One of the many aspects of Rudolf Steiner that annoy me (!) is when he harps-on about 'initiation' to a grossly excessive degree. I don't think this is helpful, and is indeed misleading - as is the related concept of 'enlightenment'.
What both of these seem to hinge-upon is the idea of a once-and-for-all breakthrough - whereby a person reaches a level of insight and understanding and from that point Is Transformed. Things are never the same again. His life is henceforward raised to a new and higher plane.
The false and misleading aspects of such ideas is that they are assumed to be permanent. The person is initiated, is enlightened - and that's that. The heavy-lifting has-been-done, from now onward he is a Different Person.
This may well have been possible and happened in the past and in other places; but I don't see anything to suggest it is possible or actually happens here-and-now.
On the contrary; those who claim (whether explicitly or implicitly) experiences of initiation and enlightenment are (it turns-out!) just like everybody else; they are not qualitatively raised, they operate in a not-significantly-different way.
We may seek special holiness, we may seek an initiate, we may seek an enlightened man in this modern world - but we will not find any such. Or, when something like this is found, it will emerge that the person has 'always been like that': in other words, innate constitution, not experiential initiation, was the cause of the difference.
I regard experiences of initiation and enlightenment as experiences like any other: that is, we need to learn-from them.
But we should not expect such experiences to 'transform' us; should not expect a life-long change in our mortal selves.
We should Not expect that such experiences will re-shape our minds and memories, change our thinking and feeling, solve our problems, raise us beyond former concerns. This will not happen - but even if it did happen, it would all be washed-away at death, or before death - by degeneration or disease.
The value of initiation and enlightenment experiences is like the value of any other experience in this, our mortal life; which is that we hope to learn from experiences such that we may benefit in our eternal (Heavenly, resurrected) life. Initiation or enlightenment may be more intense experiences than most; but they are 'just' mortal experiences - therefore transitory...
Except that 'just' experiences are potentially of ultimate, permanent and vital importance; they are, indeed, why you and I are still-alive now; rather than just incarnating and dying straight away whether in the womb or soon after birth (as have most people in human history).
In sum: initiation is something we need actively to learn-from; it is not something we are passively transformed-by.
As such; initiation/ enlightenment is a part of the evolutionary development of human consciousness towards becoming more a matter of active choice; and where we are free to learn or not; free to acknowledge reality or to deny it.
Free to choose to see-through the false world and acknowledge the vastly larger scope of divine truth; or free to choose to live-within almost any manufactured virtuality - for example by making the choice passively to surrender to external control by external (media) inputs...