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Updated: March 27th, 2020
Assembling any list like this is a necessarily incomplete task. There are old books with evergreen advice and critically important new books with information that will be obsolete in a few years, thanks to the rate of change in the digital world. As someone who is writing your own rules by starting your own business, you should read as many books as you possibly can.
The best books often feel as if they give us superpowers. Here are 5 books that will instantly upgrade your potential to generate ideas, to strategize and to understand your business.
Journalist Warren Berger’s book is an investigation into the power of inquiry. He makes the case that we’re discouraged by our parents, teachers and society in general, from asking too many questions as we get older, which stops us from having breakthrough ideas. He cites the example of Edwin Land, whose daughter, upon having her picture taken, asked ‘Why do we have to wait for the picture, papa?’ That childish question led directly to Land’s invention of the Polaroid camera. The book teaches readers how to rediscover their questioning nature, unlocking the power to come up with unexpected ideas.
The ability to predict the future would save business owners barrels of money and years of heartache. University of Pennsylvania professor Philip Tetlock shows us a group of ordinary people who have the ability to out-predict just about anyone else at an astonishingly high rate. They often do not possess any special training or expertise. These are people with traits than can be taught and learned.
An earlier book by Tetlock (Expert Political Judgment: How Good Is It? How Can We Know?) neatly debunked the premise of expertise in decision-making, demonstrating that many experts are no better at predicting the future of their field than a chimp throwing darts at a dartboard. You can learn how to anticipate the outcomes that will affect your business.
Businesses are a multi-dimensional matrix of interlocking problems. When a business fails, it is usually a system failure, and not any one particular facet of the business which has failed. Donella H Meadows has written an accessible introduction to the world of systems thinking. This engagingly written book, published in 2008, is unlikely to ever lose its relevancy. Systems follow rules, and Meadows has given us an easy to follow blueprint for how systems work. She states that ‘Systems often cause their own behavior’, and indeed, one area of a business is often responsible for the behavior of an another part of the business. Understanding how these parts relate is key. You will likely read this book every few years and find new ways to apply its insights to your business.
Readers treat most books as passive messengers of information. Thinkertoys is a different kind of book. It’s a workbook for increasing your creative potential. It is filled with dozens of actionable exercises to help you generate ideas across a range of possible applications. The exercises are open ended so it really doesn’t matter what industry you work in. Take an exercise like Future Fruits, detailed in the book. The premise of the exercise is just to generate as many possible outcomes from an action or decision as you possibly can. Say that you want to get a loan to grow your business. This exercise will help you envision every possible scenario for getting that loan, which will help you generate detailed strategies to plan for the desired outcome. Michalko’s book, together with another book of his, Cracking Creativity, outline the steps to fuel decades of inspired ideas.
Like it or not, technology is encroaching on every aspect of business. The threat of automation is likely to transform both the white collar and blue collar employment landscape. Some pundits gleefully predict a world where algorithms replace lawyers. Sci-fi writer William Gibson once said, ‘The future is here, it’s just not very evenly distributed.’ Over the next few years, it’s about to get a lot more evenly distributed. New York Times journalist John Markoff paints a picture of the present moment and tells us how we got here, and where we may be going. He characterizes advancements in artificial intelligence (AI) and augmented intelligence (IA). From personal digital assistants like Amy and Facebook’s M, to Amazon’s drone delivery and Uber’s looming fleet of autonomous taxis, the future is more or less here and it is dramatically changing the business landscape.
Samantha Novick is a senior editor at Funding Circle, specializing in small business financing. She has a bachelor's degree from the Gallatin School of Individualized Study at New York University. Prior to Funding Circle, Samantha was a community manager at Marcus by Goldman Sachs. Her work has been featured in a number of top small business resource sites and publications.