2019 Retirement Calendar – Key Dates to Help Stay on Track

| December 26, 2018

You’ve worked hard this year and it’s that time of the year again for New Year’s Resolutions. And for many of us, that means getting your finances in order. Follow the calendar below to track important deadlines and notices for your financial health.


  • 1st:Medicare Open Enrollment period begins and ends March 31st. During this period, you will have a one-time opportunity switch plans or return to Original Medicare1
  • 1st:Medicare General Enrollment period begins and ends March 31st. If you delayed enrollment, you can sign up for Medicare Parts A and/or Part B and coverage will be begin July 1st.1
  • 15th:Deadline 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


  • 1st – 31st: Medicare Advantage Open Enrollment Period continues
  • 1st – 31st: Medicare General Enrollment Period continues


  • 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 penalty.3
  • 15th: Deadline for taxes or apply for an extension
  • 15th: Deadline for payment for Q1 estimated taxes


  • 17th: Deadline for Q2 estimated tax payment


  • 16th: Deadline for Q3 estimated tax payment
  • 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: Open Enrollment Period for Individual Healthcare begins and ends on December 15th5


  • 7th: Medicare Open Enrollment Period ends
  • 15th: Open Enrollment Period for Individual Healthcare ends
  • 31st: Deadline for stocks, RMDs, itemized deductions, and gifts to count for 2019 taxes

As we approach the 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 2019. And you can rest assured that you’re not going into it alone. Call us and let us help you strategically map out your goals and make it your best year yet!

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[1] https://www.medicareresources.org/faqs/when-is-the-next-medicare-open-enrollment-period/
[2] https://turbotax.intuit.com/tax-tips/tax-planning-and-checklists/important-tax-deadlines-dates/L7Rn92V1d
[3] https://www.bankrate.com/taxes/some-taxpayers-face-a-deadline-to-make-ira-withdrawal
[4] https://thelink.ascensus.com/articles/2018/9/18/september-30-deadline-key-to-beneficary-distributions 
[5] https://www.peoplekeep.com/blog/annual-open-enrollment-periods-2015-2020