There are so many lists of books to read before you die, or before you turn 30, or before your job sucks the life out of you. But you probably wouldn’t need to depend on a list from someone else if you could just figure out how to pick your own.

The best way to get good at picking books to read is to know when you’re picking badly. And, believe it or not, this does not have as much to do with the quality of the book itself as it does with whether you are the wrong person to be reading that particular book. I’ve learned this by watching my own history of picking bad books. Here are the five biggest missteps in my literary life:

1. Nancy Drew and the Secret of the Old Clock
I was a latchkey kid with no TV. On top of that, we lived in a rich neighborhood where not a lot of other families had working moms, so kids were not allowed to come to my house, and there was no one to drive me to other kids’ houses. That circumstance put me at the library on most of my after-school days. I read a lot of great books; kids who hang out with librarians get the inside track.

But left to my own devices, I’d often pick up some Nancy Drew books. I started with number one—The Secret of the Old Clock. And I never stopped. I liked that they had an order, so I always knew which to pick next, and I could read them with only partial attention because every book was really the same story.

The reason they were such a waste of time is that what I was really looking for was a way to vegetate, escape my own reality and not have to think so much. What I was really looking for was a good TV show. I should have just told my parents. “Normal kids have a TV and we need one too, because I keep reading about the constipated relationship between Nancy and Ned and it’s bad for me.”

2. Wifey
Surely you’ve all read a Judy Blume book. And surely, you have read the two-minutes-in-the-closet scene with Philip Leroy many times. For a fourth grader, the kiss is very exciting. By the end of fourth grade I had finished all the Judy Blume books for kids. Including Forever, which really, I cannot recommend enough to girls who want to read about steamy sex between kids who your parents would think are okay to be friends with.

After Forever I still wanted more, so I wandered through the library and I found that there was an adult book by Judy Blume: Wifey. I spent many hours trying to figure out what was going on. To give you an idea of how lost I was, I spent lots of time just pondering the cover: It’s a woman’s bare stomach and she is taking off her wedding ring. I wondered and wondered: Is she wearing a bikini? I read the book twice and have no memory of what it’s about.

It is definitely good to read a little beyond your knowledge in any given subject area. But Bain Consulting has great reaserch from their mentoring program to show that you want information that is just beyond you, but not too far beyond. So Bain gives young people mentors who are 3-5 years ahead of them in the workplace. I should have done the same with my sex education books; I would have learned a lot faster.

3. The History of Tudor England. All of it.
I took modern history in high school and somehow got the teacher who was so bad at pacing that all we got through was Tudor England. I memorized every date of every head that rolled and much much more and got an A. So I took AP world history, and got the same teacher, and it seems that the AP part is just that you memorize more Tudor minutia.

Today, of course, it’s all online so I don’t need it in my head. And anyway, the teacher was fired for placing horse bets from the high school phone.

But wait. There was an important concept: Henry VIII was a religious reformer because he wanted to be able to divorce his wife and marry another woman. So Anglicanism is a pet project from him to enhance his sex life, and still, today, the British are Anglican. It is the same as the Americans who wanted to get out of British tea taxes and then, as an afterthought, started philosophizing about unalienable rights. Maybe all big ideas start out as small-minded selfish ideas.

4. The Odyssey
I actually reference this book—Wait! No! All you literature snobs, be still! I know, it’s a poem, not a book. Anyway, I reference this book all the time. I say that it’s important to have a literary canon that we all share so that we can have a common set of references to talk about other topics. For example, learning about sex with Judy Blume. Really, it’s a travesty that more people have read the Odyssey than Forever. But if you want to be part of a common language of cultural references, you need to be able to talk about the Odyssey because it’s on every college freshman reading list in the world.

The thing is you don’t really have to read the Odyssey in order to be able to refer to it in a way that tells people you share an understanding. You can just know the important characters. Don’t believe me? Sometimes people call me Pen-a-lope instead of Penelope. And I think, “You did not go to an accredited college.”

5. A Theory of Social Justice
Another great book. For someone who is going to be a philosopher. On a bad day I ask myself how I could have spent so much time reading political philosophy. It did not stop at Rawls. Ackerman, Novak, Walzer. All the big ones, all impossible to understand in one reading, and all take so much time that I could have read all of British literature in the same amount of time.

Which is my point. I should have been reading the literature, because that’s what would have really engaged me, but I was nervous that novels and poetry paved the road to nowhere. I loved reading poetry and fiction in college, but I worried that those classes were for people who were not as academically studly as I was, so I took classes just because they were hard. I knew I could get As, so I wanted to do it in hard classes. Now I see, though, that if I’m reading a book to impress someone, I shouldn’t be reading the book. Books are best for figuring out what you love and what makes you think deeper.

Of course, someone is asking, “What about having fun?” And I have written before about how fun isn’t my forte. But People magazine is fun. And I read that. And more importantly, books can fill a ton of needs, even fun, but when you read, you need to know what you’re looking for to make sure you get it. There are a lot of things to read in this world, and relatively little time to do it in, so you should pick your books carefully. Even the ones that are just for fun.