Well, I just totaled everything up in quicken and after years of being a typical debt ridden American I have acheived a positive net worth.
I made every mistake in the book aside from going bankrupt. Big credit card balances for toys and clothes, no savings, no investing, new vehicles every year or two along with financing cosmetic dentistry and medical loans. Almost had to go bankrupt after the .com bust and ended up with nothing. Even after this and getting back on my feet I didn't learn my lesson. Soon as I got a job again I got more debt.
It suprisingly only took a few years of discipline and I learned a TON about credit, cash flow, investing, home buying and everything else they really should teach you in high school.
I now have a paid for vehicle, a more modest lifestyle, a 401k, a savings account, a home and clear financial and investment goals both short and long term.
For next year I plan on getting rid of the last vestiges of credit card debt and purchasing a rental property. Note that I said I plan on, not hope to.
What turned it around and how was it done? This might be remedial for some but I'm hoping it inspires someone like me 3 years ago.
1: Take stock of your situation. For me it was sitting down, totalling up what I made, what I paid out, what I owned and what I owed. I realized that if I sold everything I had I would be roughly 20k in the hole and would make it 2 months without a paycheck. How sad is that?
2: Get in the right mindset. Defense before offense. This means you need to decide you are going to be the world's cheapest bastard. Get rid of the trappings of success because they are keeping you from being sucessful. For me this meant dumping toys like motorcycles, cars, expensive hobbies, eating out all the time, clubbing, bars, buying new clothes constantly and electronics. I sold off a lot of junk on ebay. for a while we were a single vehicle household. I still don't have a car, just a paid for motorcycle.
For hobbies I focused on inexpensive, healthy activities like hiking, camping, staying in with my wife and watching movies, lifting, mountain biking and other stuff.
3: Get a plan together. I know it is tedious. But plot out how much you earn, how much you spend and then how much you can afford to pay off debts with. Pay this first before you are tempted to buy shit. Some advise saving for emergencies, for me as the cards were paid down they could be used for emergencies which let me focus on a single goal. I started out doing $150 a check which was tough. As I shed debts (motorcycle loan, paid off medical) I was able to do more. I got promoted and do 1k a month.
4: Be disciplined. Stick to your plan. Remember that it is a marathon, not a sprint. You will be tempted to go back to your old ways. I do little rewards for myself. A cigar once a month or so. A nice dinner out. But always as a reward for doing well the rest of the time, never a lifestyle.
5: Once you're more financially sound, then start thinking and planning on investments and making money. For me that started with a no-brainer, 401k. employer matches half up to 6% of my salary and its tax free till I withdraw it. That is just free money and stupid to pass up. After that get some savings going in case of emergency. Then start reading up on investments and deciding what game you want to be in. Could be real estate, could be stocks, could be mutual funds, could be your own business, it might even be maxing out your 401k and working a job you love till retirement. I know a guy that has close to 50% of his check into 401k because he hates the taxman, has no bills but a house payment, likes working and doesn't want to F with investments. To each his own. But study up, be smart and follow your plan.
6: Next for me was quitting the rent game and buying a house. Yes its taking on a big debt and there are expenses renters don't pay. Buy what you can reasonably afford, 25%-30% of your net monthly income in a monthly payment is a good benchmark. If the rest of your bills are low you can still swing the payment if you end up between jobs and have to take up something low payment to get by. Plus you have tax advantages (interest is tax deductable), will eventually have real property and most homes steadily appreciate in value. Make this choice yourself based on the facts, the $$ involved and your position.
7: Enjoy the rewards. At this point I have a different outlook on life, work and money. I don't feel as much pressure from the financial slings and arrows life throws my way. I'm not weathly (yet), I'm not completely debt free (yet) but I'm not living paycheck to paycheck either. I realize that I really am going to be ok, in fact I'll probably retire early. I've done some things I thought would be nice but thought I'd never do like travelling overseas. I'll get to do more of those as the years roll on.
Anyhow, thats it for now. This is stuff I wish someone had told me when I was 18 and certainly at 25. Anyone can feel free to add, ask specifics, tell your own story, argue or whatever.