When is the best time of year to retire?

1 min read by Unbiased team Last updated June 28, 2024

Careful planning of retirement timing can optimize your finances, taxes, pension benefits, healthcare coverage, and Social Security income, ensuring a smooth transition into retirement.


  • Retiring before your full retirement age can reduce Social Security benefits by up to 30%.  

  • Early retirement elevates the risk of premature withdrawals from retirement accounts, resulting in penalties. 

  • Retiring at the end of a tax year can result in potential savings due to lower taxable income. 

  • A financial advisor knows all the ins and outs of retirement planning and can help you make decisions that will boost your savings.  

When is the best time to retire? 

Aligning your retirement timing with personal goals, financial needs, and employment conditions is crucial.  

The timing of your retirement can affect taxes, as retiring at the end of the year can result in lower taxable income for that year.  

Pension payouts can also vary based on your retirement date, with some companies offering better benefits if you retire at certain times. Additionally, your Social Security benefits may increase if you delay retirement. 

When deciding the best time of year to retire financially, consider your health, job satisfaction, and financial readiness.  

Planning around these factors can maximize your retirement benefits and ensure a smoother transition into your next phase of life. 

What are the tax considerations for retirement? 

It is wise to consider the best time of year to retire for tax purposes.  

Strategically timing your retirement can minimize your tax liabilities.  

For example, spreading lump-sum distributions over multiple years can prevent taxable income spikes. Also, to optimize your financial outcome, be mindful of the tax implications of your last paycheck and retirement benefits. 

For instance, retiring at the end of the year may lower your taxable income for that financial year, as you might only receive a few months' salary. This could place you in a lower tax bracket, reducing your overall tax liability.  

Conversely, retiring at the beginning of the year might lead to higher taxes, as your income includes your full salary plus any retirement payouts. 

How are pension and retirement account distributions affected? 

Choosing the best time of year to retire financially can maximize your monthly benefits, as some rules affect your retirement income and tax liabilities.  

Some pension plans offer higher payouts if you retire at certain ages or after completing specific years of service.  

Additionally, required minimum distributions (RMDs) from retirement accounts like 401(k) and IRAs must start at age 73.  

Retiring earlier might allow you to plan withdrawals more strategically, spreading them over several years to manage tax impacts. Delaying retirement can defer RMDs, potentially allowing your investments to grow tax-deferred for longer. 

What are the healthcare coverage options? 

Understanding what is the best time of year to retire ensures continuous healthcare coverage and financial protection.  

Transitioning from employer-provided insurance to Medicare or private plans requires careful timing. If you retire at 65 or older, you can enroll in Medicare, but it's essential to register during your Initial Enrollment Period (IEP) to avoid late penalties. 

If you retire before 65, you'll need private coverage until you become eligible for Medicare.  

Avoid gaps in coverage by planning the end date of your employer's insurance and the start date of Medicare or a new plan. Failing to register timeously can lead to pricey penalties and out-of-pocket expenses. 

What are the Social Security benefits? 

Deciding the best time of the year to retire for Social Security benefits depends on a few factors.  

If you retire and start benefits before your full retirement age (FRA), your monthly repayments will be permanently reduced. For example, retiring at 62 can cut your benefits by as much as 30%. In contrast, you'll receive full benefits if you retire at your FRA. 

Delaying retirement past your FRA increases your benefits by about 8% each year until age 70, resulting in higher monthly payments for life.  

Understanding these effects helps you choose the best retirement age to maximize your Social Security income and ensure long-term financial stability. 

How can you plan for a smooth transition into retirement? 

Planning a smooth transition into retirement involves several steps: 

  • Start with comprehensive financial planning, where you assess your savings. 

  • Budget for future expenses. 

  • Explore retirement income sources like pension benefits, healthcare coverage, and Social Security income.  

Transitioning work responsibilities is crucial, too: 

  • Delegate tasks and train successors to ensure a seamless handover.  

  • Communicate with your employer about your retirement plans and timeline. 

Create a detailed retirement timeline that aligns with your personal strategies and financial goals. This includes setting milestones for financial readiness, healthcare coverage, and critical retirement dates.  

Review and tweak your plan regularly to stay on track and maximize the benefits of choosing the best time of year to retire. 

Get expert financial advice  

Choosing the best time of year to retire financially can significantly impact your taxes, pension benefits, healthcare coverage, and Social Security income. Careful planning ensures you optimize your retirement benefits and minimize tax liabilities. Additionally, coordinating your healthcare coverage and preparing a detailed retirement plan are crucial steps for a smooth transition. A financial advisor can tailor a retirement plan that aligns with your unique financial situation and supports your personal goals.  

For personalized guidance and expert financial advice, get matched with a financial advisor through Unbiased. 


Unbiased team

Our team of writers, who have decades of experience writing about personal finance, including investing and retirement, are here to help you find out what you must know about life’s biggest financial decisions.