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Back in 1995-1996, I went through a bad marriage and divorce that left me $27,000 in debt. I went on CCCS and they put me on a 5 year plan to pay it off, at around $500 per month.
Just before we split up, I was starting to get a handle on the slide into oblivion, by picking up a part time job delivering pizzas. I ended up paying off that debt in about 2 1/2 years, by working my butt off and putting as much as I could toward those credit cards.
Looking back though, if I had it to do over again, I think I would've stayed with the 5 year plan, or close to it, and tried to invest more into my 401k and Roth IRAs at the time. It would've given me a few more years in the market, and a few more years to accumulate savings and compound.
But, if nothing else, the peace-of-mind feeling in getting that debt paid off was incredible.
One thing I really regret when I look back is that I didn't participate in my company's 401k when I first started at the age of 22. I worked for McDonnell-Douglas, and back then their stock was selling for around $30 per share. Well, over time it did a 3:1 split, then a 2:1 split, and when Boeing bought us out, a 1.3:1 split. And right now Boeing is going for around $68-70 per share. So my 401k would be setting pretty right now.
But, in the end I think I still turned out pretty okay. As they say, hindsight is always 20-20.
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