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mrstickball said:

Also, have you worked in IT for more than 6 months? How are you using IT on a self-employment basis? What is your masters in, exactly? What languages do you code in? Have you tried free-lancing via oDesk, E-Lance or Scriptlance?

My Masters is in Information Systems.  My BS is in Management.  I should be a system analyst somewhere, but it never happened.  In regards to doing work, I get people wanting me to do pro-bono work, if I am lucky at that.  Or straight up commission sales.  The reality is that businesses don't want to go through the headaches in this area.  It has been awhile since I actually have done any coding.  And the issue I have had is that I don't have portfolio work I can show, as it belonged with IBM when I left. 

I had experience from 1997-2004 in IT at IBM (AIX system admin, software test and some development, along with ISO type QA).  I then from 2004-2005 and then 2006-2007 as a contractor doing level 1 and level 2 helpdesk.  Since then started a non-profit, and had gone through a bankruptcy (got involved with a start up that wasn't able to raise money and burned through my 401K money in the process).  I couldn't find even any volunteer work for a non-profit so I started one.  Next up, I managed to get a social network site off the ground for games. 

When I did get oDesk, I had one of these things pop up again for straight up sales rep work, without pay, and maybe some commission.  Oh yes, and I can talk about craigslist, but people want freebie stuff there.

So, now it is onto lining up part-time office cleaning work, if that works out. 

I will say, one thing of NO benefit here is to turn this into the Book of Job and try to figure out what went wrong.  Only thing that matters is having things work.  No one has answers at all here.  Just know people can get bad luck and fall through the cracks and no one be there to catch them at all.  It happens, no matter how much of an idealist people think they are or think you can listen to Donald Trumps.  What I can tell you is I do have enough knowledge I can explain where people end up stupid.