I got lucky when I left the military and scored an entry-level job at a semiconductor manufacturer. Worked full-time and went to night school for 8 years to earn my BS in Business, company paid 60% of tuition, I carried 40% in student loans. I'm single. I'm also the opposite of others here, I've always traditionally gone into debt to buy things. Bought a house I really couldn't afford but hung on to it, always bought used cars, carried a balance on my student loans for years. Major vacations only every 4-5 years, other vacations spent at home working on improvements & landscaping. Spent all my disposable income on collectibles...garage sales, Goodwill, eBay, swap meets. Have been buying budget pinballs for years (since 2003) while scraping by, used Clay's guides to help me fix them. One bad event could have wiped me out but I made it through. House appreciated, I sold it and bought 2 more, one's a rental that's paying for itself. Car is paid for. Student loans are paid off. My collectibles are worth a lot of money. Now have a good job (QA) in a different semiconductor company where I've been for the past 21 years. I'm now buying a few expensive machines to add to the collection. Still carrying credit card debt but I'm paying it down by selling off some of the collectibles.

Some things I did well (collectibles, inexpensive pins, used cars), other things not so well (loads of debt). But I'm really happy with what I have, I think that's key.