Retirement Traps to Avoid Full Size Version Share | Related Content Should You Ever Retire? A growing number of Americans are pushing back the age at which they plan to retire. Or deciding not to retire at all. Three Key Questions to Answer Before Taking Social Security When to start? Should I continue to work? How can I maximize my benefit? Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.