Updated 8/5/17

Earlier this week I shared with The Writing Rundown crew a basic schedule I adhere to that allows me to get in 3-5 hours of reading daily.

While attending yoga classes, meeting friends for meals and hanging out, writing for 2-3 hours…and running Craft Your Content. Needless to say, I like to get a lot of time out of my days, and only occasionally “waste time” to go on day-long Netflix binges during which I never change out of my jammie pants. But oh, believe me, there are days I go on day-long Netflix binges!

The whole message came about after a friend said to me “Your GoodReads account is like my aspirational reading.”

For a minute, I was flattered, thinking my friend was gushing at my discerning tastes and brilliant literary selections.

“How do you read SO MUCH?!”

Ah, yes, the ever popular quantity over quality quandry. As recent American political discussions have shown, bragging about the size of something often evokes a more popular rapture and interest than the quality of what is at hand.

In The Writing Rundown (do you get this delivered direct to your inbox every other weekend? If not, get on that!), I discussed how I was able to make time for reading so much. Which I appreciate, because a world full of people who are making more time in their lives for reading and learning is a world I want to be a part of.

But there is a growing trend, based in part to the rise of self-publishing and Kindle and Audible, for people to consume mass quantities of books without ever really learning anything from them. Or applying the information they have learned.

Morgan Housel recently wrote for The Motley Fool about curating an anti-reading list, and knowing what to avoid:

Reading is powerful because it opens your mind up to new ideas you hadn’t thought of before. We’re all a little malleable in that way. But this can be equally dangerous if you’re reading nonsense, bull, drivel, gossip, or other stuff that opens your mind up in ways you’ll eventually regret. There’s an important difference between “reading lots of stuff from a variety of fields” and “reading every word in front of my eyes.”

What’s your favorite book?

I get asked a lot what some of my favorite books are, which is just about the meanest question that someone can ask a person who reads a lot. It’s like when people ask me where my favorite place in the world is.

You know there are a lot of places in the world, right?

Some I love because they are tranquil and inspiring. Some I love because they are chaotic and exciting. Some I love because the people I love are there.

Same for the things I read.

But, to find a bit of a compromise, I drafted up a little list of some of the most important books I’ve read in my life (so far — I assume I have a fair bit more life to live here!)

I’ve broken the list out into five different sections, so you can compartmentalize your selection process as carefully as I’ve divided my interests. The sections are not even, and some are definitely “I read this book at precisely the right time for it to impact me the way that it did.”

Here’s hoping that you get some good mileage and suggestions out of the list. It may not have a lot of the most popular books of many other lists, though there are definitely some popular ones on there. I prefer to vary my reading to just about anything I can get my hands on, rather than a niche or what is popular among the syndication circuits.

I should note, I dual majored in Creative Writing and Classical Studies (with a concentration in Latin) when I was at the University of Maine, in large part because I like learning about these things. You’ll likely note a strong leaning towards history, philosophy, creativity, classics, and essays.

I find fiction to be a vitally important component of any well-rounded reading habit. Tim Ferriss agrees, so I must be right.

Also, I’m American, and many (most) of the writers here are as well. Likely, I identify with their stories and backgrounds a bit better…having a similar story and background by being American. If you have some suggestions for non-American books that knocked your socks off, I’d love to hear about them.

Without further adieu…

The 32 Most Important Books I’ve Read in My Life (So Far)

In no particular order:

• Fiction
• Writing and Creativity
• History, Philosophy & Essays
• Business & Entrepreneurship
• Being a Better Human (Personal Development)

Fiction

The Alchemist by Paulo Coelho – I once saw some friends, who I admire and respect immensely, joking on social media that people who enjoy this book are obviously simple and a bit frivolous. It is one of my favorite fiction reads, so I took a bit of a knock on the chin for that. This is a quick one (less than 100 pages), and reads like the fables your parents read to you when you were a kid. Also where I got one of my first Life Heuristics, paraphrased from one of the recurring statements in the book – “When you want something badly enough, all the universe will conspire to help you achieve it.”

This Side of Paradise by F. Scott Fitzgerald – Yes, The Great Gatsby is Fitzgerald’s crowning-glory, and considered by many to be the greatest of the Great American Novels. While I do love me some Gatsby satire and intrigue, I’m a bigger fan of Fitzgerald’s first novel. It is a bit more raw than Gatsby (first novels generally are), and tells the story of young Amory Blaine as he comes of age, loves, learns, loses, and finally comes to know himself as a literature student at Princeton and a bayonet instructor in World War I.

The Circle by Dave Eggers – You know those books that you stay up until 4 AM reading because you just can’t put them down? I did that with The Circle. The book, broken into three sections, definitely starts a bit slow. PUSH THROUGH TO SECTION TWO! You won’t be disappointed. It tells the story of Mae Holland, who lands a coveted customer experience position at a tech company that seems like the fictional love-child of Google and Facebook. As she gets sucked further into the excitement the company fosters, both with users and its workers, we learn about the thrills and dangers of a technology system that permeates personal boundaries and develops culture, and are left to wonder when transparency may (or may not) go too far.

Ovid’s Metamorphoses – In fairness, this was my capstone project for the Latin concentration of my Classical Studies program — translate 250 myths, totaling approximately 78K Latin words, into English, in a semester. So I spent a fair bit of time with the text. But if it was good enough to inspire the likes of Shakespeare and Dante, it is worth reading as a seminal work of fiction. For history buffs, reading through the mythology and pairing with the events and non-fiction writings of the era will provide a fascinating peek into the power of narrative to explain the world around us. Plus the writing is poetic and beautiful, a good example of writing about current events via creative narratives.

The Hitchhiker’s Guide to the Galaxy by Douglas Adams – When I mentioned on a date that at age 27, I had never read Hitchhiker’s Guide, I was immediately eliminated from consideration for a third date. To rectify potential future snafus of this nature, I immediately delved into the trilogy (of five books?) and loved them all. If you want to know why you should read this book, the answer is 42. But you will learn in the reading, that if you want to know the answer to questions, a better understanding of why you are asking the question is in order. Also, life is short so be wacky and have fun.

The Rosie Project by Graeme Simsion – This would likely be classified as chick lit if it were written by a woman. But since it is written by a man, it’s a romantic novel. And it’s a damn good romantic novel. Don’t take my word for it, Bill Gates wrote about how he appreciate this book so much he has gifted this book to at least 50 of his friends. From his description (which sums it up so well I don’t feel any need to write differently): “It starts when a geneticist who may or may not have Asperger’s Syndrome decides to put together a double-sided, 16-page questionnaire as the obvious first step to finding a wife. Ultimately the book is less about genetics or thinking too logically or the main character’s hilarious journey than it is about getting inside the mind and heart of someone a lot of people see as odd—and discovering that he isn’t really that different from anybody else.”

Pride and Prejudice by Jane Austen – Just as The Rosie Project may help you to understand a bit more about modern personal interactions and human psychology, Austen’s works are a deep exploration of the complexities of social life. The book is about what happens in the upper and middle classes of Regency England, especially when you insert (wait for it….) emotions and game-playing like pride and prejudice into otherwise lovely relationships and friendships. It will certainly make you think twice about “first impressions” (the original title for the book), and how quickly you judge and view others.

Fahrenheit 451 by Ray Bradbury – Before The Hunger Games was warning us what happens in a world where technology and vapid entertainment are more valued than intelligence and free thinking, we learned that 451 degrees fahrenheit is “the temperature at which books burn.” It follows the heroic arc of fireman Guy Montag, as he goes from a public servant commissioned with the burning of outlawed books and shaming of their owners to a man who questions the implications of these actions for moralistic and quite realistic reasons. There’s a quite interesting exchange with his fire chief, Beatty, who explains that as people’s attention spans were trained to become shorter and need more sensational, hedonistic, stimulation, they began to devalue individual thoughts and ideas. The book, written in 1953, eerily predicts the environment we’ve seemed to work ourselves into as a society.

The Bookshop on the Corner by Jenny Colgan – My runaway favorite fiction read of 2017, I recommend this to anyone asking for ideas on a good novel to devour. Bonus for the audiobook, which has one of the best narrations I’ve listened to before, by Lucy Price-Lewis. This is a story for people who love stories, about a librarian who is made redundant (down-sized for the American readers) and takes on a crazy idea and whim to open a mobile bookstore…in the Scottish Highlands. It’s also the story of what happens when you are foolish and think that life should be like the stories we read, and why it is not.

Writing and Creativity

On Writing: A Memoir of the Craft by Stephen King – I have a pretty blind faith devotion to Stephen King, in large part because we both attended the University of Maine in Orono and majored in writing. Basically, I am convinced one day we will become friends, if he were to ever learn of my existence. Fangirl gushing aside, this is one comprehensive and raw look at a massively successful, talented, and prolific writer’s creative process and journey. From when he was a child, copying his favorite horror tales and short stories by hand to learn “how to write”; to fueling his early authorial inspiration through cases of beer and a myriad of illegal and pharmaceutic drugs; to his sobriety and current writing routines and habits, which include a mind-boggling 2K words a day, consistently; On Writing is part memoir and part “learn what to do for yourself by learning what worked (and what didn’t) for me.”

Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content by Ann Handley – When people ask me for advice on how to write better content and articles, I immediately direct them to Ann’s book on the process (before talking to them about signing on as a client). Of course, Ann does know of my existence and we are friends, so it should be no surprise that I greatly value her opinions and knowledge on waging wars against content mediocrity. If you are looking for a guide that gets right into the how-tos and actionable steps, this is your modern writing bible.

Daily Rituals: How Artists Work by Mason Currey – This book is another “learn from others” rather than “how-to” guide for developing rituals and routines in your daily life. Routines are huge for me, as I can easily fall down rabbit holes that suck hours from my existence and I have no idea what I did with the time — sound familiar? These small snippets of productivity and habits from other creative and entrepreneurial minds will not only give you some tips for structuring your days, but it will also inspire you to find the beauty in routine and get some epic shit done.

Deep Work: Rules for Focused Success in a Distracted World by Cal Newport – This is an example of one of those “right book at the right time” reads, and I will reference for years to come as the reason that CYC changed in 2016. As I was working on new site content at the end of February and doing some serious self-reflection on the values I wanted to focus on, professionally and personally, I happened to hit Deep Work next on my Kindle queue. Remember how the universe conspires when you really want something? This book focuses on the importance of deep work and brilliant thinking in a world that unfortunately does not always focus on such things. It calls creatives, academics, entrepreneurs, and other innovators in similar pursuits to return to a place and time when we took pride in the work that we put out and focused on quality over quantity.

Thinking, Fast and Slow by Daniel Kahneman – Why is this book on decision making and cognitive processes in a section on creativity and writing? Because while haphazard creative whims and projects can produce life-altering works of art and legacy (thinking fast), there is also the magnum opus that a creative or writer can produce with careful and deliberate research and focus (thinking slow). Understanding the two “speeds” of our thinking brains, and how they can apply to our creative endeavours and writing pursuits gives you a huge advantage to understanding what you are working on and how to allocate that time.

The Paradox of Choice: Why More Is Less by Barry Schwartz – Similar to Thinking, Fast and Slow, this is another book that most would probably not think of as “creative” — but that’s precisely why it must be read with a mindset of honing your creativity. Creatives and writers will often speak about blocks and dry spells, in which they are paralyzed and unable to find momentum or take the next step. More often than not, when I am working with clients on this (or struggling with it myself), I discover it is actually a case of being overwhelmed by choices and possibilities. This book teaches you how to focus on the choices and possibilities that matter, let go of the ones that don’t, and discover the discretion necessary to know the difference between the two.

The War of Art: Break Through the Blocks and Win Your Inner Creative Battles by Steven Pressfield – Artistic process, repurposed through the process and ancient teachings of Sun-Tzu on war? Yes please. Because writing and creativity are absolutely battles that must be waged, yet often your adversaries do not lurk behind enemy lines. They creep up into your subconscious thoughts, like evil little demons lingering on your shoulder whispering their terrible little thoughts into your ear until you believe them yourself. Does your snotty literary or entrepreneurial friend spew on about their struggles with their internal Resistance? They got that from this book, but if they are snotty about it, they likely didn’t get too much more.

Mastery by Robert Greene – I’m a recovering sales person who read The Art of Seduction primarily to learn how to lure people into buying situations. But it was Greene who seduced me into his web, and this quintessential read (not just because it is his 5th book), that profiles some of the greatest leaders and thinkers in history breaks down exactly what it is that made them masters in their fields. If you are someone who wants to be seen as an authority and influencer in your world, whether that is your family or your company or your industry or your planet, find inspiration and get some aspirations from these folks who have already set the path.

Leonardo’s Notebooks: Writing and Art of the Great Master by Leonardo Da Vinci – Ah yes, the Renaissance — when art and writing and philosophy were rushing back into the world after the Dark Ages of war and minimal scientific or methodical advancement. Perhaps no greater representative of the time can be identified than Leonardo da Vinci, an almost pure embodiment of the term Renaissance Man. A writer, a painter, a sculptor, an inventor, an entrepreneur, a scientist and mathematician, who carefully documented years of thoughts and theories into notebooks upon notebooks. Luckily, you can read through it all, and maybe become a bit of a Renaissance thinker yourself. Or at least understand why a well-rounded sphere of interests and knowledge is so damn important to legacy-impacting creativity. (If you don’t have at least Kindle Fire or similar device, get the printed version of this book. Da Vinci’s greatest works of art were not meant to be appreciated on a paperwhite.)

Everybody Behaves Badly: The True Story Behind Hemingway’s Masterpiece The Sun Also Rises by Lesley M.M. Blume – Do you sometimes wonder how fiction writers get their ideas for novels and inspiration? No surprise, the true story behind Hemingway’s first novel was more autobiography than creative license. Also, for anyone in the digital nomad space, replace “Paris” and “writers” for “SE Asia” and “entrepreneurs” and it’s almost the same story, with bullfights. I wish more people would write biographies of novels, it’s pretty much like a documentary for fiction.

Honorable mention to Careless People: Murder, Mayhem, and the Invention of The Great Gatsby by Sarah Churchwell, a similar book that tells the story behind F. Scott Fitzgerald’s best known novel.

History, Philosophy & Essays

The History of the Decline and Fall of the Roman Empire by Edward Gibbon – You know that one book you were forced to read in school but actually got something out of? For me, that was this book. And by book, I mean huge effing volumes of work that clock in at over 1300 pages by most printings. But somehow only $1.99 on Kindle when this post was published?! Considered by most to be the most comprehensive analysis of what brought the Roman Empire crashing down, the thing I found most fascinating about the book is how every “empire” that has risen since then has indulged the same fallacies and had the same precursors to its demise — in a much more abrupt and shocking collapse than the slow crawl of the Roman Empire to its eventual fate. Truly, this is a book about power and civilizations as much as it is about the Romans specifically.

Self-Reliance and Other Essays by Ralph Waldo Emerson – This book starts with the argument that inside each of us is a genius, desperate to share his or her gifts and skills with the world. Yet we often fall into the trappings of traditionalism and conformity and are too scared to step outside the confines of what we know and rely on from our own intuition and experience — our very selves. Plus who wouldn’t love a book that includes the phrase: “A foolish consistency is the hobgoblin of little minds, adored by little statesmen and philosophers and divines.”

(Honorable Transcendentalist mention here to Walden, often cited as a more popular source of similar messaging — though if pushed I’d still recommend Emerson’s essays over Thoreau’s narrative on seclusion to a cabin to find simplicity and individualism in his world.)

The Prince by Niccolò Machiavelli – Is it creepy how much I was adored The Prince? Maybe a little. It made waves in European society not only because of its departure from Catholic teachings and suggestions that those without power could rise to power in a very classist structure, but it also was published in the more modern Italian language rather than Latin, a nod to its eschewing of traditional mores and politics. The book itself is a series of philosophical case studies of sorts, profiling the various “princedoms” that one can hold dominion over, how one comes to power, and how that power can be taken away.

Letters from a Stoic by Lucius Annaeus Seneca – Pretty much exactly what it sounds like, a series of letters and teachings from Seneca the Younger, a Roman statesman and philosopher. The Stoics were a school of ancient Greek and Roman civilizations, who believed that for one to live a good life, they must live in harmony with and understand the rules of the natural order. This book is almost like a primer for a student, explaining in relatively short (though some ridiculously long) letters and essays “How To Be a Stoic.” If reading isn’t your jam, Tim Ferriss recently released the entire collection as an audiobook/podcast series titled: The Tao of Seneca: Practical Letters from a Stoic Master.

Beyond Good and Evil by Friedrich Nietzsche – I’m gonna say it…Thus Spoke Zarathustra is a fluffy novelistic approach to the book Nietzsche really wanted to write. Zarathustra is widely accessible as a narrative piece (and still a damn good book) but Beyond Good and Evil takes off the gloves and pulls no punches on his takedown of previous philosophers who tried to paint clear black and white parameters around the concepts of good and evil, while often cloaked in a moralism that was skewed by their allegiances to various faiths or political systems. Instead, Nietzsche argues, our concepts are based in our own perspectives and experiences, and shaped by our tenuous relationship with knowing our own selves.

Business & Entrepreneurship

Lean In: Women, Work, and the Will to Lead by Sheryl Sandberg – Man, I feel like a woman that half my friends loathe for loving this book. Heralded by some to be a Feminine Mystique of the modern waves of feminism, the book by Facebook’s COO and working mother Sheryl Sandberg, encourages women to lean into their futures and fight to take their seat at the C-Suite tables. I did not read the book to be a “this is what the world could look like for all women” tome, as that would be idealistically foolish. I did, however, come away with a most important lesson, and that is man or woman, no one can “have it all” without enlisting a system of support and delegation in both our personal and professional lives.

The End of Jobs: Money, Meaning and Freedom Without the 9-to-5 by Taylor Pearson – This one probably seems like cheating, and maybe it is, as we edited the book for Pearson and had at least a bit part in refining its message and narrative. In a modern world where traditionally published manuscripts are polished and stripped to appeal to the most massive of audience markets, this self-published exploration into the shifting revolution of workforces and systems reads like a philosophical and historic essay series leading readers to one vital conclusion — jobs, as we have known them for the past century, will soon cease to exist in their current manifestation. It helps that I’ve seen this coming for a few years now.

Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek – To be honest, I didn’t love the writing style of this book. It got a bit repetitive at times (I get it…Apple has a great story foundation…jeez…) and could have dug much deeper into some concepts. But the main message of the book and some of the processes suggested are worth the price of admission. To develop any sort of lasting and prolific brand and business, you must start with the why. Why you are doing thing, why it matters, why it will make a difference…the how’s and the what’s will come in due time, but a solid foundation will do a much better job of serving your vision.

Being a Better Human (Personal Development)

A Million Miles in a Thousand Years: How I Learned to Live a Better Story by Donald Miller – Miller was in a rough spot after the success of his book Blue Like Jazz. Then Hollywood came knocking, and he was asked to adapt the book into a screenplay. Forced to edit the events of the movie, he began to analyze his own current life under the concepts of narrative and structure, and determined that he was not living the story we would want to write about. Another “right time, right place” books, I read this just after I began leading a workshop series I called Being The Author, which taught people how to use creative writing techniques and exercises to uncover the deepest desires they had for life and how they might go about manifesting them.

Some Thoughts About Relationships by Colin Wright – A fast read, I like that it doesn’t pretend to be some all-encompassing manifesto on the relationships in your life. Instead, it is a series of essays and thoughts on the rules and frameworks Wright has developed in his own life for making interpersonal-connections work. The policies, while being exact in their explanation, all strive towards similar goals. Be yourself, be happy with who you are, seek someone who will make you even happier, have open and honest communication with them, be direct, don’t assume, and don’t try to make people or relationships something they aren’t (aka don’t hold them up to unrealistic expectations).

The Art of Happiness: A Handbook for Living by Dalai Lama (via Howard Cutler) – Cutler, a psychologist who was granted audience with the Dalai Lama, posed a series of questions and gathered the answers (with some musings and explanations of his own) into this book. The takeaways are simple: Happiness cannot be manifest through any outside means (it is something that we can only find within ourselves), but we can experience our own happiness (once various basic needs have been met) by training our hearts and minds to make it so.

The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life by Mark Manson – Mark has been a favorite modern writer of mine for a long-while, and I waited with anticipation for this debut title, and it did not disappoint. At the top of best-seller lists across the boards, others seem to have the same opinion. In life, we must choose carefully the number of fucks we give, and make sure that those we do are things that really matter. But really, read the book to learn how to actually do that, not just read it in a sentence on a website. (As a bonus, you can listen to my hella-long convo with Mark about writing, including working on this book, in an old episode of Writers’ Rough Drafts!)

Fortunately This List is Always Changing

Much like tastebuds and waistlines change over time, so does our reading material and preferences (thanks caramelized-onion cream sauce and vanity sizing).

In five years, who knows where I’ll be (seriously, I don’t even know where I’m living in May right now!) and what I’ll be doing. Perhaps I’ll be delving into a whole new area of study and stimulation.

But as of this week, as I reviewed my GoodReads accounts and Amazon order history, while racking my brain for university assignments I read over a decade ago, these are the books that stand out as having an impact on some vital piece of my life and thinking.

Though I do understand why people enjoy the quantifiable accomplishment of declaring their dominance over a massive quantity of titles, there is definitely something to be said for paying attention not only to the quality of what you are reading but what you are learning from it — and how you can apply that to both your prior knowledge and current life decisions.

The thing I love is that the more I read, the more I know. The more I learn, the more places I’ll go (thanks Dr. Suess!)