I apologize, my previous comment must have been quite poorly written for you to have misunderstood it to the extent that is apparent. I didn't intend to make an

I apologize, my previous comment must have been quite poorly written for you to have misunderstood it to the extent that is apparent. I didn't intend to make any assertions about writing books or wearing suits, and I certainly do not object to $100/hour rates (having charged more than that in markets much smaller than Chicago). The crux of my point was that freelancing isn't the optimal way for most people to pick themselves up from nothing. It's not helpful to suggest that a person just needs to go check out the local $INSERT_PROGRAMMING_LANGUAGE_HERE developer meetup and ask people to hire them for freelance work--that sort of environment is not the norm in most of North America. Of course freelancing is a perfectly viable option for lots of people, and I will generally agree with your party lines (ie. businesses typically value developer skills on a completely different axis than programmers do, and programmers typically underestimate their ability to provide that value) but offering it up as a panacea to someone who's on the verge of homelessness seems... a bit strong.