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.

Miguel de Cervantes
Miguel de Cervantes

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.


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

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.

Portrait of Black Labrador Retriever

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.

Moby Dick, Herman Melville
Moby Dick by Herman Melville

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

11984George OrwellNovel11:22
2A Brief History of TimeStephen HawkingNon-Fiction5:46
3A Confederacy of DuncesJohn Kennedy TooleNovel13:32
4A Game of ThronesGeorge R.R. MartinNovel33:46
5A Good Man is Hard to FindFlannery O’ConnerShort Stories7:36
6A Heartbreaking Work of Staggering GeniusDave EggersMemoir13:28
7A People’s History of the United StatesHoward ZinnHistory34:08
8A Scanner DarklyPhilip K. DickNovel9:12
9A Separate PeaceJohn KnowlesNovel6:08
10A Visit from the Goon SquadJennifer EganNovel10:07
11A Wrinkle in TimeMadeleine L’EngleNovel6:27
12All the President’s MenBob WoodwardMemoir12:55
13American PastoralPhilip RothNovel15:05
14And Then There Were NoneAgatha ChristieNovel6:01
15Anna KareninaLeo TolstoyNovel35:35
16Battle Cry FreedomJames MacphersonHistory39:40
17BelovedToni MorrisonNovel12:03
18Brave New WorldAldous HuxleyNovel8:00
19Chronicles: Volume OneBob DylanMemoir5:49
20Crime & PunishmentFyodor DostoevskyNovel20:28
21David CopperfieldCharles DickensNovel33:54
22Don QuixoteMiguel de CervantesNovel39:37
23Drinking Coffee ElsewhereZ.Z. PackerShort Stories6:50
24East of EdenJohn SteinbeckNovel25:23
25Edgar Allan Poe: The Complete Short StoriesEdgar Allan PoeShort Stories16:34
26EmmaJane AustenNovel18:25
27FactotumCharles BukowskiNovel5:08
28FaustJohan Wolfgang von GoetheNovel12:45
29Fear and Loathing in Las VegasHunter S. ThompsonMemoir6:00
30Fear of FlyingErica JongNovel11:45
31Fifty-Two StoriesAnton ChekovShort Stories20:13
32For Whom the Bell TollsErnest HemingwayNovel16:17
33Friend of My YouthAlice MunroShort Stories10:03
34From Here to EternityJames JonesNovel36:50
35Goodbye to All ThatRobert GravesMemoir4:58
36Harry Potter and the Sorcerer’s StoneJ.K RowlingNovel8:18
37HatchetGary PaulsenNovel3:42
38HousekeepingMarilynne RobinsonNovel6:24
39How to Win Friends and Influence PeopleDale CarnegieNon-Fiction7:15
40In Cold BloodTruman CapoteNon-Fiction14:27
41Jane EyreCharlotte BronteNovel19:10
42KidnappedRobert Louis StevensonNovel7:20
43KimRudyard KiplingNovel11:54
44King Solomon’s MinesH. Rider HaggardNovel8:27
45Lady Chatterly’s LoverD.H. LawrenceNovel13:05
46Less Than ZeroBrett Easton EllisNovel5:37
47LolitaVladimir NabokovNovel11:28
48LullabyChuck PalahniukNovel7:15
49Midnight’s ChildrenSalman RushdieNovel24:29
50My LifeAnton ChekovNovel3:57
51Never Let Me GoKazuo IshiguroNovel9:40
52Of Human BondageW. Somerset MaughamNovel25:53
53One Hundred Years of SolitudeGabriel Garcia MarquezNovel14:04
54Over the Edge of the WorldLaurence BergreenNon-Fiction6:13
55PerfumePatrick SuskindNovel9:00
56Seven Habits of Highly Effective PeopleStephen R. CoveyNon-Fiction13:04
57So Long, See You TomorrowWilliam MaxwellNovel6:02
58Stranger in a Strange LandRobert A. HeinleinNovel16:17
59Team of RivalsDoris Kearns GoodwinHistory41:32
60Th Brothers KaramazovFyodor DostoevskyNovel43:06
61The Adventures of Augie MarchSaul BellowNovel22:13
62The Adventures of Huckleberry FinnMark TwainNovel9:44
63The AlchemistPaulo CoelhoNovel4:00
64The Amazing Adventures of Kavalier & ClayMichael ChabonNovel26:20
65The Autobiography of Benjamin FranklinBenjamin FranklinMemoir6:35
66The Best and the BrightestDavid HalberstamHistory37:04
67The CorrectionsJonathan FranzenNovel21:53
68The CrossingCormac McCarthyNovel14:41
69The Crying of Lot 49Thomas PynchonNovel6:14
70The Executioner’s SongNorman MailerNon-Fiction42:37
71The Guns of AugustBarbara W. TuchmanHistory19:09
72The Hitchhiker’s Guide to the GalaxyDouglas AdamsNovel5:51
73The Hunchback of Notre DameVictor HugoNovel22:15
74The Killer AngelsMichael ShaaraNovel13:44
75The Kite RunnerKhaled HosseiniNovel12:01
76The Liars’ Club: A MemoirMary KarrMemoir4:08
77The Lion, The Witch, and the WardrobeC.S. LewisNovel4:21
78The Long GoodbyeRaymond ChandlerNovel13:25
79The Maltese FalconDashiell HammettNovel7:05
80The MoonstoneWilkie CollinsNovel18:45
81The Naked and the DeadNorman MailerNovel26:14
82The Picture of Dorian GrayOscar WildeNovel8:35
83The Right StuffTom WolfeHistory15:42
84The Rise and Fall of the Third ReichWilliam L. ShirerHistory57:11
85The Secret HistoryDonna TarttNovel22:03
86The Selfish GeneRichard DawkinsNon-Fiction16:12
87The Sound and the FuryWilliam FaulknerNovel8:51
88The Spy Who Came in From the ColdJohn le CarreNovel7:00
89The StandStephen KingNovel47:47
90The StrangerAlbert CamusNovel3:27
91The Sun Also RisesErnest HemingwayNovel7:46
92The Thirty-Nine StepsJohn BuchanNovel3:53
93The Three MusketeersAlexandre DumasNovel23:32
94The TrialFranz KafkaNovel8:53
95The Wealth of NationsAdam SmithNon-Fiction36:43
96The Wind-Up Bird ChronicleHaruki MurakamiNovel26:11
97The Year of Magical ThinkingJoan DidionMemoir5:05
98This Boy’s LifeTobias WolffMemoir10:01
99To the LighthouseVirginia WoolfNovel6:37
100Tropic of CancerHenry MillerNovel10:01
101UlyssesJames JoyceNovel27:16
102UnderworldDon DeLilloNovel31:22
103Valley of the DollsJacqueline SusannNovel17:39
104Waiting for GodotSamuel BeckettPlay2:02
105White TeethZadie SmithNovel18:38
106Wuthering HeightsEmily BronteNovel12:32