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Is it ever beneficial to decide on a meditation topic before beginning to meditate? For example, say I want to deal with a specific problem in my life, e.g. hatred towards a specific person, cravings for food, stress about my job, etc -- something I'm aware of as an ongoing, personal problem that I want to deal with proactively rather than to merely observe it when and where it pops up.

Is it a good idea to plan and say, "ok, during this meditation session, I'm going to think about problem x," and then proceed to meditate on that subject? Or is it better to begin with breath meditation and to observe thoughts as they develop naturally.

How should one ideally structure such meditation so that it remains controlled, calm, objective, and appropriately focused?

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    "I'm going to think about problem X" is thinking, not meditating [in the buddhist / vipassana sense]. – Thiago Feb 22 '15 at 23:54
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One shouldn't practice that way if one is practicing Vipassana. The sole goal of Vipassana meditation is to be able to directly see the reality in front of you, so setting up other goals doesn't fit.

If one is having a persistent problem in meditation one can switch over to other techniques to deal with them however. For example, if a meditator keeps having angry thoughts towards people coming up in meditation practicing loving kindness meditation is an effective antidote.

Generally though if you are practicing Vipassana you should only apply these remedies as needed to overcome distractions instead of trying to work them out ahead of time.

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    Not contradicting what you said. I found it occasionally useful to state a resolution before formal practice (such as "may I see my anger/depression/whatever clearly"), then forget about it, and practice as usual. Sort of pre-conditioning of the mind. – eudoxos Feb 23 '15 at 16:51

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