THEORY AND PRACTICE: AN ODD COUPLET
I'll leave WHICH books you should be reading for another time. Today, let's look at how you should mix theory and practice. The answer varies with the individual and where you are on the poker learning curve.
For example, if you have never (or hardly ever) played, it would be silly to start playing for money without doing a LOT of reading. In the old days, people got their poker educations in the school of hard knocks, usually by losing until they figured out a thing or three.
Today, there is absolutely no excuse for risking anything more than irrelevant nickels and dimes without first doing some reading. I firmly believe that a good poker book pays for itself many times over; just how many times depends on how often you play and what kind of stakes for. (A bad book can cost you far more than the cover price, too, so that's why it's important to stick to the good ones)
You can, however, take this concept too far. I think it would be unreasonable to read 20 poker books before you ever sat down in a game for money. You just wouldn't have the context, the actual game experience, to make the books work for you. The difference between theory and practice is usually bigger in practice than it is in theory.
A SUGGESTED APPROACH
I like the "read one or two books, play a session for money, and then go back and reread those exact same books" approach for starters. In that way, you get your basic grounding, you get to take it out for a spin, and then, by rereading, you will probably pick up all kinds of things that went right over your head the first time through. "Oh, that's what he meant by that," you'll probably hear yourself thinking.
Once you get past your first couple of books and your first few sessions, it's time, if you find you really do like this game, to expand your library. You don't have to buy the 30 best books all at once; you might change your mind, or you might find that despite the best of intentions, you just don't have the knack to apply what you read. Maybe five more good ones at this point, and while I still like the "read-play-reread" approach, it's also OK, at this point, to read a new one, play, read a new one, play, and so on. Just make sure you get to the rereading before you expand your library any.
I've heard it said that rereading is the hobgoblin of little minds, that a smart person should be able to absorb a book in one reading. I think that's nonsense for the vast majority of the population. There are probably a few people running around who can get everything they are ever going to get out of a poker book on the first read, but my guess is that's less than 1% of the population.
There are some books I have read five or six times, at different intervals of my career, and each time I go back, I either see the book from a new perspective, or I get reminded of something I used to know to do but have forgotten to do.
DON'T FORGET COMPUTER SOFTWARE
I haven't addressed computer software (as McManus often does). I think software can be incredibly helpful, but my belief ? and I know reasonable people who disagree with me ?that software primarily benefits people who have reached the intermediate and advanced stages of their poker careers. It is true that software will let you simulate quite a few things, and let you grow accustomed to how certain kinds of hands tend to develop, but I think software is the tool that comes in after you've bought that second round of perhaps five books.
Finally, you need to figure out a stake level to play as you are learning. Some authors counsel the lowest possible stake, but I disagree. If you're a millionaire, it is going to be exceedingly difficult to place value on the money involved in a $1-$2 game. I think you should play for low stakes, no question, but I also believe you should play for the lowest stake in which the outcome actually matters to you.
If fifty bucks matters to you, by all means, start out playing $1-$2. If you've a six figure income, you might want to start at least at $4-$8. I'm not fond of players (especially beginning players) continuing on after they've lost 50 big bets in a session, and at $4-$8, that's $400, which should be enough to matter to someone with a six figure income.
The poker literature these days is so much better than what was available when I was first learning, it's almost spooky. Some of those "best poker books" you'll be reading about soon can turn an intelligent person into a pretty decent player in just one reading. Read and reread the right books, and you'll probably dominate the more "experienced" college frat boy who thinks poker is about male machismo by the second time you sit down.