As you observe yourself, you will naturally find the task rather daunting. Before you know it, you're already in thinker mode again, thinking things like "this is impossible" or "I can't possibly succeed at this".
Being able to constantly remain in observer mode takes practice, and usually when you start doing this, you would travel back and forth between thinking and observing. Thats great, it's the natural course of things.
As Tolle puts it "The moment you realize you are not present [in thinker mode], you are present [in observer mode]". Paraphrased, we can say, the more you 'realize' you aren't observing, the better. So just keep on realizing and realizing.
When I started observing myself, one key that proved really useful was plain acceptance - to accept that my state of mind was simply as it was. To be 'impartial' about it. Without judgment.
So doesn't that kill the purpose you may wonder? Well consider this. Say you are trying to observe your mind but you find your mind is bloated with thoughts of all kinds. Being irritated about it would really get you nowhere - in fact it would add more thoughts to the already bloated mind. For example, if you're observing, and you see the bloated mind, and think, "what a bloated mind I have", then you have just introduced a new thought through the 'back door', and you have returned to thinker mode.
To conclude, when you are observing yourself, the best is to accept, let go, and realize when you have fallen back into thinker mode. Trust me, when you have this positive mental attitude towards your practice, its effectiveness will increase significantly.
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