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I was introduced to meditation many years ago through a short course and a book. Essentially I tried the mindful breathing meditation. I kept at it for a couple of years after which different circumstances resulted in me forgetting all about the meditation. Maybe it was due to my not noticing any discernable effects. But now I am trying to pick it up again. Currently I am following the book "Wherever you go, there you are" by Jon Kabat-Zinn. However, I have a few questions:

1) Everywhere I keep reading stuff of the kind "Observe your thoughts without judgment". What does that really translate into in practice? How do you observe without judging? I mean, if you get sad thoughts, you get sad too. Thats why they are called sad thoughts. I never understood how to actually follow this advise.

2) Again, I keep reading "Observe this particular moment", "be in this moment" etc. What other moment are we normally in? What special tasks do we need to undertake to be in this moment? I mean, as long as you don't daydream about the future or wallow in the past, you're in the moment, right? This is something I again fail to comprehend clearly.

3)"Observe the breath". Do I feel the breath? Or note that I am breathing? Or count the breath? It just feels like more thinking.

4) How do you ever "know" that your meditation is working right? Or how do you even know your practice is headed in the right direction? I got tired after 2 years of it and nothing in return. Okay maybe I did it wrong, but how would it have been had I done it right? Is there a time frame within which you can expect some sort of result if you do it right?

5) There seem to be many kinds of meditations, each with its own set of fanboys. Are these different types simply different paths to the same goal? Or are they meant for different goals? Moreover, are their learning curves different? How do I know what is right for me? Does this analysis even matter at all or am I just complicating things needlessly? My aim is to be able to concentrate and think clearly without getting overwhelmed.

Clearly I am doing it wrong, for I feel no difference. The meditation books are full of hollow cliches and deep-sounding mumbo-jumbo which isn't helping at a practical level.

Just to put the facts out: I am a mathematics grad student deeply interested in algebra and computing, and a Hindu by birth. I find religion and mythology fascinating from a historical perspective though am not spiritual or too keen on the underlying philosophies. I have also faced recurrent issues with OCD and clinical depression and insomnia, but medication, therapy and most importantly, time, have made things better. I am, and have always been curious about meditation, but have not been too successful or consistent with it. I am not opposed to religious imagery or artefacts in the meditation practice, though I'd prefer it to be as objective as possible.

Any advise/suggestions would be great. Thanks!

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I think you did a really good job of breaking down your doubts into individual points.

1) Everywhere I keep reading stuff of the kind "Observe your thoughts without judgment". What does that really translate into in practice? How do you observe without judging? I mean, if you get sad thoughts, you get sad too. Thats why they are called sad thoughts. I never understood how to actually follow this advise.

In Buddhism we separate the initial thought from the emotion which we apply to it. The thought isn't a bad thing until we start to apply our ideas to it, we call it sadness and we want to get away from it, we start to think of how good life would be if we could avoid sadness. It is only after we apply our ideas that this thought becomes bad.

As humans it's very hard not to see sadness as a bad thing, we cannot immediately control our reactions to avoid labeling sadness as bad. When beginning with meditation we practice allowing the sadness to be present in the mind and not try to get rid of it.

2) Again, I keep reading "Observe this particular moment", "be in this moment" etc. What other moment are we normally in? What special tasks do we need to undertake to be in this moment? I mean, as long as you don't daydream about the future or wallow in the past, you're in the moment, right? This is something I again fail to comprehend clearly.

You're right that thoughts about the future and past are not part of the practice but sometimes we get distracted without going to the future or past. For example if we see a bar of chocolate we have sight in the present moment; then we might get distracted and start to think "Where are these chocolates made?" or "How many calories are in the chocolate?". These thoughts aren't about the past or future but we are now lost in thinking and we are not in the present moment.

As an extra note, if you change from seeing chocolate to thinking "How many calories are in the chocolate?" then the present moment changed from sight to this thought about calories, you could remain in the present by observing the thought but observing a thought is different from just thinking it.

3)"Observe the breath". Do I feel the breath? Or note that I am breathing? Or count the breath? It just feels like more thinking.

Some of the suggested techniques do involve more thinking than others. One aim of meditation is to reduce the amount we get caught up in thoughts. Just feeling the breath involves less thought than counting the breath, in that way feeling is better than counting. You know from meditating that it is difficult to stay aware of the breathing, some people are so stressed that they have to count their breath, it is too difficult to only feel the breath. For these people counting is a good idea until they are calm enough to just feel the breath.

4) How do you ever "know" that your meditation is working right? Or how do you even know your practice is headed in the right direction? I got tired after 2 years of it and nothing in return. Okay maybe I did it wrong, but how would it have been had I done it right? Is there a time frame within which you can expect some sort of result if you do it right?

If you are doing meditation correctly then you should notice an improvement in your reactions to things. Maybe before when a person shouts at you then you get angry and shout at them, after meditating for months when a person shouts at you then you notice your anger and you don't immediately think that you have to shout.

5) There seem to be many kinds of meditations, each with its own set of fanboys. Are these different types simply different paths to the same goal? Or are they meant for different goals? Moreover, are their learning curves different? How do I know what is right for me? Does this analysis even matter at all or am I just complicating things needlessly? My aim is to be able to concentrate and think clearly without getting overwhelmed.

Largely the different meditations are different paths to the same goal. Any meditation which involves observing an object (the breath, the body, a coloured disc, a flame) the object is unimportant because eventually in deep meditation you will not be able to see/feel the object. Because breath meditation is so popular there are many many variations of how to watch the breath but you just need to find the one that works best for you. The only way to know what is right for you is to experiment with different types, a month should be long enough to know if you like it. None are perfect so just find one that is good enough for you.

Last bit of advice: Meditation involves letting go of what is happening. If you are trying very hard to follow your breath then you are preventing yourself from being relaxed. Ideally you should not require effort to remain aware of the breathing, you just won't get distracted by other things because you are calm.

I hope that some of these answers help you to develop a fruitful practice.

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1) Everywhere I keep reading stuff of the kind "Observe your thoughts without judgment". What does that really translate into in practice? How do you observe without judging? I mean, if you get sad thoughts, you get sad too. Thats why they are called sad thoughts. I never understood how to actually follow this advise.

When any thoughts arise there is a feeling accompanying them. Thei can be pleasant (happy throughs) or unpleasant (anger, sad, fear) or neutral.

On cognizing a mind-object with the mind,
one investigates the mind-object that the basis of mental joy,
one investigates the mind-object that is the basis of mental pain,
one investigates the mind-object that is the basis of equanimity.

Dhātu Vibhaṅga Sutta

If they are pleasant this leads to craving / covetousness and if they are unpleasant they lead to aversion, which you should avoid.

 a monk dwells exertive, clearly aware, mindful,
 observing the mind in the mind,
 removing covetousness and displeasure in regard to the world

Mahā Sati’patthāna Sutta

Non judgemental way is not to have any attachment or aversion to the pleasant, unpleasant and knowing the nature of neutral sensations arising from the thoughts.

the latent tendency to lust reinforced by being attached to pleasant feelings;
the latent tendency to aversion reinforced by rejecting painful feelings;
the latent tendency to ignorance reinforced by ignoring neutral feelings.

Pahāna Sutta

pleasant feeling is pleasant when it persists, painful when it changes;
painful feeling is painful when it persists,   pleasant when it changes;
neutral feeling is pleasant when there is knowledge of it, 
    painful when there is no knowledge of it

Cūla Vedalla Sutta

If you do become judgemental this leads to attachment or aversion which should be avoided.

Taking the painful as pleasurable

Vipallasa Sutta

when the latent tendency of lust takes over, we are lustful;
when the latent tendency of hate takes over, we are hateful;
when the latent tendency of ignorance takes over, we are delusive

Pahāna Sutta

If you are non judgemental where by maintaining complete equanimity and towards any sensation knowing their impermanence, you will not be overcome by latent tendencies.

Also it is the sensations as there are many Suttas which are assertive about it:

all mental states flow along with feeling - Vedanā samosaranā sabbe dhammā

Kiṁ Mūlaka Sutta

and

Ānanda, two kinds of feeling, relatively speaking [by way of instructing], have been spoken of by me.
Three kinds of feeling, too, relatively speaking, have been spoken of by me.
Five kinds of feeling, too, relatively speaking, have been spoken of by me.
Six kinds of feeling, too, relatively speaking, have been spoken of by me.
Eighteen kinds of feeling, too, relatively speaking, have been spoken of by me.
Thirty-six kinds of feeling, too, relatively speaking, have been spoken of by me. 
One hundred and eight kinds of feeling, too, relatively speaking, have been spoken of by me.
Thus, Ānanda, has the Dharma been shown by me in a relative manner.

Pañcak’aṇga Sutta

Also see this answer for a more generic description and more references.

2) Again, I keep reading "Observe this particular moment", "be in this moment" etc. What other moment are we normally in? What special tasks do we need to undertake to be in this moment? I mean, as long as you don't daydream about the future or wallow in the past, you're in the moment, right? This is something I again fail to comprehend clearly.

Your thoughts tend to roll and be preoccupied in the past and future most of the time than the present and many of these thoughts are either pleasant or unpleasant leading to craving and aversion. There are times you mind is in the present also dwelling in pleasant or unpleasant thoughts which also should be avoided.

Thus, there are thirty-six such preoccupations with craving regarding the past, 
preoccupations with craving regarding the future, 
and preoccupation with craving regarding the present, 
making 108 preoccupations with craving

Tanhā Jālinī Sutta

Being is the present means to be aware of the sensations resulting from thoughts and mental activity observing their arising and passing nature.

All sensations are unsatisfactory. This is the key point which links to the 1st Noble Truth in the 4 Noble Truths and the main link (among the 12 links) which you can break the vicious cycle of Dependent Arising. In this specific case every thought that arises in your mind you should try to understand the working of Dependent Arising and 4 Noble Truths at the experiential level. This is not a logical thinking exercise just keep looking at the arising and passing of the sensations due to your thinking and metal activity.

3)"Observe the breath". Do I feel the breath? Or note that I am breathing? Or count the breath? It just feels like more thinking.

You should not count, visualise or verbalise as this leads to creating verbal fabrications.

Breath meditation at early stages involve Vitarka and Vicara which is like thinking and pondering.

4) How do you ever "know" that your meditation is working right? Or how do you even know your practice is headed in the right direction? I got tired after 2 years of it and nothing in return. Okay maybe I did it wrong, but how would it have been had I done it right? Is there a time frame within which you can expect some sort of result if you do it right?

There are many measures of progress. See these answers one answer on progress, another answer on progress. Also if you are too concerned with the progress this will lead to excessive efforts and also resentment which hinder progress.

5) There seem to be many kinds of meditations, each with its own set of fanboys. Are these different types simply different paths to the same goal? Or are they meant for different goals? Moreover, are their learning curves different? How do I know what is right for me? Does this analysis even matter at all or am I just complicating things needlessly? My aim is to be able to concentrate and think clearly without getting overwhelmed.

Many meditation have different goals. E.g. Samatha does not deal with ultimate peace but limited to mastery over the mind. There are many types or Kammaṭṭhāna. Vipassanā is what aims at ultimate peace and happiness. This also has been thought in different ways with some techniques being effective than the other overall. Also a technique that works for one may not be the best suited for another. You have to figure what works. If you have not already tried it have a look at:

which follows the tradition of Ledi Sayadaw, Saya Thetgyi, Saya Gyi U Ba Khin, Webu Sayadaw.

In addition there are lineages and tradition which you might be able to find from:

Notable other traditions are:

Also do not change your practice too often. Give any type of meditation and ernest and fair trial for about 6 months to 1 year and if it does not work more on. If you see that one technique is working and you are making continuous progress then stick to it without changing.

Also validate if the theory and practice is congruent and the practice validates the theory.

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You have asked your question systematically. However, as a practitioner, in conclusion, you do not find the right way. "Observe your thoughts without judgment"... "Observe the breath"... etc., this so-called techniques however does the one advocated it really understand, try and prove? For example, counting the breathe, many people misunderstand it by counting from 1, 2... 100 and on, like counting sheep for sleep. No. Counting breathe (隨息) it should count like: 1, 2... 10; then 10, 9... 1. And it's not like counting breath-in: 1, breath-out: 2... No. It should be counting breath-in, hold-on, mindless/mindfulness, concentrate on your nose-tip, until release: 1; repeat: 2. I shouldn't say too much in breathe technique since personally I'm not so interested in this at the moment. The other called "observe your thoughts" etc will take too much time to explain. But as what you reported in your question, those are wrong.

One less complex method you may try, chanting "Om, Ah, Hum". Either just concentrate to listen to the sound you chant, or with thought on: "Om" is vibrating in your head, "Ah" is vibrating in your heart, "Hum" is vibrating in your abdomen. Mantra chanting maybe is an easy way to follow if you don't have a real teacher and you can't read the Dharma text. There are many Buddhist Sutras and techniques in Classical Chinese however I doubt if these are translated into English or any language for you; if the translation is correct.

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