Books That Matter to Charlie Gilkey

Books matter to us. They change our world views and outlooks. They light up alternative realities. They crack open our hearts.

Today marks our debut feature for Books That Matter. Books That Matter is our 8-week series that showcases influential wonder-trackers’ relationships with books that matter to them. We’ll feature people from a variety of backgrounds and perspectives.

Our first focus: Charlie Gilkey.

charlie-gilkeyFounder of the business advising firm Productive Flourishing and author The Small Business Lifecycle, Charlie Gilkey is a pragmatic philosopher-king of business advisors.

Don’t let the philosopher scare you off. Gilkey can pull back, survey a business landscape, and then suggest practical and inspired strategies for any solo-preneur or business owner to advance.

He’s like Plato (theory of forms) mixed with Aristotle (what makes us happy & productive on a daily basis) and a little get-out-of-your-own-way Taoist sage in one.

My business advisor for the past year, Charlie as of late is now author of  The Small Business Life Cycle: The Guide for Taking the Right Steps at the Right Time for Your Small Business ranked the #1 Kindle book in Entrepreneurship its first week out.

You can find out below what book has mattered most, his predictions for publishing, and what factors contributed to his publishing such a successful first book.

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What one book most took off the top of your head (Dickinson on poetry) or was “the axe for the frozen sea within” you (Kafka) or otherwise just changed something profound within you? What did it do for you? Maybe a book that lit you up as a child or that turned you on as a young adult or last week that salved some pain or turned your thinking upside-down.

The book that I read that changed me was the Tao Te Ching; I read it about every month and it still continues to stir things deep within me. Verses that were inscrutable a year ago are now crystal clear. Lines that had one meaning a decade ago have multiple layers of meaning now. It points to deep fundamental truths that you can’t put words to, thus simultaneously showing the power and feebleness of language.

I’ve lost count of how many times and versions of the Tao Te Ching that I’ve read. My favorite version, by far, is Derek Lin’s from Skylight Press, for it separates Derek’s commentary from his extremely accurate translation. Many versions – including the far more popular version by Stephen Mitchell – replace the Sage’s words with their own.

Survey: Roughly what % of books do you read digitally versus in paper? (What’s your preferred reader?)

Physical books still make up about 60% of my reading, although I am quickly increasing my digital reading. I don’t have any particular emotional attachment to the physical form of books – I understand that people find cuddling up with a book to be emotionally more satisfying than cuddling up with a Kindle, but my preference for physical books is largely practical. Most of my reading is non-fiction (by choice) and I know where things are in the book by feel; I can pick up a book I’ve read and find what I need in 5-10 seconds. I’ve yet to be able to do this quickly in a  digital book.

My preference being based on practicality rather than aesthetics also explains my gradual adoption of digital reading. I’m a voracious reader and usually have 3-5 books that I’m reading at time. I can’t carry all of them with me and I have a mobile lifestyle, so I simply read more digitally. I also find reading a book on my iPhone far more constructive and relaxing than other alternative uses. And, I’ll be honest: I like the price and instant gratification of digital books.

My preferred reader, though, is no longer available: it was the KindleDX. I used one and returned it because an iPad was in my future and I thought I could just read on the iPad as well as the DX and couldn’t justify the price of the DX at the time. I was wrong about the reading experience; the size of the DX made me read faster with less effort and I could still “unplug” and read outside. I do have a Kindle, but the screen size is noticeably smaller.

It’s rather ironic, really: I have more ways to read my digital purchases and it also increases the choices that would prevent me from reading. Do I take the Kindle today? Would I rather read faster and be able to leave reviews easier on the iPad? Do I just want to take my computer?

I avoid that whole dilemma by just grabbing a physical book and throwing it in a bag.

It’s a wonderful time to be an author and reader. It’s a terribly disruptive time to be an author and reader.

In a sentence or two, what’s your forecast for the future of publishing?

We’re at the end of the post-Guternberg publishing world and at the beginning of a new iteration of storytelling. This new synthesis will have the connection orators once had with their listeners with the impact that only works created in private can have.

Small-Business-Lifecyclex300What 1-2 factors most helped you write your latest book The Small Business Lifecycle?

I embraced the opportunity provided by this disruption we’re in and actually listened to what readers, analytics, clients, and students were telling me and asking for. When I saw that what I had now was what people wanted now and that I could ship it now – and that the reasons I had for not doing so weren’t particularly good ones – it was a fairly straightforward process. (I’d also be remiss to add a third factor: asking for help from the right people who were there the whole time.)

The book I am most embarrassed to say I’ve never read isn’t a book, but, rather, fiction.

Obviously, I read fiction, but not to the degree that I read non-fiction books. I read anywhere between 10 and 25 books a month but, at most, 4 or so novels a year. Last year was an outlier year because I went on a science fiction and fantasy binge and read 9 books over the course of a couple of months. My wife (Angela) will read a novel a week, though.

At times, I think it’s a shame I don’t read more fiction, for Portland’s libraries are top-notch and it’s not that I don’t have access. Most of the time, though, I read what I enjoy to read, which is non-fiction that ranges from the business to gardening to philosophy to music to creativity to writing to …

If I had the time, talent, grit, and support, the book I would write is a complete mystery to me.

When I think big, it’s not about particular books or products or things, but, rather, my body of work over the course of my life and the impact that body of work has made. In that respect, I’d most like to be like Peter Drucker.

His body of work fundamentally changed the landscape of business for the better; what was foggy became clear and he had the intellectual and artistic conviction to tackle the hard subjects with a breadth and depth we’ve yet to see since his passing. He did it in his own way and style, as well – you know when you’re reading Drucker.

Two years ago, I lamented because Drucker would not be published today; today, I’m excited because there’s no barrier preventing the Drucker’s-in-training from getting their work out there.


What philosophy or business books have mattered most to you? Offer your responses, questions, and queries for Charlie here.

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