Is There a Best Day of the Year to Retire?
Taking into consideration the time of the month and the time of the year can make a difference in your retirement income.
![A businessman looks at a calendar while also using his laptop at his desk.](https://cdn.mos.cms.futurecdn.net/ByQMS78LF54hQrfN8yaeU6-415-80.jpg)
This common question comes from those who are fortunate enough to have the flexibility to decide. The reality is that the date is often a compromise between you and your employer. A combination of that employer’s benefits, as well as IRS rules, should help you decide which day makes the most sense for you. In today’s article, we are going to cover three options and the potential benefits that come with each.
July 31
As a general rule, the end of the month is good for those with pensions, as those often start on the first day of the month after retirement. In this scenario, retiring on the 31st means that you won’t have a gap in pay.
The midyear strategy has to do with condensing all income into one calendar year so that you’ll see a drop in taxes the following year. This could be accomplished on December 31 if it weren’t for the lump sums that are often paid out in the months following your retirement. This may include bonuses, commissions, unpaid vacation and sick leave.
![https://cdn.mos.cms.futurecdn.net/hwgJ7osrMtUWhk5koeVme7-200-80.png](https://cdn.mos.cms.futurecdn.net/hwgJ7osrMtUWhk5koeVme7-320-80.png)
Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
If you see a significant drop in your tax bracket in the following year, you should evaluate Roth conversions and capital gains recognition. This is a tax sale.
December 31
As above, December 31 has the benefit of a full month of income with the pension starting the next day. This is a common date for federal employees, who are the kings and queens of gaming the retirement system. Retiring on December 31 is likely to maximize your unpaid annual leave check.
There’s a drawback, though: That lump sum will come next year. So, between that and your pension, you are unlikely to see a big drop in income taxes.
January 1
Pensions seem to be a recurring theme. Certain employers’ pension plans credit a year of service, for calculation purposes, on January 1. Similarly, you may get a cost-of-living adjustment by staying until January 1. This varies by employer.
This one makes sense for those who are retiring after required minimum distribution age. The money in your current employer’s retirement plan was exempt from RMDs due to the still-working exception. However, that RMD starts in the year you retire, even if that’s December 31.
In other words, if you retire on December 31, 2023, you will have two RMDs from your employer plan in 2024. The 2023 RMD will have to be taken by April 1, 2024, and the 2024 RMD by December 31, 2024.
If you retire on January 1, you’ll have only the 2024 RMD in December.
Other considerations
Vesting of retirement plans. I have seen six-figure sums left on the table by walking away before employer matches in retirement plans are fully vested. You will always get the money that you contributed. However, the employer match will follow some sort of vesting schedule that you need to outlast in order to keep that money.
Vesting of stock options. Stock options are a retention tool. Any unvested options will be forfeited when you are no longer retained. Here’s the thing: This is a moving finish line. Typically, employers will keep issuing new options on an ever-extending vesting schedule. At some point, you just need to pull off the Band-Aid.
Health care. This maze will be a topic of a future article. The most important thing for our clients is to ensure you have a plan between retirement and Medicare eligibility. Often, COBRA serves as the bridge. If that’s the bridge you want to use, you’ll need to work backward from age 65 to see when you can retire, based on how long your COBRA coverage will last.
People spend too much time trying to game this system. Of course, you don’t want to leave free money on the table, but it’s more important to ensure that you have enough than it is to decide between December 31 and January 1.
If you want one final check of your math, you can use this free software to see where you stand.
Related Content
Get Kiplinger Today newsletter — free
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.
After graduating from the University of Delaware and Georgetown University, I pursued a career in financial planning. At age 26, I earned my CERTIFIED FINANCIAL PLANNER™ certification. I also hold the IRS Enrolled Agent license, which allows for a unique approach to planning that can be beneficial to retirees and those selling their businesses, who are eager to minimize lifetime taxes and maximize income.
-
Eight Key Steps to Take When Investing in the Stock Market
The stock market can be a confusing place for beginners, but it doesn't have to be.
By Kiplinger Advisor Collective Published
-
Confused by Annuities? Making Sense of the Different Types
Many investors aren't sure if annuities are a good option for meeting financial goals. Let's look at the different categories, along with their pros and cons.
By Kris Maksimovich, AIF®, CRPC®, CPFA®, CRC® Published
-
Confused by Annuities? Making Sense of the Different Types
Many investors aren't sure if annuities are a good option for meeting financial goals. Let's look at the different categories, along with their pros and cons.
By Kris Maksimovich, AIF®, CRPC®, CPFA®, CRC® Published
-
Talkin' 'Bout My Generational Wealth: Baby Boomers
With retirement, each generation has different priorities and challenges. For Baby Boomers, it's a matter of ready or not, here it comes.
By Alvina Lo Published
-
How to Avoid a Big Hassle if Your Financed Car Gets Wrecked
How an insurance check is made out for repairs can cause a world of problems if the lienholder is left out.
By H. Dennis Beaver, Esq. Published
-
Estate Planning Strategies to Consider as Election Nears
Are big changes in tax laws coming soon? Not likely, but you might want to take advantage of higher estate and gift tax exemptions well before the end of 2025.
By David Handler, J.D. Published
-
How to Get Your Money's Worth From Your Financial Adviser
A good financial adviser will focus on how your financial planning and investment strategy align with your lifestyle and aspirations.
By Pam Krueger Published
-
Think of Prenups and Postnups as Financial Planning Tools
These contracts provide a clear framework for asset management and protection and are especially useful if you get married later in life.
By Andrew Hatherley, CDFA®, CRPC® Published
-
Congratulations on Your Raise: Three Things to Do With It
We're not saying you shouldn't spend it on a new car, but there are some considerations to guard against lifestyle creep and to help ensure a comfy retirement.
By Andrew Rosen, CFP®, CEP Published
-
Check Off These Four Financial Tasks to Finish 2024 Strong
The new year is a popular time to set financial goals, but now is the ideal time to check how you're doing. Four tweaks could make a big difference.
By Daniel Razvi, Esquire Published