October 18, 2025
20 BOOKS

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A Reading List for the Grafters and Dreamers
By Tommy Kennedy IV — www.tommykennedyiv.com

Twenty books that’ll toughen your mind, feed your heart, and remind you that strength isn’t just in your hands — it’s in the words that stay with you. These stories aren’t school stuff. They’re life lessons dressed in paper and ink.

You’ve just finished a long shift. Cement dust on your boots, knuckles sore from the bag. You drop into a chair, the world humming round your head, and you wonder what it’s all about. These books — twenty of them — are your sparring partners. They’ll make you think, laugh, fight, and feel. Some will jab your heart, some will heal you slow.

Let’s step into the ring.

1. Of Mice and Men — John Steinbeck
Two men chasing a dream that keeps slipping away. Friendship, loyalty, and the ache of hope when the world’s stacked against you. Short, sharp, and straight to the gut.

2. The Catcher in the Rye — J.D. Salinger
Holden Caulfield’s seventeen, angry, lost, and fed up with fakes. You’ll get him right away. It’s that restless feeling you know too well — stuck between the life you’ve got and the one you’re chasing.

3. The Old Man and the Sea — Ernest Hemingway
An old fisherman takes on the sea with nothing but pride and grit. Every hit knocks him down, but he keeps swinging. That’s boxing. That’s bricklaying. That’s life.

4. Trainspotting — Irvine Welsh
Raw, filthy, and real as concrete dust. A gang of lads chasing highs and losing hope in Edinburgh. Makes you thankful for your own fight, for every hard-earned breath.

5. 1984 — George Orwell
Truth under attack, freedom strangled by power. Orwell saw it coming. Read it and you’ll see the world differently — who’s pulling strings, who’s asleep, and who’s awake.

6. A Clockwork Orange — Anthony Burgess
A violent, mad ride through rebellion and control. The slang feels strange till it sings. It asks if being forced to be good makes you less human. Deep, dark, unforgettable.

7. The Road — Cormac McCarthy
A father and son walking through a dead world. No comfort, just love and survival. You’ll feel the cold in your bones but the warmth in your chest. It’s about keeping your inner fire burning when everything around you’s gone.

8. Down and Out in Paris and London — George Orwell
Before he was famous, Orwell was skint, scrubbing dishes and sleeping rough. He saw what struggle really looks like. Every line smells of sweat, smoke, and survival.

9. To Kill a Mockingbird — Harper Lee
A young girl watches her dad stand up against hate and lies. Quiet courage, the kind that doesn’t need shouting. Teaches you about justice, decency, and what it means to stay human in a loud world.

10. The Outsiders — S.E. Hinton
Gangs, loyalty, heartbreak, and pride. Written by a teenager about teenagers. Ponyboy’s tough and tender all at once. It’s working-class youth with all its scars and heart.

11. The Grapes of Wrath — John Steinbeck
Families on the move, hungry but proud. Dignity in the dirt. A masterpiece that reminds you what it means to keep your head high when the world wants you crawling.

12. Shantaram — Gregory David Roberts
A convict on the run finds redemption in the chaos of Bombay. Big, bold, and full of heart. It’s about falling, forgiving, and standing tall again — the fight to stay human.

13. On the Road — Jack Kerouac
Freedom, jazz, open highways, and a restless soul. The urge to move, to break out, to live wild before life tames you. Makes you want to chase your own truth before it fades.

14. The Power of One — Bryce Courtenay
A small boy learns to box and to fight hate with brains as well as fists. It’s courage, discipline, and destiny in one punch. Every page feels like training for something bigger than the ring.

15. One Flew Over the Cuckoo’s Nest — Ken Kesey
A madman in a mental ward shakes up the system. It’s about rebellion, spirit, and refusing to let authority break your soul. You’ll be cheering by the end.

16. Lord of the Flies — William Golding
A bunch of boys stranded on an island turn savage. You see how thin civilisation really is — one bad day away from cracking. Brutal, clever, and honest about what humans are capable of.

17. The Brief Wondrous Life of Oscar Wao — Junot Díaz
Fast, funny, tragic, and wild. A cursed life full of love and pain, told with swagger and rhythm. You’ll read it like a heartbeat — fast and alive.

18. A Kind of Loving — Stan Barstow
A northern lad trying to balance love, work, and small-town pressure. Honest as a bruise. Every wrong turn feels like your own. It’s about class, pride, and growing up the hard way.

19. Fight Club — Chuck Palahniuk
It’s not really about fighting. It’s about men searching for something real in a fake world. Raw, funny, brutal, and smarter than you expect.

20. The Alchemist — Paulo Coelho
A dreamer follows the signs across the desert, only to find his treasure was inside him all along. Simple words, deep truth. It’ll light something in you if you let it.

Final Round
These books aren’t homework — they’re life training. Each one teaches you how to fight, think, love, and stand taller. Read them between shifts. Between rounds. Between the noise.

Because stories build you from the inside out.

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