Books for Sharpening Your Strategic Mind

Recently someone asked me which books every brand strategist should read.

It’s a surprisingly loaded question. The first thought that popped into my head was an embarrassingly butchered-up version of that Haruki Murakami quote: “if you only read the books that everyone else is reading, you can only think what everyone else is thinking.” Cheesy, but true.

So, naturally, I reached out to a few friends, former colleagues and other strategists that I admire immensely to ask them which books have helped them sharpen their thinking. You can find the full thread of their recommendations here, but a few notable things that I thought were worth pointing out:

a. Don’t spend all of your time reading strategy books. Early in your career, it makes sense to dive head first into books on account planning and brand strategy. Learn the trade, develop the skills, know the processes. It’s always good to revisit these types of books over the years to refresh your thinking and how you approach your work. You need a foundation. But don’t forget that foundations are meant to be built on.

b. Find your ‘fuck yeah’. Part of becoming a better strategist is becoming a more interesting person. And that means stretching your brain across different creative outlets that you personally find intellectually stimulating. My friend Jonathan Colmenares has recommended architecture books like S,M,L,XL and Towards A New Architecture. I know Rob Estreitinho is all-in on philosophy with writers like La Rochefoucauld, Alain De Botton and the rest of his Salmon Theory work. Eugene Hwang goes deep on game theory and design. Whatever makes you a more multi-dimensional thinker and overall inspired person.

c. Use obscurity to your an advantage. Strategists are weird people. In the best way possible. They obsess over odd ideas and conversations. They probe deep on overlooked or ignored concepts and implications. And part of this means becoming experts on specific topics interest them. That’s why I wasn’t at all surprised when Sam Fowler suggested Churchill’s war diaries, or when Peter Spear brought up The Secret Life of Puppets, or when Julian Cole told me he was reading about the history of geography and trade along the Silk Road. It’s less about ‘if’ or ‘how’ this stuff will ever be relevant in your professional or personal life, and it’s more about the brain processing behind learning something entirely new. Embrace it.

d. Look far forward and look far back. A lot can be learned from the past, but it seems like a lot of strategists today don’t know much about their industry before, say, 2006. Books like A Masterclass In Brand Planning: The Timeless Works of Stephen Kind, Changing The World Is The Only Fit Work For A Grown Man, even 100 Ways To Create A Great Ad can help give us good perspective on where we’ve been. But, just as importantly, we need to build up our superpower of peering into the future. Wiemer Snjiders mentioned futurists like Duncan Watts, Ben Kunz suggested Superintelligence by Nick Bostrom and Murray Calder recommended a lot of solid Sci-Fi writing, all good starting points for us to start thinking about tomorrow.

e. Don’t flub on fiction. I once read an article from Neil Gaiman when he said, “Fiction gives us empathy: it puts us inside the minds of other people, gives us the gifts of seeing the world through their eyes. Fiction is a lie that tells us true things, over and over.” No, I didn’t memorize that. I had to look it up. But my point is, don’t discount the novel. Gareth Price put out high praise for John Dos Passos, Jeremy Busch suggested Charles Baxter, and I personally believe stories like Nicholson Baker’s The Mezzanine have some weird, meditative, dark art ability of making us more skilled observers of our world.


I. Five books for students (or aspiring strategists)

Let’s assume you’re a student. You want to learn more about strategy and you want to begin developing a basic skillset. But you’re also paying for tuition, spending an obscene amount of money on caffeinated beverages, and (understandably) aren’t too keen on dropping a ton of dough on buying books. Here a five recommendations to start the journey.

Chris Kocek’s The Practical Guide to Account Planning makes for a good appetizer. It’s short enough to read in one day, and it’s a good introductory book for some of the things account planners actually do day-in and day-out. You’ll probably also want to pick up John Steel’s Truth, Lies and Advertising because it’s basically become the planner’s bible. Most strategists have a copy sitting somewhere on their bookshelf. I’d also recommend picking up Paul Feldwick’s The Anatomy of Humbug. It’s less about the craft of account planning, and more about how advertising works, which, you’ll find, actually helps you with the craft of account planning. Plus, it gives you some much needed history on the advertising industry without getting too painfully dry. Next, find a book that will recalibrate the way you think about ideas. You can’t really go wrong with Edward De Bono’s Lateral Thinking or James Webb Young’s A Technique for Producing Ideas. One or the other, or both if you’re feeling saucy. They’re classics, and they‘ll get all the regions of your brain to fornicate with each other. And finally, pick up a book that stretches the way you think about culture, media, technology, humanity, whatever. Something fun and something that’s genuinely thought-provoking. I recently finished Derek Thompson’s Hit Makers and thought it was delicious. But you could also substitute that with a few alternative options given to me by others:

Adrian Mediavilla: Curious by Ian Leslie

Tom Morton: Enlightenment Now by Steven Pinker

Cristina Sarraille: Wired for Culture by Mark Pagel

Gareth Price: The Secret of Our Success by Joseph Henrich

Chris Gilfoy: Stranger Than We Can Imagine by John Higgs

II. Five books for mid-level strategists

Let’s assume you’re a junior or mid-level strategist looking to nerd out on some books that will take you to the next level in your career. You don’t mind going a little deeper on things that can be immediately applicable to your day-to-day work. Here my five recommendations to level-up.

Let’s start with some marketing science. How Brands Grow by Byron Sharp has, in my opinion, become mandatory reading for any ad strategist today. It’s chock full of data, it dispels myths you probably hear from clients every day, and it will change the way you think about your own work. Next, I’d strongly recommend Richard Rumelt’s Good Strategy, Bad Strategy. It’s an ejection seat from advertising books, and it helps breathe some sanity back into what strategy actually is and is not (you could always substitute this with HBR’s 10 Must-Reads on Strategy, but the former is less, well, Harvard-y). Thirdly, I’d strongly recommend a very practical book on some sort of skillset development. I found Erika Hall’s Just Enough Research a hugely helpful book in teaching me more about conducting any sort of research project (and The Field Study Handbook is supposed to be excellent, too, if you’re currently sitting on a fat wallet). Next, I say, go deep on behavioral economics, psychology, evolutionary biology, etc., so you can understand the human condition and all of it’s beautiful quirks. The Elephant In The Brain, The Advertising Effect or Descartes Error are all good options to choose from. Finally, pick up a book that will make you better with words. This might seem odd, but the truth is, every presentation, every creative brief, every conversation you’ll have in your day-to-day job will be drastically improved with better mastery of language. On Writing by Stephen King will get you well on your way, but really, any book that’s ridiculously well-written can pay off in spades. I’m a huge Anthony Bourdain fanboy, and Kitchen Confidential taught me a lot about writing with a stronger voice (by the way, the New Yorker story that originally put him on the map years and years ago is still one of the greatest articles ever written, in my opinion).

III. Five books other strategists keep recommending

Let’s say you’re beginning to think I’m a bit douchey sounding, and you’re starting to seriously question my personal tastes. Look, I get it. That’s why I asked a bunch of friends, former colleagues and other strategists that I really admire about what they’ve been digging lately. You can find the full thread here, but here are five books that seemed to pop up most frequently:

  1. Understanding Comics by Scott McCloud

This one came recommended from my old boss, Eugene Hwang. And Rachel Mercer also said, “this is basically the best way to think about deck-writing.”

2. Sapiens: A Brief History of Humankind by Yuval Noah Harari

I haven’t gotten around to this one yet (or Harari’s follow-up Homo Deus), but I’ve listened to a handful of podcasts from the dude, and I like what he’s preaching. Plus, I’ll trust whatever Thomas Wagner and Ben Kunz tell me.

3. Critical Mass by Philip Ball

I personally haven’t read this one, but Faris Yakob and Eric Woning both put it back at the top of my Amazon queue (this is probably a good time for a message from my unofficial sponsor today: public libraries).

4. Attention Merchants by Tim Wu

One of the themes I noticed from other strategists is their fascination with technology and where it’s all heading. Ben Perriera and others reminded me of Tim Wu’s work, along with a few other Kevin Kelly-type of thought leaders.

5. Dark Matter and Trojan Horses by Dan Hill

I admittedly had never even heard of this one, which isn’t all that surprising because Patrick Tomasiewicz and David Carr are both always leaps and bounds ahead of me on pretty much everything.

IV. Five books no one talks about but should

Let’s say you’re a real scholar. Maybe you’ve already read all of these books, and you’re looking for some stuff further on the fringes. Fine. I’ll give you a few books that made a pretty big impression on me despite the fact I never really hear anyone else mention them. Here are five more books that might surprise you.

The Art of Thinking Clearly by Rolf Dobelli

You can probably imagine my mental state when I decided to buy this one. Turns out, it wasn’t the proper medicine, but it’s still become one of the most useful books for me. A collection of 99 short chapters (1–2 pages max) each focusing on different cognitive biases — it’s a nice briefer and Cliffnotes overview of a lot of behavioral economics and psychological theories of other more notable researchers and writers.

The Next America by Paul Taylor

I grabbed a copy of this one when I was living in Brooklyn and starting to feel the symptoms of big-city bubble and hipster monoculture creeping into my consciousness. It’s a data heavy snapshot of American culture from the people at Pew and it will begin to remind you why Trump is president, why Baby Boomers still matter, and why a place like TGIFriday’s is still in business.

Thank You For Arguing by Jay Heinrichs

I started highlighting passages and scribbling notes in this one, and before I knew it, every page of this book started looking like a kindergartener’s art project. There are so many nuggets of timeless brilliance in here that will make you rethink how you present, how you speak and how you listen.

The Happiness Hypothesis by Jonathan Haidt

Jonathan Haidt has a fascinating brain. His ability to remain objective and breakdown why people do what they do, think what they think and feel what they feel is fascinating. His other book The Righteous Mind: Why Good People Are Divided By Politics and Religion is fascinating. Yes, fascinating is good.

How To Win Friends and Influence People by Dale Carnegie

You’ll find this gem in virtually every book store. You may even feel slightly embarrassed when other people witness you purchasing it. But it’s one of the best books on social media, persuasion, one-to-one marketing, or whatever other trendy bullshit is out there today… all despite the fact that it was originally published in 1936.

APPENDIX: The (Unfinished) List

Please add any others in the comments section below.

For understanding ideas (and your own creativity):

  1. Lateral Thinking by Edward De Bono
  2. A Technique for Producing Ideas by James Webb Young
  3. Ways of Seeing by John Berger
  4. Understanding Comics by Scott McCloud
  5. The War of Art by Steven Pressfield
  6. The Creative Habit by Twyla Tharp
  7. Ego Is The Enemy by Ryan Holliday
  8. Whatever You Think, Think The Opposite by Paul Arden
  9. This Will Make You Smarter by John Brockman
  10. Making Ideas Happen by Scott Belsky

For understanding persuasion, rhetoric, behaviors and psychology:

  1. Influence by Robert Cialdini
  2. The Advertising Effect by Adam Ferrier
  3. The Elephant In The Brain by Kevin Simler and Robin Hanson
  4. Behave by Robert Sapolsky
  5. Thinking Fast and Slow by Daniel Kahneman
  6. Misbehaving by Richard Thaler
  7. Descartes Error by Antonio Damasio
  8. Decoded by Phil Barden
  9. The Choice Factory by Richard Shotton
  10. How To Think by Alan Jacobs

For understanding media, modernity and technology:

  1. The Inevitable by Kevin Kelly
  2. Present Shock by Douglas Rushkoff
  3. The Attention Merchants by Tim Wu
  4. Play Anything by Ian Bogost
  5. The Platinum Age of Television by David Bianculli
  6. The News by Alain De Botton
  7. The Four Dimensional Human by Laurence Scott
  8. Everybody Lies by Seth Stephens-Davidowitz
  9. Economic Science Fiction by William Davies

For understanding our world:

  1. Factfulness by Hans Rosling
  2. Hit Makers by Derek Thompson
  3. Homo Deus by Yuval Noah Harari (or Sapiens)
  4. Curious by Ian Leslie
  5. Critical Mass by Philip Ball
  6. The Secret of Our Success by Joseph Henrich
  7. A Short History of Nearly Everything by Bill Bryson
  8. Ultrasociety by Peter Turchin

For understanding hypnotism:

  1. On Writing by Stephen King
  2. On Writing Well by William Zinsser
  3. Save The Cat! by Blake Snyder
  4. Draft №4 by John McPhee
  5. Why I Write by George Orwell
  6. The Etymologicon by Mark Forsyth
  7. Bird By Bird by Annie Lamott
  8. Any book of poetry

For understanding business strategy:

  1. Good Strategy, Bad Strategy by Richard Rumelt
  2. HBR’s 10 Must-Reads on Strategy by Harvard Business Review
  3. The Art of Action by Stephen Bungay
  4. Key Strategy Tools by Vaughan Evans
  5. Value Proposition Design by Alex Osterwalder
  6. Brand Relevance by David Aaker
  7. Positioning by Al Ries and Jack Trout
  8. Measure What Matters by John Doerr
  9. Zero to One by Peter Thiel
  10. Be More Pirate by Sam Conniffe Allende

For understanding research, rigor and hard skills:

  1. Just Enough Research by Erika Hall
  2. The Field Study Handbook by Jan Chipchase
  3. Don’t Make Me Think by Steve Krug
  4. Beautiful Evidence by Edward Tufte (or anything from Tufte)
  5. Good Thinking by Wendy Gordon
  6. Guide To Information Graphics by Dona Wong
  7. Interviewing Users by Steve Portigal
  8. Hooked by Nir Eyal
  9. The Design of Everyday Things by Donald A. Norman
  10. Presentation Zen by Garr Reynolds

For understanding marketing science:

  1. How Brands Grow by Byron Sharp (and Part II)
  2. Marketing In The Era of Accountability by Peter Field and Les Binet
  3. The Hidden Power of Advertising by Robert Heath
  4. Numbers And Nerves by Scott Slovic and Paul Slovic
  5. Advertising Works by the IPA
  6. System 1 by John Kearon et. al.
  7. The Advertised Mind by Erik Du Pleissis
  8. Viral Marketing by Karen Nelson-Field

For understanding the craft of account planning:

  1. The Practical Guide to Account Planning by Chris Kocek
  2. A Master Class In Brand Planning by Judie Lannon and Merry Baskin
  3. Truth, Lies and Advertising by John Steel
  4. Under Think It by Adam Pierno
  5. Paid Attention by Faris Yakob
  6. How To Plan Advertising by Alan Cooper
  7. Space Race by Jim Taylor
  8. 99% Pure Potato by John Griffiths
  9. The Advertising Concept Book by Pete Barry
  10. Brain Surfing by Heather LeFevre

For understanding the ad industry and its history:

  1. The Anatomy of Humbug by Paul Feldwick
  2. The Book of Gossage by Howard Luck Gossage
  3. Changing The World Is the Only Fit Work For A Grown Man by Steve Harrison
  4. Damn Good Advice by George Lois
  5. Tibor by Peter Hall
  6. From Those Wonderful People Who Brought You Pearl Harbor by Jerry Della Famina
  7. Where Did It All Go Wrong? by Eaon Pritchard
  8. The Belief Economy by David Baldwin
  9. Hoopla by Warren Berger
  10. Madison Avenue Manslaughter by Michael Farmer
  11. Propaganda by Edward Bernays


I’m sure there’s more, but I’m exhausted.