A Fruitful Retirement: Social Security Benefit Taking your Social Security benefits at the right time may help maximize your benefit. Share | Have A Question About This Topic? Name Email Address Question Thank you! Oops! Related Contents Preparing For the Ultimate Vacation Make your retirement as exciting as your next vacation. Social Security: The $64,000 Question One of the most common questions people ask about Social Security is when they should start taking benefits. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.