What I learned reading 50 books a year for 7 years

And why “reading” isn’t a secret to success


I’ve read over 300 books since the beginning of 2011, not counting the many I started but didn’t finish and the endless content we all read online.

90% of this was non-fiction. I’ve read about topics ranging from Buddhism to business, philosophy to physics, and writers ranging from feminists to pick-up artists (and even Trump’s “Art of The Deal.”) I’ve read old books, new books, books with illustrations and fancy charts, a lot of books from which I got nothing and I handful of books I still love.

Here’s what I’ve learned in all that reading time — and some of my favorite books from my 20’s.

Truly good books are few and far between and priceless

The are two camps of “good books” and both of them are rare.

  1. The first is good content. They deliver a message that stands on its own. The writing only needs to be good enough to allow you to follow.
  2. The second is good craft. It doesn’t matter as much what the content is because the writing is so goddamn beautiful it all but sings off the page.

(Writing that offers both, it should be said, is the incredibly rare and precious gem indeed.)

When it comes to choosing between them, as we must, I personally prefer the former over the latter. I’m not here to be romanced.

(That being said, some of my favorite “good craft” writing is by way of essays and/or out of writers such as Barnes, Keegan, and Solnit.)

Here’s one such excerpt. You obvs don’t have to read it.

Rebecca Solnit, A Field Guide to Getting Lost

Regardless of which direction you go, though, the truly good book is a thing to cherish.

On the flip side: there’s a lot of garbage out there

My least favorite books are what I call “bullshit business books” — the theoretical fluff written by people who have never actually done the thing beyond a purely academic or “consultative” position. They’re professors, or founders of “think tanks,” or heads of “organizations,” and they make it their business to compile all the notes they’ve seen from other people’s actual businesses and pawn it off as “expertise,” like some armchair anthropologist reporting on “life in the Congo” because he visited once, and now he “knows.”

In other words: most of the shit sold in airport book stores.

I read a truly unfortunate number of these books before I got fed up enough to swear them off forever, like dumping that big-talk lover who promises you the moon but then just leaves dirty dishes in the sink.

Bullshit business books aren’t the worst books out there, of course. Because even worse than books written on topics about which their authors know nothing, and not to mention most self-help books and books that conflict with your own beliefs, there are truly bad publications, deplorable in both content and craft. This is especially true as the barrier to entry becomes lower. Tread lightly, my friends.

If we’re not careful, reading can easily become just another form of consumption — and procrastination

Sure, there are studies about how it makes our brain smarter. And how all the most successful people read voraciously.

And then we get people who are only trying to be successful — and maybe even making a business out of talking about it— and they take up reading because they hear it’s clutch, and then regurgitate it on down the chain.

It disappoints me that we perpetuate this nonsense.

I’m not saying successful people don’t read — many of them do, I’m sure, and they might even chalk their success up this, in part. But reading isn’t the secret to success.

I started and built my own business in late 2015. I had read dozens of books on marketing and entrepreneurship and customer segmentation and sales and product and design and everything else under the sun.

But when it came to decision-making, the biggest impact was my own experience. At some point, “research” is just a distraction from real tasks.

Entrepreneur Gary Vaynerchuk wrote a fantastic piece on this, pointing out:

“How many books from these ‘experts’ do you need to read before you can actually do something? You can only read so much and at some point, you just have to do. Stop being a student.”

If you *are* reading for growth, read to get answers on specific questions

From books for healing (especially after loss or heartbreak) to engineering books with specific models or formulas to resolve a design question, books are an excellent resource for specific questions

My favorite book this year was The Will To Change (hooks), because I was coming off a bad breakup and looking for lessons and growth. I may not have gotten as much out of it two years ago.

Once you get enough of an answer to act on, stop reading and start doing. Otherwise it becomes, as one of my bosses (a cofounder of 2 companies) put it, “an academic exercise.”

Listen to people who have firsthand experienced or accomplished the thing

My absolute favorite types of books are autobiographies and memoirs from people I admire — with top slots going to Zero to One (Thiel), Big Magic (Gilbert), Fashion is Spinach (Hawes), The Hard Thing About Hard Things (Horowitz), and Man’s Search for Meaning (Frankl), and honorable mentions going to all of the dozens of autobiographical pieces I’ve read (Vaynerchuk included.)

I’ll take a firsthand account with “B-minus” writing over flowery garbage that says nothing any day. And when it comes to learning more about someone, I’ll take any autobiography over any biography. The reason being that I want to get to know the person. I don’t want facts; I want their thought process.

Some of my favorite non-autobiographical pieces are still-solid firsthand thought pieces like Rework (and pretty much any thing else Fried and/or Hansson put out) and The Law of Success (Hill), the latter of which includes a chapter on leadership that is by far one of my favorite pieces on management philosophy.

As an aside: the only few pieces I hold in the same tier as firsthand accounts are well-researched and rich books on the human mind, such as Flow: The Psychology of Optimal Experience (Csikszentmihalyi) and Blink (Gladwell).

Context and timing is king

Maybe we’d eventually like a certain book, but we’re just “not ready for it,” or right now’s not the right time.

A guy I dated once let me borrow his copy of Sartre’s Nausea but warned me “that might not be where you’re at right now.” He was right. I didn’t finish. Maybe someday it might offer something, but it didn’t then.

This was also true of philosophy overall. When I first tried to wander in through its unlocked side door in my early 20’s, I felt like I’d walked into the middle of a heated debate with big words and no context — and philosophy isn’t a conversation where many are willing to pause to get you up to speed.

But when I came back to philosophy a few years later, with very specific questions I wanted answers, I had a much more fruitful experience.

Confirmation bias, the risk of influence, and the fact that no writing can be totally objective

Writers are people. Be careful what you read.

No matter your viewpoints, you can find a writer who agrees. There are feminist writers, there are man-hating writers, and there are self-sabotaging writers who use big words like “strong women” while simultaneously cutting themselves down with the task of “winning a man.”

You can find angry writers, sexist writers, delusional writers, depressed writers, writers from all walks of life. So if you’re out there to get someone to make you feel better or more validated, you can.

That doesn’t make any opinion — yours included — right. And we have to remember this while reading, especially when we’re looking for “answers to questions” and already have an idea of what answer we want.

Similarly, it might be tempting to forget that any single piece of work is only the viewpoint of a single person. It’s not everything — only their lived experience (or, at worst, what they’re trying to sell you regarding yours.)


All of this being said, reading is a personal journey

One person’s bargain bin find is another person’s salvation.

One of my dear friends became enraptured with Rupi Kaur’s Milk and Honey, and recommended it to me with that zeal with which we always throw beloved books at other people. I read through half a dozen pieces and, much to the disappointment I could see fill her previously-eager eyes, they just didn’t do anything for me.


Some of it’s personality and values and individuality. Some of it’s just context, and where we’re at in our journey.

Reading can be an enjoyable escape, if that’s what we want. It can also be intellectually rewarding — but only if approached in a way that supports, rather than distracts us from, our growth.

Edit: a few readers have asked for recommendations.

My answer is: “it really depends on what you’re looking for” (see above) But:

  • If you only read one book, my top pick is: Laws of Success (Hill.) I’ve read that shit like once a year since 2012.
  • For mindset: Man’s Search for Meaning (Frankl)
  • For romantic relationships: All About Love (hooks)
  • For creative work: Big Magic (Gilbert) and Rework (Fried, Hansson)
  • For something beautiful: A Field Guide to Getting Lost (Solnit)


This story is published in The Startup, Medium’s leading publication for entrepreneurs and startups.

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