Dear Rusty: Help!! The Social Security Administration says I didn’t pay enough into my Social Security account, despite being a business owner and paying taxes. What can I do?” Signed: Self-employed American Dear Self-employed: For all potential SS beneficiaries, it is very important to know how Social Security determines if you are eligible for retirement benefits: Everyone (including the self-employed) must have earned at least 40 “quarter credits” contributing to the SS program, which is usually about 10 years’ worth of earnings.