The most decisive event in your life is when you discover you are not your thoughts or emotions. Instead, you can be present as the awareness behind the thoughts and emotions.
When you continuously know and sense yourself as the space of consciousness rather than what appears in consciousness - sense perceptions, thoughts, emotions - then it can be said that you are enlightened... except that you wouldn't think or speak of yourself as 'enlightened', because that would instantly create another mind-based conceptual identity and so it would be the end of 'your' enlightenment.
Here is a new spiritual practice for you: don't take your thoughts too seriously.
Pay attention to the gap - the gap between two thoughts, the brief, silent space between words in a conversation, between the notes of a piano or flute, or the gap between the in-breath and the out-breath. When you pay attention to those gaps, awareness of 'something' becomes - just awareness. The formless dimension of pure consciousness arises from within you and replaces identification with form.
Most people spend their entire life imprisoned within the confines of their own thoughts. They never go beyond a narrow, mind-made, personalized sense of self that is conditioned by the past.
Observe your thoughts, don't believe them.
I am not my thoughts, emotions, sense perceptions, and experiences. I am not the content of my life. I am Life. I am the space in which all things happen. I am consciousness. I am the Now. I Am.