"would you be ok going to the atm, withdrawing $50, and throwing it in the trash each month" That's sound advice for all investing. Never bet what you cannot afford to lose! Also, I'm not a financial adviser but I have heard that it is a better idea to pay off all of your debts before you think of investing!
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Umm that depends on the interest of your debts. With low interest now days. The s&p 500, since it's creation, has increased in value 6-8% yearly on average. If you're only paying 3% on your loan I'd say max out your retirement first, but that's just my opinion.
I follow the thinking that investments are a risk, paying off debts is a guaranteed return.