As the title states this is going to be pretty tl;dr. Sorry in advance. If you do read it, there's a good chance that at some point you're going to want to berate me and call me a huge idiot and all that. It's certainly warranted, but I'm hoping the discussion will be focused on solutions rather than the problems. There are Cliff's at the bottom. I'm 23 and I've put myself in the hole, literally and figuratively. I didn't go to college for various reasons and after my initial ideas failed I worked odd jobs, lived off a credit card for a little while, etc. I landed a decent gig a couple years ago with a base salary of $37k with, 401k, good insurance, 2 weeks vacation, 1 week sick, etc. through my mother, who was very close with the executive in charge at the company. Not long after being hired good things started happening for me. I was able to move out and furnish a condo, had spending cash after expenses and savings, and was a very important employee at work. My job was in education and while I wasn't a teacher I interacted with the students on a daily basis. These students happened to be 18-28 year old women, and I happen to be a bit of a wallflower who was starting to break out of his shell. I ended up getting honey where I got my money which is a big no-no and was basically the only thing I could get fired for as I had a cushy safety net through my mother if any issue arose. My direct supervisor was the most hated person in the company but due to some office politics she wasn't going anywhere regardless of her job performance. Going back to the part about me being a wallflower, I had a few friends in high school but I had confidence issues and my parents were really restrictive about where I could go. When I was 14 I went to the mall with a friend after school and while walking home from the mall with my friend, my mother sped beside us and made a big spectacle about me not calling her to let her know where I was; I was supposed to call her about 20 minutes prior and forgot. After that I never had friends over or anything. As I got a little older my friends would go to parties on weekends but I never went. I couldn't think of a good way to lie to my parents about going to parties, even if I didn't drink. My dad was abusive and a bit of an alcoholic, and when he said he'd beat my ass if he found out I'd been partying, he meant it. I did sneak out a couple of times but decided the risk wasn't worth it. When I was 20 I started breaking out of my shell but I worked by myself/with mature adults from age 18 up until then, and I didn't really have any people my age in my social network. I also found something else around that time... I've played card games my entire life, playing online poker when I was 13-14 during summer instead of working a job. I stopped playing when I was 15ish but decided to try again at 19. I got decent at it; enough that I supported myself with poker for about 6 months prior to my new job starting. I found strategy forums and after participating in the communities I had myself a group of friends. Maybe they weren't "real" because at that time I had not met them in real life, but I talked to them on Skype all the time, swapped money from poker site to poker site with them, basically trusted them and treated them just as I would a "real" friend. When my job started, I was rollin'. I was making a couple thousand a month from poker in addition to what I made at work. Two streams of income seems like a good problem to have, but when you've grown up a pauper and were taught how to manage money by people who live paycheck to paycheck and on a host of credit cards (my parents) all that cash is a catalyst for disaster. I paid off my consumer debt and was living well, but I never saved money. I bought a drumset, clothes (I discovered StyleForum at that time and developed an addiction to Common Projects), basically all things I wanted but could never have before. In August of 2010 I signed a backing arrangement for my poker play. Under the contract, my backer would supply buy-ins for all live and online poker tournaments, and would pay for the hotels when I traveled for poker. In exchange, I would get 50% of the profits, but I'd have to win back any buy-ins lost before we split any profits (this is known as makeup). With this agreement in place I could I decided it was time to meet a few online players in real life at last, so I went to Vegas in October of 2010. I played a couple of tournaments for my backer but mostly came to meet friends and enjoy the things that 20-somethings enjoy in Vegas -- booze, drugs, gambling, strippers, dining and the parties that go down in Sin City. I was in Vegas for about five days and I spent a lot of money, most of it on my credit card because my credit union locked my checking account after a good-sized withdrawal at a Vegas strip club and I neglected to call the bank about it. Around this time I had some things cooking at work with the ladies. A couple dates, a couple nights out, two trips to Vegas and one big night where I threw down with two other guys for a table, bottles, all that good stuff at a popular club on the strip. The two guys never paid and I got stuck with the bill, which I put on my credit card because I was cash poor. During these few months of degeneracy I got deep in debt, about $40k worth, but I wasn't terribly concerned because I had poker and a job and I'd be okay. Around March of 2011 things were rough for me at work. The girl I was seeing (one of the students) and I broke things off in bitter fashion, and it greatly affected my personal and professional life. I dreaded showing up every day and seeing her, and instead of being an adult and dealing with the mess I created by getting involved in the first place I let the break up eat at me. My workload was steadily increasing and I found myself doing accounting and managerial tasks in addition to my usual duties. Thankfully poker was going pretty well and although I was only playing part time, I had won nearly $50k. After makeup and the profit split I had just over $20k to put toward my debt. Then on April 15th the US government seized the major poker sites along with player funds. I'm personally owed five figures that I'll likely never see. I slipped into a cycle of hating work all day, coming home and smoking a lot of weed and watching TV. I spent basically everything I earned on weed and dining out, and I just made the minimum payments on my remaining debt because I simply didn't care. In late 2011 I had a meeting with my supervisor at work and was informed that someone had seen me out with a student. I bullshitted my way around it in the meeting, but I figured that was it. I was caught, and to save my mother the embarrassment of me getting fired for it, I subleased my condo, sold my car, quit my job and with about six months of living expenses saved up I moved out of the country to play poker online. I played for a few months, didn't do very well and have accumulated some makeup. I'm not terribly concerned about the makeup figure and can clear it in a month or two. I can also ask my backer for money for living expenses if I need it, but I'd rather just go home than do that. I recently came home to assess my life and try to make the best decision I can for myself at this point. Here are what I consider to be my options: - Go back to school. I wasn't a good student in high school and will likely have to take some classes before I can enroll full-time and work towards a degree. I'd be going to community college and then transferring to university. I have a decent idea of what I'd like to study, but I'm not certain yet. I don't know how I'd fund this short of student loans as my parents have no money, I don't qualify for many (if any) scholarships or grants right now. I have part time work lined up already and it can become full time, but it won't pay very well. I'd have to live at home (which I don't mind too much but it could be a problem) and even then I wouldn't make much of a dent on my debt which is $400/month for the minimum payments right now. Going back to school would also put me in contact with people my age and give me an opportunity to make friends and be somewhat normal. I've found that I'm not a freak, I just struggle to make friends my age because I put myself in so few situations to meet them. I feel like if I don't find a way to interact with my peers I'm never going to develop those kinds of skills and it's going to affect other parts of my life too. I like this option best but graduating college with student loans and a heap of credit card debt seems scary. I do have a good amount of work experience and am qualified for a lot of positions which pay decently, though. - Go back to work full time. Through industry contacts I can get myself a full time job, but again I don't see this helping me with my credit card debt too much. Despite possessing the qualifications most firms require, it's unlikely that I'll find a job that pays similar to my old one without a degree, and my parents will be much less reluctant to let me stay at their house if I'm not in school. What this will do for me long-term depends on what the position is. My last job had zero upward mobility, any future employment should have something I think. - Move abroad again. I can live abroad for about $400/month more than what I'd spend if I stayed home and went back to school. I'm a winning player over a sample greater than 3 million hands, so I have a high level of confidence that I'd be able to make money but the game is quite volatile and I could easily go another month or two without making a dime. I could comfortably live abroad for at least three months on the savings I have. The work is isolating, hard on the body, stressful, and it's hard to find a work/life balance in poker. The feeling that I have to win is not a good one, and the added pressure surely had a negative effect on my play during my last trip abroad. Poker is a means to an end and if I choose this route I want to be out of the game within a year or so. - A combination of things. I can move for a month or two with the intention of coming home, working full time until school starts in the fall and then adjusting my work hours if needed. If poker doesn't work out, I can quit the game and won't owe the makeup until I decide to play again, but I'll have used up a decent chunk of my savings on the flight, living expenses, etc. Cliffs: Got good job. Did a terrible job of managing my money and myself. Quit job. Have about $20k credit card debt and six months living expenses. Have a few options but not sure what's right for me.