Money Matters

2020’s Dates to Remember

7 Jan 2020 by: Matt Showley 

As we prepare for this new year and new decade, we wanted to summarize and share some important dates to remember. While we enjoy staying on top of all the changes coming our way, we know that remembering these dates may not be top priority for everyone. Please use this as a reference to keep you prepared for 2020. Additionally, we encourage you to do a free credit check through Experian, Equifax and TransUnion.

Health Care

  • January 1 to March 31: Medicare General enrollment period*
  • January 1 to March 31: Medicare Advantage open enrollment period (NEW)
  • April 15: Last day to fund a Health Savings Account (HSA) for 2019
  • October 15 to December 7: Medicare Advantage and drug plan open enrollment
  • November 1 to December 15: Affordable Care Act (ACA) open enrollment
  • September to December: Keep an eye out for your employer’s open enrollment dates to review and make changes to your benefit elections

*Only if you have not already signed up when you were first eligible for Medicare or if you were not eligible for a special enrollment period.


  • January 1: First day to fund your retirement savings for 2020
  • January 15: Estimated taxes for Q4 2019 due
  • April 15: Last day to file income taxes or apply for an extension
  • April 15: Last day to contribute to a Roth IRA or a Traditional/Rollover IRA for 2019**
  • April 15: Estimated taxes for Q1 due
  • June 15: Estimated taxes for Q2 due
  • September 15: Estimated taxes for Q3 due
  • September 30: Last day to determine beneficiaries after an IRA owner’s death
  • October 1: Extended trust and estate taxes due
  • October 15: Income tax deadline if you filed an extension
  • December 31: Last day for stock sales, Required Minimum Distributions (RMDs), itemized deductions, and gifts to count for 2020 taxes

**IRAs for small business owners must be funded by the employer’s tax filing deadline, which may include an extension.


  • June 30: Last day to file the Free Application for Federal Student Aid (FAFSA)
  • October 1: First day to file the FAFSA for college financial aid

Birthday Milestones

  • Age 50: Eligible to begin catch-up contributions to retirement plans
  • Age 55: Penalty-free distributions allowed from 401(k)s (under certain rules and restrictions)
  • Age 55: Eligible to begin catch-up contributions to HSAs
  • Age 59 1/2: Penalty-free distributions allowed from IRAs and qualified plans, and Roth IRAs that are at least five years old
  • Age 60: Can apply for reduced Social Security under deceased spouse’s earnings record
  • Age 62: Can apply for reduced Social Security under own earnings record (benefits reduced)
  • Age 65: Can apply for Medicare (Parts A and B) beginning three months before birthday
  • Age 66-67: Full retirement age for unreduced Social Security benefits
  • Age 70: Apply for Social Security at this age to get maximum benefits
  • Age 72: Must start IRA Required Minimum Distributions (RMDs)

While we know that not all dates and ages are applicable to each situation, it is good to have a general idea of what to expect.  Things will continue to change but we wanted you to be aware of the updates for the coming year. Give CCMI a call if you need help answering your questions as it relates to the items above or to other new developments such as the SECURE Act and how it may impact your retirement.

CCMI provides personalized fee-only financial planning and investment management services to business owners, professionals, individuals and families in San Diego and throughout the country. CCMI has a team of CERTIFIED FINANCIAL PLANNERTM professionals who act as fiduciaries, which means our clients’ interests always come first.
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