Jonathan Weissberg

I had said: "But as ever, one can become fully aware not only of one’s coming nonexistence, but to its place in life." I had meant it is good to become fully aware of one's coming nonexistence square on, with no ifs, buts, or maybes, no fogginess and no denials. And its place in life is only terminal point of life. Conducting one's life never shunting awareness of the coming end is a rationality in life (and tuning one's priorities in projects and relationships with one's present expectation of the termination time of one's life---some decades from now versus two months from now---is part of that rationality).
Have you by chance read the book The Denial of Death by Ernest Becker? It's been a while since I read that, but as I recall, it's quite good.

“Thou hast become dark and cannot hear me. When I die shall I not be like Enkidu? Sorrow enters my heart. I am afraid of death.”—The Babylonian epic of Gilgamesh.
  This awareness seems to affect people differently at different points in their life:
"For some of us the fear of death manifests only indirectly, either as generalized unrest or masqueraded as another psychological symptom; other individuals experience an explicit and conscious stream of anxiety about death; and for some of us the fear of death erupts into terror that negates all happiness and fulfillment." - Staring at the Sun, Yaalom.
Yaalom thinks that we find ways to 'repress' this fear, although I would distinguish between dealing with this fear by finding rational meaning that makes life worthwhile on its own and irrational attempts at finding meaning through what he calls 'immortality projects' like having children or seeking to create another kind of legacy (specifically when motivated by this fear, rather than some other reason).
 
I quote this before, but it's relevant again:
  See Also 'Death of Ivan Illych':     So rational values pursued, internalized and embodied lead one not to even raise these kinds of questions is my take-away. One can setup irrational 'defense mechanisms', i.e., unreal explanations and life projects engaged in out of fear of this death rather than love of life, which reality constantly presents counter evidence for, and which eventually will result in an 'existential meltdown' (Like a Jim Taggart moment).   In what sense did you mean one becomes aware of the place of one's own eventual non-existence in one's life? That would be a case for what Yaalom is claiming when he says that it's important to "derepress" this fear if it has been smothered with irrational coping mechanisms.        

I've seen this a lot. Someone experiences an "existential meltdown" / a nervous or mental breakdown and they are suddenly deep into (usually mystical) philosophy. Behind the scenes is an intense focus on death, which the Russel Brand quote captures well. Apart from comedians, it happens to successful businessmen, athletes, friends, anyone. Why is it usually mystical philosophy that is pursued? Because God is Dead:    
God is dead. And philosophies that are mystical offer comfort, if you can buy into their premises. A more naturalistic, this-worldly-only philosophy like Objectivism is rare, but it would also be a much more potentially bitter pill to swallow at first—because what if it's too late? what if you can't make meaning?
Of course everyone's answer to this experience varies, but the experience usually prefigures significant psychological change.     What is going on here in philosophic terms? The best understanding I could make of it is that there is (forced) complete re-evaluation of values, of one's life, and that the judgement is negative. If one has lived by (and is embodying) what one now judges as wrong values, has one ever really lived or only meaninglessly existed? will one still have a chance to experience living?     
  There is some complication here because, as far as I can tell, it's not only a complete re-evaluation of values that leads one to this state: Unless by this he means that the situation forcefully leads to the re-evaluation of all values.
  What are the two most basic motivations man can have? a love of life, of (his) values or fear of death, fear of dis-value. If one is stripped of values then all that remains is to stare into the abyss? But saying this feels like a mathematically deductive reductio ad absurdum not appropriate to this enquiry. Why the intense focus on death that many experience in the wake of an "existential meltdown?" 

My summarized take after reading all your responses:
The Benevolent Universe Premise describes an attitude that views man as empowered to survive in an intelligible universe: he can discover facts, causal connections and the unknown. He is equipped with a tool that, when applied correctly, allows him to build an ever-growing context of knowledge which, rather than being threatened by new knowledge, is strengthened by it.
It's also helpful to make a few distinctions that clarify thinking about the kind of world we live in: (1) the metaphysical vs. the man-made; (2) the unknowable vs. the unknown;
With respect to distinction #1: The differences between men and objects are consequential enough (a badly styled outfit is capable of being visually irritating, a badly developed soul is capable of murder) to separate them out for analysis.
 
 With respect to distinction #2: A quote from John Galt's speech describing the feeling of living in an unknowable universe:
 
Actually, this is something I had in mind originally too. According to the quotes below we consider “accidents” as not being the essence or the “norm” of human life. It’s still not really clear to me what kind of conceptual stepping stones I need to jump over to be fully convinced of this. I can see that we have a tool to discover the unknown, but there is still the unknown—and the unknown can include causes of negative, deadly consequences and this fact is "in the nature of existence." I don’t think I’ll get an answer until I explore lots of real-world examples of how men actually dealt with the unknown, e.g., the case of discovering blood types compatibility and how that unfolded. This is what Greg pointed out with exploring “positive reinforcements” too.
Some quotes:
With respect to distinction (1), the man-made:
Rearden reflecting in Atlas Shrugged:
“The Inexplicable Personal Alchemy:"
With respect to distinction (2), an unknown as opposed to unknowable universe:
Leonard Peikoff's lectures:
 

Thank you Boydstun & StrictlyLogical for clarifying this. Here is my summarized understanding after having read both your replies.   The assumed context here is that man survives by a particular method of thought and action.You cannot evaluate an object when it is obtained by irrational action because it is moral principle that sets the context (a commensurable standard) for evaluating that object in relation to your other values. You can evaluate the method as good or bad, i.e., this is for my life or against my life, but not the object. Similarly, in epistemology, a proposition accepted on faith cannot in some sense be evaluated on its own, but in terms of method.    An example with StrictlyLogical's breakfast:  If I obtained the breakfast by cheating a shop keeper and he later hits me with a rock does it make sense to say the breakfast was good because I enjoyed it while it lasted? Or what about if I suffered no immediately perceivable consequences but began obtaining more things in the future through fraud? In either case I can't really make sense of the situation by looking just at the breakfast (evaluating the object in terms of my other values) but only by looking at how I obtained it (against moral principle, bad when evaluated in terms of action or method).

Thank you Boydstun & StrictlyLogical for clarifying this. Here is my summarized understanding after having read both your replies.   The assumed context here is that man survives by a particular method of thought and action.You cannot evaluate an object when it is obtained by irrational action because it is moral principle that sets the context (a commensurable standard) for evaluating that object in relation to your other values. You can evaluate the method as good or bad, i.e., this is for my life or against my life, but not the object. Similarly, in epistemology, a proposition accepted on faith cannot in some sense be evaluated on its own, but in terms of method.    An example with StrictlyLogical's breakfast:  If I obtained the breakfast by cheating a shop keeper and he later hits me with a rock does it make sense to say the breakfast was good because I enjoyed it while it lasted? Or what about if I suffered no immediately perceivable consequences but began obtaining more things in the future through fraud? In either case I can't really make sense of the situation by looking just at the breakfast (evaluating the object in terms of my other values) but only by looking at how I obtained it (against moral principle, bad when evaluated in terms of action or method).

@Easy Truth, @MisterSwig, @StrictlyLogical
Sorry, I see there were some typos and inaccuracies in my original post. Eiuol filled in the blanks and was correct. There's more context I could've originally provided so I'll do it now. The rest will take me some more time to think through before replying. Keep in mind the majority of what I'm about to write was in the context of a discussion about asking the question of "will this flight that I'm about to catch crash?" and how to think about such a statement.   Yes, I meant to say man is non-omniscient and fallible. LP said fallibility is addressed by logic. And that non-omniscience is addressed by specifying the context, i.e., by implicitly acknowledging for complex items of knowledge (inductive generalizations) that your statement is preceded by “within the available context of my knowledge”. He states that this does not mean anything else is possible or “maybe I will discover something to upset this”, but only: “everything now known supports this and I acknowledge there is more to learn. If my method is right, the more I learn will not contradict what I have so far.” The more knowledge you have that’s relevant to your current context will simply mean the addition of new conditions, e.g., the discovery of the Rh factor blood as relevant for blood type compatibility (from the OPAR chapter on Reason.)   LP says that there are two ways to be wrong: (1) you’ve applied the method of objectivity correctly and specified a context, but new knowledge teaches you a qualification which doesn’t contradict the old context; or (2) you’ve erred in your method and new knowledge will contradict your old knowledge.    Metaphysical possibility and epistemological possibility are different concepts. LP says that metaphysical possibility refers to a capacity or capability or potentiality, e.g., a plane has the capacity to crash but a feather does not. A metaphysical ‘possibility’ is a statement about the nature of the entity and an epistemological possibility refers to advancing a hypothesis about a situation. You cannot say it's impossible for the plane to crash metaphysically, but you can say it's impossible epistemologically with no evidence of causal factors or conditions that actuate that metaphysical possibility.   Yes, I think this is what I was getting at. 'Certainty' is epistemological. A plane crash is metaphysically possible, but may be epistemologically impossible. If, on principle, you're concerned about the metaphysically possible as a guide to action but with no evidence of epistemological possibility then you end up paralyzed and unable to act.

After listening to Peikoff's 'Art of Thinking' Lecture, I've been thinking a lot lately about the importance of hypotheticals and specifically the kind of hypotheticals one asks and how that affects the quality of one's actions and decisions. I have some questions from this lecture which I'm going to number. Feel free to answer only one or whatever interests. 
(1) Why does ‘metaphysical’ possibility not imply ‘epistemological’ possibility in any given case? 
Paraphrasing LP: ‘Context does not eliminate the possibility of error. No philosophy is going to make you infallible. You can follow the method to the utmost that is originally possible to you, you can specify your conclusion and still be wrong.’ 
Let’s assume no error in method, but a situation where some unaccounted for factor is causally relevant. We know that such a situation is metaphysically possible, so then why do we not say given this general fact, it ‘may’ be possible in any given situation?
Isn’t there some similarity here to statistics, which is applicable to concretes of which you have no knowledge? So the metaphysical knowledge of possibility is applicable to your ignorance of unknown causal factors (just as statistics is applicable to concretes which you are ignorant of). 
My understanding is that ‘epistemology’ is about method and if we were to use our minds to consider something which we cannot consider, e.g., an unknown factor that is causally relevant, we then cannot mentally function since we will be paralyzed on any given inductive generalization for fear of the ‘possibility of being wrong.’ Is this correct? That we dismiss ‘possibility’ epistemologically on the basis of it not allowing us to function well?
(2) Given the above, does it ever make sense to consider a hypothetical of metaphysical possibility but epistemological impossibility for the purpose of informing action?
I think no because then you’d need to consider a meteorite hitting you when leaving the house and you’d be completely paralyzed. LP later says statistics applied when there’s no basis to hypothesize some specific phenomenon results in total paranoia so I assume this applies. 
(3) What’s the epistemological status of “Eat, drink, and be merry, for tomorrow we die?”
I recently overheard a conversation in which someone was talking about working hard to save money and the other person replied that they should just make sure they spend it all before they go into the grave which might be tomorrow because who knows. What is the epistemological status of such a statement? 

(4) Why is it only philosophy that makes long-range predictions? 
LP makes the case that long-range predictions, e.g., 50 years out or longer, are out of the question because so much can change and many new factors relevant to your prediction cannot be anticipated or accounted for. But he says that this is not true for a philosopher making a prediction like “this country will ultimately become a dictatorship?” What is the justification for this? My understanding is that a philosophical prediction has fewer conditions to consider in making such a generalization, but even so aren’t those few conditions dependent on the free will of many people, which one cannot predict?
(5) Without an explicit theory of induction, is error inevitable?
We are both omniscient and fallible. Specifying context addresses omniscience, logic fallibility. Given that there’s no explicit theory of induction, then isn’t error an inevitability when making inductive generalizations, just as it was pre-Aristotle’s discovery logic when discovering new knowledge?
 

Most certainly, the second. "...forming all kinds of concepts". The reason we find art, all art, valuable is that it yields to one's mind the meeting between reality and man's consciousness--as typified by a specific artist. We catch an insight into his re-created world, a particular view of existence which is supremely significant to he/she. Whether one is in metaphysical accord or not with their depiction, one gains and takes away from their creation for one's own purposes (by conceptualization). Here is a corrupt or bleak or impotent or petty view of life and man's mind - there is the antithesis: I.E. existence is knowable and valuable, and man is able to know it and appreciate it. But the bad/ugly/trivial/etc. do exist in others' minds and actions and it's a denial to not conceptualize those as well. Strength of mind depends on the confidence to stay true to rational convictions, not be subjugated to any random input from any other, artists' works in particular.
A "good author"- especially the good Romantic Realist, while not exclusively - doesn't try to make it easy for the reader, imo. His plot and characterization needs to be authentically realist if we are to believe his narrative. He puts across the competing, dark forces against e.g. reason and individualism, freedom and success and so on, which readers can relate to from their experience, creating that necessary "tension" which his protagonist, whose acts we identify with, eventually overcomes through conviction, independence and rationality. (Or succumbs to by futility and weakness, in other depictions). For myself I look for that "tension" in art. I think like in all things real, one needs a challenge from artworks to have to conceptually grapple with, or the art may become prosaic or sentimentalist or ornamental. That personal effort put in by reader/viewer is what gives a work its 'sticking power' in a mind. The darkness, of imagery and writing (and music) can 'fit' my moods on occasion, all the while resting in the knowledge that shadows don't exist without light. Penetrating questions, Jonathan.

Simply, dark moods happen. As with anyone experiencing periods of deep introspect, it's personal. But, as it relates to the arts, certain music is appropriate in such moments. Some authors are more appropriate. When I read Edgar Allen Poe's The Raven, it is helpful to find a virtual friend in shared experience. Nietzsche, as I understand him, was a guide to those who recognize the more frustrating aspects of modern life. His "man going under" is the man who is only able to rise above man, to becoming the "superman." Well, if one is going to be exhausted or depressed as times, one may as well rise above it stronger for the experience. I think there is a great body of works in our times that channel the introspective individual downward, but not necessarily guide him back to focus on any constructive purpose. I'm too old to appreciate Goth culture, but I understand the appeal. I only hope for the sake of such individuals who stare into the abyss that they find the strength to rise again. That's why I read Ayn Rand.

I don't think it's necessary to repress yourself in the pursuit of anything rational. If there is a "function of nihilistic" art, I'm not entirely sure I can answer that; I can only speak for myself. Nihilism and/or realism in bold artistic statements of human imperfect gives me a sense of connection with the outraged and frustrated others, as so many of us feel in moments of alienation. I find it's something that can help me to explore or sink to the depths of my own darker moods with music or other "culture for misfits" that reflects some sort of macabre aesthetic, or noir realism. Dark moods are a part of life. Dark moods won't guide your life, unless you allow them. Rationality can be inspired through art as well, however, art that inspires rationality and heroism is rare in these desperate times, so you have to seek it. My observations have been that some people only consume the sort of culture that inspires darkness and meaninglessness. They immerse themselves in it. It's always a matter of choice. Rising from out of the depth of darkness, to live again, is very rational.

Although not quite a "sense of connection" with those, I agree it makes for an insight into their cynicism or nihilism or "ressentiment" and quite valuable for one's understanding of general trends, moral and artistic. My opinion is one needs to look at the dark side in art too. One emerges stronger and more certain for the experience I think (like one's intellectual, artistic "immune system" is enhanced from the exposure). Naturalism, that broad category, holds merits, often technical and stylistic, and at least as a foil to romantic realism. Best put, maybe, that one comes to finely discern the light from the darkness, while noting/appreciating the shades between them.
The art content and presentation by extremely capable artists or authors will usually hold several enjoyable take-aways which, if nothing else, heighten the capability to *see* (and conceptualize).
E.g. Any well-crafted novel but the most boring, naturalist, ones always has a prominent and often absorbing individual character, typifying individualism, but - he/she may be the doomed-Byronic type, having volition "in regard to consciousness, but not to existence"; or on the other Classical Romantic side, he succeeds in his ambitions but does so without an expressed reason: possessing volition "with regard to existence, but not to consciousness". Then rarely, one finds the authors and their characters who combine both elements, in greatly refreshing romanticism-heroism for one's spirit. I advise to read and view them all and find out/identify/enjoy for oneself. An art 'echo chamber' is needlessly self-constrictive and limiting.

I'm not ignoring all your questions but I will only answer the one's that I think I have thought about adequately:
That means that if the child used his mind to infer something, you would infer that same something if you had that child's mind as in his "field of awareness", his perspective, or his capability to understand. So what he sees is valid i.e. it is from a child's perspective.
He could not be limiting it to the perceptual field especially when he is including how you organize them into concepts. That which affects your field of awareness can't be limited to perception (to what you sense/perceive) it has to include concepts/previous conclusions and perhaps other things that I may not have mentioned.
The lense, his eyesight (capability to see), and his assumptions are some of those things. These affect what he sees. The lense is obvious, bad eyesight as in color blindness would cause him to see what he sees, and his assumptions can skew his view or conclusion about what he is seeing. (his political leanings may influence it too LOL) These examples are not "definitions" that he holds, but they do affect the understanding/identification of what is perceived.
Because my definition of perspective is broader that "spacial, or visual perspective", yes it is the same thing. But if your definition of perspective is limited to "where you are in relations to the object" then no, context is far more broad.

The point that I have been focusing on is the subtle difference between concept formation (so-named in Objectivism) and concept-acquisition (what I’m saying is not part of ITOE or OPAR, and I’m not sure about secondary writings on the topic – there is no such thing as “concept-acquisition” in Objectivism). There are two big questions: “What is the proper means of forming concepts?”, and “What are the actual methods that men use to learn existing concepts?”. In our discussion, I pointed to the difference between the abstract nature of logic and knowledge, versus the practical methods of gaining knowledge; you asked, is it not the domain of philosophy to set out the fundamental practical methods for gaining knowledge? I would say “no” to that question, given a particular view of what “philosophy” is as distinguished from “science”. Philosophy provides the foundation for science: it defines the basic terms and questions that allow specialized scientific research to be conducted rationally. It says what it means to be a concept, to be a proposition, to be knowledge, what “identity” is and so on. Philosophy identifies the nature of “concepts” and “logic”. In ITOE p. 289, Rand presents the essence of the distinction between science and philosophy:
Philosophy will tell you what “integration” and “logic” are, but it does not directly say how a child learns to integrate, it simply accepts the undeniable fact that children do so. Philosophy provides the conceptual foundation for science to conduct specialized research, calling on knowledge of statistics, specialized techniques for observing children, a framework for recording data, and so on – these are non-philosophical matters that depend on a philosophy. It is not a philosophical question whether a picture is worth a thousand words or the opposite, that is a practical, individual matter of what method of learning is most effective for a particular person. Philosophy is relevant to the enterprise because it focuses your attention on “asking the right questions”. It helps you understand the concept “proof”, by demanding that you ultimately be able to reduce “proof” to undeniable perceptions. If I ask my neighbor to reduce the concept “proof” to the axiomatic, I will get a blank stare, because for the neighbor, the idea of “reduction to axioms” is just a bunch of words.
I have a suggestion: please reduce the concept “proof” to the axiomatic. As a prelude, please briefly state what it means to reduce a concept to the axiomatic. As a guiding procedural rule, don’t look anything up. A secondary rule: please report back within 48 hours (that is, you should limit how extensively contemplate the answer – my own scheduling problems explain why it took me so long to spend the hour needed to write this). I believe that this will make the contextual nature of knowledge very clear, since I predict that there will be some concept that you depend on, which you don’t yet understand. This is not a failure, this is a discovery: there’s something that you need to understand better. An example is that in the course of studying Objectivism, I expanded my knowledge of “logic”, which was originally just the standard Philosophy 150 formal method of deduction. I read the part that says “Logic is the art of non-contradictory identification”, which encapsulates the nature of logic, but does not magically give you full knowledge of logic when you have learned those essential words. I thus gained a better knowledge of the nature of “logic”, and can now better identify “logic”. If at the end of this you reflect on what you learned about “reduction”, “learning”, and “proof”, you should have a basic theory of the learning process that you asked about.
I'm not too sanguine about my attempts to take a highly technical subject and make it comprehensible for the layman, when my goal is to do a highly technical logical analysis and reduction-to-experience for people whjo know the field. But perhaps...

Close, but I think the way you wrote this is worded a bit funny. Context is everything connected to what you refer to when you use a concept or idea. Sometimes, as with language learning, it might include how you say the word, when you use the word, grammar rules, and so on, on top of what the word refers to. Context is also something like the boiling point of water is 100°C, but that assumes the context is sea level. Context will constrain our referents or what we are talking about in reality. As a result, when we are trying to form new concepts, it will be easier to remember and focus on the stuff in reality we are talking about. 
Definitely. As long as the discussion also includes real-life examples. 

I think it is important to remember two contextual factors regarding concepts. First, every concept is a mental integration… which means, it’s in your head. Second, proper concepts in your head arise by applying logic to valid conclusions, given some premises, so to the extent that the facts out there are the same, we all learn the same concept “dog”. Concepts are objective, not subjective. The science of psychology is concerned with the nature of a concept in the brain, whereas philosophy is concerned with the abstract nature of concepts which anyone can grasp using reason. Epistemologically primary concepts are those that can understood through direct experience, words with ostensive definitions (“That is a dog; this is yellow”). Philosophy is usually about very high-level concepts such as “cause”, “rights”, “logic” and so on, things that you can’t just point at. Because the connection between a word and what it refers to in philosophy is much more distant, explicit definition and deeper scrutiny of logic is necessary in order to establish that there exists a valid path. Ayn Rand engaged in that enterprise and thus had a valid logical connection between axiomatic propositions and conclusions about the concept “rights”. A number of others have also studied this and now grasp that same relationship. Pretty much everybody has some concept of “rights”, but the definition and what it integrates varies wildly in the English-speaking world (insert alternative words like droit and Recht to expand the range of definitions). Objectivism presents an integrates theory of existence under which we can say what a “right” is and show why that is a valid conclusion, but the same cannot be said for the theory that “a right is that which I want to have”. Even though that analysis has already been done (can be objectively presupposed), you should do it too. You too should discover the fundamentals and how logic and experience yield conclusions about “rights”. (Within limits: I don’t advocate that everybody should validate the concept “neutron”, “electron”, unless you’re a physicist, or have lots of spare time).
Again, there is an essential difference between the abstract nature of logic and knowledge, which is the domain of philosophy, and the practical methods of gaining  knowledge, which is the domain of the science of psychology. It is not very common for a person to actually create a concept from the ground up, instead we are generally faced with the task of understanding a concept that was already created by someone else (hopefully, by induction). Infants start by first learning the label, words like “dog”, “ball” and so on, and then use contextual experience to arrive at conclusions about what “dog” refers to. The psychology of infant learning is a very difficult scientific subject, but we do know what they end up with – it’s just unclear how they got there. Infants do not induce the (adult) concept “rights”, “inference”, “elaboration”. The logic of concept formation, as set forth in ITOE, is that similarities and differences are perceived, leading to the conclusion “these things have something in common that distinguishes them from those things”, and eventually that concept is assigned a name. The overall point that I’m making here is that knowledge and concepts need to be studied from two perspectives, the logical and the psychological, that is, how do we actually learn this stuff.
Regarding the words versus sounds question, you respond “So learn and master sounds first before proceeding because they are the fundamentals which everything presupposes, on which you build mastery of the language”. Yes and no, in a way that relates to the preceding. You cannot first learn the sounds and then learn the words, but that is a fair description of the existential nature of sounds and words (the logical relation between words and sounds). From the psychological perspective – how do I learn this – you have to start with some words. Not all of the words, some of the words. That is a basis for reaching initial conclusions about the sounds of the language. You then learn some more words and validate – or correct (elaborate) – your conclusions about the sounds, and the words. This is a cyclic process, where you continuously increase your knowledge by increasing your axiomatic experiences (hearing the language) and make non-contradictory identifications. So, not only is it impossible to learn all of the words and then draw higher order conclusions about the sounds, it is impossible to first learn the existential primitives (sounds) free of the context where they appear (words), and then learn the words. As an aside, I’m currently working on a paper that explicates the nature of the cyclic, integrated system of reasoning for discovering the sounds of a language.
To summarize my points, there is a hierarchy of concepts and propositions that constitutes your knowledge. You do not learn the elements of that hierarchy by starting at the bottom and seeing how e.g. quarks lead to the concept of proton or neutron, which lead to atoms, which lead to molecules, then cells, dogs, mammals and living being. The entry point into this logical hierarchy, in Objectivism, is not the quark or the concept “living being”, it is the directly perceptible – the dog, and then dogs qua concept. Sounds are the atoms of words (and they are actually made up of smaller stuff, just as atoms are not indivisible existential primaries). Words are the epistemological primaries – the things that we directly experience.

Personally, mastering the sounds of a language has been way more important than learning words by categories. Sometimes I practice Spanish by reading out loud complete paragraphs of books, even if I barely know at all what was said. It helps when I have a native speaker to correct me. It's also good because by reading books in Spanish, I'm exposing myself to words and getting a natural sense of which words are more common than others. On top of that, since I'm picking my interests through the books I choose, it's much easier to fold those words into memory. 
Of course, immersion around native speakers in settings where you need to communicate is the best way to learn a language. But if you want to supplement your learning, or if you can't immerse yourself, some variation of 2 would be best. Really, I'm advocating what I would call "learning in context". 
Learning words by categories doesn't provide context. It's detached from usage, detached from how language is used. Because of this, it makes it much more difficult to cue your memory of different words, not to mention that they are not being used with grammar. With a context, there are many many many more opportunities to cue your memory for words, your memory for grammar rules, plus practice communicating your thoughts. Learning about sounds first is a form of context, which you can keep reusing as you learn more about the language. Immersion is the ultimate form of learning in context, but that's not always possible. As you're saying, strong mental and emotional links are extremely valuable.
These same ideas apply to learning any subject. You don't want to just have a list of concepts by category as a study tool. You don't want just a list of definitions. They might help with which concepts to look out for, but you're still missing context. Essentially, you would be a parrot reciting what it has heard without having any conceptual understanding. You're on the right track I think by mentioning a frequency list, but that's not really necessary, because whatever primary sources you use, you get a natural sense of word frequency through simply reading them. Rather, seeing a word a lot means that the writer thinks that it is important. You could approach it that way, trying to figure out what the context is for those concepts after you've read that work at least one time. 
Part of learning in context is discussing what you have read, without worrying that you will make a mistake. Talk about how concepts are used. Try applying concepts to different contexts and seeing how they measure up. Be a devil's advocate and argue against the concept with someone equally or more knowledgeable. Listen to the writer themselves in public settings using their own ideas. At some point, you'll just "get" what the concepts mean. To be sure, it takes effort, but it's gradual.
In this post alone, I used the word "context" a lot. Think about how I use the word. Did it ever appear strange? Did you change how you thought about the word? Since I talked about "context" as related to language learning, did it make more sense? Clearly I think the word is important, but can you figure out why I think it is important? These are all great questions to essentially immerse yourself in the "language" of philosophy. 
@DavidOdden is a professor of linguistics, he probably would have more to say on the language connection you are thinking about.

[In response to Jonathan's original post]
I don't think one can learn philosophy in the same way that one learns a foreign language. When you learn a foreign language, you are mostly learning new words (and grammatical constructions) for concepts that you already know, such as learning that the Japanese word テレビ is "television" and so forth. You don't learn anything new about televisions by learning the word テレビ.
That's a fundamentally different process from the one you would use to learn entirely new concepts, and it's also different from the process you would use to add "depth of understanding" to concepts you already know. These are the processes in play when you learn a philosophy.
For these, it seems like the important thing is being able to give examples of a concept, and being able to identify the concept from examples of it. It might also be important to be able to identify that some things are not examples of a concept, and why they are not.
Knowing how to define the concept will help a great deal with this. (Recall, the "definition" of a concept serves to distinguish the concept from other concepts, and is usually written as "genus" and "differentia.")
I think reduction can also be helpful, but I'm not sure it's fundamental.
For learning a new concept, consider how you would explain "television" to someone who had never seen one before.
For adding "depth of understanding," consider how your understanding of "television" would change if you learned how to build one.
p.s. On further thought, I want to recommend Ayn Rand's Introduction to Objectivist Epistemology as a good book to read through.

I dunno if this will be useful in your quest to better integrate Objectivism in your life, but I do have a perspective on language learning. I will start by saying that technique 1 doesn’t work for me, in fact it is logically impossible for any human, if taken seriously and literally. Technique 2 is somewhat defective because of the use of ‘then’, but that’s fixable.
I am betting that you can’t learn the words ተኹላ, ጠለበዱ, ወዐግ, ድቢ, ምራኽ, ዳንጋ, ገመል, ድሙ, ጫቚት, ከልቢ, ኣድጊ, ሓርማዝ, ወኻርያ, ኣጋዚን, ጢል, ኡማሬ, ፈረስ, ገንሸር, ነብሪ, ኣንበሳ, ጋውና, ህበይ, በቕሊ, ብዕራይ, ቅንፍዝ, ማንቲለ, ደዕል, ኣንጭዋ, በጊዕ which are just the names of mammals, and it will only help a little if you get the English translations (African wild dog, antilope, ape, bear, calf, calf, camel, cat, chick, dog, donkey, elephant, fox, giraffe, goat, hippo, horse, lamb, leopard, lion, male baboon, monkey, mule, ox, porcupine, rabbit, ram, rat, sheep). I am betting (but it’s impractical and complicated to try to demonstrate this here) that you can learn the sounds composing the words, wich is the basis for learning the words. There are millions of words in the language, and dozens of sounds. The Objectivist epistemology is constructed so as to lead you to follow technique 2, because humans have a relatively small ኳኽ (the name of a bird). Technique 1 ignores the perceptual level and goes straight for the conceptual and propositional levels.
I believe that there is a general tendency to not correctly grasp the two kinds of fundamentality, namely existential versus epistemological fundamentals. Quarks are existentially fundamental, dogs are epistemologically fundamental. On this point, I commend to you Binswanger’s How we know, because he has a good psychological perspective on epistemology (“good” doesn’t mean “infallible”). We do not take “animal” or “mammal” as a perceptual given and then reduce “animal” through an elaborate set of differentiations to “… and huskies, like this and that”. We don’t actually know what the acquisition process is (this is a scientific question, not a philosophical one), in fact I don’t think we even know how to find out. It might be that mice and motorized toys are initially indistinguishable to infants.
Validating a concept by reducing it to (true) axiomatic knowledge is a very adult thing to do (not what children actually do), and presupposes that you actually grasp the concept. You cannot validate the concept ተኹላ if you don’t grasp it: what do they have in common, how they different from ከልቢ? Can you correctly integrate and differentiate ክ, ኮ, ኩ, ከ, ካ? My suggestion is to start by explaining one of these concepts – defining it, by saying what it refers to, and see which words you have to use to set forth that definition. You definition should make clear that “it’s these things, excluding those things. These things are similar in ___”. Start with “existence”, then move to “action”.
My own “acquisition” experience regarding your word list is that even though I knew all of these words, I didn’t correctly grasp their role in (Objectivist) philosophy. My suggestion about “explaining” existence and action is intended to provoke a bit of widening of your list. While it is true that you are hosed if you ignore the meaning of “context” in Objectivism and just treat it as a floating abstraction, frequency of occurrence is not what make the term important. What I found most important is understanding the epistemological concept “presuppose” (probably because it is a fundamental concept in linguistic semantics). Galt’s Speech and specifically the “Existence exists” part ought to be in front of you as you take on this task.
The only thing I would add to Eiuol's suggestions about language learning are (a) it is important to have cooperative conversation partners (dial it back, dude!), and (b) it actually takes a lot more than 2 similar examples and 1 dissimilar example to acquire a linguistic concept (e.g. "a sound").

Not to get hung up on ice cream flavors or other sense-perception tastes, but having such preferences for this over that (or that, not at all) has an objective base when one pays it mind, I think. Saying this, because many a time we hear that these are "subjective" tastes and values. One finds out from experience that strawberry is tastier for you than chocolate, or 'agrees' with you better. This might be a minor variation in the arrangement of taste buds specific to you or a digestive system that reacts to chocolate, for all I can tell. (Then if strawberry isn't available, your taste hierarchy might point to the next flavor in line. The category "ice cream" has pleasure-value over the flavor). The major point imo being that this taste and its enjoyment likely has a source in your biological nature and a corresponding value - and that you know it - therefore, is objective and "personal" - not a contradiction. Forcing yourself to eat carrots you heartily dislike over an ice cream treat, that could be subjective and a value-sacrifice (if you weren't starving). Up the line in magnitude to where it really counts, the greater values in your rational, self-full hierarchy maintain their order also, since "you know" them (conceptually) too and wouldn't sacrifice a higher value to a lesser one.

"Perfect practice makes perfect. If you practice a mistake long enough, you'll get very, very good at it." — Miss Byrd, piano teacher.

Jonathan, A hierarchy of values you've seen indicates that many objective values are of lower/higher value "significance" in the greater scheme of things to one (for whom his/her life and its entirety is the supreme, objective-value significance).  Why then to declare a cut-off point, between: this is a moral choice, that is non-moral? I can see no advantage and only downsides. These minimally important things are what sometimes give our simplest rewards in anticipation, enjoyment, a sense of well -being. We could see this input as the maintenance and sustenance of a huge range of material values and human values, for the 'spiritual' values they repay us with.
The choices then, I think, are all "moral" -  pertain to a rational morality. What varies tremendously is the discovered values, which will have most-more-lesser-neutral significance, which one best identifies in order to best evaluate. In effect, this is one's precious life, nothing that touches on it passes muster and evaluation.