In January, 1968, Leonard Cohen received a fan letter from Deirdre Anzalone, a high-school junior from Long Island.

At 33, Cohen was already a poet of renown, had recently broken through as a musical artist and was getting plenty of fan mail. Most of it was written in a rambling, mystic style mimicking his own verse.

Some letters were remarkably informal: "Dear Leonard Cohen, Please come to our house for supper some day soon. … We just learned how to use our new pressure cooker."

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Others were of the gentle lonely hearts variety. One of them ends, "Be careful not to find me – I love you too much."

A few were more direct. One of those includes a sultry black-and-white portrait photo of a woman, a pornographic poem in rhyming couplets and a letter of explanation from the man who forwarded the crush letter along, Cohen's publisher Jack McClelland.

"I expect you will agree with me that poetry is not her strongest suit," McClelland wrote. "All I can say is that this publishing business sometimes leads one into the strangest activities."

At the time, amidst a new commitment from academic institutions to gather up the writings of contemporary authors, Cohen had began selling some of his written material to the University of Toronto. The fan letters are cataloged amongst a great deal of correspondence.

The collection spans most of his life, but the bulk of it covers the lean years he spent stretching a small Canada Council grant on the Greek island of Hydra.

In the parlance of librarians, the 23 boxes of Leonard Cohen Papers at the Thomas Fisher Rare Book Library contain five metres of material – which is to say, the length they take up on a shelf. It is not much space to contain a life.

Amidst so much verbiage, Anzalone's letter stands out because it is so charming.

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"The main reason for my writing is that recently I have listened to your song Suzanne, and although I have tried very hard I have not been able to understand it," Anzalone wrote in a looping, girlish scrawl. "I would deeply appreciate if you would answer my letter and tell me: Who is Suzanne? What happens in the song? What does this song mean?"

Cohen never did write back to tell her who Suzanne is, but something in Anzalone's letter made him want to hang on to it.

When I called Anzalone (now Surber) a couple of weeks ago, she didn't need to reach back to recall a letter written 50 years ago. She remembered it quite precisely.

She laughed at the idea of her overserious teenage self, and asked for the letter to be read back to her. Over the line, I could feel her holding her face in her hands at the most earnest parts.

But she was clearly delighted by the idea of her words being held in an important collection, theoretically forever, still accessible long after she is gone.

"I can't believe he kept it," Surber said wonderingly. "Why do you think he did that?"

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Cohen's presentation to the world can be found in his work, but his interior self is contained in these random pieces of paper he squirrelled away.

Like Cohen, we all have our own boxes – of love letters, photo albums, concert tickets, Polaroids, all the detritus of experience, most of it printed, that one accumulates through a lifetime. But few of us have taken this much trouble to preserve it.

Cohen was a committed collector of his own ephemera. He kept corrected drafts of his work, notebooks, letters received and copies of ones sent. He kept postcards, including those he'd written out, stamped and never sent. He kept a copy of his Greek driver's licence, telegrams, cancelled cheques and written records of his disappointments and loneliness.

"My publisher refused my novel," he wrote to a friend. "Since hearing the news I have been strangely exultant. I feel free again, the way I felt before a line of mine was ever published."

And then shortly thereafter, to someone else: "God it was good to hear from you. … Nobody here knows what a poem is."

At times, he nagged friends and relatives for money. He kept a copy of both the begging letter and the one in which he thanked his mother for sending him five dollars.

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Through an odd alchemy of time gone by and Cohen's fame, these documents have taken on a holy cast. You can't just walk into the library and rummage through them. You have to go through an application process.

The boxes are brought out singly or, if the librarians like the look of you, two at a time. You cannot bring a phone or a pen into the sepulchral reading room ("Pens sometimes explode," one attendant warned.)

Each box is about the size of a briefcase and is subdivided into manila folders. As you flip you through the first few, the librarian on duty stares a hole through you, assuring herself that you are not too rough with the sacred parchments.

While you shift self-consciously through the first papers, a young woman sitting across from you uses a tape measure to assess the dimensions of a tiny illuminated Bible.

There is nothing particularly remarkable about the Leonard Cohen letters, other than that they were written by Leonard Cohen. Like all of us, he was a chameleonesque correspondent – cajoling with some, winsome with others, flirty and teasing, sad and self-conscious by turns.

To one of his contacts at the CBC: "Speak to me, Harry. How slants the rain?"

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In an unfinished letter to a New York writer he probably wanted to impress: "We have several images of ourselves. It is a surprise to see which one we assume."

It was in letters to his mother that Cohen seemed his truest self – another commonplace: "I suppose you have your reasons for keeping this long silence. … You know how quickly months become years, and years can harden misunderstandings in such a way that they can never be repaired."

What strikes you about spending an afternoon time travelling through Cohen's coming-of-age isn't its uncommonness, but its familiarity. We have all been this person. We've all begged our parents for money, whined to our friends that we don't see them enough or tried to initiate a romance through text.

Maybe we haven't aspired to Cohen's lyricism …

(One typed letter is nearly a haiku:

"Dear Mariette, Does this reach you?

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I don't know your last name.

You didn't put a return address on your letter.

Tell me where you are.

Love, Leonard")

… But we've tried.

The urge to collect your own relics is strongest when you are young, and establishing all your firsts. Most of the stuff that represents your paper trail through the world – your few metres of shelf space – will be from your youth. Were future archeologists to get hold of your boxes and try to reconstruct your life, it's likely they'd think of you as perpetually 17 years old.

As you get older, you collect less. Possibly because whatever you collect, you eventually have to pack in a box and carry up a flight of stairs every time you move. The garage or attic or hall closet fills up with stuff that is intensely you, but not immediately useful.

You write less as you get older – to others and, crucially, for yourself. Technology is steadily whittling away at whatever urge remains. Letters became e-mails, then texts, and then photos with emojis in place of words.

A Skype call takes the place of a long, confessional missive sent from foreign parts. And so the written record of yourself begins to vanish.

At its root, writing is the result of a feeling of disconnectedness, and reaching out. All of us are connected now, all of the time, but in a way that encourages facile brevity. Convenience of communication is antithetical to depth.

Few people take the trouble to save their electronic communiqués.

How many times have you cleared your inbox without taking the trouble to think about what was in there? It'd be like someone a century ago pulling a pile of papers from a desk drawer and tossing them in the fireplace without first sifting through them, and yet we do it.

A month later, your inbox is filled again, giving you the illusion of meaningful communication.

Still, you manage to fill your boxes. Occasionally, you'll come across one of them when you're up in a corner of the house looking for an extension cord or an appliance warranty.

Once every three or five years, you'll sit down amidst a pile of junk on a Sunday and go through all the signatures in your senior yearbook or read your old letters. It can be a macabre experience because you are not so much one changing person all your life, but many different iterations of a person. It is often too uncomfortable go back and meet that earlier version of yourself, one who is now gone.

Only the most self-aware people share their boxes with others when they are still in the prime of life. At the opposite end of the spectrum, some will feel the need to censor their boxes as they grow older, lest their children or grandchildren stumble upon them and be alarmed by the notion that the person they think they know was once someone else, with different desires, obsessions and priorities.

Your boxes will lie in mouldy basements until you die. As soon as that happens, they become a library of their own, and grow reverent through death.

Somebody will inherit your house and your car, but this valueless collection of the things you thought to keep is all that's left of you. We can speak mystically about living on in the memories of those you loved, but after too short a while, memories require a reference point. Your boxes are that.

Not that we think of them that way. Most of what we consider heirlooms are things with a dollar figure attached.

And though someone will mow your grave and clean your tombstone, no one will tend your boxes. The best you can hope for is that they be distributed willy-nilly to relatives, no longer coherent and so, no longer encapsulating the fullness of whomever you were.

That's what you're thinking as you go through the Leonard Cohen archive.

Not about Cohen, although he was a person of significance (isn't everyone to someone?). But about yourself and everyone you care about. What's in your box? What's in theirs? If you laid it all out in manila folders and assuming anyone would care to look, what would a stranger think of you?

Who were the Deirdre Anzalones in your life – people who drifted by at a time, even glancingly, but made some impression, enough of one that you wanted a keepsake to remind you of it? Have you kept those things?

The Thomas Fisher library is a glorious structure – hollowed out through the middle, a half-dozen storeys high and bathed in soft, green light. Sitting at its base and looking up, an image of Borges' Library of Babel floats to mind. It's a place that contains not just every book ever written, but every possible book.

That's what this is: a vast collection of boxes and experience, every sort, reaching back centuries to a time when people could barely conceive of writing memoirs. All they wanted was to leave something tangible behind. These are the lucky few whose bequests are prized enough to survive.

The rest of them are out in the world, scattered and lost, but no less meaningful.

Box No. 3 of Cohen's papers contains, amongst other things, the typescript drafts of early poems. One of them begins this way:

"There are some men who should have mountains to bear their names to time.

Grave markers are not high enough Or green, And sons go far away …"

Cohen was only 27 when he wrote it, but he already knew that he would leave something behind. One wonders when the rest of us do, and if it's too late.