Choosing the Best Month to Retire, Ep#216

Retirement is the beginning of a new story, and the decisions you make leading up to your last working day can significantly impact your financial well-being and peace of mind. On the show this week, I focus on the importance of timing your retirement and how choosing the specific month to retire can significantly impact your finances, taxes, and benefits. 

 

There are various financial and emotional factors to weigh—ranging from optimizing pensions and bonuses to health insurance coverage and even non-financial considerations like climate and seasonality. Careful planning avoids costly mistakes, such as unnecessary taxes or missed income opportunities. I also explore listener questions, covering topics such as whether to pay off your mortgage before retiring, how much cash to keep on hand, how to develop a withdrawal strategy, and how to plan for inherited IRAs, to empower you to make informed choices as you approach or navigate retirement.

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You will want to hear this episode if you are interested in...

 

• [01:45] How the timing of retirement affects financial outcomes

• [05:55] Timing retirement with bonuses

• [12:11] Timing retirement for tax benefits

• [16:32] Paying off mortgage before retirement

• [18:50] Premature 401 (k) withdrawal tax mistake

• [26:44] Benefits of early Roth conversions

• [31:49] Planning a tax-free legacy

• [41:54] Understanding annuity and IRA rules

 

The Right Month to Retire

 

One concept discussed was the surprising significance of when in the year you retire. Many people pick their retirement date based on sentimental reasons—such as a birthday or simply reaching the end of a fiscal quarter. In actual fact, the month you retire can swing your benefits, taxes, and overall income.

 

There is a financial advantage of retiring early in the year, particularly in the spring. Retiring after you’ve earned just a few months of income keeps you in a lower tax bracket for the year. This allows you to maximize Roth IRA or 401(k) contributions, capitalize on the year’s HSA limits, and possibly stack up a payout on unused vacation and PTO in a low-income year—saving you thousands in taxes. Conversely, retiring near the end of the year—after most income is already earned—often means higher taxes on lump-sum payouts and fewer options for account contributions.

 

Retiring into spring, particularly in colder climates, can offer a positive mental boost, making the transition out of work more enjoyable compared to the isolation of a winter retirement.

 

Don’t Leave Money on the Table

 

Specific benefits such as bonuses, profit sharing, and pension calculations are often tied to your official retirement date. For instance, certain pension plans count an additional year of service if you retire in January rather than December, potentially increasing your monthly payout for life.

 

Bonuses commonly paid in the first quarter motivate many to extend their tenure until after the check clears. Health insurance is another major factor—timing your departure can determine whether you maximize employer contributions or face high premiums through COBRA or private options, especially if you retire before becoming Medicare-eligible at 65.

 

Mortgage Decisions: To Pay Off or Not to Pay Off?

 

A popular listener question is whether to pay off your mortgage before retirement. While there’s no one-size-fits-all answer, many self-made millionaires pay off their homes early. Without a mortgage, your required monthly income drops—granting financial flexibility and security.

 

Rushing to pay off your mortgage by tapping tax-deferred accounts while still earning a high salary can lead to hefty tax bills—sometimes costing tens of thousands extra. Instead, consider timing large withdrawals for when your income is lowest to minimize taxes, especially in your first year of retirement.

 

Making Your Money Last

There are many different approaches to withdrawing funds in retirement, like proportional withdrawals across tax buckets, or spending from traditional IRAs first and Roth IRAs last, and they can have drastic long-term tax implications. 

 

Legacy goals further complicate the equation. If leaving tax-efficient inheritances or charitable gifts is important, incorporating those aims into your withdrawal strategy early makes a huge difference for heirs. Mapping out these decisions alongside a financial planner can mean hundreds of thousands in potential savings. Retirement is a complex transition that deserves a thoughtful, strategic approach. The months and years leading up to your last day at work hold opportunities (and pitfalls) that can greatly affect your financial future. 

Resources & People Mentioned

 

• 3 Steps to Retirement Planning

• Ramsey Solutions 

 

Connect With Gregg Gonzalez

 

• Email at: [e-mail]

• Podcast: https://RetireStrongFA.com/Podcast

• Website: https://RetireStrongFA.com/

• Follow Gregg on LinkedIn

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• Follow Gregg on YouTube

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