Monica, first of all, no you do not have to have enough experience before entering a monastery. That is a worldly view. St. Therese of Lisieux entered a monastery at the age of 15, with the permission of the pope, and died and reach holiness at the age of 24.
She even homeschooled, so had no experience of the world whatsoever.
I would strongly, not recommend you to have experience of the world. The world is our enemy, not our friend.
You know, there was this nun, who hurt me badly (that is why I do not have the courage anymore try to enter a monastery), who said I should have enough experience of the “world” before entering a monastery and regret it. She said to have satisfied your desires of the world first, then enter a monastery.
How foolish is that? however, at that time, I was blinded by her counsel and I complied. Thus I entered university, choose a very wordly subject (interior design), spent much money frivolously, be “fashionable”, commited many horrible sins, including adultery, go back to pornography, have worldly friends, It was “HORRIBLE”
What made it more horrible is that it happened
after my conversion. So I have to convert all over again. The Diary of St. Faustina Kowalska helped me a lot in my second conversion. By it, God wanted to show his mercy for me.
And I went to confession, with full contrition, crying my eyes out.
So, no, you
shouldn’t have the experience of the world before entering a monastery.
And about your fright, about where your parents/family will go. Me too. I have those frights for my whole family and relatives. There are
none who love Jesus, everyone live according to their own taste and will, and very wordly. Even though they are not cruel. But they forget God, and search for money and pleasures. They have decent jobs, my mother is a dentist, my father is an engineer, my aunt works as a director in a big company, they are… rich. In their thought. But very poor spiritually. And worse, they are like the pharisees who go to church every sunday, yet commit these horrible sins. And no, they don’t go to confession, my mother and grandmother make justifications that the priest is a sinner. I think no one taught them, or they are just disinterested in God, because of their past heart wounds (their family hurt them).
And I comply to these fright by praying for the conversion of my whole family and relatives, even my servants who are affected badly by their worldly behaviour. I do mortifications and penances, unite them with the most sorrowful passion of Jesus, and offer it for their conversion.
Jesus told St. Faustina, that there is only one thing by which souls are bought, through sacrifices (suffering offered for love of Jesus) and prayers.
By these, I still have those frights, but it has been reduced, and I have peace, about what God will do to their soul. I let the grace of God to work in their souls.
St.Anthony Mary Claret said that mortifications and penances impart graces. Graces for salvation. Do not fear, trust in the mercy of Jesus.
If you pray for them, Jesus will hear you.
Ask mother mary to pray for them. And for your sake, they will be blessed.
Offer little mortifications for them, even mortification of the will. Unite them with the sorrowful passion of Jesus, and offer it for the conversion of your family.
For example, eating chocolate. “Oh, I would not eat that chocolate, I renounce it, for love of Jesus. I offer this as a sacrifice, I unite this with the most sorrowful passion of Jesus, and offer it for the conversion of my family.”
Holy obedience “I offer this holy obedience, as a sacrifice, I unite this with the most sorrowful passion of Jesus, and offer it for the conversion of my family.”
That’s how you do it.
And before every rosary and divine mercy chaplet, just say this prayer, Jesus I pray for the conversion of sinners, perserverance of the just, relief for souls in purgatory, conversion of myself, and my family.
They are miraculous
These three intentions (conversion of sinners, perserverance of the just, relief for souls in purgatory) was practiced by St. Anthony Mary Claret at each and every devotion he had, whether rosary, litany of the saints, holy mass, holy communions, divine office. I imitate him, and the result have been marvelous, for my soul and the souls of others.
I pray for you and your family

Please pray for mine too
Check out these pages
saintsarefamily.blogspot.com/
saints.sqpn.com/
May the merciful Jesus bless you