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 Content A Bucket Plan to Go with Your Bucket List A bucket plan can help you be better prepared for a comfortable retirement. When Should You Take Social Security Monthly Social Security payments differ substantially depending on when you start receiving benefits. My Retirement Savings Estimate how long your retirement savings may last using various monthly cash flow rates.