I confess, I do not know a lot of freelancers personally. Not career freelancers, who pay all their bills, make doctor appointments and who are not artists waiting for a "big break", anyway. That said, there is a certain "Joie du Travail" element to the idea, no? Being your own boss, a part of the growing "Gig Economy", choosing your own projects and timelines... it all sounds sexy to this nine-to-fiver. The allure, I suspect, is control: the ability to take charge of your own career success and schedule without a manager or supervisor middleman.
Going down this path of daydreams invariably leaves me feeling anxious, though. What if my skill set is too narrow to build a business? What if I'm a terrible rainmaker? What do I know about advertising or an IRS 1099-MISC? Branching out on one's own is scary in so many ways, but I really start to twitch when I think about whole no-safety-net thing. But are those the only two options available: Working for the Man or flying solo? While that was once the case, a new path is beginning to emerge.
For example, did you know that there was a Freelancer's Union? Their mission is based on strength in numbers, specifically "helping the diverse self-employed community build a powerful voice - in politics and in markets." The Freelancer's Union offers members a wide array of resources, including health insurance, tax advice, corporate discounts, retirement planning and, perhaps most importantly, community. In many ways, they are creating a safety net for all the freelancers out there who work independent of a business, government or non-profit organization. (They claim as many as 1 in 3 in the American workforce.)
There is also a wealth of books out there - both traditional and electronic - on how to survive the shift from cubical proletarian to freelancer. Many are simplistic and outdated, so spend some time at the library to limit your investment in unproductive boredom. Here are just a few that peak my interest and are in the queue: