On Advaita Vedanta: Knowing that you will lose, fight as if you have already won

The following excerpt is from a samvaad (dialogue) session with Acharya Prashant.

निद्राया लोकवार्तायाः शब्दादेरात्मविस्मृतेः ।
क्वचिन्नावसरं दत्त्वा चिन्तयात्मानमात्मनि ॥

nidrāyā lokavārtāyāḥ śabdāderātmavismṛteḥ
kvacinnāvasaraṃ dattvā cintayātmānamātmani

Without granting for a moment even a toe-hold for sleep, gossip, verbal exchanges, etc., and self-forgetfulness, meditate on the Self in the self.

~ Adhyatma Upanishad, Verse 5

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Questioner (Q): I am not sure if I understand what is meant by meditating on the Self in the self. The first Self has a capital ‘S’, and the second self has a small ‘s’. As I understand it, the little cannot know of anything beyond its littleness. Me being what I am, even the infinite remains an image. Every method or direction taken seems to be within the same little dimension. It’s almost as if the ‘I’ wants to be the enjoyer of even its own dissolution. What is being advised here in this verse, and how should it be applied?

Acharya Prashant (AP): The verse says, “Meditate on the Self in the self.” For the sake of clarity, I will take the big Self as Truth; otherwise, there is no way I can differentiate between the two in a spoken way. So, meditate on the Truth in the self. Now the self is the small self, the ego. Meditate on the Truth in the ego. And the contention is, that the ego cannot know anything beyond its limited boundaries, so how will it meditate on the Truth or the great Self?

That is exactly the intention of this exercise: give the ego a task beyond its capacity. What will happen? The ego is a machine. It can only do what it is conditioned to do, designed to do. When you start pushing a machine to do something that it is not designed to do, what happens to the machine? It breaks down. That’s the purpose of all meditation. That’s the method of all spirituality: bring the ego to a point where it attempts something that it just cannot do…