I don’t usually come down hard on books. I mean, I like to point out when something falls short or misses the mark, but my last read, Right Thing, Right Now, left me cold. Part of it, I think, is because I expected more from Ryan Holiday.
When I look at a book, I judge it by one simple thing—whether it makes me want to read it again. In short, does it have a strong re-readability quotient? If it pulls me back in, my money and time were not wasted. That’s what good books do. They stick with you.
A classic remains a classic because it draws you in, even years later. Picture a book you once found in your grandfather’s personal library. You read it, loved it, and shared that love with your father and grandfather. As you grow older, you read it again, and it shows you something new.
Then, one day, long after your grandfather is gone, you’re working, raising kids, and you stumble upon that same book. Without thinking, you pull it off the shelf and start flipping through it. It still has something to offer, just like it did before. The only difference is what you learned as a kid is different from what it teaches you now.
The Lindy Effect and Timeless Books
This brings to mind something Nassim Nicholas Taleb wrote about in his 2012 bestseller Antifragile. He called it the Lindy Effect: the longer something has been around, the more likely it is to stick around. This applies to books in an almost magical way.
A book that grips you never fades away. It’ll always be passed from one reader to the next. Bookshops will keep stocking it. Professors won’t stop praising it. Writers in the future will look back and reference it, fortifying its legacy. And, publishers will keep their presses whirring, year after year, printing more copies.
Take George Orwell’s 1984. Written in 1949, the book paints a grim picture of a dystopian future, yet it feels more relevant now than ever. That’s the Lindy Effect in action.
A book like 1984 wasn’t just important in its time—it has outlived its era. It continues to shape how we talk about power, control, and surveillance. Each time a new generation picks it up, they find something new to worry about or think about. And that’s why it lasts.
1984 has become part of our collective consciousness. The durability of its influence lies in its ability to adapt and remain relevant as the world changes. That’s what gives it its staying power. You don’t just read 1984 once, you read it again as the world shifts around you, and each time, it says something different, something new.
Identifying the Next Timeless Classic
This brings me to a book I’ve just started reading, The Hard Thing About Hard Things by Ben Horowitz. It’s a decade-old book, but I’ve already seen it start to work its way into conversations the same way the classics do.
I never read it when it first came out, but I kept hearing about it. Podcasts, book recommendations, conversations with colleagues—it seemed like everyone who’s had to navigate the difficult, messy realities of building and running a business was talking about it.
That’s the Lindy Effect at work again.
A good book finds its way into the hands of people who need it, and before long, it becomes part of the conversation, passed from one person to the next.
What struck me about The Hard Thing About Hard Things is that it’s not just about business principles—it’s about life, leadership, responsibility, fear, and failure. These are things people will always face, whether they’re running a startup today or leading a company fifty years from now. That’s why this book is a contender for Lindy’s legacy.
I see The Hard Thing About Hard Things becoming a classic for future generations of entrepreneurs. People will keep recommending it, and it will keep getting referenced in business schools, documentaries, and articles. It’s a book that will stay on shelves for years to come, not because it’s flashy or trendy, but because it offers something deeper, something lasting.
What Books Do You Think Deserve the Lindy Legacy?
Good books transcend their time. They survive, not because they were popular at one point, but because they offer something essential that readers need repeatedly. It’s why we keep returning to books like 1984, and I suspect we’ll be talking about The Hard Thing About Hard Things for years to come.
So, what books do you think deserve the Lindy legacy?
Which stories keep drawing you back, offering something new each time? I’d like to hear about them. As for me, I’ll be finishing Ben Horowitz’s book soon and will share my thoughts. From what I’ve read so far, it seems like a book that will stick with me.
©BookJelly. All rights reserved
Lindy effect? I like it. My vote goes for Jane Eyre and To Kill a Mockingbird.
Hi Pam, Before citing 1984 as an example, I had ‘To Kill a Mockingbird’ in mind. Funny how that happens.