Each list takes one field and puts its books in order, from the easiest to read to the hardest, with the hours each takes. Start at the first star and climb.
Where to start with philosophy
18 books · 133 hours · difficulty 29 to 86
From What Does It All Mean? by Thomas Nagel to Critique of Pure Reason by Immanuel Kant.
Where to start with Nietzsche
10 books · 66 hours · difficulty 57 to 76
From The Antichrist by Friedrich Nietzsche to Beyond Good and Evil by Friedrich Nietzsche.
Where to start with the Greek myths
16 books · 72 hours · difficulty 21 to 64
Where to start with Dostoevsky
12 books · 129 hours · difficulty 40 to 64
From White Nights by Fyodor Dostoevsky to Demons by Fyodor Dostoevsky.
Where to start with physics and the universe
13 books · 59 hours · difficulty 22 to 44
From Astrophysics for People in a Hurry by Neil deGrasse Tyson to A Brief History of Time by Stephen Hawking.
Where to start with the classics
18 books · 132 hours · difficulty 34 to 71
From Of Mice and Men by John Steinbeck to Moby-Dick by Herman Melville.
Where to start reading again
15 books · 57 hours · difficulty 24 to 43
From Girl with a Pearl Earring by Tracy Chevalier to Misery by Stephen King.
Where to start with economics
13 books · 125 hours · difficulty 26 to 66
From Nudge by Richard H. Thaler to The General Theory of Employment, Interest and Money by John Maynard Keynes.
Where to start with psychology
17 books · 128 hours · difficulty 24 to 66
From Influence by Robert B. Cialdini to The Denial of Death by Ernest Becker.