Hey, Stephen, welcome to the forum!
Leonard is very ironic guy, as well as very deep and multi-layered: a lot of things that he says are tinged with self-deprecation and excessive humility, and thus one cannot simply take a random interview quote at face value, without considering the context and/or subtext of the discussion, as well as any number of possible things that he may have meant in any given utterance. It is also relevant to consider the difference between an interview and something that Cohen wrote in a poem, book, or song: in the former, he might make more off-the-cuff remarks compared to something he was writing (well, I suspect that Leonard considered his words carefully, even in interviews, but there would not have been the same level of meticulous scrutiny and revisions that he gave to his written words).
The quote you mentioned, I assume, is
"How can I begin anything new with all of yesterday in me", from
Beautiful Losers, which was written in the mid-1960s (and which was fictional, more or less). I do not know what year Cohen made the remark about failing at the venture (of zen? Of Buddhism? Of being a full-time monk at Mt. Baldy?...) , but I suspect it was later than the 1960s (more like 2000s maybe?). I vaguely recall him saying something to that effect, but I also recall, as alluded to, that there may have been a good dose of self-deprecation involved, and/or Cohen may have been referring to a range of things (related to living at Mt. Baldy, perhaps?), and not just "zen" itself. Can you provide a link to the youtube video you saw, or further information to identify it, to give us some context?
I think that it is accurate to say that Cohen is not, and never was, just one thing: he and his beliefs were made up of myriad different elements derived from many different sources -- he did, after all, study deeply in the religions and the philosophies -- and thus it is reasonable to assume that he assimilated, and perhaps at times rejected, various elements, ideas and practices of the many schools of thought which he explored throughout his life. There will also undoubtedly have been ebbs and flows, with him perhaps leaning more to some things than others at different times in his life, and thus the religions or philosophies (and/or elements thereof) that he may have felt more strongly connected to may have changed and/or evolved throughout his life. Thus, any given thing that he may have said or written should perhaps be viewed as being representative of a particular context and time-frame within Cohen's life, rather than being a definitive statement applicable to the entirety of his existence.
I am not sure exactly what episode in Leonard's life you are referring to, but if you mean his time at Mount Baldy, then he makes some comments about it in this interview:
https://www.npr.org/2016/10/21/49881042 ... -monastery
In the linked interview, Cohen makes some interesting remarks related to some of what you are saying (I think), and here is an excerpt:
GROSS: Did you become a Buddhist because your desires were so dominant?
COHEN: Well, I never became a Buddhist, to tell you the truth.
GROSS: Should I just use the word practicing meditation?
COHEN: Well, I don't even - I bumped into a man many years ago who happened to be a Zen master. I wasn't looking for a religion. I had a perfectly good religion. I certainly wasn't looking for a new series of rituals or new scriptures or dogmas. I wasn't looking for that.
I wasn't looking for anything exalted or spiritual. I had a great sense of disorder in my life of chaos, of depression, of distress. And I had no idea where this came from. And the prevailing psychoanalytic explanations at the time didn't seem to address the things I felt.
So I had to look elsewhere. And I bumped into someone who seemed to be at ease with himself. It seems a simple thing to say he seemed to be at ease with himself and at ease with others. And without ever deeply studying at the time what he was speaking about, it was the man himself that attracted me.
GROSS: How did you decide it was time for you to leave the Zen center?
COHEN: I don't know. I'm never sure why I do anything, to tell you the truth. I don't know if I could tell you the whole story because it's very private. But I felt the reason I'd gone to see Roshi and had become a monk - it was appropriate to become a monk because if I was going to be in his scene, that was the uniform.
As I've often said, if he had been a teacher of, you know, physics in Heidelberg, I would've learned German and studied physics in Heidelberg. So it was appropriate for me to become a monk. But the life was very - is very rigorous. I mean, it's designed to overthrow a 21-year-old. So I was already in my, you know, 60s and late 60s.
So there was that part of it. But I had the feeling that it wasn't doing any good. And it wasn't really addressing this real problem of distress, which seemed to be the background of all my feelings and activities and thoughts.
So I began to feel that this is a lot of work for very little return. That was a kind of - the kind of feelings - the kind of superficial feelings I had. There were other feelings that are ambiguous and too difficult to describe. They deserve or probably should be described in song or poetry rather than conversation.