By failing to prepare, you are preparing to fail.  — Ben Franklin

Before I became a poker pro, I was a tournament chess player.  In chess, you would never imagine making a move without considering how your opponent is going to reply to that move, and how YOU are going to reply to that reply.  So why would you do that in poker?

Tricky mate in 3 — hover over for answer

Do you often catch yourself making a bet, getting raised by your opponent, and then saying, “geepers…what do I do now”?  If so, you need to update your vocabulary; nobody says “geepers” anymore.  But after that, you need to accept that you have a long way to go in your poker education.

I guess this is why so many strong chess players excel at poker.  Because thinking ahead comes naturally to them.  In a given chess position, you might sometimes be considering 5 different moves (we call these “candidate moves”).  To each of these, your opponent might have 5 or more serious replies that have to be considered.  To these, you might have 5 possible replies.  You can see how it grows exponentially.

In poker, we’re fortunate to only have three possibilities – bet, call, fold – to worry about.  Obviously, bet sizing can complicate things a little, but the tree of possibilities doesn’t grow nearly as fast as chess.  In fact, folding could be compared to checkmate — it ends the hand, so we don’t have to worry about any “moves” beyond that.

Playing with a plan means having a strategy for the entire hand.  You can verbalize these in your head if it helps.  Some examples might be:

• I’m not prepared to play this medium strength hand for all my chips.  But it could win a medium-sized pot.  And I do need to bet or he’s going to take the pot away from me.  I’m going to try to control the pot with smallish bets, hoping to keep some hands I can beat in his calling range.  If I get raised, I’m going to fold.
• I have a big draw.  I like my hand, but if all the chips go in, I want to make the last bet.  I’m going to bet about ½ the pot.  This way, if he raises, I’ll go all-in, and will still have enough chips to have some fold equity.
• I think I have the implied odds to call this bet with my straight draw.  If I miss my draw, I’m going to fold on the turn if he bets a sizeable amount again.  If a flush card comes on the turn and he checks to me, I’ll bluff at it.  Otherwise, I’ll check behind him and take the free card.

That’s the kind of thinking you should be doing on every hand.  Notice how I made a plan for the entire hand, as soon as the flop came out.  Sometimes, you can even start planning pre-flop.  If you aren’t planning ahead, this is the single most important thing you should be working on!

I remember a time back in middle school when I dreamt of calling up a certain girl, Amy, and asking her on a “date” (in those days that meant my mom driving us to the mall or something – exciting stuff).  Before cell phones this involved calling her house, getting past the initial line of defense (the parents), a little small talk, and then the dreaded moment of the actual request.  I say “dreaded” because, for those of you that have been there, the worst case scenario is always foremost in your mind at that moment – she laughs at you, tells everyone at school, and you’re forced to move to Australia to escape from the shame. 

For months I dreamed about making this phone call, but never got the guts to do it, until one day my best friend, Adam, who was twice as big as me, got tired of hearing me talk about it and told me that I would pick up the phone and call her right then or he would kick my ass.  He was dead serious.  So I called her, my heart racing.  I made the ask; she agreed (although didn’t sound entirely enthusiastic about it).  The “date” was uneventful – as I recall we wandered around the mall for a couple hours that Saturday evening, and that was the end of it. 

From middle school drama to the poker table, making a big bluff feels a lot like asking a girl on a date.  The worst case scenarios swirl in your head.  I’ll get called.  They’ll laugh.  They’ll tell everybody else what a terrible player I am.  I’ll be the laughingstock of the entire poker community and Donk Illustrated will run the story.

Of course, rarely does that actually happen (occasionally it does — keep reading).  Nor do prospective girlfriends generally mock us when we ask them out on a date.  What usually happens is quite the opposite – even if the end result is not what we hoped her, we feel brave, powerful, able to conquer the world, just because we had the guts to do it. 

Unfortunately for most of us, we don’t have Adam threatening to kick our ass when we’re at the poker table.  We have to muster up the courage to make these big bluffs when they feel right, knowing that it’s the only way we’ll get more comfortable with the idea in the long run.

About ten years ago, I remember the biggest bluff of my life to that point.  The pot was big enough that it was going to require an all-in, $350, a lot of money at the time.  The actual cards held aren’t that important.  The point is that I missed my draw and had absolutely nothing on the river.  But several factors lead to me to believe that a bluff, a big bluff, would be successful in the situation.  I just had to get the nerve to make the play.  Surely, there was the possibility I would get called, and ridiculed by the other players.   

The amazing thing is, that’s exactly what happened.  He had made an incidental wheel on the river and I got called right away.  He slammed the cards down and basked in his glorious superiority as he raked in the pot.  The room erupted with a collective “WTF?” when they saw my cards; a few players ever stood up as they pondered $350 wasted on such trash.  $350 was a nice TV, six months of auto insurance, or 443 bean burritos at Taco Bell. 

The point is, oddly, I continue to relish this wonderful bluff, even if the end result was bad.  You know why?  Not for the “rightness” of the bluff, but because I had the balls to do it, when no one else would have.  I drove home that night penniless, yet I felt like a bigger champion than I had ever been before.  I was on top of the world for days afterwards, and my poker game has benefitted immensely for this reason:  I have never again questioned whether I have the guts to make a particular bluff. 

The lesson is this: only when you get outside of your comfort zone do you have a chance to improve yourself as a poker player (and, as it turns out, as a person as well).