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Must Read Books On Risk Taking

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This article showcases our top picks for the best books on risk taking. We reached out to industry leaders and experts who have contributed the suggestions within this article (they have been credited for their contributions below).

We are keen to hear your feedback on all of our content and our comment section is a moderated space to express your thoughts and feelings related (or not) to this article This list is in no particular order.

The Art of Risk by Kayt Sukel

This product was recommended by Ajmal Dar from Moccasin Guru

A well-written book, an excellent read! I couldn’t disagree if other readers thought it’s a combination of intensive research and storytelling. It is! And that made it enjoyable as you turn pages. I like the straightforward way of defining what a risk is and the fact that the author interviewed several professionals to come up with this masterpiece.


Unstuck by Craig Lemasters

This product was recommended by Susan Stitt from Front Edge Publishing

Many industries worldwide are stuck as they struggle to survive and grow. Stuck businesses do not react, pivot and redirect, which can be catastrophic. In Unstuck, Craig Lemasters shares techniques he has used in a lifetime of helping Fortune 500 companies fill their knowledge gaps—using reciprocity, strategic planning, rapid cycle learning and make-it-happen coaching through direct connections with enlightened resources. The wisdom in this book is for far more than Fortune 500 executives. “We all get stuck sometimes,” writes futurist Rita J. King in her Introduction to the book. Community leaders, teachers, networkers, entrepreneurs—and anyone who works with others in companies and organizations—will find powerful tools in these pages. Craig makes that promise in his dedication page: “to everyone who feels stuck.” He addresses all of us throughout the book. Why is this book timely? Because leaders are facing more disruption and seemingly insurmountable barriers than ever before. In the opening pages, Craig writes: “For most of human history on this planet, change has consistently been gradual. … Now, change has accelerated so rapidly that it poses a formidable challenge to the acquisition of timely knowledge, let alone accumulating the depth and range of knowledge needed to get ahead of change. My goal, and my full-time vocation, is to meet leaders in that moment of stuck and share a way to get unstuck.” This book is divided into two sections. Part 1 is “Stuck,” because getting unstuck depends on clearly understanding the complex forces leaders are facing. In this section of the book, Craig draws on his own experience as a Fortune 500 CEO leading digital transformation. Readers learn the symptoms to look for when organizations are getting stuck, how expectations differ from reality and how our internal bank of wisdom may not be broad enough to meet emerging challenges. Part 2 is “Unstuck,” which is possible once an organization has diagnosed the problem. Readers learn about defining and filling knowledge gaps in an organization and many other practical techniques for leading teams and connecting with others, both locally and around the world. When you can acknowledge being stuck, you’re ready to overcome it. Craig shares his definition of wisdom and how it can help you overcome the knowledge gaps keeping you stuck. Learn practical techniques for leading teams and connecting with others. The stories and ideas Craig shares in these pages have been proven throughout his own career as an executive—and have been finely tuned through his years of consulting with Fortune 500 companies around the world. The key is a practical return to the foundations of leadership in business: knowledge and experience producing timely wisdom. As Craig puts it: “The multiplied power of knowledge and experience, wisdom, helps us leaders get back to making choices with confidence. That is, choices made with speed and clarity which lead to decisive action. The choices that we avoided while we were stuck. With wisdom, we get to reclaim our primary role as leaders and shepherd our teams through flawless execution of our initiatives.”


The Hour Between Dog And Wolf by John Coates

This product was recommended by Brian Conghalie from My Open Country

It’s a fascinating book I definitely recommend it. The book really is about how the brain works and some specific effects driving decision-making. After reading this book, I am convinced of the mind-body connection and the many ways we may think with our bodies. I enjoyed the descriptions of the various parts of the Human Brain and their ‘inputs’ to the process of investing. The characters and their successes and failures were well-drawn. I could feel the despair at the failures. The successes were a bit more muted but still plausible. It’s quite an eye-opener for those who like a bit more substance.


Managing Risk in Organizations by J. Davidson Frame

This product was recommended by Michael Hammelburger from Cost Reduction Consultants

This is a great book on risk that every CEO must read. If you want to explore more on the PMBOK, this is a great resource. The discussion and samples simplified the complex concepts of Monte Carlo Simulation and Expected Monetary Value (EMV) – two of the very important ideas that executives need to learn. For CEOs like me who want to run their organizations at the optimized level, it’s a must-read especially in today’s new normal period.


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