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Working May Decrease Your Social Security Benefits Many taxpayers currently underemployed due to recent economic conditions may consider applying for social security retirement benefits earlier than they previously planned to supplement their income. But, continuing to work while receiving those benefits may cause their benefits to be reduced below the anticipated amount.   Assisting Grandchildren with College Costs Contributing to a Section 529 college savings program is a great way for grandparents to help their grandchildren pay for college.   Federal Taxation of Social Security Benefits With millions of baby boomers close to retirement age and job losses inflicting financial strain on additional millions, many taxpayers are looking to social security benefits for financial assistance.