The primary risk of entrepreneurship and other free agent lifestyles is not financial or even social — it is the risk to a person’s very self-concept as someone who does what they set out to do. In entrepreneurial endeavors that depend just as much on luck and timing as intelligence and hard work, this feels like a terrible gamble. And it’s a gamble with odds you can’t improve through careful preparation and planning (in fact, too much planning will probably worsen your odds). This sort of risk is not any less threatening in cultures that are relatively tolerant of failure, like the U.S. If
...more

