@ds30055407 - I would just back off a tad on your first suggestion; to "Save 'til it hurts". I would suggest either "Save until it almost hurts" or "Save 'til it hurts .. then back off a tiny bit." Anything a person feels forced to do "until it hurts", can very easily become the reason they lose their motivation .. whether that's saving money, working out, or anything else.
Many community colleges have "Investing 101" type classes that are inexpensive; sign up for a couple.
Google "Investing for Dummies" or go to Barnes & Noble; for ~ $15 you can get a paperback copy & start learning about the market.
Find yourself a VERY reputable brokerage & broker with patience, who'll answer your questions & explain things simply, and help you select the right investment for your level of risk tolerance. Don't get sucked in by promises of well above-average returns, or any broker who wants you to think what he can do is "magic"!