The world at large has no shortage of armchair philosophers.

What is my purpose in life? What is the meaning of life? How does consciousness work? What is being? How can we truly know anything?

If you’re human, you’ve probably wondered about these things at some point or another. Maybe after a few glasses of wine, an ego-shattering trauma, or while staring pensively into the spacious night sky.

Maybe the expansive uncertainty of the question quickly overwhelms you, like it often does to me, and you quickly avert your attention to the latest shenanigans happening on Twitter or Instagram.

Swoosh. Your mind automatically coalesces back into the unending stream of digital status games.

It’s easy to pile in on the latest Snowflake IPO or TMZ controversy. It’s much more uncomfortable to traverse the unraveling strings of larger questions that slide you down a bottomless pit of uncertainty.

Lately, i’ve been pining to surrender to this bottomless pit. Since quarantine, i’ve felt the once omnipresent nature of life stuffed into browsers, Zoom calls, and text bubbles.

The gravity towards these form factors usurp the serendipity of face to face conversations that delightfully turn deep. The moments of philosophical awe transpired from a melting sun or expansive forest.

Despite living through one of the most existential periods in human history, there’s less surface area in life to think deeply about the questions that arise when we’re truly alone with ourselves.

How do we make more room in our lives to ponder deep questions without slipping helplessly into a bottomless pit?

With some structured guidance hopefully.

Writers like Tim Ferris, Mark Manson, Alain de Botton and Ryan Holiday have all attempted to make philosophy accessible to the “modern person”. (btw, where are the women??)

In line with our diminishing attention spans, listicles are made on “The top quotes on Stoicism” or “Plato’s thoughts on productivity”. Even reading articles like mine right now. Like fast food, one might feel “enlightened” after reading this content. But the “philosophical high” quickly fades in lieu of a deeper grasping of its core foundational underpinnings.

So why not go straight to the primary source?

I decided recently to create a philosophy syllabus for myself completely comprised of essays and books (by dead people, preferably - the deader the better). Here’s a few resources I used to build my book list:

• Reddit: I’m interested in philosophy where should I start?
• Reddit’s recommended philosophy reading list here and here
• MIT’s linguistics and philosophy course and Introduction to Philosophy: God, Knowledge and Consciousness
• OpenSyllabus.org scrapes college curriculum across 6,059,459 syllabi and you can look up what books top colleges are using in their philosophy curriculums
• I also enrolled in my dad’s college-level “Intro to Philosophy course” - all currently online.

For the next few issues, I plan on sharing what i’m learning and my personal syllabus of collected books.

Learning in public hopefully keeps me accountable and attracts more weirdos like me into my orbit (No hard feelings if you want to unsubscribe 😆).

Signing off with a few questions for you:

• Do you feel intellectually satiated with the content you’re reading today?
• Is there something you want to make time to learn deeply?
• What are some recent deep questions you want to lean into? How can you make it more comfortable to do so?

If yes, hit reply. I’d love to hear about it and share your deep musings in the next newsletter (anonymously of course!) :)

- Patricia