Lately I have found an interest in philosophy. I would love to dig deeper into it when I get the time.
I just started reading Seneca's Letters from a stoic and plan to read Tao te Ching next, as I always wanted to implement thoughts from Stoicism and Taoism in my life.
I'm aware that, randomly reading different philosophical works won't give me much in-depth knowledge.
I want to know what's a good way to go about it and the resources I could use.
Not as in-depth as reading books of course, but it's very pleasant to listen to and you'll get a rough overview of who's who and can then go on to reading something referenced in the podcast that interests you.
Agreed, it was my gateway to philosophy. It's gives you a good idea of who the most famous philosophers were, and their greatest contributions. It's very superficial, because you can only say so much in a 20 minutes format, but it's a great start to find who you want to get into.
I want to thank you so much for suggesting this. I'm almost caught up with all the episodes of the podcast and I'm hooked. I just wish I had the time to follow up each episode with supplementary reading.
Don't think PhilosophyTube has been mentioned. Abby's great at taking complex topics and condensing them down to understandable discourse, and the videos are funny to boot. She used to do videos focused on philosophy but now applies that philosophy to popular subjects.
If you're still not very knowledgeable, "Sophie's World" by Jostein Gaarder is an awesome read. Don't let the fact that it's a novel fool you, it's perfect to understand who's who across philosophy's history.
Study it. Go to a university or community college. There are several offerings for adult education out there. This is 'the best' way to do it.
In case you don't want that: Take another form of couse or read a book that is made specifically to teach about the subject or give a proper introduction.
randomly reading different philosophical works won't give me much in-depth knowledge.
I'd rate reading different philosophical works much higher than reading modern summaries of philosophical movements.
I've rarely found that the generalization of an ancient philosopher brings much into my life, but often found that a specific turn of phrase or idea in their actual writing has offered a great deal.
As for recommendations, my top recommendation is Plato's The Apology which can be read in an afternoon and does a wonderful job in capturing the value of Socrates' commitment to rejection of false positives and negatives while also contextualizing the depth of that commitment against social pressures.
After that I'd recommend Leucretius's The Nature of Things mostly for the fact it's the only extant work from antiquity to have effectively proposed evolution nearly two millennia before Darwin - a detail that's frequently overlooked in the modern discussions of Epicureanism which tend to focus on its broader discussion of hedonism in the face of death.
I'd strongly recommend reading the philosophers themselves directly, sampling from each and continuing to read those that resonate with you, taking pearls of wisdom where you find them. And skip those you find insufferable to read.
This is going to sound dead obvious, but I'd honestly recommend some Intro to Philosophy/Logic/Ethics books, e.g. Logic: A Very Short Introduction or The Logic Manual. I know you're not necessarily looking at logic specifically, btw, but it's one of the regular recommendations with philosophy more generally, especially if you branch out to other thinkers.
Also a somewhat common introductory text that I personally didn't care for is Sophie's World, which acts as a narrative historical overview of Western philosophy. If you want that sort of thing you may be just as well with a text like A Little History of Philosophy, which might be available via your library.
Finally, for ethics, you might look to Hornbook Ethics and/or Justice: What's the Right Thing to Do? Besides A Little History of Philosophy, if memory serves all of these I've linked to have at one point or another been required texts for different philosophy and ethics courses depending on where one attends, so in reading these independently you'd basically be getting some intro level course education on the cheap.
Honestly though, I'd say reading the primary texts as you're doing isn't a terrible way to go about it, as that's what many philosophy courses would have you do anyway. What I would recommend alongside that is the same as I'd recommend for any older text then, which is to read up on the historical context to get a better sense of what may have influenced their writing, how they were received by their peers and broader community (if they were noticed at all during their life), and develop your understanding from there.
Sorry if this is a bit much, but I hope it helps! Be sure to check your local libraries for any of these before buying them btw, as they may have hard copies available despite not having digital copies. Also remember that college/university libraries may be an option too, albeit likely more costly if they do offer a library card to borrow materials.
Start with a survey book or course. Do not start by diving directly into the primary literature.
As far as where to start - that’s really something that should be driven by your interests. You don’t need to start with the Greeks and work your way forward.
I’d say to start with an overview of modern philosophy. It will likely be more familiar to you in terms of the problems and the thinking patterns, and might apply more directly to problems you’re interested in. If you find something that you want to learn more about, turn towards “Intro to X,” and from there branch out into the individual philosophers and their works.
I'd probably start with Socrates-Plato-Aristotle. They weren't the first, but they basically formed the framework through which we think about philosophy. As you look into specific ideas in that context, you'll find references to people who disagreed with, reinforced, and transformed their ideas. That's when I'd start going down rabbit holes one at a time based on interesting historical responses.
As a person that started by randomly reading different philosophical works, I'd actually start with general overviews. Like, you might be interested to know that the Tao Te Ching is a response to the strict rituals of Confucianism. Introduction to Classical Chinese Philosophy is an excellent book in this regard. It's like putting all these different Chinese philosophies side by side, seeing how they grew out of each other, and you get to decide which you agree with and why.
I think the context is important because you get an idea of why they said what they said. The Tao Te Ching kinda seems like it's own book, a unique ahistorical perspective of living. But, if you think that (as too many people do), then you don't understand its limitations and its strengths. So, if you don't know what problem Confucian rituals are trying to solve, then you won't really understand why the Tao Te Ching eschews rituals in favor of "living in accordance with nature". It'll just sound like some hippy nonsense (which is, admittedly, very attractive on its own).
You might do the same for Stoicism, though I don't know any resources like the above for stoicism.
If you're already at the Tao te Ching, then the Tao of Pooh is a very popular exploration of Taoism using Winnie the Pooh as an exemplar of Taoist principles.
In that vein, there are about a zillion "X and Philosophy" books, where X is a pop culture franchise, e.g. "Star Trek and Philosophy," "Star Wars and Philosophy," "Watchmen and Philosophy." All of these are collections of essays by various authors discussing philosophical subjects through the lens of popular culture. I find that it's very useful to have a set of characters and plots with which you're already familiar to use as a vocabulary to talk about heavier philosophical subjects.
I don't know as I would recommend going directly to the primary texts first off. Some of them can be read on their own merits by someone otherwise unfamiliar with the subject, but many are written in archaic or academic language that can be daunting. A class or book club can help in that regard, but just sitting down and trying to read Aristotle all by yourself may not be the easiest of going.
There are a lot of good resources in this thread, but nobody has mentioned the single most important part by far:
actually practice philosophy
Study is worthless if you don't engage in the practice of philosophy. Find people to debate with, preferably ones who have a formal grounding (and I mean a real debate, where you make reasoned arguments and investigate the truth of a matter, not the bullshit-flinging points game that gets popular online). Write arguments, revise them, give them to people to tear them apart.
The literature is good, but it will only teach you (a) how philosophers approach questions, (b) what arguments and counterarguments have been successful or popular, and (c) what the big questions are. If you do not practice philosophy, you will never learn philosophy; you will only learn what philosophers have said.
The YouTube channel Then and Now is pretty good for beginners.
CCK Philosophy is good for Nietzsche, Marx, and postmodern / continental philosophy broadly, but you'll get more out of his work after reading a bit of those first.
Ben Burgis is a Marxist who teaches logic. He's not always a great public speaker, but he's very affable and generally on point. Will interview interesting people too.
Philosophy is more of a meta science. It's people commenting on other people's thoughts all the way down.
So you won't get any actual answers on how to live, you might find how a lot of people tangled with different aspects of reality and producing their views.
If you like the ideas of stoicism and taoism you can read on those subjects. If you want a philosophic approach you learn about idea structures leading up to them and contemporary with them, like epicureanism and confucianism.
There's plenty of good advice in this thread already, so take your pick! I always found a cool vibe between presocratics and Taoist thought.
Has almost a decade of videos covering all sorts of topics. His videos are academic and to the point. He'll usually discuss the topic and motivations for the philosophical thought, then discuss any criticisms and counter examples.
Lots of good recommendations already, but my personal favorite is PhilosophyTube, both on YouTube and Nebula. The terribly depressing reality of many topics is couched by elaborate theatrical sets and costumes. At this point, there is a huge back catalog of topics that cover everything from traditional Socratic thought to modern social issues and everything in between.
Yeah but still... there's something really nice and basic about getting to know the primary sources. You can find a lot of secondary literature / handbooks / online courses / ... but it just can't compare to the original (albeit in translation). If you would ever decide to start studying philosophy in-depth you'll be glad you're already familiar with some fundamental works.