Spending your savings can be a lot more complicated than building them up. Many chronic health conditions are associated with higher medical costs in retirement, including diabetes, high blood pressure, high cholesterol, arthritis and heart disease, according to a study by Vanguard and Mercer Health and Benefits. Make a plan to replace your paycheck Investing in retirement. The stock market entered a downward spiral just as the Longs were tapping into their retirement savings. Life insurance. It often indicates a user profile. In this situation, your chances of running out of money go down.