What are the tollhouses?

Saint John of Shanghai and San Francisco wrote:

When “the books are opened” (Revelation 20:12) it will become clear that the roots of all vices lie in the human soul. Here is a drunkard or a fornicator. When the body has died, some may think that sin is dead too. No! There was an inclination to sin in the soul, and that sin was sweet to the soul. And if the soul has not repented of the sin and has not become free of it, it will come to the dread Judgment also with the same desire for the sweetness of sin and will never satisfy its desire. In it there will be the suffering of hatred and malice. It will accuse everyone and everything in its tortured condition, it will hate everyone and everything. There will be wailing and gnashing of teeth of powerless malice. (Sermon on the Last Judgment)

The passions and unrepented sins that we tolerate in this life are not healed on the spot by our passing from the body; death is not an instant sanctifier. Forgiveness and the grace of reconciliation are always available to the servant of God in this life. But “How shall we escape, if we neglect so great salvation?” (Hebrews 2:3)

The resurrection of all the dead and the Final Judgment have not yet occurred, so when we are separated from the present mortal body, we will be brought to a place where we will await the resurrection, in a condition reflecting the actual state of our souls. (See Luke 16:19–31). This is called the Particular Judgment.

The saints have metaphorically represented this judgment as a path through tollhouses, where one is challenged by demonic accusers of the sins committed in this life. Here is how a few of the saints have described this:

Saint Hesychios the Priest (5th c.), On Watchfulness and Holiness, Philokalia Vol. 1, p. 188:

If the soul has Christ with it, it will not be disgraced by its enemies even at death, when it rises to heaven’s entrance; but then, as now, it will boldly confront them. But let it not tire in calling upon the Lord Jesus Christ, the Son of God, day and night until the time of its departure from this mortal life, and He will speedily avenge it in accordance with the promise which He Himself made when speaking of the unjust judge (cf. Luke 18:1-8). Indeed, He will avenge it both in this present life and after its departure from its body.

Sunday Midnight Office, Tone 1, Sessional Hymns after Ode 6, Theotokion

Guide aright my wretched soul, O pure one, and have pity on it. For by the multitude of my transgressions, my soul has stumbled headlong into the pit of destruction, O most immaculate one; and, at the dread hour of my death, rescue it from the accusing demons and from every torment.

Saint John of Karpathos (7th c.); For the Encouragement of the Monks in India who had Written to Him: 100 Texts, Philokalia Vol. 1, pg. 303-4:

When the soul leaves the body, the enemy advances to attack it fiercely reviling it and accusing it of its sins in a harsh and terrifying manner. But if a soul enjoys the love of God and has faith in Him, even though in the past it has often been wounded by sin, it is not frightened by the enemy’s attacks and threats. strengthened by the Lord, winged by joy, filled with courage by the holy angels that guide it, encircled and protected by the light of faith, it answers the malicious devil with great boldness: ‘Enemy of God, fugitive from heaven, wicked slave, what have I to do with you? You have no authority over me; Christ the Son of God has authority over me and all things. Against Him have I sinned, before Him shall I stand on trial, having His precious Cross as a sure pledge of His saving love towards me. Flee far from me destroyer! You have nothing to do with the servants of Christ.’ When the soul says all this fearlessly, the devil turns his back, howling aloud and unable to withstand the name of Christ. Then the soul swoops down on the devil from above, attacking him like a hawk attacking a crow. After this it is brought rejoicing by the holy angels to the place appointed for it in accordance with its inward state.

Father Jeremy McKemy has written this helpful and pastoral summary:

You won’t make it through the toll houses later – you’re struggling through them right now. Through the prayers of our holy fathers and a life of confession and repentance, we ascend through them right now. The elaborate toll house metaphor is almost like a replay of your life but with spiritual spectacles on. If you continuously struggle against sin and never hold on to any of it, then you’ll make it through. The demons of the toll houses will have nothing on you because the record has been cleansed by God’s mercy and your repentance. As seen in the visions, the prayers of others can help spur us toward repentance and even cover our sins. That’s one of the mysterious ways in which God’s mercy works. Our prayers for one another actually make a difference! These prayers are expressed in the metaphorical vision as “payments” to get us through.

So, rather than thinking about the toll houses as something that’s going to happen to us later, we should see that we’re already going through them now. Our ascent to heaven occurs in this life; our struggle through the toll houses is happening now. Either we fight our sin and repent – or we give in and find out later that the demons of the “toll houses” had us all along. May God bless our struggle.