Well this section is about poker, not career guidance. I'm talking about when you should raise in poker. And there's a fairly straightforward, and generally correct answer (in my opinion) that is easy to see logically. You should raise when you think that your probability of winning after players have responded to your raise (by folding, calling, or raising) is greater than 1 / the number of players you think will call your raise. (well actually you should take into account the house rake). Say you're playing $1-$2 poker and you estimate a 1/4 chance of winning with 5 people (including you) calling your raise. Then there will be 3 times you lose 1 extra dollar for every 1 time you gain 4 dollars. Thus your raise is worth 25 cents. Putting it another way--not raising costs you 25 cents (long-term of course).
I think that's pretty straightforward but sometimes it seems counterintuitive. Often you should raise when you think you're beat, and that doesn't seem reasonable. But I think it's correct play. And you also have the slight chance of removing players who would have beat you on top of my analysis. Obviously there are other considerations besides the ones I've mentioned...but as a general rule can anybody dispute my analysis?