Because both choices carry a cost, there are decisions that become difficult precisely. Staying where things are familiar can offer security, while taking a chance can leave a person facing an outcome that cannot be predicted. Jeff Bezos encountered that dilemma in the 1990s, when he was working at the investment firm D. E. Shaw began considering an idea built around the rapidly expanding internet. Leaving a well-paid job for an online bookseller was hardly a guaranteed route to success. Bezos knew the business could fail. What mattered to him was a different possibility: that years later, he might look back and wish he had given the idea a chance. He eventually left his job and founded Amazon . The decision became one of the defining moments of his career, but the reasoning behind it came before anyone knew how the company would turn out.
That can distort what Bezos was actually deciding in 1994. Bezos was describing the way he weighed the risk of leaving his established career. He did not know whether Amazon would succeed. In fact, he considered failure a realistic possibility. Amazon did not begin as a plan to create a vast technology and retail company. It began as an online bookstore. The first version of the business was focused on selling books through a website at a time when buying something online was still unfamiliar to most people. Within its first weeks, Amazon had shipped books across the United States and to customers overseas. The catalogue also gave the business an advantage that physical shops struggled to match. It could offer a huge range of titles without having to keep every book on shelves. Rather than trying to predict every detail of the future, he imagined reaching old age and looking back at the choice. From that imagined future perspective, he considered which decision was more likely to cause regret. The framework simplified the problem. If Amazon failed, Bezos could return to the job market and continue with his career. If he never tried, he might spend years wondering whether the business could have worked. Failure produces an answer. If a business closes, a person knows that a particular approach did not work. If an application is rejected, there is a definite outcome. Even an unsuccessful project can reveal what needs to change.
It is easy to view the original Amazon through the scale of the company that exists today.