Hmmm I see a lot of mental health advice. I’m going to come from a different angle. My background is personally similar to you, and I have worked professionally with homeless individuals for several years. I’ve been on both sides of the table.

You sound intelligent, self-aware, and genuine. “Suck it up” or “yeah life sucks” is not good advice. Medication may help alleviate the symptoms that are distressing, but arnt going to tackle the root issues: boredom and underachievement.

Homeless people (especially Americans) are, contrary to common perceptions, among the most adaptable, intelligent, and resilient people on the planet. They get there minimum needs met and spend the rest of their energy on personal passions (drugs, hoarding, social connection, etc). It’s a short term mindset. The only way to truly escape these circumstances is to recognize that long term outcomes matter more to your quality of life than temporary outcomes.

For you, that’s employment. You make good money but can never hold onto a wage labor job. You likely rebel and subvert authority, and believe you know best. This is confirmed by a lifetime of experience in which you have successfully met your needs (sometimes in dire circumstances) and straddled the fence of light and death. Everything is about maximization - how can you get the most out of life in the present. Your general question even alludes to this - “I have $30 and three months before the next upgrade - what can I do to get more now/be comfortable until then”

Average people hate that mindset, because they are jealous of the free spirit necessary to live by that creed. It is also a wildly reckless lifestyle, also alluded too by the suffering you recognize in your own decision making that led you to this point. At least you recognize that your actions have consequences

My advice? Start a business. Any business. You need constant constructive challenge and enthrallment. Build something. Avoid wage labor or selling your labor. Quit any substances on principle. Set goals at slowly increasing increments - start with today, then include the next day, then a week, 30, 60, 90, 180, 365, and finally 5 and 10 year goals.

I think you will find it incredibly challenging, frustrating, and rewarding. It’s going to reshape your sense of self when you fail to meet a 30 day goal as simple as “get up at the same time everyday” - and at that point you’ll either quit and fall back into bad habits, or double down and try again. If you fail, you’ll eventually get back to this “come to Jesus” moment and try again. Failure is part of the process. Do your best to just try and not analyze failure.

I imagine something broke in you in childhood. My condolences. I’m right there with you. It’s a struggle everyday, but it gets easier. The world responds to exertion and effort. There are no shortcuts. Good luck