Works that might be good to read repeatedly.

Besides, of course, the Gospels, the Psalms, and a synaxarion. Don't choose all of them, of course, choose a few and know them. Reading all of them will make you crazy or something. The point here is to stick to the basics rather than reading 100 different books, so offering 100 different books would be counterproductive.

• Indication of the Way into the Kingdom of Heaven. Perhaps not this edition, I'm sure there's a nicely typeset one somewhere. Could probably be split over a week or two.
• St Augustine's Confessions. A bit long for this purpose, sure. But you would greatly profit each time you read it.
• Orthodox Funeral Service. Nice and short, possible to read over in full every day.
• The Rule of St Benedict. Not terribly different from Eastern monastic rules in substance, as it borrowed from them. There's a tradition of reading from it every day, so why not? It isn't too advanced.
• The Rainbow Series Catechism. Everybody could use more readings from the catechism. Very basic stuff. I'm not going to pretend Fr. Tom is on the same level as St Augustine, but going over the basics is very good.
• The Forgotten Medicine: The Mystery of Repentance by Fr Seraphim Aleksiev is a very good book on preparing for confession. Nice and short. It is perhaps a bit too small to use continuously for this purpose, but it is very good and you could use it every time you prepare for confession (break it up over a couple days). This might end up being the most valuable book in the list, as it will help you make a good confession.
• The Way of the Ascetics by Tito Colliander. Very good, very practical, might be a bit much for some people. A modern classic. Not sure how much we can trust it, though, given that the Finns are on the New Paschalion.
• EDITED TO ADD: Beginning to Pray by Metropolitan Anthony. A very good book. I cannot believe I forgot to put this on because it is one of my favorites.

I considered a few other additions, like St John Cassian's Collationes, but that gets rather advanced (or obscure) at points and it is rather long. Reading a little bit every day for several years in a row over dinner, as the name suggests, would certainly be salutary, it's just too much for the purpose of this list.

Anyway, the point of this list is to provide some of the "basics" so you're not trying to make a meal out of popcorn and getting burnt out on web-logs, radio shows, and poorly-written convert books pushed out by Conciliar Press. These should perhaps only be invested in after reading the daily scripture readings and the synaxarion is not enough for you (possible exception: the confession book, as it is quite practical, and reading over the funeral service should be okay since it is an actual service of the church and you should be familiar with it (don't want the first time you hear it to be when you're dead)).

I'm sure people who know better than me and who have decent, valid opinions about your spiritual life might have different, better suggestions for what you should read. There is much more to the spiritual life, of course, than reading a couple prayers in the morning and at night, reading the day's scripture readings (you can have them e-mailed to you - you have no excuse), and reading a bit from a book you've read several times before, but this is a much more sane place to start from. Your real activity is what goes on in between, that is where the hard asceticism, real Orthodoxy (rather, Christianity) begins. Humility, love, all that nonsense. You'd learn more from reading Tozer than you would from the chattering of web-logs, and I don't recommend Tozer because he's a Protestant. I don't recommend chattering, either. HTH. HAND. Let me know of any other very good books that might serve this purpose, because opinions may vary and I'm at the point where I can probably afford to read at least one more good book in my lifetime. Or, heck, good books that don't serve this purpose (if you're doing that, though, make sure it's something I probably haven't read).