A Bucket Plan to Go with Your Bucket List A bucket plan can help you be better prepared for a comfortable retirement. 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. When Should You Take Social Security Monthly Social Security payments differ substantially depending on when you start receiving benefits. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.