In this video attorney Francis Jackson of the law firm of Jackson & MacNichol conducts a live Q & A session on Social Security Disability Training and answers the question: If a young man is receiving Supplemental Security Income and Social Security Disability Income and working, how much can he earn each year? Whatever he earns is going to apply to the SSI portion of his monthly payments. For the SSI piece, they will look at your income every month and they will evaluate whether you got paid enough or too much.