Being comfortably in middle age, something I’ve wanted to do for years is conquering one of those 100 books everyone should read lists. They’re all over the internet, from Esquire, to Business Insider, and everywhere in between.

Problems, Problems, Problems

The problems for me though are myriad. First, I’m a slow reader. Sometimes it takes me several weeks to slog through a book that’s easy to read, let alone a magnum opus like The Brothers Karamazov or Don Quixote, which could take several months. At that rate I’d spend the rest of my life and only make it halfway through the list.

Secondly, like many people, I don’t have an endless amount of time to devote to reading. I have a wife and kids and I can’t lock myself away night after night for years on end just to read. Something had to give, and up to this point in my life, it’s been reading.

Still, I’m determined to enrich and empower and educate myself, and there is no better avenue to accomplish those goals than reading. A while back I attempted something similar, challenging myself to read twenty books in a year. I failed miserably. I barely finished five books and found myself disgusted by the lack of commitment to my goal.

Solutions

The following year, I challenged myself again, this time upping the ante to twenty-five books. The difference was I wasn’t going to read the books, but I was going to listen to them instead, on Audible.com.

This solved two of my biggest problems. First, listening helped me avoid the problems associated with slow reading. When I read, my mind can wander, and I end up flipping through pages and reading different passages over and over. When all I’m able to do is listen, this problem is eliminated. My mind stops wandering to concentrate on what’s being said. Plus, there’s no easy way to go back and read sections repeatedly.

Listening instead of reading allows me to do two things at once. My day typically starts with a thirty-minute walk. Instead of just walking, I realized I can “read’ as well. I also take Dublin, my black Labrador Retriever, for several walks a day. That adds even more time to read.

Driving While Listening

I also have a job that requires a lot of driving. Instead of listening to mindless sports radio debates, I began listening to audio books. This added another five hours per week to my “reading” time with no other cost.

Overall, I had about ten hours a week where I could “read” that didn’t stop me from doing things I was already doing. Listening to audio books allowed me to effectively multi-task. This allowed me to achieve my goal of finishing twenty-five books in a single year.

Part of me thought listening instead of reading was cheating. I felt guilty that I was listening instead of putting my head down and doing the challenging work of reading. Studies have shown however, that when it comes to comprehension there isn’t any significant difference between listening and reading. For my goals of enriching and educating myself, I didn’t see any point in making a distinction.

The Plan

With that thought in mind, I put together a five-year plan to listen to 100 books. That works out to twenty a year, and since I’d already listened to twenty-five in a year once before, that seemed like a realizable goal.

The next step was choosing 100 books to read. Most book lists I’d come across included a number of classic books that I’d read in high school and college. I had no interest in re-reading any books, so this eliminated twenty or so books from most existing lists right off the bat.

Culling together titles from a number of sources, I finally produced my very own list of 100 books to listen to. I like to think my list covers a wider gamut of books than most other lists out there. My list includes a fair share of classics, but also includes history, memoirs, and other types of non-fiction books. Modern books are part of my list as well. While some of these books might not be viewed as classics today, hopefully in time they will. Overall, my list is quite diverse and well-rounded, and hopefully will allow me to broaden my horizons and expand my point of view over the next five years.

The Final List

One other thing, my list turned out to be 106 books. I found drawing the line and keeping it to just 100 hard to do. As I start reading these books, if the inspiration strikes or if I feel like I have insight to share, I do plan to offer additional commentary on this blog.

Without further ado, below is my list of 106 books to listen to over the next five years.

106 Books Every Middle-Aged Man Should Read

#	Title	Author	Type	Duration
1	1984	George Orwell	Novel	11:22
2	A Brief History of Time	Stephen Hawking	Non-Fiction	5:46
3	A Confederacy of Dunces	John Kennedy Toole	Novel	13:32
4	A Game of Thrones	George R.R. Martin	Novel	33:46
5	A Good Man is Hard to Find	Flannery O’Conner	Short Stories	7:36
6	A Heartbreaking Work of Staggering Genius	Dave Eggers	Memoir	13:28
7	A People’s History of the United States	Howard Zinn	History	34:08
8	A Scanner Darkly	Philip K. Dick	Novel	9:12
9	A Separate Peace	John Knowles	Novel	6:08
10	A Visit from the Goon Squad	Jennifer Egan	Novel	10:07
11	A Wrinkle in Time	Madeleine L’Engle	Novel	6:27
12	All the President’s Men	Bob Woodward	Memoir	12:55
13	American Pastoral	Philip Roth	Novel	15:05
14	And Then There Were None	Agatha Christie	Novel	6:01
15	Anna Karenina	Leo Tolstoy	Novel	35:35
16	Battle Cry Freedom	James Macpherson	History	39:40
17	Beloved	Toni Morrison	Novel	12:03
18	Brave New World	Aldous Huxley	Novel	8:00
19	Chronicles: Volume One	Bob Dylan	Memoir	5:49
20	Crime & Punishment	Fyodor Dostoevsky	Novel	20:28
21	David Copperfield	Charles Dickens	Novel	33:54
22	Don Quixote	Miguel de Cervantes	Novel	39:37
23	Drinking Coffee Elsewhere	Z.Z. Packer	Short Stories	6:50
24	East of Eden	John Steinbeck	Novel	25:23
25	Edgar Allan Poe: The Complete Short Stories	Edgar Allan Poe	Short Stories	16:34
26	Emma	Jane Austen	Novel	18:25
27	Factotum	Charles Bukowski	Novel	5:08
28	Faust	Johan Wolfgang von Goethe	Novel	12:45
29	Fear and Loathing in Las Vegas	Hunter S. Thompson	Memoir	6:00
30	Fear of Flying	Erica Jong	Novel	11:45
31	Fifty-Two Stories	Anton Chekov	Short Stories	20:13
32	For Whom the Bell Tolls	Ernest Hemingway	Novel	16:17
33	Friend of My Youth	Alice Munro	Short Stories	10:03
34	From Here to Eternity	James Jones	Novel	36:50
35	Goodbye to All That	Robert Graves	Memoir	4:58
36	Harry Potter and the Sorcerer’s Stone	J.K Rowling	Novel	8:18
37	Hatchet	Gary Paulsen	Novel	3:42
38	Housekeeping	Marilynne Robinson	Novel	6:24
39	How to Win Friends and Influence People	Dale Carnegie	Non-Fiction	7:15
40	In Cold Blood	Truman Capote	Non-Fiction	14:27
41	Jane Eyre	Charlotte Bronte	Novel	19:10
42	Kidnapped	Robert Louis Stevenson	Novel	7:20
43	Kim	Rudyard Kipling	Novel	11:54
44	King Solomon’s Mines	H. Rider Haggard	Novel	8:27
45	Lady Chatterly’s Lover	D.H. Lawrence	Novel	13:05
46	Less Than Zero	Brett Easton Ellis	Novel	5:37
47	Lolita	Vladimir Nabokov	Novel	11:28
48	Lullaby	Chuck Palahniuk	Novel	7:15
49	Midnight’s Children	Salman Rushdie	Novel	24:29
50	My Life	Anton Chekov	Novel	3:57
51	Never Let Me Go	Kazuo Ishiguro	Novel	9:40
52	Of Human Bondage	W. Somerset Maugham	Novel	25:53
53	One Hundred Years of Solitude	Gabriel Garcia Marquez	Novel	14:04
54	Over the Edge of the World	Laurence Bergreen	Non-Fiction	6:13
55	Perfume	Patrick Suskind	Novel	9:00
56	Seven Habits of Highly Effective People	Stephen R. Covey	Non-Fiction	13:04
57	So Long, See You Tomorrow	William Maxwell	Novel	6:02
58	Stranger in a Strange Land	Robert A. Heinlein	Novel	16:17
59	Team of Rivals	Doris Kearns Goodwin	History	41:32
60	Th Brothers Karamazov	Fyodor Dostoevsky	Novel	43:06
61	The Adventures of Augie March	Saul Bellow	Novel	22:13
62	The Adventures of Huckleberry Finn	Mark Twain	Novel	9:44
63	The Alchemist	Paulo Coelho	Novel	4:00
64	The Amazing Adventures of Kavalier & Clay	Michael Chabon	Novel	26:20
65	The Autobiography of Benjamin Franklin	Benjamin Franklin	Memoir	6:35
66	The Best and the Brightest	David Halberstam	History	37:04
67	The Corrections	Jonathan Franzen	Novel	21:53
68	The Crossing	Cormac McCarthy	Novel	14:41
69	The Crying of Lot 49	Thomas Pynchon	Novel	6:14
70	The Executioner’s Song	Norman Mailer	Non-Fiction	42:37
71	The Guns of August	Barbara W. Tuchman	History	19:09
72	The Hitchhiker’s Guide to the Galaxy	Douglas Adams	Novel	5:51
73	The Hunchback of Notre Dame	Victor Hugo	Novel	22:15
74	The Killer Angels	Michael Shaara	Novel	13:44
75	The Kite Runner	Khaled Hosseini	Novel	12:01
76	The Liars’ Club: A Memoir	Mary Karr	Memoir	4:08
77	The Lion, The Witch, and the Wardrobe	C.S. Lewis	Novel	4:21
78	The Long Goodbye	Raymond Chandler	Novel	13:25
79	The Maltese Falcon	Dashiell Hammett	Novel	7:05
80	The Moonstone	Wilkie Collins	Novel	18:45
81	The Naked and the Dead	Norman Mailer	Novel	26:14
82	The Picture of Dorian Gray	Oscar Wilde	Novel	8:35
83	The Right Stuff	Tom Wolfe	History	15:42
84	The Rise and Fall of the Third Reich	William L. Shirer	History	57:11
85	The Secret History	Donna Tartt	Novel	22:03
86	The Selfish Gene	Richard Dawkins	Non-Fiction	16:12
87	The Sound and the Fury	William Faulkner	Novel	8:51
88	The Spy Who Came in From the Cold	John le Carre	Novel	7:00
89	The Stand	Stephen King	Novel	47:47
90	The Stranger	Albert Camus	Novel	3:27
91	The Sun Also Rises	Ernest Hemingway	Novel	7:46
92	The Thirty-Nine Steps	John Buchan	Novel	3:53
93	The Three Musketeers	Alexandre Dumas	Novel	23:32
94	The Trial	Franz Kafka	Novel	8:53
95	The Wealth of Nations	Adam Smith	Non-Fiction	36:43
96	The Wind-Up Bird Chronicle	Haruki Murakami	Novel	26:11
97	The Year of Magical Thinking	Joan Didion	Memoir	5:05
98	This Boy’s Life	Tobias Wolff	Memoir	10:01
99	To the Lighthouse	Virginia Woolf	Novel	6:37
100	Tropic of Cancer	Henry Miller	Novel	10:01
101	Ulysses	James Joyce	Novel	27:16
102	Underworld	Don DeLillo	Novel	31:22
103	Valley of the Dolls	Jacqueline Susann	Novel	17:39
104	Waiting for Godot	Samuel Beckett	Play	2:02
105	White Teeth	Zadie Smith	Novel	18:38
106	Wuthering Heights	Emily Bronte	Novel	12:32