Thought experiment: You wake up tomorrow, and you find that you have all of the qualities that normally disqualify us from having a self (see the Anattalakkhana sutta below). Do you have total confidence that you have a self? Why or why not?

Thus have I heard. On one occasion the Blessed One was dwelling at Baraṇasi in the Deer Park at Isipatana. There the Blessed One addressed the bhikkhus of the group of five thus: “Bhikkhus!”

“Venerable sir!” those bhikkhus replied. The Blessed One said this:

“Bhikkhus, form is nonself. For if, bhikkhus, form were self, this form would not lead to affliction, and it would be possible to have it of form: ‘Let my form be thus; let my form not be thus.’ But because form is nonself, form leads to affliction, and it is not possible to have it of form: ‘Let my form be thus; let my form not be thus.’

“Feeling is nonself…. … Perception is nonself…. Volitional formations are nonself…. Consciousness is nonself. For if, bhikkhus, consciousness were self, this consciousness would not lead to affliction, and it would be possible to have it of consciousness: ‘Let my consciousness be thus; let my consciousness not be thus.’ But because consciousness is nonself, consciousness leads to affliction, and it is not possible to have it of consciousness: ‘Let my consciousness be thus; let my consciousness not be thus.’

“What do you think, bhikkhus, is form permanent or impermanent?”—“Impermanent, venerable sir.”—“Is what is impermanent suffering or happiness?”—“Suffering, venerable sir.”—“Is what is impermanent, suffering, and subject to change fit to be regarded thus: ‘This is mine, this I am, this is my self’?”—“No, venerable sir.”

“Is feeling permanent or impermanent?… Is perception permanent or impermanent?… Are volitional formations permanent or impermanent?… Is consciousness permanent or impermanent?”—“Impermanent, venerable sir.”—“Is what is impermanent suffering or happiness?”— “Suffering, venerable sir.”—“Is what is impermanent, suffering, and subject to change fit to be regarded thus: ‘This is mine, this I am, this is my self’?”—“No, venerable sir.”

“Therefore, bhikkhus, any kind of form whatsoever, whether past, future, or present, internal or external, gross or subtle, inferior or superior, far or near, all form should be seen as it really is with correct wisdom thus: ‘This is not mine, this I am not, this is not my self.’

“Any kind of feeling whatsoever … Any kind of perception whatsoever … Any kind of volitional formations whatsoever … Any kind of consciousness whatsoever, whether past, future, or present, internal or external, gross or subtle, inferior or superior, far or near, all consciousness should be seen as it really is with correct wisdom thus: ‘This is not mine, this I am not, this is not my self.’

“Seeing thus, bhikkhus, the instructed noble disciple experiences revulsion towards form, revulsion towards feeling, revulsion towards perception, revulsion towards volitional formations, revulsion towards consciousness. Experiencing revulsion, he becomes dispassionate. Through dispassion his mind is liberated. When it is liberated there comes the knowledge: ‘It’s liberated.’ He understands: ‘Destroyed is birth, the holy life has been lived, what had to be done has been done, there is no more for this state of being.’”

That is what the Blessed One said. Elated, those bhikkhus delighted in the Blessed One’s statement. And while this discourse was being spoken, the minds of the bhikkhus of the group of five were liberated from the taints by nonclinging.

-Anattalakkhana sutta SN 22.59

Yes… this is the dilemma.
It is impossible to have doubt about “Whether you attained” if you really did truly attain.
On the other hand, if you are on your first “experience of thinking you are enlightened”, odds are it is upkilesa (false enlightenment).
So you have a choice…
You can be one who is absolutely sure he is enlightened but probably not.
You can be skeptical that you actually attained our of fear of being a “difficult to talk to” falsely enlightened one… this skepticism and fear disqualifies you right on the spot.

The solution is to have a good teacher looking over you.
If he is able to convince you you are not enlightened, then you are definitely not enlightened.
If you meet the checklist from your teacher and don’t get offended, then one should keep practicing to attain higher paths and fruits. Because upkilesa is part of the path progression, you have nothing to lose from the experience as long as you continue to practice.
Unfortunately, part of the checklist is , “nothing will cause your concentration to fall down”. Because of that, “not practicing”, or “being made busy” is part of the checklist.

The best advice… give up lay life and ordain.

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Thank you, Venerable. If I ever think I’m an arahant, I will follow your advice!

On the other hand, with this thought experiment: What about if one wakes up with a self, and immortality? If one woke up immortal and in full control of their body and mind (things that disqualify us from declaring a self normally, as per the Anattalakkhana sutta), does one declare: “I have a self!” ?

I think that Devas and surely Brahmas might think they have indeed a self.
Ignorance would prevent anyone including normal earthly people from knowing.

They would need to look at their many past lives in order to see this as suffering…
However, even so, they might conclude they have reached the end.

It depends.

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Thank you, Venerable. I agree.

My thinking is that it would always lead to a vicious infinite regression. Even a being a hundred times smarter than a human could still be wrong, and one day simply die, or lose their power, or find out that only beings a hundred times smarter than them can really know they have a self, or that the apparent self is part of an illusion, and so on, ad infinitum.

In other words, one could never safely say they have a self.