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? Address Thank you! Oops! Related Contents Tuning Your Social Security Benefit When should you take your Social Security benefit? Social Security: The $64,000 Question One of the most common questions people ask about Social Security is when they should start taking benefits. Retirement Plan Distributions There are a number of ways to withdraw money from a qualified retirement plan.