I have been having a problem losing money in sessions where I should have got up long time ago. There's only 1/3 NL available where I am, unless I want to travel 1 hour or so. Anyways, there's this promo thing that a local casino has: 1 hr. of live play = 1 Raffle ticket. Every friday starting at 7pm, they draw a ticket every hour. 7pm,8pm = $75 9pm, 10pm = $100, 11pm, midnight = $150 and 1AM = $175 and 2AM = $200. Thing is I get caught up in getting hours, that I end up busting out.

Example #1:

Bought in for $100. 3.5 hours later, built it to $440. Get involved with set over set and my stack goes down to about $200. Should just leave, but continue anyways, and end up losing to a suck-out.

Example #2: Bought in for $60 (I occasionally do this just to see how the table is playing) Ended up busting out, but gained some valuable info. Re-Loaded for $150. Ran it up to $570. Getting it in pre-flop AA vs. 99 and lose, he has me covered.

Example #3: Bought in for $100. Ran it up to $310. I feel that I should just leave, so I announce that I will play till UTG (2 hands away). Very NEXT HAND, I pick up KK. Get it in on the turn KK vs. 10's and he spikes the river.

I am getting a little frustrated here. I feel that maybe I run it up 3x buy in that I should leave. I am not sure, but something I am doing is wrong and needs to be corrected. The majority of the time, my sessions are really good, it's just the time and cards that kill me. Is there a good rule of thumb dealing with this issue? I get this feeling that maybe I should get up, but for some reason I ignore it and just continue playing. It's also hard to to play for hours.
If you have been winning for a while, and doing your best to stay out of trouble, wouldn't a cooler be overdue? I would rather bust out with 1 buy-in and reloading instead of running it up to $500. Thoughts? Advice?? HELP?!?

No.

You seem to feel that if you have been doing well, you should leave, because you are due to do poorly. This is not how it works. Poker is one long session.

You may be getting bored, tired, anxious, etc, these are all good reasons to leave. Being due for a downswing is not one of them.

But what does any of this have to do with bankroll management?

Also, the only reason you should "do your best to stay out of trouble" is if your image is somewhat out of line. But if you've been winning for a while you're image is usually great and you should do your best to stay "in trouble" (not trouble obv, but get yourself into more spots where you can be aggressive).

You should be able to play longer sessions after winning and shorter sessions after losing, even though people tend to do the opposite. You should quit if you feel uncomfortable playing after winning big. But you have to understand that it's all in your head and it's costing you money. You are equally likely to run into that cooler the first hand of your next session so quitting for that reason doesn't really save you from anything. Just try to make the best decisions each hand and try not to think about what you won or lost.

If you are playing underrolled you are going to be uncomfortable playing long sessions so make sure you have at least a 20 buy-in bankroll for live poker.

Read "The Poker Mindset". Everything that you're feeling is discussed in the book.

Short answer is: Downswings do not exist. You are not "due" for a change in luck. Every hand is a random event. It is human tendency to try to find a pattern, even in random events.

You got your money in good. The ONLY thing the three examples have in common is getting sucked out on by people who had you covered. If you are playing well, why stop? However, if you must stop, may I suggest cashing out, grabbing a meal, and getting back in a game with a standard buy-in?

I don't know, I just feel that when I used to play online, I would play till about 3x my buy in, then leave for another table. Maybe it is just me though. So when you sit down, when is it enough then? When do you guys decide it's time to go home?