This is a little long but worth reading I think.
I've been in the process of going to the monastery for about 3 years now and I am still in the process. First and foremost it is a vocation God gives you and it is not a path for everyone! I eat, sleep and dream monasticism, it's on my mind most of the day and it kills me to be in the world. Not because I have to pay bills or go to work, but because I think the world and everything in it is a waste of time and it keeps me from Christ. I want to give my life to Him by dying to the world and everything in it. For some people it's their careers or family or entertainment. To me, that all is just a big waste of time, not to put anyone down who do those things, that's just the way God made me. That's a sign that the monastic life may be your vocation, God gives it to you and it is a part of your life.
I am a convert, so I had to wait a little while to make sure this wasn't "convert zeal." Also I had to make sure I wanted to do this for the right reasons. My parents whom aren't Orthodox think I am just throwing my life away and giving up on responsibility and am taking the "easy road" out. I had to make sure my reasons were pure and not selfish, and those reasons are because I want to give all of myself, all my life and time and energy to Christ. The pain I have in my heart not being in a monastery is like being away from a loved one, a wife, gf or child. After realizing that I had to start somewhere. However, sadly I followed my own will and I picked a monastery that was closest to me, I talked to the Abbot and built a relationship with him over a time of a year. Within that year I visited the monastery three different time on what are called vocational visits. You live there with the monks as if you were a monk, working and praying all the services and you do what the Abbot says, and this is to see if you like the monastery and you figure out if it is a good fit for you. Read the book "My Elder Joseph the Hesychast" and you'll see that not all monastery's are the same and you might do better at one than you would the other. After my third visit the Abbot said he wanted me to join his monastery. But since I picked this monastery out of my own will and didn't have a spiritual father I was concerned that it wasn't the place God wanted me to be. So I asked for help from a very well respected 77 year old schema-archimandrite what I should do. He told me I was NOT to join this monastery because it was to easy there, and the monks were lazy and I might lose my salvation there. He said I needed to go someplace harder. (Which isn't easy to find in America)
After that I picked a spiritual father who is a monk in my town (thankfully God lead me to a spiritual father who is from Mt Athos). I was told to be OBEDIENT to him for 1 year to make sure I was serious about monastic life. By this point I was going crazy because I thought I would have been in a monastery 2 years earlier. Have you ever wanted to go somewhere really bad but your were told you can and had to wait a year!? It's not fun lol. Well I remand obedient even in times I didn't want to because I felt like he was keeping me back from the monastic life. But thankfully I listened, obedience is the most important thing. If I wasn't obedient to my spiritual father I would only be playing monk in some monastery somewhere with a lazy abbot and I'd be losing my salvation, and most likely I would have given up and walked out. But thinks to God and obedience my spiritual father is getting me ready for the monastic life so I will be in it for the life long run. He said he doesn't care where I go, that's up to God, he just wants to make sure I reach salvation.
I wanted to join the monastery when I was 26, I am now 28 and it feels like an eternity but it's not up to me, it's up to God. I pray and pray for Him to lead me into the monastic life. Before I prayed that he would put me in such and such a monastery. But now, after all this time, I just pray He doesn't forget me and my vocation and He puts me anywhere He sees fit for my salvation. I still don't know where I am headed and I don't know how much longer I'll be waiting, but I have faith that God knows what's best for me.
Keep in mind however, everyone's path is different. My spiritual father went to Mt Athos and prayed as a laymen to the Icon of the Theotokos "who is quick to hear" and he became a monk 3 moths later. I have a friend in St Anthony's monastery in Arizona who's spiritual father told him his salvation was at that monastery and so out of obedience he went and has been there for almost 20 years now. My journey is different also, but the key is to have faith that God, not man, will know the right time for everything in your life.
Now you might ask, "but how do I know when God is talking to me?" I asked the same thing, and what I was told is this, that's why you have a spiritual father, to help you. And God will open that path, take for example, if I wasn't obedient to that elder whom I spoke to, I'd be in the lazy monastery doing God knows what, but because I was obedient to the elder, I was obedient to God and through that event, God is leading me to where He wants me. Obedience is the most important thing, always listen to your spiritual father (unless he goes against the bible). There is a saying, it is better to disobey God than it is to disobey your spiritual father, why? Because if you disobey God, He will forgive you, but if you disobey your spiritual father, he may leave you, and then who would you have to help you? When you are obedient to your spiritual father, you are obedient to God. This counts with all things, tonsure and vocation a like.
If you are looking to be a monk, the best advice I can give you is this. Find an elder who you would trust your life with and who you want to be like because the son ends up being like that father. Be obedient to them and do everything they say. While in the process of going to the monastery (which can be years) and through the blessing of your father, live like a monk as best you can in the world. Get rid of all that stuff you don't need like all your material items (either put it in storage or if you can sell it or donate it all, that's what I did). Stop watch tv, reading the newspaper, stop reading popular books, stop going out to eat, stop going to movies, stop talking and looking at girls, get rid of your computer if you can, move into a small studio apartment. Go to all the Church services and pray more, ask your spiritual father for a daily prayer rule (you'll have plenty of time now that you don't have distractions.) Then just trust in God and eventually He'll lead you where He wants you to be, or maybe He'll let you know that the monastic life isn't your vocation. I once heard a nun say "be the best monastic you can be, and sooner or later the Church gives you more clothes)
Also keep in mind this, you may get to the monastery and years later realize it isn't your path (talk to the abbot about this because it can be the devil trying to pull you away) the monastery gives you time of discernment to figure out if it's your path or not. The ranks (depending on Russian or Greek) go like this:
Worker - You first join the monastery and live there for up to a year. You aren't considered part of the brotherhood and you still wear normal clothes. You can freely leave at anytime
Novice - You are given monastic clothes and are part of the brotherhood. This rank can last normally up to 2-3 years, it all depends on God's will. St. Seraphim of Sarov was a novice for 8 years. You don't take vows as a novice and you can leave at anytime
Rassaphore - You are given more clothes, your hair is cut and you are given a new name, however you do not take vows and still can leave at anytime. This rank can last up to 5 years or more, again it depends.
Stavrophore aka Little Schema - At this point you are considered a monk, you take vows and shouldn't leave the monastic life.
Great Schema - Highest level of monasticism, you are like a walking angel on earth. Some say you get a second guardian angel to watch over you and all your sins are forgiven.
Think of it like this, as a novice you are dating Christ, as a Rassaphore you are engaged to Christ, and as a little schema you are married to Christ and you shouldn't break that marriage because you took vows not to and God knows their judgement in Heaven, those who break their vows to Christ.
(Greeks don't have the the rank of Little Schema, great and little are the same thing in Greek monastic life, as far as I know anyway)
Also, ranks and when you get to that rank in Orthodox Monasticism is unlike the Roman Catholics. It's dependent on God, for example, Elder Ephraim went from Novice to Great Schema in less than a year, that's crazy fast! But God knows what He is doing!
Hope this helps, and please if you can, pray for me that God will lead me there soon!