Navigating Financial Changes in Anticipation of Your Upcoming Retirement

By Marc C. Shaffer

For many, a new year means a fresh financial start. For those nearing retirement, it means another day closer to a momentous transition. Whether you have your retirement date circled on the 2024 calendar or coming up in the next few years, the new year can be a great time to get your financial ducks in a row and make sure you’re checking the right boxes before the big change.

One of the first conversations we have with clients is their time horizon. We want to be aware of the big milestones planned for the future and determine a strategy that makes sense to help meet those milestones when they occur. The strategy for a retirement in five years could look very different than a retirement that isn’t planned for another thirty.

The 2023 Retirement Confidence Survey showed that only 18% of workers felt very confident about retirement. And this occurs at every level of wealth. The survey also shows that 6 out of 10 workers report a problem with debt. Even if you make a high salary, if your spending increases at the same level as your income, it doesn’t leave much room for saving and investing for the future. Cash flow management can be a critical component in raising these confidence numbers for yourself. A balanced spending approach and watchful eye on the cash flow, among other financial planning components, could help increase confidence in a comfortable retirement.

While retirement can be a main focus of your financial planning, there are financial milestone ages that might trigger a closer look at your situation. A few of these milestone ages include:

Age 50 – At this age, you become eligible to make catch-up contributions in your retirement accounts.

Age 55 – You become eligible to make catch-up contributions to your Health Savings Account (HSA).

Age 59 ½ – You have the option to start making withdrawals from your retirement plans.

Age 65 – You could be eligible for coverage under Medicare (assuming timely application).

Age 70 – This is the age that you can receive the maximum Social Security benefit payout if you delayed starting your benefits.

Questions to ask as you near retirement:

  • Are you assuming the right amount of risk on your investments?
  • Are you maximizing (by timing) your Social Security benefits?
  • Does it make sense to consider annual Roth conversions as soon as your income moves into a lower tax bracket?
  • Is your estate plan up to date?
  • Have you factored items such as extended care into your retirement projection?
  • Will you be retiring with too much debt?
  • Are you preparing physically and mentally for retirement?
  • At any time during retirement, do you plan to change your residence?
  • Do you expect to have large Required Minimum Distributions?
  • Will your charitable giving goals change?

Don’t let an upcoming retirement catch you unprepared.



Please remember that different types of investments involve varying degrees of risk, and there can be no assurance that the future performance of any specific investment, investment strategy, or product made reference to directly or indirectly in this content, will be profitable, equal any corresponding indicated historical performance level(s), or be suitable for you or your portfolio. Due to various factors, including changing market conditions, the content may no longer be reflective of current opinions or positions. Moreover, you should not assume that any discussion or information contained in this newsletter (article) serves as the receipt of, or as a substitute for, personalized investment advice from Searcy Financial Services, Inc.

The content of this letter does not constitute a tax or legal opinion. Always consult with a competent professional service provider for advice on tax or legal matters specific to your situation. To the extent that a reader has any questions regarding the applicability of any specific issue discussed in this content, he/she is encouraged to consult with the professional advisor of his/her choosing.  

Published for the blog on January 15, 2024 by Searcy Financial Services, your Overland Park, Kansas Fee-Only Financial Planner and Investment Manager.