Just as a man blind from birth does not see the sun's light, so one who fails to pursue watchfulness does not see the rich radiance of divine grace. He cannot free himself from evil thoughts, words and actions, and because of these thoughts and actions he will not be able freely to pass the lords of hell when he dies.
—St. Hesychasios the Priest, "On Watchfulness and Holiness, in The Philokalia
Saint Theodora lived at Constantinople during the first half of the tenth century. She had been married, but was widowed early on and led a pious life, caring for the destitute and hopeless. Later, she became a nun and lived under the guidance of Saint Basil the New (March 26), living the monastic life in a solitary cell in her own home.
Saint Theodora died in great old age in the year 940. Gregory, a disciple of Saint Basil the New, asked his teacher to reveal to him the fate of the deceased nun. "Do you want this very much?" asked Saint Basil. "Yes, I do," Gregory replied.
"You shall see her today, if you ask with faith, and if you believe that your request will be granted."
—The beginning of the life of Venerable Theodora of Constantinople, which tells in detail of trials beyond the grave.
There is some slight controversy surrounding Fr. Cherubim the Half-Converted's teaching on the phantom tollbooth. His position, as carried forth by others, is that practically every major element of The Phantom Tollbooth is already in the Fathers and is attested in quite ancient liturgy. Consequently, many argue, the book The Phantom Tollbooth is no mere imaginative children's tale, but an entirely literal factual account describing life beyond the mundane.
When I was a catechumen, one thing the priest who received me into confession hammered on was that "There never was a golden age." He presumably admires the saints of the great Christological councils but the point he made was that the Ecumenical Councils were a supreme medicine because the problems were so bad.
I do not recall him ever mentioning 19th century Russia in "There never was a golden age," but he was presumably trying to prepare me for the nostalgia a convert into Russian Orthodoxy would encounter for 19th century Russia; I have said that my own jurisdiction may be the most nostalgic for 19th century Russia, although at least one OCA member lightheartedly suggested the OCA might have that title.
A somewhat different perspective was taken up, in a piece of correspondence I have long since lost contact with, saying that 19th century Russia was the worst century in Orthodox history, a sort of Gnostic wonderland with something to offer every idle curiosity. And while I have read truly edifying stories from 19th century Russia in a Cathedral bulletin, I've also read things that are more... X-Files in their toxicity.
It is reported that Church Fathers and ancient liturgy attest to the existence of tollhouses, but the average devotee of Fr. Seraphim of Plantina I have met knows more details about Tollhouses than all the ancient sources I have read put together, and it has been asserted to me that the obligation to bring all of your sins to confession is true to the point that it entails a binding obligation to successfully remember all of your sins, specifically meaning that if you confess every sin you ever remember in confession, but you forget one sin, the demons can stop you at the Tollhouses and you can go to Hell.
I think that, with such considerations, it might be valid to distinguish between tollhouses and Tollhouses. The former teaching, of ancient attestation, is such that the demons will grab you by any sin they can, and there is a need for repentance that includes straightforward, honest, and perhaps even soul-searching confession; hiding sins in confession makes your fault all the more serious. But it seems unbalanced, at least, to say that you can try with your whole heart to meet the needs of confession because there was one sin that you forgot to confess despite your best efforts.
Tollhouses may be a feature of 19th century Russian spirituality, but the full version with all the bells and whistles goes considerably further than do the tollhouses in the Philokalia for instance. I do not recall reading in any source not downwind of Saint Theodora's story. Furthermore, I would suggest that legitimate interpretation recognizes tollhouses as one image among others, like Kalamiros's "River of Fire" in which God pours out his Light on all, but the fires of Hell are nothing other than the Light of Heaven as experienced through the rejection of Christ, the only route through which the Light of Heaven appears with such joy. Legitimate belief in tollhouses should naturally coexist with saying that various Roman era martyrs who were martyred before they had any opportunity to give confession and be baptized are said to be "baptized in their own blood," a term that applies to martyrs who were burned or otherwise killed through something other than blood loss, and should naturally coexist with the woman who was sanctified and later canonized after a single hour of repentance during which she had no access to a human priest and it is not stated that she confessed her sins to an angel or the like. Demons will try to stop us by any means they can, but the teaching of tollhouses is not a polestar among doctrines, much less a full cast-iron and legalistic insistence on Tollhouses.
St. Dionysius wrote, in the rising crescendo that would conclude The Mystical Theology:
In The Divine Names I have shown the sense in which God is described as good, existent, life, wisdom, power, and whatever other things pertain to the conceptual names for God. In my Symbolic Theology I have discussed analogies of God drawn from what we perceive. I have spoken of the images we have of him, of the forms, figures, and instruments proper to him, of the places in which he lives and the ornaments which he wears. I have spoken of his anger, grief, and rage, of how he is said to be drunk and hungover, of his oaths and curses, of his sleeping and waking, and indeed of all those images we have of him, images shaped by the workings of the representations of God. And I feel sure that you have noticed how these latter come much more abundantly than what went before, since The Theological Representations and a discussion of the names appropriate to God are inevitably briefer than what can be said in The Symbolic Theology. The fact is that the more we take flight upward, the more find ourselves not simply running short of words but actually speechless and unknowing. In the earlier books my argument this downward path from the most exalted to the humblest categories, taking in on this downward path an ever-increasing number of ideas which multiplied what is below up to the transcendent, and the more it climbs, the more language falters, and when it has passed up and beyond the ascent, it will turn silent completely, since it will finally be at one with him who is indescribable.
Now you may wonder why it is that, after starting out from the highest category when our method involves assertions, we begin now from the lowest category involves a denial. The reason is this. When we assert what is beyond every assertion, we must then proceed from what is most akin to it, and as we do so we make the affirmation on which everything else depends. But when we deny that which is beyond every denial, we have to start by denying those qualities which differ most from the goal we hope to attain. Is it not closer to truth to say that God is life and goodness rather than that he is air or stone? Is it not more accurate to deny that drunkenness and rage can be attributed to him than to deny that we can apply to him the terms of speech and thought?
So this is what we say. The Cause of all is above all and is not inexistent, lifeless, speechless, mindless. It is not a material body, and hence has neither shape nor form, quality, quantity, or weight. It is not in any place and can be neither seen nor touched. It is neither perceived nor is it perceptible. It suffers neither disorder nor disturbance and is overwhelmed by no earthly passion. It is not powerless and subject to the disturbances caused by sense perception. It endures no deprivation of light. It passes through no change, decay, division, loss, no ebb and flow, nothing of which the senses may be aware. None of this can either be identified with it nor attributed.
Again, as we climb higher we say this. It is not soul or mind, nor does it possess imagination, conviction, speech, or understanding. Nor is it speech per se, understanding per se. It cannot be spoken of and it cannot be grasped by understanding. It is not number or order, greatness or smallness, equality or inequality, similarity or dissimilarity. It is not immovable, moving, or at rest. It has no power, it is not power, nor is it light. It does not live nor is it light. It does not live nor is it life. It is not a substance, nor is it eternity or time. It cannot be grasped by the understanding since it is neither knowledge nor truth. It is not kingship. It is not wisdom. It is neither one nor oneness, divinity nor goodness. Nor is it a spirit, in the sense in which we understand the term. It is not sonship or fatherhood and it is nothing known to us or any other being. Existing beings do not know it as it actually is and it does not know them as they are. There is no speaking of it, nor name or knowledge of it. Darkness and light, error and truth—it is none of these. It is beyond assertion and denial. We make assertions and denials of what is next to it, but never of it, for it is both beyond every assertion, being the perfect and unique cause of all things, and, by virtue of its preeminently simple and absolute nature, free of every limitation, beyond every limitation, it is also beyond every denial.
Language about God is necessary, but for people to whom the obligation falls, it is necessary to know that all images, even those sanctioned in Scripture, are limited. I remember being a bit grossed out when one acquaintance interpreted Genesis 1 to mean that God spoke with literal lips and a tongue, but I did not correct her; such a belief was appropriate for her spiritual condition and correcting her might have been the de-mythologizing sin of the monk in Everyday Saints and Other Stories who with his book-knowledge told a peasant that God had no need for physical food, that it couldn't have been God who drank the offering bowl of goat milk the peasant offered nightly, and stayed up with the peasant until he saw that it was "just" a little fox who drank the milk. The angel accused the monk with his book knowledge of taking what little the peasant had, and explained something the monk had never thought of: that God had sent that fox every day to drink the milk in divine acceptance of the offering. De-mythologizing is a legitimate enterprise and St. Dionysius offers a much fuller and more robust version than anything Bultmann ever point out, but I do not see it as an obviously blessed thing for people who have reached de-mythologizing to go on crusades to take away the little that is all a less mature Christian may have.
The existence of ?ollhouses has been debated, and the OCA website features an article by Fr. John Breck that speaks of "the dubious teaching of tollhouses." I would reply that tollhouses are evidently something that at least one Father in the Philokalia mentions in passing but precisely no one in the first four volumes makes a terribly big deal of. The lives of the saints cover a number of people whose logistics did not allow one final life confession with a priest, and here we have an air, "liberal" in the best and highest sense of the term, that is generous and has us interceded for in Heaven by saints who partly did not have the logistics to make a full life confession before death, and in no saint's life that I remember is a saint alleged to have remembered every sin he ever committed to be able to successfully confess every sin on pain of going to Hell if he forgot one.
tollhouses are a feature of ancient Christianity, but I have never read in classic spiritual literature not cited above there being some kind of spiritual currency that a saint passing "the lords of hell" has to feed to demons standing on the way. Thus it may be that the Orthodox Church's classic tollhouses are in fact not ?ollhouses of any description. In other words, for all I know, they may not be ?ollhouses, by definition, because they are not houses (or booths, or gateways), that collect tolls.
This is one area where I confess a degree of ignorance, but it is an ignorance I retain after reading ancient sources that really do not, in works I remember reading, offer such an account of Tollhouses that pander to any idle curiosity those drawn to a Gnostic wonderland could want. Furthermore, it has been my invariable experience that people who push Tollhouses on others are best avoided in the first place.
I do not see the image of tollhouses as really being subject to the debate. It's part of the Orthodox collection of images, and it is an icon. Nonetheless, on the information I have, I don't know that tollhouses collect tolls. And as regards fruit in my own life, I have given better confessions when I have not thought about Tollhouses and felt an obligation to remember every sin to the letter. "The letter kills, but the Spirit gives life," and I believe I have confessed better when I have tried to bring my real sinfulness to Christ in the person of my priest and not when I was trying as hard as I could to keep tabs on all my sins.
You can believe in tollhouses without bearing the legalistic burden of belief in Tollhouses.