There is a constant that all pre-retirees and retirees have in common: planning is crucial to financial success and being prepared pays dividends.


  • Begin collecting your tax documents (W-2s, 1099s, K-1s, 1098s, etc.)
  • While gathering data for your 2019 return, look for ways to cut your 2020 tax bill.
  • Put more into your 401(k) for 2020.
  • Consider contributing to a traditional IRA, Roth IRA or both. Maximum total IRA contribution for 2020 is $6,000 ($7,000 if you are 50 or older).
  • Medicare Advantage open enrollment is January 1st – March 31st.
  • The Part A/Part B general enrollment period is January 1st – March 31st.
  • Fourth-quarter estimated tax payments for 2019 must be made by January 15th.
  • If you receive social security, any cost-of-living adjustment (COLA) change will be reflected starting with your January check.


  • If you have a flexible spending account (FSA) and your employer offers a grace period to use up FSA funds from the previous year, it expires March 15th.
  • Review your auto and home insurance coverage. Sites such as and provide quotes from various insurers.


  • For those who turn 70 ½ in 2019, you must take your first required minimum distribution. All subsequent RMDs must be taken by December 31st. With the Secure Act passing in late 2019, the RMD age changed from 70 ½ to 72. For 2020 and on, RMDs must be taken in the year in which you turn 72. Those who have just turned 72 in a given year have until April 1st of the following year to start taking their RMDs. After that one-time extension, subsequent payments must be made by the end of the calendar year.
  • 2019 IRA contributions can be made up until April 15th.
  • Tax returns must be filed by April 15th for the 2019 tax year.
  • 1st Quarter estimated tax payments need to be made by April 15th.
  • April is Financial Awareness month. Take some time to review your budget and overall retirement plan. Meet with your financial advisor to ensure your plan still aligns with your goals and risk tolerance. Share any new events that have transpired that may impact your plan or any changes you wish to have made. Check your understanding regarding any recent legislation and how it may impact your financial goals.


  • 2nd quarter estimated tax payments must be made for 2020.
  • Check your credit report. Visit to claim your free annual report and check for errors or signs of fraud.


  • Perform a mid-year tax checkup. Look for ways to lower your taxable income for 2020 such as making additional contributions to tax-advantaged accounts or health savings account (HSA).


  • Check your withholdings to avoid underpayment penalties. (Pay at least 90% of the current year’s tax owed or 100% of the prior year’s tax owed to avoid penalties.)


  • 3rd quarter estimated tax payments must be made for 2020.
  • Look in your mailbox for your “annual notice of change” (changes in cost or coverage) from your Medicare Advantage or Part D prescription – drug plan.


  • Tax return extensions are due by October 15th.
  • Medicare open enrollment starts and ends on December 7th. You can switch between traditional Medicare and Medicare Advantage or choose new Advantage and Part D plans. Coverage is effective in 2021.
  • Review your estate planning documents (wills, POAs, medical directives, beneficiaries) because October is Estate planning awareness month and you want to ensure these documents are up to date with changing legislation and aligned with your current wishes.
  • Cost-of-living adjustment (COLA) figure will be announced. It is essentially the “raise” that seniors may receive that is aimed at keeping up with inflation.
  • The Free Application for Federal Student Aid for the 2021-2022 school year should be released on October 1st. You will have until June 30, 2021, to submit the form for federal aid, but it should be completed as soon as possible since many states/schools award money on a first-come, first-served basis.


  • Retirees in many states can buy 2021 health coverage via exchanges under the Affordable Care Act from November 1st through December 15th.
  • Review your portfolio for tax-loss harvesting opportunities.
  • Open enrollment for health insurance benefits provided by employers typically takes place in November. You can also pick a plan from the individual market and Medicare at this point in time. Evaluate your options to ensure you get the plan that suits your needs at the lowest cost.


  • The annual five-star Medicare Advantage enrollment period is December 8th – November 13th.
  • Make sure you have taken your RMD prior to year-end. If you are making a qualified charitable distribution, begin the process by the first week in December to ensure the charity receives the money by December 31st.
  • Ensure you have made all charitable gifts, gifts to family (annual gift exclusion of $15,000), and any additional contributions to your retirement account prior to December 31st to decrease your 2020 tax bill.


Sources: Kiplinger/ MarketWatch/ Forbes

© Geier Asset Management, Inc. January 2020. Gregory Palacorolla, CFP ® is Director of Wealth Management for Geier Asset Management, Inc., a Registered Investment Advisor. The articles & opinions expressed in this material were gathered from a variety of sources, but are reviewed by Geier Asset Management, Inc. prior to its dissemination. All sources are believed to be reliable but do not constitute specific investment advice. The views expressed are those of the firm as of January 2020 and are subject to change. These opinions are not intended to be a forecast of future events, a guarantee of results, or investment advice. Any advice given is general in nature and investors must consider their own individual circumstances. In all cases, please contact your investment professional before making any investment choices. Geier Asset Management, Inc. is not responsible for any damages or losses arising from any use of this information. Past performance is no guarantee of future results.