> Does anyone have a recommendation or a reading list in the classics (perhaps a Coursera or something) where I can self-study? I'm tech by trade and education but I would love to read the greats through the last several millennia in the western canon.

I'm "well educated" in the classics by most standards (I studied Latin for the better part of the decade, can spot recite poems and speeches, &c) and I think that reading "the greats" as a whole is a kind of category error: classical antiquity is a period of 1.5 millennia spread across the better part of Southern Europe and Northern Africa. Reading them as a uniform narrative is like trying to draw a line from the beginning of the Ottoman Empire to the California Gold Rush: the history is all there, but a thematic connection is tenuous.

If you want to read classics in general, I suggest picking a subject you like (plays, epics, poetry, military history) and expanding in circles. You can even pick a modern author as a guide; I can personally recommend both SPQR[1] and Introducing the Ancient Greeks[2] as excellent histories of their respective cultures.

[1]: https://www.goodreads.com/book/show/28789711-spqr

[2]: https://www.goodreads.com/book/show/23316534-introducing-the...