Philosophers often say that the highest form of knowing is "I know that I don't know" - the realm of known unknowns. But mysticism teaches that there are also things we don't know that we don't know - unknown unknowns.
I've experienced this in at least two areas of wisdom: first, when I "accidentally" found myself waking up from the prison of the egoic mind; and second, when I encountered Chabad Chassidus and began learning its teachings and practices.
Until then I didn't know what I hadn't known. As for Chassidus, I was even naive enough to erroneously consider it subrational, while in truth it is suprarational. Subrational lowers us beneath reason into confusion, while suprarational lifts us above reason into wonder.
I was also fortunate enough to meet Chabad Chassidus, which many sages, both insiders and outsiders, regard as the most sophisticated form of Jewish suprarationality - also known as mysticism or nonduality.
These two precious experiences taught me the importance of humility as the single most essential character trait for turning unknown unknowns into known unknowns, and eventually into known knowns.
My life so far has also shown me at least two very different pathways to humility. One is through conscious effort - humility can't be learned conceptually (that may even make you arrogant), but through spiritual practices such as meditation and prayer. The other is by hitting rock bottom and having your ego shattered - in the most extreme case, losing everything you thought you were.
This is exactly what happened to me and forced me to become (more) humble, as it made me realize so clearly that what I used to think I was was nothing but a collection of ego's illusions. This must be the reason why it is often said that the broken heart is the best preparation for studying Chassidus.
These discoveries were not just personal insights; they transformed my whole direction in life. I even decided to leave academia and become a Jewish life coach, then a Jewish "gardener of the soul", to help others liberate themselves from this prison through the teachings of Chabad Chassidus.
It didn't take me long, however, to face an enormous challenge: trying to convince those who still don't seem to know what they don't know not only to study but even to try for free what I have to offer.
Even after struggling for several years, I haven't found any magical formula for this. I've asked a number of like-minded people, especially teachers of Jewish life wisdom, but none of them has been able to give me such a formula, either.
Then I suddenly realized that this very effort stemmed from the ego - or the spiritual ego, to be more precise - though it may not appear so at first glance.
This has been a very humbling realization, showing me again and again that even the best life coach or teacher cannot compete with a most powerful contender called life itself and that everyone and everything have their own timing.
This realization, which naturally came in perfect timing, ;-) is also very encouraging. I don't have to worry too much when what I want to achieve is not achieved so easily. Perhaps the greatest unknown unknown is the timing of life itself - hidden from us, yet unfolding with perfect precision!