There's not really a lot of detail to target advice to. You don't even share what roles you're applying for at the companies you list. From the sounds of thing

There's not really a lot of detail to target advice to. You don't even share what roles you're applying for at the companies you list. From the sounds of things you don't sound unhireable as you've had several jobs. You just quit them for perhaps bad reasons? Even in a situation where I have a good social safety net I wouldn't quit a job I needed unless I had something else lined up. > I need a job with decent health/dental insurance. Medicaid is useless. I might be homeless soon. Pragmatically you need to deal with these material needs first. It's going to be exponentially harder to reach for the jobs you think you deserve if you aren't able to take care of your physical needs properly. I really sympathize here though, the healthcare system is the US is a joke. Practically I think you need to make a couple of plans: 1) Short-term: How to stabilize your own life so you meet your living needs. You as you say you need a steady job and some level of health coverage. Go through the usual things of making sure your applications match the roles and so on. 2) Long-term: You sound like you want an entry level software engineering or cyber-security role in a high status company. You need to put down a realistic assessment of where you are and a realistic plan of how to get there. This probably requires swallowing a bit of pride and admitting to your current faults. Ideally for both bits try and find someone you trust and will listen to who you can give you advice based on an unvarnished account of where you are at now. Reading between the lines it sounds like you need a bit of a reality check but that's obviously hard to do without knowing more about you.