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2020 Retirement Calendar

December 23, 2019

The New Year marks the opportunity for a new beginning. It’s a time to reflect, refresh, and recommit. A great way to start may be with solid financial resolutions that can help you reach your goals. You can start by making a list, but the key is creating actionable steps and sticking to them. Below are important deadlines to help you stay on track.


  • 1stMedicare Open Enrollment period begins. During this time, you’ll have a one-time opportunity to switch plans or return to Original Medicare1
  • 1stMedicare General Enrollment period begins. If you delayed enrollment, you can sign up for Medicare Parts A and/or Part B and coverage will be begin July 1st1
  • 15thDeadline for Q4 2018 estimated tax payment2


  • Begin organizing your 2018 taxes
  • 1st – 28th: Medicare Open Enrollment Period continues
  • 1st – 28th: Medicare General Enrollment Period continues


  • 31st: Deadline for Medicare Advantage Open Enrollment
  • 31st: Deadline for Medicare General Enrollment


  • 1st: If you turned 70 ½, this is the last day to withdraw your first IRA required minimum distribution (RMD) to avoid a hefty tax penalty3
  • 15th: Deadline for taxes or apply for an extension
  • 15th: Deadline for payment for Q1 estimated taxes2


  • 15th: Deadline for Q2 estimated tax payment2


  • 15th: Deadline for Q3 estimated tax payment2
  • 30th: Deadline for determining designated beneficiaries of an IRA or employer-sponsored retirement plan4


  • 15th: Deadline for extended individual tax returns
  • 15th: Medicare Open Enrollment period begins and ends December 7th


  • 1st – 30th: Medicare Open Enrollment Period continues
  • 1st – 15th: Open Enrollment Period for individual health insurance5


  • 7th: Medicare Open Enrollment Period ends
  • 15th: Deadline for Open Enrollment for individual health insurance
  • 31st: Deadline for stocks, RMDs, itemized deductions, and gifts to count for 2020 taxes

As we approach a new year, it’s a great time to reflect on this year’s finances and to also be prepared for what’s to come in 2020. Call us and we can help you prioritize and plan to get you from where you are now to where you want to be.


This document is for educational purposes only and should not be construed as legal or tax advice. One should consult a legal or tax professional regarding their own personal situation. Any comments regarding safe and secure investments and guaranteed income streams refer only to fixed insurance products offered by an insurance company. They do not refer in any way to securities or investment advisory products Insurance policy applications are vetted through an underwriting process set forth by the issuing insurance company. Some applications may not be accepted based upon adverse underwriting results.  Death benefit payouts are based upon the claims paying ability of the issuing insurance company. The firm providing this document is not affiliated with the Social Security Administration or any other government entity.

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