Fernando Pessoa's heteronyms were deeply tangled with the idea of posthumousness.

In The Book of Disquiet, he describes how characters from novels, particularly Mr. Pickwick and Mr. Wardle, are more real to him than living humans.

The heteronyms existed on the stage of Pessoa's life as characters, but also as friends, as costumes he could slip into and flaneur across the page. 

[The self is a friend to some of us; ideas become our favorite company.]

In a letter dated 8 February 1918, Pessoa wrote:

There is only one event in the past which has both the definiteness and the importance required for rectification by direction; this is my father's death, which took place on 13 July 1893. My mother's second marriage (which took place on 30 December 1895) is another date which I can give with preciseness and it is important for me, not in itself, but in one of its results – the circumstance that, my stepfather becoming Portuguese Consul in Durban (Natal), I was educated there, this English education being a factor of supreme importance in my life, and, whatever my fate be, indubitably shaping it.

After losing his father and infant brother at a young age, with the sounds of his most recent birthday party in the background, Pessoa found life changed quickly: his mother fell in love with another man, who worked from Durban. In the final year of living in Lisbon, when Pessoa was six years old, he wondered in his diary, of this time:

"Is anything sacred? is anything permanent?"

This is a question that plagues writers and theologians. Is anything sacred across time. Is the notion of sacredness sustainable in application to eternity.

. . . Pessoa would move to Durban with his mother and family the following year. Stability is built into our idea of sacredness.

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How Pessoa was described by a fellow classmate in his early teens:

I cannot tell you exactly how long I knew him, but the period during which I received most of my impressions of him was the whole of the year 1904 when we were at school together. How old he was at this time I don’t know, but judge him to have 15 or 16. [...]

He was pale and thin and appeared physically to be very imperfectly developed. He had a narrow and contracted chest and was inclined to stoop. He had a peculiar walk and some defect in his eyesight gave to his eyes also a peculiar appearance, the lids seemed to drop over the eyes. [...]

He was regarded as a brilliant clever boy as, in spite of the fact that he had not spoken English in his early years, he had learned it so rapidly and so well that he had a splendid style in that language. Although younger than his schoolfellows of the same class he appeared to have no difficulty in keeping up with and surpassing them in work. For one of his age, he thought much and deeply and in a letter to me once complained of "spiritual and material encumbrances of most especial adverseness". [...]

He took no part in athletic sports of any kind and I think his spare time was spent on reading. We generally considered that he worked far too much and that he would ruin his health by so doing.

Pessoa's sister, Henriqueta Rosa Dias said, of Pessoa as a child: "Reality was constantly being transformed, and we were the protagonists of his reverie."  

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Charles Robert Anon.

At eighteen, Pessoa stepped into Charles Robert Anon to excommunicate all churches in a notebook piece titled "Excommunication":

His favorite book was Charles Dicken's The Posthumous Papers of the Pickwick Club, of which he said:

"The women of Dickens were cardboard and sawdust to pack his men to us on the voyage from spaces of dream. The joy and zest of life does not include women . . ."

[This, in contradistinction to fellow heteronymer, Antoine Volodine, who gives women a central role in the posthumous frays and fictions.]

Pessoa acknowledged in a 1935 publication that he had created a fictional world around him since childhood - to make friends. To make friends by making them. [More on this on p. 116 of Pessoa biography.]

The heteronym enlarges this world with possibilities by making real the hope of another one.

I would call it Pessoa’s promiscuous posthumous mode. I’m interested in writer’s relationship to his heteronyms, per loyalty, allegiance, identification, etc. as compared to writer’s relationship with his characters.

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Alberto Caeiro.

Everything was subject to fiction – and characters gained biographies, became letter-writers, created a stage for themselves. Each heteronym was nurtured as its own creation. Pessoa  practiced their signatures, carefully distinguishing them from his own. A signature was a man's word, a gentleman's honor in correspondence. It was a high-status pledge to deliver in that relationship. Pessoa invested signatures with a sort of magical power,  even as he subverted their conventional bonds.

In the past, literary alter egos had been adopted by adults (usually males) once they had already established writing careers. The purpose was to separate particular texts from their public personas and reputations, as seen in Kierkegaard, Yeats, Machado, Valery and others. But Pessoa created his collaborators when he was young, almost as a sort of initiation into writing, a reason for writing itself, rather than to balance a work against reputational considerations.

In "Aesthetics of Artificiality," Pessoa articulates his relationship to artifice as a mode of being: "I live aesthetically as someone else...” An excerpt (with my line breaks for reading purposes):

Life hinders the expression of life.

If I actually lived a great love, I would never be able to describe it.

Not even I know if this I that I’m disclosing to you, in these meandering pages, actually exists or is but a fictitious, aesthetic concept I’ve made of myself.

Yes, that’s right. I live aesthetically as someone else. I’ve sculpted my life like a statue made of matter that’s foreign to my being.

Having employed my self-awareness in such a purely artistic way, and having become so completely external to myself, I sometimes no longer recognize myself.

Who am I behind this unreality?

I don’t know. I must be someone.

And if I avoid living, acting and feeling, then believe me, it’s so as not to tamper with the contours of my invented personality.

I want to be exactly like what I wanted to be and am not.

If I were to give in to life, I’d be destroyed.

I want to be a work of art, at least in my soul, since I can’t be one in my body.

That’s why I’ve sculpted myself in quiet isolation and have placed myself in a hothouse, cut off from fresh air and direct light –where the absurd flower of my artificiality can blossom in secluded beauty.

Sometimes I muse about how wonderful it would be if I could string all my dreams together into one continuous life, a life consisting of entire days full of imaginary companions and created people, a false life which I could live and suffer and enjoy.

Misfortune would sometimes strike me there, and there I would also experience great joys.

And nothing about me would be real. But everything would have a sublime logic; it would all pulse to a rhythm of sensual falseness, taking place in a city built out of my soul and extending all the way to the platform next to an idle train, far away in the distance within me…

And it would all be vivid and inevitable, as in the outer life, but with an aesthetics of the Dying Sun.

In order to have the friends and camaraderie he wanted, Pessoa had to invent them, and it.

One suspects many writers find themselves returning to the page in order to have conversations, or feel kinned to others. The person one becomes when writing is kindred. 

Pessoa, writing as Bernando Soares in The Book of Disquiet (with my line breaks):

To know nothing about yourself is to live.

To know yourself badly is to think.

To know yourself in a flash, as I did in this moment, is to have a fleeting notion of the intimate monad, the soul’s magic word.

But that sudden light scorches everything, consumes everything. It strips us naked of even ourselves.

Pessoa loved the visionary scope of John Keats, how he wrote from what he imagined rather than what he saw. 

His last known writing, dated November 29, 1935: "I know not what tomorrow will bring".

Pessoa died next day, on November 30.

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Alberto Caeiro once more, as translated by Eduard Roditi, and published in Poetry Magazine in 1955.