It comes with a lot of the same problems as getting hired by a company as an employee. Meeting with clients when you can't travel easily is a challenge. Living

It comes with a lot of the same problems as getting hired by a company as an employee. Meeting with clients when you can't travel easily is a challenge. Living in a homeless shelter puts you on the schedule of the shelter (there are in and out times that are strictly enforced at most of them, if you aren't in by the curfew, you don't sleep in a bed that night), which conflicts with the erratic schedule of an IT contractor. You need a phone that is reliable, and the ability to take calls and emails at any time, which being homeless does not really allow; my friends who are homeless often live by day in coffee shops and libraries and by night in shelters if they're lucky enough to get a bed. Also, though I don't like it, the reality is that black folks in IT are also facing subtle discrimination on a daily basis. Getting hired as a contractor often has none of the same protections that large companies have in place for people of color being hired as employees (government contractors are an exception in that the government has guidelines in place to help insure minorities are well-represented, but selling to the government is a whole other set of skills that he may not have, and may not be able to obtain given his circumstances). Among people of color (and women) that I've discussed it with, they tend to prefer applying for jobs and working jobs in major companies because the HR processes are designed to be less discriminatory. Small firms, even when they intend to not discriminate often make "culture fit" decisions that exclude women and minorities. He's also older. Smaller IT firms are infamous for hiring young and overlooking older candidates. I live in an RV (I did it for four years, traveling full-time, and now I'm back to it after a couple years of stability), and I'm being reminded of all of the ways it makes a "normal life" difficult. And, I'm not dealing with the kind of stuff he is: I have a vehicle and money to travel, I have a phone and reliable Internet, I have a private home where I can have phone/skype conversations with co-workers, etc. Getting out of homelessness is really tough, is what I'm trying to say, and being homeless makes a lot of things that are obvious solutions to problems for you and I much tougher when you don't have the stability and savings and such to fall back on that you or I have.