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…