As a counterpoint, see The Trouble With Optionality [1] as a critique of keeping your options open to forestall a single "decisive mistake": > This emphasis on

As a counterpoint, see The Trouble With Optionality [1] as a critique of keeping your options open to forestall a single "decisive mistake": > This emphasis on creating optionality can backfire in surprising ways. Instead of enabling young people to take on risks and make choices, acquiring options becomes habitual. You can never create enough option value—and the longer you spend acquiring options, the harder it is to stop. > The Yale undergraduate goes to work at McKinsey for two years, then comes to Harvard Business School, then graduates and goes to work Goldman Sachs and leaves after several years to work at Blackstone. Optionality abounds! > This individual has merely acquired stamps of approval and has acquired safety net upon safety net. These safety nets don’t end up enabling big risk-taking—individuals just become habitual acquirers of safety nets. The comfort of a high-paying job at a prestigious firm surrounded by smart people is simply too much to give up. When that happens, the dreams that those options were meant to enable slowly recede into the background. For a few, those destinations are in fact their dreams come true—but for every one of those, there are ten entrepreneurs, artists, and restaurateurs that get trapped in those institutions. [1] https://www.thecrimson.com/article/2017/5/25/desai-commencement-ed/ https://www.thecrimson.com/article/2017/5/25/desai-commencem...