These are the books I regularly turn to for advice:
“As complexity rises, precise statements lose meaning and meaningful statements lose precision.” (Lofti Zadeh)
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Skin in the Game (Taleb)
Fragile stuff breaks, when exposed to volatility. Robust stuff doesn´t care about volatility in it´s environment. Antifragile stuff gains (what?) from volatility. The thoughts Taleb presents here under the heading of barbell-strategies are seminal to my thoughts about innovation management and long term strategies, potentially providing an answer to Christensen´s Innovator´s Dilemma.
It is an essayistic collection of reflections and observations on randomness & volatility - and definitely one of my favourite books.
The Innovator´s Dilemma (Christensen)
Based on the work and research done for his PHD, Christensen sheds light on why large companies are hesitant to pursue options in what Taleb (above: Antifragile) would call the fat tails. By studying e.g. Kodak´s demise this book illustrates, how disruptive innovation as a phenomenon might come into being and why it is so difficult for incumbents to fight it off.
The fourth economy (Davison)
This book was initially published purely as e-book. After going somewhat viral within certain circles, it is now aswell available as paperback. It is a very long story, illustrated beautifully by carefully researched examples all along - the basic proposition made within this book is fundament to my conviction, that the ability to deal with complex problems will be seminal to the success of people and organizations within the 21st century.
Maps of Meaning (Peterson)
How did humanity end up waging unseen wars against one another in the 20th century? It is this question that initially got Jordan Peterson thinking and wrtiting about what came to be "Maps of Meaning" and probably one of the most clicked lectures shared online at the University of Toronto. To me it is a cautionary tale against violence and on how humans orient themselves within reality derived from the close observation of many civilizations.
Why would you praise people for what they have achieved? Why would you praise them even if they haven´t achieved what they were aiming for? Based on the research for her PHD Carol Dweck writes a story on the effects of subtle differences in communication that has changed how I converse (with family, friends and in the professional sphere). If I could only give a single book to people as gift for the remainder of my life: I´d pick this one for all of them.
Finite and Infinite Games (Carse)
The difference between games you play to win (finite games) and games you play to continue playing them (infinite games) is fundamental! I believe this book was probably of inspiration to Simon Sinek´s Book "The infinite Game" - which I have not yet read, but based on his talks: Sinek is iterating what Carse put down here in writing and combining it with his golden circle thinking. For me this book illustrates the difference between project thinking (finite) and product thinking (infinite), wicked and tame problems, and wicked and tame learning environments.
Miteinander Reden (Schulz von Thun)
Schulz von Thun elaborates over 3 volumes on how we might (mis-)understand what others (are trying to) tell us. This book helped me to differentiate between the factual content and perceived offensiveness of feedback and critique. Together with phenomenological writings within french philosophy it fundamentally changed how I conceptualize reality.
On the question whether hyperspecialization is a reasonable strategy for coping with a complex world. It probably is within tame learning environments, and that is how the 10´000 hour rule gained its internet-fame - it probably however is not for those learning to dance with ambiguity.
Information Rules (Shapiro & Varian)
Platform Business-Models are ubiquituous nowadays - here is a brilliantly principled disection of their mechanics relative to information technology written towards the end of the last millenium - timeless in its content! If you ever want to do something that ends up producing money in the www - you should read this book. If you want to understand why certain players (google, twitter, facebook) have become so powerfull - read this.
Zero to One (Thiel)
Thiel as part of the "pay-pall mafia" reflects on the difference between autochthonous new value propositions and copy cats in all of their different forms of appearance.
I beg your pardon for the comparison, yet: Probably due to Thiel´s experience reading this book was to me as if one switched from a bird's eye view to ego-shooter mode in one of the good old computer games: You observe the same events, but the relevance for yourself becomes much more tangible.
Trust Me I´m Lying (Holiday)
People ask me why I refuse to read newspapers. It's partly because I've read this book and the others by Nassim Nicholas Taleb. It is very helpful to understand how blogging, twittering, and "news" work. And it hints at a possible explanation for why certain topics I maybe would consider interesting will never be headline.
Tübinger Einleitung in die Philosphie (Bloch)
I love to recommend this book. Sadly there is no english translation available, however his essays on the philosophy of Music are beautiful and the book traces is one I like to read single sections of every now and then. Coming to think of Philosphy of Music, have you ever encountered any writings by Glenn Gould? I think he never really published big writings but there are single essays letters and scribbled thoughts you may track down in the internet - or right here!
What Jake Knapp put into writing here literally went viral amongst the workshoppers & design thinkers. People focused on product and service design alike have turned to this book again and again to structure their sessions and get some inspiration. What was born as the google venture sprint now is being re-invented and re-issued under thousands of different names.
Designing Your Life (Bill Burnett & Dave Evans)
Based on the learnings of what some claim to be the most successful course being taught at Stanford, Bill Burnet & Dave Evans present their answers to the question of "How to build a well-lived joyful life".
Designing Your Life Workbook (Bill Burnett & Dave Evans)
This workbook is a neat composition of all the materials layed out in the above "Designing Your Life" Book - it does not provide revelatory news - but for those who really put the advice above to good work it might be worth buying it instead of having 20 different worksheets flying around your deskt loosely.
The Start-Up of You (Ben Casnocha & Reid Hoffman)
Another book that has its roots within the paypal mafia. And reasonably argues that you should shift gears and join the infinite game club. What Peter Thiel sketched out in his book Zero-to-One (see above) is explicitly applied to the personal perspective here.
Principles (Ray Dalio)
Ray Dalio - founder and "shaper" of one of the most successful businesses in history shares his perspective and frame of how to build not only a reliable business, that works (refer to "work the system below") in general - but actually shares the specific principles he and his colleagues have been relying on in decision making for the last few years. The book is headed by a short auto-biography and thereafter lays out Dalio's principles for his decision making concering the private- and business-realm of life.
Work the System (Sam Carpenter)
Sam Carpenter describes his "down-trotten-life" prior to reframing what he was doing from "checking of to-do's" to "working-the-system". He advocates building systems you can rely on instead of only being the firebrigade in your life that attends to whatever is currently crying out the loudest for attention. Goes well with Ray Dalio's principles (above) and/or David Allen's Getting Things Done (below).
Getting things done (David Allen)
When the above books greatly argue on the meta level about how important it is to build systems you can rely on, this is the proven step-by-step guide to implementing it step-by-step. The book I initially read talked about paper-based-filing-systems, but do not let this distract you, the system you need and want to build will be exactly the same if you use apps or slack-channels etc.
Change by design (Tim Brown)
The basics of Design layed out clearly by one of the founding fathers of design thinking as explicitly described method.
9 lies about work (Marcus Buckingham & Ashley Goodall)
A beautiful book, that is especially enjoyable to read, because the single lies it uncovers (9 of them, as you correctly guessed) are very well rounded stories and chapters of their own. It does go against the grain of common misconceptions - or at least points out the important exceptions to what appears to be rules according to common wisdom. 9 reframes that will change how you think about work.
Indistractable (Nir Eyal)
With increasing distractions being described precisely at book length - the power not to be distracted seems to become a superpower. Avter initially describing how digital products actually create their habit-forming-powers (see hooked below) this book is the antidote: How to keep yourself focused on whatever you deem to be relevant and worth your time and effort.
Hooked (Nir Eyal)
Nir Eyal's book "Hooked" carefully disects how Facebook, LinkedIn and co are able to lure us onto their platform yet again and again. The hook-model he presents and illustrates allows you not only to understand how social platforms are tuning into your brain's way of establishing habits but - in reverse - also is insightful if you yourself are aiming to create a habit forming product yourself. It does however not clearly provide an antidote to this cycle. For this you'd need to turn to the above mentioned book "indistractable".