding your way into the worlds that call you, or into deeper layers of the worlds you’ve already begun exploring.
Setlist: Wild Thing, Smoke on the Water, repeat
But our instincts, and our society, point us away from going deeper. Between a natural aversion to discomfort and awkwardness, and devices that offer infinite novelty, we tend to go wider, rather than deeper. We keep grabbing at novel forms of the familiar and known, instead of entering new worlds. It’s just easier to flip to your news feeds, or put on another true crime podcast, than it is to try to read Aristotle or develop your singing voice.
How to enter a new world
You already know of some worlds you want to live in: that of the competent guitar player, the reader of thick history books, the baker of golden pastries, the speaker of conversational Spanish, whatever.
You might need to find instruction, but that’s not the hard part. Books, courses, and information abound.
It’s when you follow the instruction, when you start doing the thing itself, that the hard part happens. You encounter awkwardness, confusion, and tedium. The entrance to the new world does not allow for easy movement. It confronts you, with unresolved puzzles, awkward sensations, and frequent snags.
Passable with some careful figuring
Meanwhile, the mind is always hunting for a smooth sense of progress and easy gratification. But those can’t be found in this new world yet, only in the old one. If you give in to this urge to grasp at ease — let’s play Wonderwall again, let’s play the *Iron Man *riff again – you just go wider instead of deeper, and never gain access.
These cravings for ease can be used as cue to go deep instead. You can pick your way through the thicket by applying a kind of slow and careful attention to the new world’s mental puzzles and physical demands.
For reading old books, that means slowing down your pace, and being satisfied with a few well-read pages at a time. That might mean reading aloud, and taking those winding Victorian sentences again when they lose you.
For playing guitar, it means carefully forming those awkward chord shapes, relaxing into the tension the best you can, and patiently working out each trouble spot.
A portal
Entering a new world requires repeated delves into its weeds and brambles, wielding that slow and careful attention as a tool, or a lantern. This kind of work is more than tolerable in short, regular sessions. But you have to make those sessions happen, and for their duration you have to deny the mind’s craving for quick and smooth progress.
The good news is that moving through any given brambly patch (e.g. a cramped chord position, the thick prose of Victorian novels) doesn’t take many “delves” to make it familiar, but each world is huge and there are a lot of places to go.
The fruit comes with thorns, the thorns come with fruit
Never embarking – staying home in the Shire, so to speak – seems like the worst possible choice. Imagine the guitarist who lives and dies without ever learning to play, or the writer who never wrote a story. Maybe you don’t have to imagine.
We all have lifelong desires to enter certain worlds we think we belong in, and we know it’s possible. Which castaway has been at the helm?
What’s a world you’ve always wanted to enter?
***
Pick a world and go
If you want a guided journey into a world you’ve always dreamed of entering, there’s still time to join the winter One Big Win group.
Each participant designs a quest into a new world of their choosing, and makes small, manageable delves into it, until it’s a part of them. Repeat for other worlds as desired.
A portal and a map