When does one commit the sin of despair?

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I worry very often that I commit the mortal sin of despair when I become very anxious at the thought of hell and begin to wonder if I am truly saved. I try to ward these thoughts off, but sometimes my fear gets the best of me, and they grow until I wonder if my own self–not everyone–being saved is nearly impossible. Please note the word nearly. I know in my heart that Jesus can save anyone, if only we let Him. But are these thoughts bordering on the sin of despair?
 
I worry very often that I commit the mortal sin of despair when I become very anxious at the thought of hell and begin to wonder if I am truly saved. I try to ward these thoughts off, but sometimes my fear gets the best of me, and they grow until I wonder if my own self–not everyone–being saved is nearly impossible. Please note the word nearly. I know in my heart that Jesus can save anyone, if only we let Him. But are these thoughts bordering on the sin of despair?
I think that you need to have a good priest for spiritual development. You need someone to help you through this.

Secondly, psycological help may be good if spiritual help does not help you understand and give you comfort.
 
Sounds like scrupulosity or perhaps OCD. No need to answer, but if you have a diagnosis, then speak with doctor about controlling your symptoms. If it is spiritual, then speak with your confessor. Maybe both.
 
Despair isn’t a mortal sin. I dunno who told you that but they are wrong, or a liar.
 
Pray the Divine Mercy Chaplet. And trust Jesus. Read about the Divine Mercy Devotion, especially its promises, it’s just fitted for the scrupulous. It seems you have more scrupulosity than despair.
 
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I worry very often that I commit the mortal sin of despair when I become very anxious at the thought of hell and begin to wonder if I am truly saved. I try to ward these thoughts off, but sometimes my fear gets the best of me, and they grow until I wonder if my own self–not everyone–being saved is nearly impossible. Please note the word nearly. I know in my heart that Jesus can save anyone, if only we let Him. But are these thoughts bordering on the sin of despair?
Sr. Josefa Menendez (1890-1923) -Jesus’ Message to the World of His Mercy for All

“I would like these [those living with sin] to understand that it is not the fact of being in sin that ought to keep them from Me. They must never think that there is no remedy for them, nor that they have forfeited for ever the love that once was theirs… No, poor souls, the God who has shed all His Blood for you has no such feelings for you!”

“It is My intention also, to show souls that I never refuse grace, even to those who are guilty of grave sin; nor do I separate them from the good souls whom I love with predilection. I keep them all in My Heart, that all may receive the help needed for their state of soul.” -Jesus to Sr. Josefa Menendez

 
I worry very often that I commit the mortal sin of despair when I become very anxious at the thought of hell and begin to wonder if I am truly saved. I try to ward these thoughts off, but sometimes my fear gets the best of me, and they grow until I wonder if my own self–not everyone–being saved is nearly impossible. Please note the word nearly. I know in my heart that Jesus can save anyone, if only we let Him. But are these thoughts bordering on the sin of despair?
Prayer to the Shoulder Wound of Jesus

It is related in the annals of Clairvaux that St. Bernard asked Our Lord which was His greatest unrecorded suffering and Our Lord answered: “I had on My Shoulder, while I bore My Cross on the Way of Sorrows, a grievous Wound, which was more painful than the others and which is not recorded by men. Honor this Wound with thy devotion and I will grant thee whatsoever thou dost ask through Its virtue and merit. And in regard to all those who shall venerate this Wound, I will remit to them all their venial sins and will no longer remember their mortal sins.”

This revelation and promise of Our Dear Savior is another proof of His unlimited mercy. You are urged to say these prayers daily and to promulgate this prayer on a continuous basis, so that others may share in this blessing.

The Prayer

O Loving Jesus, meek Lamb of God, I a miserable sinner, salute and worship the most Sacred Wound of Thy Shoulder on which Thou didst bear Thy heavy Cross, which so tore Thy Flesh and laid bare Thy Bones as to inflict on Thee an anguish greater than any other Wound of Thy Most Blessed Body. I adore Thee, O Jesus most sorrowful; I praise and glorify Thee and give Thee thanks for this most sacred and painful Wound, beseeching Thee by that exceeding pain and by the crushing burden of Thy heavy Cross to be merciful to me, a sinner, to forgive me all my mortal and venial sins, and to lead me on towards Heaven along the Way of Thy Cross. Amen.

Imprimatur: Thomas D. Beven, Bishop of Springfield, Ma.

Pope Eugenius III, at the earnest request of St. Bernard, has granted three thousand years Indulgence to all who with a contrite heart, recite the Lord’s Prayer and Hail Mary 3 times, in honor of the Wound on the Shoulder of Our Blessed Redeemer.

http://brizek.com/prayer/pieta.htm#shwound
 
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“It is obvious that a mere anxiety, no matter how acute, as to the hereafter is not to be identified with despair. This excessive fear is usually a negative condition of soul and adequately discernible from the positive elements which clearly mark the vice which we call despair. The pusillanimous person has not so much relinquished trust in God as he is unduly terrified at the spectacle of his own shortcomings of incapacity.”
From the Catholic Encyclopedia (I think)

There’s a case of a despairing soul saved by Jesus in the Diary of St Faustina (of Divine Mercy Fame)
 
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I worry very often that I commit the mortal sin of despair when I become very anxious at the thought of hell and begin to wonder if I am truly saved. I try to ward these thoughts off, but sometimes my fear gets the best of me, and they grow until I wonder if my own self–not everyone–being saved is nearly impossible. Please note the word nearly. I know in my heart that Jesus can save anyone, if only we let Him. But are these thoughts bordering on the sin of despair?
St. Faustina Divine Mercy Diary

I desire trust from My creatures. Encourage souls to place great trust in My fathomless mercy. Let the weak, sinful soul have no fear to approach Me, for even if it had more sins than there are grains of sand in the world, all would be drowned in the unmeasurable depths of My mercy. (1059)

Say unceasingly the chaplet that I have taught you. Whoever will recite it will receive great mercy at the hour of death. Priests will recommend it to sinners as their last hope of salvation. Even if there were a sinner most hardened, if he were to recite this chaplet only once, he would receive grace from My infinite mercy. I desire that the whole world know My infinite mercy. I desire to grant unimaginable graces to those souls who trust in My mercy. (687)

http://www.divinemercy.org/index.ph...mercy/82-diary-passages-about-the-novena.html
 
Despair only becomes sinful when it leads you to renounce God, or do something like Judas did. You’re a long way from that.

Speak to a priest, pray for confidence in Our Lord Jesus. Padre Pio said Pray, Hope and Don’t Worry.
 
One commits the sin of despair at the moment one loses all hope with God.
 
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