@CharlesW986326 First, I would review the eligibility requirements for any of your employer's benefits (i.e., defined benefit pension, 401 K match, profit sharing, any bonus payments, etc.). For example, some employers who sponsor profit sharing plans may operate on a calendar year basis. So, profits, if any, may not be known until after December 31st. Payments, if any, may be issued in February. Also, you may accrue vacation (i.e., 4 weeks, etc.) annually. Will you receive vacation pay in lieu of time off? With regard to health insurance, the ACA provides subsidies if your income is below certain thresholds. You need to review those threshold for your status (i.e.,single, married, dependents,etc.) in the year you loose employer sponsored health insurance. If your income is above the thresholds, take a look at COBRA continuation coverage thru your employer's Plan. Based on all of the above, there may be an advantage to retire in the beginning of the year.