Does spiritual awakening happen one time or can it happen more than once at different points in you life?

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It’s a question of terminology. Ego has a tendency to think it is much further along on the spiritual path than it actually is. Every ego tends to think that, and mine did too.

Most people who say they’re enlightened or self-realized merely had an awakening experience. Awakening experiences can happen multiple times, many times, in fact.

Self-realization can only happen once, by definition. It’s the ultimate realization, it has no degrees or gradations. You either made it or not. Most self-realized people naturally assume they’re enlightened, and there’s nothing left to do.

Enlightenment, which is the final cessation of all dreaming activity of the mind can also only happen one time, and there’s nothing beyond it. There’s no spirituality beyond enlightenment, it renders everything obsolete except the experience of however many years that are still ahead of you.