7 hours ago, oso said:
The biggest problem in my life has been procrastination and a lack of self-discipline. For many years I thought that the source of this problem was a lack of training in self-discipline and that the solution would be additional will power. Despite knowing that procrastination is irrational and destructive in the long term, I’ve continued to struggle with it. Until recently, whenever I allowed myself to procrastinate I would tell myself that my failures had been a result of personal weakness. That’s true to an extent, but it’s not useful. What has finally been useful to me is understanding what it is about myself that leads me to choose to procrastinate. I don’t know yet, but I think that self-knowledge along with will power and philosophy is what’s needed for success.
Since discovering Ayn Rand and Objectivism, I had felt that it would give me the tools I needed to be happy. I think this is true, in the sense that Objectivist morality is valid and practical, but Objectivism doesn’t tell you how to become a person able to hold yourself to proper moral standards.
I don’t know whether this comparison will be useful to you or not, but consider the goal of… I don’t know, playing some complex piece of music at a concert (perhaps by Rachmaninoff, of whom I believe Ayn Rand was fond). So I give you the sheet music along with a manual which describes a piano, and which shows you how to orient your fingers in order to strike the keys properly, and…
What? You sit down and play the piece flawlessly?
I think that there is much valuable knowledge and insight in Objectivism, without which happiness would be much more difficult to achieve. But no, there is far more to “being happy” than “being an Objectivist.” I have heard it said that Ayn Rand occasionally suffered from sadness/depression. I don’t know whether that’s true, frankly, but if it were true, I would not think less of the philosophy (or its creator) for it.
7 hours ago, oso said:
Objectivism doesn’t tell a damaged person how to heal himself. That’s the realm of psychology, not philosophy, but unfortunately for me, it has been a long road from discovering philosophy to realizing the importance of psychology and self-knowledge.
I’m curious to know, has Objectivism lead you to self-knowledge?
To me, this is akin to asking whether Objectivism has led me to… knowledge of the stars. Given the fundamentality of philosophy, a proper philosophy (i.e. Objectivism) is invaluable for having the right approach in gaining such knowledge, but for the stars to be known they must be studied. There are no shortcuts. For the self to be known, the self must be studied.
To answer directly, I think that Objectivism has assisted me in an effort to “know thyself” which began before reading Ayn Rand and continues to this day.
7 hours ago, oso said:
Do you think that the errors I’ve made are easy to make?
I think this is impossible to answer without a far more extensive knowledge of personal context than would be feasible (or appropriate) on this forum. But I think that many people make similar errors, at least.
For myself, I struggle greatly with an explosive anger. I don’t know whether it’s an error “easy to make,” in general, but it certainly is for me! 
7 hours ago, oso said:
If so, is there potentially a dearth of discussion of self-knowledge, psychology and childhood experiences within Objectivist literature and communities?
I believe that Nathaniel Branden has written a deal on psychology, though I’ve not personally read much by him. As “Objectivist literature and communities” typically deal with philosophy, and as what we’re talking about is psychology, then I’m not entirely certain that there’s a greater call for discussion of psychology in such literature and communities. (Though neither do we have to shy away from it, necessarily, just as we may discuss specifics of art or science or etc.)
But what we can say, perhaps, is that a person needs to know more than philosophy alone to be a successful/happy/flourishing human being. Perhaps that, and the importance of psychology specifically, is a point deserving of greater emphasis.
7 hours ago, oso said:
These things seem particularly important in regards to the subject of happiness, especially since we live in a world where so few people have had entirely healthy childhoods.
I agree.