On how to learn philosophy
Hello Forum,
I havent a degree in philosophy (accounting and finance instead, 2023 graduate) but Im highly, highly interested in it. I want to engage dialectically to an academic standard. I have, over the last 3 - 4 years, as a hobby, familiarised myself with topics such as ethics, epistemology, modality, existentialism, logic, political philosophy etc Ive read a few key texts and other contemporary papers, books, articles. However , I want to arm myself with the academic (philosophical) rigour that one would gain in a BA.
Im capable of engaging in Philosophical discourse, but I want to being able to critically engage; for my own sake, better than the above average laymen
Do you know any which way I would go about this , or have any must read, key texts to engage in. Over the course of a few months to a year or so
Im happy with essentially starting from scratch and re-building my foundations up properly
Thank you all for your advice
I havent a degree in philosophy (accounting and finance instead, 2023 graduate) but Im highly, highly interested in it. I want to engage dialectically to an academic standard. I have, over the last 3 - 4 years, as a hobby, familiarised myself with topics such as ethics, epistemology, modality, existentialism, logic, political philosophy etc Ive read a few key texts and other contemporary papers, books, articles. However , I want to arm myself with the academic (philosophical) rigour that one would gain in a BA.
Im capable of engaging in Philosophical discourse, but I want to being able to critically engage; for my own sake, better than the above average laymen
Do you know any which way I would go about this , or have any must read, key texts to engage in. Over the course of a few months to a year or so
Im happy with essentially starting from scratch and re-building my foundations up properly
Thank you all for your advice
Comments (43)
An Essay on Metaphysics by RG Collingwood. You should be able to find this free online.
The Metaphysical Foundations of Modern Science by EA Burtt.
If youre interested in the philosophy of science, heres a link to an article that really changed the way I thinkMore is Different by PW Anderson.
https://cse-robotics.engr.tamu.edu/dshell/cs689/papers/anderson72more_is_different.pdf
If you hang around here on the forum, youll find I also have a strong interest in Taoism. But we wont go into that here.
Do you have any advice with regards to engaging in text, and improvement on Philosophical dialectic ?
Sounds like you want to move from reading philosophy to doing philosophy.
It might seem that a forum such as this would be ideal, but while it might help, there is a lot of very poor work hereabouts. Caution is needed. Autodidacticism can lead to eccentricity, or worse.
Philosophy is a discipline, and there's nothing better than spending time with professional philosophers. I'd suggest some sort of post grad study, perhaps a coursework MA if you are serious, or just seeing if you can audit a few courses at a local university. Something with face-to-face time. I'd personally commend a basic logic course above all else, but breadth is also a very important part of understanding how the subject works.
This view will probably not be popular. Folk tend to forget that philosophy is a discipline.
But also, write. Get your ideas down on paper. Spin your arguments out, make their structure explicate, and get someone to read them critically. These days, that can even be an AI.
Good luck.
Thank you mate. Ill do the best I can. Unfortunately I doubt Id be able to enrol in a course, *maybe* online, but I work full time. Now, I understand that this comes with its difficulties - Im trying to parse them as best I can.
Your point on writing my own work and formulating my ideas is crucial to learning how to engage outside of just reading. So I will do that too.
I may shadow an open source curriculum and enhance as such.
Quoting Banno
As an eccentric autodidact, Id have to agree with this. Hes left out the monomaniac contingent...
Quoting KantRemember
One issue with doing philosophy is that there are a plethora of views about what this discourse actually is, and many camps seem to resent or denigrate other camps. Some see it as a rigorous pursuit of truth, others as a language game, and still others as a form of personal or ethical guidance or self-help. Philosophy seems to be a tricky subject because its methods, goals, and even subject matter are endlessly contested, and what counts as philosophical in one tradition may be dismissed in another.
Why are you interested?
A few really good resources I can think are:
The Oxford Very Short Introductions - they can vary in quality, but they are generally quite good. They are on quite specific topics, which is helpful. The one on objectivity is especially good.
The Routledge Contemporary Introductions to - these are pretty good topical introductions. They are generally quite biased towards later analytic thought. However, since historical surveys are always incredibly thin, they're still better than attempting some sort of chronological slog (and I say this as someone who is not particularly hot on analytic philosophy).
The Teaching Company - they do a lot of lecture series on various topics. The one on mind-body philosophy and philosophy of science are particularly good, as is the one on the Platonic dialogues by Segrue. The one on information theory is also neat, if not quite philosophy. They're hideously overpriced on their site but on Audible they aren't that expensive and I think a number are free with a membership at any given time. Or the site Wonderium had them fairly cheap and I discovered that if you do a trial and then cancel they give them to you at a steep discount.
The Modern Scholar - Sort of the parallel to the Teaching Company. They have a good series on Plato and Aristotle, and one on speech act theory that I didn't get to finish that seemed good. The guy who does the Divine Comedy and other epic literature is great too (Timothy B. Shutt).
And then for stuff I know is up online:
I really like Eric Perl's Thinking Being for metaphysics, although being a survey it is quite broad. That one happens to be up on Google right now: https://afkimel.wordpress.com/wp-content/uploads/2018/06/eric-perl-on-metaphysics.pdf (IDK, maybe it isn't supposed to be, but it's been one of the top search results for ages now so I assume I'm not doing any harm by pointing it out).
Pierre Hadot's Philosophy as a Way of Life on how ancient philosophy was practiced (very different from modern philosophy is also interesting, and it's essays so you can dip into it: https://ascetology.wordpress.com/wp-content/uploads/2016/09/pierre-hadot-philosophy-as-a-way-of-life-spiritual-exercises-from-socrates-to-foucault-1.pdf
I normally recommend Robert M. Wallace's Philosophical Mysticism in Plato, Hegel, and the Present because I think it's a really great introduction to the broadly "Platonic" tradition in quite accessible terms. If you ever get into Hegel (which I wouldn't at first lol), his book on Hegel is really great (so is Houlgate's commentary on the Logic and Gary Dorrien's Kantian Reason and Hegelian Spirit as an introduction on German Idealism, at least the first parts of the book).
And lastly, Boethius' Consolation of Philosophy is a really beautiful book.
Oh, and Fukuyama's Origins of Political Order is quite encyclopedic on theories of state development (political theory), although it is a bit of a "whig history" in favor of liberalism.
In so far as directly engaging with original texts goes, I found it helpful to record reactions, note parallels, and keep track of references as one proceeds. Apart from whatever direction I have gone, the practice I began at the beginning has been a gift to my future self. It started out as marginalia and then a notebook linked to marginalia, and then linking to indexes in specific works. I developed a kind of marginalia in those indexes that still helps me decades later.
Everyone has their own style, but some form of this discipline helps one keep building on previous learning.
Sure.
it might help us identify some good on line stuff if you list your interests.
I highly commend the EdX philosophy and critical thinking course. See https://thephilosophyforum.com/discussion/13633/page/p1
The Ethics Centre has various courses, and on line conversations.
Look for stuff by actual working philosophers.
Okay, here's how i look at it: there's informal philosophy. This is anything: "What is life"?
And the there's formal philosophy, related to specific thinkers, which ends up being academic philosophy.
The two are not totally separate practices, but what we can call "non-philosophy" are specific and technical matters. "Did you wash the dishes?" is not philosophy. Philosophy deals with general ideas and abstractions primarily...and that's why your "average person" tends to hate it.
But is there a point to this other than to join some imagined club of sophisticated thought?
Sure it is great to launch into the usual Grand Tour of the history of philosophy as another subject to study. But do you really want instead to become skilled at critical thought? To gain skills beyond mere philosophising?
Quoting KantRemember
I'll tell you my secret. Start by finding some question you really want answered. Then start reading around that. Make notes every time some fact or thought strikes you as somehow feeling key to the question you have in mind, you are just not quite sure how. Then as you start to accumulate a decent collection of these snippets stumbled across all most randomly as you sample widely begin to sort the collection into its emerging patterns.
Look for the more general things that connect up a lot of particular things. Delete what starts to seem irrelevant. Begin reading much more about anything that starts to really seem to matter. Keep adding the snippets and sorting them into their natural clumps. Eventually you will find you are coming at your original question from all its many angles. You really begin to see an answer emerging as a fully structured whole.
And doing that not only answers your question to the degree that it can be it is also teaching you critical thinking of the valuable real world kind.
My own first question was "how could the human mind have evolved so suddenly?". I had been a good enough student at school and university, but never the slightest bit stimulated to engage beyond passing everything with minimum effort. But this is how I got hooked on really learning. And it is incredibly efficient as you are turning a morass of what everyone has ever thought and said, then zipping through looking for only the ideas that properly connect as a whole, while discarding vast chunks of guff that only clutter up the view of what matters.
Even with a day job as a magazine editor, I had generated a tightly reasoned book in a couple of years. I was off to the races.
Do you want to wade through all of philosophy much of which is sophisticated guff? Arguments for the sake of arguments. Tiny amendments to disputes of increasing irrelevance.
Do you want to have random arguments with random strangers with a random array of opinions?
Probably not. So what is some really difficult but pointed question you would want to tackle in a thorough manner, and thus learn your own limits when it comes to critical thinking.
You can't just invent answers off the top of your head. And you can't learn answers by asking around or reading diligently, as there are just any number of answers that will be offered. You have to turn yourself into an efficient search algorithm with an end in mind and a method that sifts the wheat from the chaff.
Quoting Tom Storm
That is the start point. How do you begin with the something worth doing and not a vague hope of becoming more learned?
Quoting Paine
Yep. It is about a method with that built-in feedback of condensing and reacting. Then reacting to that reaction with even more distilling. With an infinity of texts available, the ones to read next start popping out.
Quoting ProtagoranSocratist
This is a good summary of how people tend to divide. Either they wander around picking up on what seems interesting. Or they will treat it like being back in school or joining an impressive institution.
Either too unfocused to be something that personal, or too focused on what some institution has decided is the proper course work to master and parrot.
So that is why I recommend a middle road. Find that interesting thing. Then make full use of the institutional knowledge and support that exists. Have the best of both worlds. And undertaking a structured search task is the best way to emerge out of it as a proper critical thinker.
I have learned many things through it but have often come to question their summaries when reading actual texts. Probably the fate of all attempts at classification.
The only philosophy course I took in college was Logic. And that was a math requirement. My interest in philosophy, post college, was mainly in looking for a substitute worldview to replace my childhood religious indoctrination. But I never had time to get into philosophy seriously until after retirement. And most of my autodidact education since college has been obtained from science books with a philosophical inclination.
I've had minimal communication and interaction with other philosophers, until I started posting on intellectual forums. Some on TPF have formal academic training, but most seem to be what I call "amateur" philosophers, and self-taught, like me. But, you are not likely to get training that is up to "academic standards". Also, as warned : " Autodidacticism can lead to eccentricity, or worse".
I assume he would put me in that category, since I have a shallow & narrow focus on a few topics of interest to me, but don't fit neatly into any of the traditional philosophical viewpoints, such as Idealism or Realism. Instead, I call my personal worldview Enformationism, which is unconventional, idiosyncratic, and mostly science-based : e.g. quantum physics & information theory & systems theory.
My ideology doesn't conform to any of the authoritative doctrines & systems*1, but has some affinity with several, including A.N. Whitehead's Process Philosophy. Like you, my retirement hobby has touched on a variety of scholarly topics, but with little academic rigor. Do you see yourself becoming a Platonian, or Kantian or Hegelian or Marxist, or Existentialist, or a master of some other formal system of thought?
Some TPF posters are offended by my unorthodox views, but most accept a bit of oddity as typical of independent thinkers. So, since your time is limited, you might find that this forum will give you access to a variety of views, and experience with having your beliefs challenged. You may have thin skin at first, but it will toughen as you endure critical analysis of your favorite values & assumptions. :smile:
*1. Philosophical systems are comprehensive, interconnected frameworks of thought that offer structured perspectives on fundamental questions about existence, knowledge, ethics, and reality, such as Plato's Idealism, Aristotle's Logic, Kant's critical philosophy, Hegel's absolute idealism, Whitehead's process philosophy, and Ervin Laszlo's Systems Philosophy. These systems provide a lens to understand the world and shape cultural beliefs, offering foundational principles and a coherence that allows for interpretation of complex phenomena.
https://www.google.com/search?client=firefox-b-1-d&q=philosophical+systems
Confessions of a Philosopher by Bryan Magee is probably your best bet. He covers most of the great figures quite accurately in great, easy to grasp prose. I can't think of a better introduction.
His book on Schopenhauer is also very good and will help build more critical thinking skills.
Beyond that, there's a lot of stuff, it depends on what you like. Russell's History of Western Philosophy, though uneven, is a great reference.
Once you see a topic click, you can read intro books, lectures or just begin to read the classics. I think it's important to note that you never really finished with Plato or Descartes or Wittgenstein, it's a lifelong thing. So don't pressure yourself in mastery of the subject. It comes with time and changing perspectives.
Shout out to T Clark for mentioning The Metaphysical Foundations of Modern science by Burtt. Knowing a bit about the history of the time period helps A LOT. What may seem silly to us now, was perfectly reasonable for the time, given what they knew. That's also a good book for the early-modern period in philosophy, which contains the most important figures outside of Antient Greece. It's a great book too.
Not always offended, but puzzled that you would be resistant to learning of the philosophers and scientists already saying much the same thing in a more nailed down fashion.
It is a good case as my own investigations into biosemiosis put me among a community of about 100 researchers trying to figure it all out. They had a number of discussion boards and the level of discussion could be both friendly and rigourous. Welcoming to independents making an effort.
And also occasionally so violently acrimonious that one discussion board got simply deleted with its many years of posts by its admin who didn't think it was sticking close enough to the view of his own particular recently deceased mentor. Professors are only human too. :grin:
Anyway, there was even one philosopher there John Collier who had coined your term enformation. He defined it dichotomously as the opposite of intropy and firmed it up with the suitable mathematical equations.
See Causation is the Transfer of Information (1997).
So this is my point. One could get mired in philosophy as some whole cosmopolitan edifice of collective human wisdom. Or at least a history of certain leading questions and the endless acrimonious splits that they created. A soap opera of endless fissions and not much helpful consensus.
Or one can go the "independent" route which at best can only end up with you repeating the semi-obvious in a suitably obscure way.
And then there is always an informed community who have narrowed down the search space in some robust fashion. They are surprisingly welcoming as they are always pleased to find someone sort of on the same page. But also their tongues are sharp, their tempers sometimes explosive. A contest of ideas is what it is about. And then a few virtual beers after the fray.
But having the discipline of a research mentality is the only way to reach the inner circles of current thought. And that is just the way it is.
Philosophy, like any art, is about expression. Any intake is unnecessary. Just take it out and give it to the world.
I think this is the single best reason why I love philosophy over science.
My interest came primarily from 3 things. 1. My desire to learn, think critically, and challenge myself, 2. A want to understand the nature of reality, and 3. It started a few years back with a deconversion from faith when questioning the rationality behind it all - that led to questions on morality, theology, which, naturally, led me down to ontological thought, and further, what it meant to know something. This has developed further into an interest regarding all things Phil. Mind, matter, more so the analytical stuff rather than continental - but I see a large value in both, and I do not know enough about either to confidently say which has more value in general.
I am VERY happy to help if you want? It is probably most worthwhile picking a question and exploring different ways you could answer it.
If you are in your 20's I would recommend getting a reasonable idea about the science behind our understanding of reality in terms of physics, the cognitive neurosciences and general anthropology.
Feel free to DM me :)
My interests are:
Logic. I'm familiar with informal logic and very vaguely so with formal logic , but I need to deep dive on what actually, seriously, makes a good logical argument - being able to spot arguments in any body of text, critically engage and follow the premises towards the conclusion and question effectively whether they follow, what they pre-suppose etc. /
metaphysics: I believe this to be foundational and commonplace in many philosophical discussions and readings. I want to seriously be able to understand what is being talked about and effectively contribute - further to this, with metaphysics being so broad and widely applied, having an understanding on this will help me down the line with any of the granular topics that follow from it.
Ethics / morality: I already hold my own positions on moral realism, ethics, the good etc, however I'd like to strengthen these rigorously, question my own world view, critique it, and be able to formalise it.
Language: I find that in my own experience, a lot of philosophy is lost and/or found in semantics. I view language as the medium by which thoughts are expressed and that in itself holds its own weight.
I think I am already on the right track, but again, the structure is what I believe I am lacking.
I've heard Hegel Is a shit show at first. I find idealism interesting, but I don't see the value in engaging is such technical prose at first. I'm aware that I more than likely won't be able to grasp Hegel in full until maybe the 90th read.
I'm also a semi-academic philosopher, but I'm still on my way to becoming one. In my opinion, a child can utter a philosophical formula that rivals a master in its content, but academic philosophy is more about rigorous explanation. I believe some philosophers are so engrossed in this that it's unbearable to read. For example, Heidegger is wonderful, but unbearable to read. His ideas are magnificent, but formulate them in three or four paragraphs and something that makes them "philosophical" evaporates.
For me, philosophizing means living within a philosophical paradigm, constantly asking myself questions, constantly critiquing my own ideas, and constantly consulting with people, the participants of this forum, authors of philosophical works, and even AI.
So the very pursuit of philosophy is philosophy itself, but it requires the use of tools for purity of thought. For myself, I define philosophy as "astonishment before the self-evident."
Thank you. Yes, that all sounds understandable. I believe that a deconversion can leave some with a big hole to fill. A lot of former Muslims and Christians often end up looking for foundationalist justifications in philosophy. Although I also find it interesting how often they rest for a while alongside New Age or Pagan groups- a kind of methadone program for hard core theism. What people believe and why is always interesting.
In terms of why I like philosophy, please refer to my replies to Banno/Tom storm.
in terms of what my goals are; as superficial as it is, I want to be able to reach that level of being able to read philosophical text, separate the sense from the non-sense and make sense out of the arguments and propositions. I want to also be able to provide meaningful , non shallow insight in discussions I partake in. Im aware that this will take years but my love for philosophy and study gives me time for that. The only downside is that it is almost entirely autodidactic.
I should note. I believe myself capable of providing interesting opinions. Its more so Ive reached a stage where, as previously mentioned, I want to move from reading philosophy, to doing philosophy. Being self taught means lacking guidance. I think Ive had enough of briefly reading supplementary texts on a plethora of topics and much rather would like to seriously hone my skills.
As to whether there is a point outside of some imaginary sophisticated club of 'smart people', that is up for debate. for now, at least, I motivated by my desire to engage and understand. I feel as though I am learning for learnings sake, but at present, that satisfies me.
I will have to have a hard think about a question in the same vain as yours that I want to seriously grasp though.
I find it much more interesting trying to understand reality for what it is than attributing everything to a divine cause. That isn't to say doing so is wrong or there is no value in doing so, but I love the epistemic pursuit of figuring things out for ourselves.
Fair enough. I tend to think of reality as a human construct, a kind of secular version of God, serving as a foundational justification for all our ills. Theres a lot of searching for the "really real" in philosophy, it seems to me. By temperament, Im more drawn to the view that humans are meaning-making creatures who cant help but explain things through gods, science, karma, or whatever framework they inherit or (less commonly), choose. They all work to a point, depending on ones culture and axioms. I tend to think Ive chosen to step aside from that impulse and not concern myself too much with explanations, except the provisional or pragmatic kind that help me as I go about my business.
Quoting apokrisis
I think this is excellent advice. I would add: When you encounter a point of view that seems, on first reading, just nonsense, immediately stop and try to enter that "nonsensical" point of view. Why would this (presumably respected and published) philosopher write such a thing? What could they be thinking, meaning? Don't move on until you feel you've made progress in understanding this alien way of thinking. I believe the single biggest error that newbie/amateur philosophers make is to fail to read generously and curiously. This leads to the kind of autodidacticism you've been warned about, and reinforces our natural unfortunate tendency to be dismissive of people we disagree with, without actually understanding how or why the disagreement comes about.
I'm a retired professional architect, and an part-time amateur philosopher, working a retirement gig to make ends meet. So I have very limited time or inclination for academic discipline. And no ambition to "reach the inner circles of thought". That's why my "resistance to learning" may be more charitably termed "time management".
My current "research" is mostly Googling names and terms I'm not familiar with. I Googled "John Collier" and got nothing relevant. But I would invest some time to see what he has to say about Enformation. Back when I started writing-up my Enformationism thesis, the term Informationism was already being used in a different context. So, I added the initial "E" to emphasize the Energy & Entropy aspects.
If you have the time to scan the website*1 & blog*2, you may see that I have already done considerable "research". Most of my references are scientists, so the philosophical inferences are my own amateur musings, not the "nailed down" conclusions of professional metaphysicians. But if you know of something I've missed, please let me know. :smile:
*1. Enformationism :
This website is a place to explore the meaning and ramifications of a new philosophical and scientific hypothesis that I have chosen to call Enformationism. The term spelled with an "I" had already been used elsewhere in various contexts and meanings, so I looked for an alternative name. Since the new scientific term Enformy was already in use, with a meaning similar to what I had in mind, I simply chose to change the spelling of my proposed coinage.
https://enformationism.info/enformationism.info/
*2. Introduction to Enformationism :
Yet, its based on the emerging evidence that invisible Information, instead of tangible Matter, is the fundamental substance of everything in the universe, including Energy, Matter, and Mind.
https://bothandblog6.enformationism.info/page80.html
:up: :up:
In @Gnomon's case: ... too often in a confused and un/mis-informed way (i.e. full of woo-woo).
Quoting Gnomon
:sweat: Yeah, it shows ...
Just click the link I provided,
Thanks for the link. I scanned the long, technical document, and found it was mostly over my amateur head. But the AI summary revealed that some of the concepts covered are compatible with my non-professional thesis. For example "Causation as Information Transfer" is equivalent to the Information = Energy sources in the thesis. Collier's "The Role of Form" is essentially the same as my usage of Platonic Form. Also "Quantification of Form and Complexity" is basically what the Santa Fe institute is doing. And "The Negentropy Principle of Information" is what I call EnFormAction or Enformy*1. So, it seems that we are thinking along the same lines. :smile:
*1. Enformy :
[i]In the Enformationism theory, Enformy is a hypothetical, holistic, metaphysical, natural trend or force, that counteracts Entropy & Randomness to produce complexity & progress. [ see post 63 for graph ]
1. I'm not aware of any "supernatural force" in the world. But my Enformationism theory postulates that there is a meta-physical force behind Time's Arrow and the positive progress of evolution. Just as Entropy is sometimes referred to as a "force" causing energy to dissipate (negative effect), Enformy is the antithesis (physicists call it Negentropy), which causes energy to agglomerate (additive effect).
2. Of course, neither of those phenomena is a physical Force, or a direct Cause, in the usual sense. But the term "force" is applied to such holistic causes as a metaphor drawn from our experience with physics.
3. "Entropy" and "Enformy" are scientific/technical terms that are equivalent to the religious/moralistic terms "Evil" and "Good".
https://blog-glossary.enformationism.info/page8.html
Hack yourself to pieces, and then put yourself back together.
I would say this approach is completely impossible.
It is not possible to view oneself from the "View from Nowhere", completely devoid of everything except one's rational faculties.
We are placed in systems of hierarchies and traditions into which we are "thrown", which are "givens", to us, and with which we have to deal.
They must be reviewed, repaired, sometimes challenged, but they cannot be escaped, as if we can place ourselves in sterile laboratories of reason.
I think this is good advice:
Quoting apokrisis
The mind engages most deeply what it is interested in, so it is best to begin with what you are already interested in. It is there where you will be able to be attentive to your own thinking and to the different views on offer, and to effortlessly exert the energy required to grow philosophically.
Similarly, when you encounter a point of view that strikes you as nonsensical, just move on. Be honest with yourself, and don't contort yourself to try to make yourself see something that you do not see. Move on to contrasting views that have intelligibility, and can be assessed with earnestness and genuine curiosity. Only later on should you move to try to examine nonsense.
Interesting, but i don't think that's the right way to think about it: a "view from nowhere". Objectivity emerges from the sum of all subjects. The more subjective perspectives one can experience, the more objective the resulting singular composite metaperspective becomes. Nothing exists objectively without the substance of the subjective. "View from Everywhere" would probably have been a better title for Thomas Nagel's book (hadn't read it though).
Quoting Colo Millz
I never said or implied anything about escaping anything other than personal ignorance. The rest of what you said i'm fine with.
What I am seeking now is a more coherent structure. That is to say, I want to know what it is I'm talking about, analytically, outside of my own personal opinion.
To @punos's point earlier, my goal is to ' hack myself to pieces and put myself back together again.
I have spent years wondering around in the name of curiosity, I now want to synthesise that with structure, competence, understanding and background, only to then wonder around again with the same curiosity that set me on this journey in the first place.
I've learnt (Barely) First Order Logic and Informal logic, I'm now in the midst of rigorously going through the consensus on Ethics, with further study in mind on other key areas of philosophy that will eventually give me the breadth of understanding I'm looking for (Undergraduate level), and then, while on this journey, discover new things that spark my interest. Be it the daunting Hegel, or the prose-full Simone De Beauvoir.
Someone I've recently stumbled upon who addresses this in detail and in an accessible way is Nathan Jacobs. For example, "The most important question," or "What to do with moral truth?"
Especially in that latter video he talks about what he believes to be the best way to reshape yourself rationally, and it is based on his "four levels of discourse."
Edit: Although Jacobs focuses on issues that pertain to morality or practical reason, his approach is applicable to theoretical reason as well (and issues of "level one discourse" such as realism and nominalism always implicate theoretical reason rather directly). His advice to move into deeper levels of discourse is salutary. One place where I think he is weak is in recognizing the importance of the shallower levels of discourse in informing and interacting with the deeper levels of discourse. In my opinion what one needs to do is not merely move deeper, but to be continually moving back and forth along the ladder of levels of discourse. Quips or aphorisms, for instance, are examples of the way in which the levels are not altogether separable.