10 Books That Will Help You Creatively


First off, I love reading. Especially in the last year, I’ve read more than anyone I’ve met. This is not to brag, but it feels like it. This means a few things. It means I feel like I am an in a privileged position to recommend books that are comparatively good to other books I’ve read. It also means that if you recommend a book, it is very likely that I’ll try to read it. Please recommend books to me.

Reading with the intention to improve your creative thinking doesn’t really work. You have to stumble upon it. Reading a book about creativity won’t really help you think creatively. What does it mean to think creatively anyway? Well, it helps to expose you to new approaches to thinking about old problems. Not even old problems, it helps expose you to new approaches of thinking, period. You can then contrast this with the old ways of thinking, the old ideas you had about things. By approaching new ways to thinking about something and exposing yourself to enough points of view, you will start to have new ideas. Your new ideas will flirt with old ideas, and then some idea magic happens and you will have truly insightful ideas. Your new idea babies are the keys to creativity.

Outside sources and material can’t tell you how to be creative. Creativity doesn’t come externally – the job of the external influences is to open up a space for you to think and create. To create this space, you have to expose yourself to many different and novel points of view. You have to open up a space to let your mind run wild. If the space is too big you can’t really decide what direction to go. If the space is too small, it’s a straightjacket – a glass ceiling to your ideaphoria.

The following books helped me open up this space.

1. Zen and the Art of Motorcycle Maintenance

Robert Pirsig’s theories on everything. On how the world works – morality, philosophy, metaphysics, etc. They are incredible and you may have to read them multiple times. He uses biography of a seemingly ordinary person as a means of anthropological cultural analysis and exploration while at the same time criticizing anthropology while at the same time explaining all of existence in terms of his critique on anthropology and biology.

2. The Book On the Taboo Against Knowing Who You Are

Alan Watts is Amazing with a capital A. He would have been a cool uncle to have. This book singlehandedly changed the way that I view the world more than any other sum of books I have ever read. It also unlocked a whole separate category of literature for me – spiritual and metaphysical texts. Written simply enough to give you the tools to have an intelligent conversation about enlightenment with someone else. And maybe even feel it for yourself.

If it feels like you are walking a tightrope in your life trying to get to some better destination, this book will make you jump into the abyss and show you that you can fly over it if you want to.

3. Play it Away

Charlie Hoehn talks about ridding himself of his anxiety and workaholism by reengaging with his childlike ability to play and playing homerun derby. I know, I know, this sounds stupid at first. The book is actually more of a philosophical text on how to start playing more in our lives and doing things that we enjoy regularly. When you play, you aren’t really trying. You lose all societal inhibitions. You aren’t thinking about other people’s opinions. Combined with Alan Watts’ book above, this is a great text to figuring out how to get more “play” in our life.

4. The Short Stories of Ernest Hemingway

Good short stories are amazing. They let your imagination run wild. What the hell was it about? How many different themes is it tapping into? Because of the ambiguity and variability of the interpretation of short stories, good short stories give you the room to ponder about what a short story was trying to say.

5. On the Road

Jack Kerouac is pure flow. Poetry. Once sentence can stretch to a several page long word vomit not dissimilar to freestyle rap or jazz or whatever else it is that people do in flow. He wrote the original version of this book in twenty days. TWENTY DAYS. This gives you a taste of how to completely uninhibit yourself when you are doing something. To not think about it and just jump in and start letting what will happen, happen.

6. Infinite Jest

This thing is a behemoth. There is so much to it. I think David Foster Wallace’s real goal was just to make us self-aware, but the way in which he does it is to expose us to many different versions of ourselves that can resonate with us. This book is the ultimate Rorschach test. You find yourself in it no matter what. You find out more about yourself by finding out what in this book resonates with you and what you remember about the book.

7. The Tim Ferriss Collection

Tim Ferriss redefines what is possible in our ordinary lives. Part self-help, part career advice, part creativity expert himself, what Tim can do more than anything is help you wonder what you can do differently in your own life. He presents interesting ideas between differentiating between success and effectiveness, too. An extremely intelligent person who himself has been exposed to many different points of view, he his an excellent reference if you need inspiration for or want to figure out how to do, well, anything.

8. Demian

I love Herman Hesse. His novellas are awesome. He delves into different levels of the self and chronicles how a boy grows up from a primary school youth to a university student and how his understanding of life changes at each phase in his development. Similar to Boyhood (which everyone, really, everyone, needs to see), but deeper.

9. Intuition: Knowing Beyond Logic

So, so easy to read. This doesn’t detract from the book. It actually adds to it. That is the genius of Osho, and similarly to Alan Watts he will make you start to recognize parts of yourself that you never knew existed. A how to guide for listening to what your intuition is telling you. And you do have intuition. It’s really hard to describe this book in a blurb.

10. Steve Jobs

Monumental. This biography is amazing. A very polarizing how-to-guide for how to do things and how not to do things like Steve Jobs. His intensity, intuition, and no bullshit attitude allowed him to almost single handedly revolutionize six different industries. Really, this is just a guide on how to trust yourself.

I need new book recommendations.