If you were born in May 1959, you are turning 66 in 2025. This puts you right at the doorstep of traditional retirement age. When you can retire depends on your Social Security eligibility, Medicare enrollment and, most importantly, your financial readiness. While age 66 is often associated with retirement, full retirement age (FRA) for those born in 1959 is slightly higher, making careful planning even more important.
A financial advisor can help you assess your options and determine the best timing for a secure and comfortable retirement.
Average Retirement Age
The average retirement age in the United States is 65 for private industry workers and 60 for state and federal employees, according to the Bureau of Labor Statistics. However, when you can retire largely comes down to personal financial circumstances more than age. If you were born in May 1959, you’ll need your savings and benefits to support you for 25-30 more years. That’s why it’s important to consider the long-term impacts of when you retire.
Can You Afford to Retire?
Saving enough to retire comfortably is critical. Financial experts often suggest a common benchmark of 70% to 80% of your pre-retirement income each year to maintain your lifestyle.
For example, if your current salary is $80,000, you would likely need around $56,000 to $64,000 per year in retirement income. That could come from a combination of savings, Social Security, pensions or other income sources. Retirement calculators can help estimate how much you’ll need based on your specific goals.
If you miss these benchmarks, consider part-time work, delaying retirement, or lifestyle adjustments that fit a more modest budget. A financial advisor can provide even more personalized guidance.
What About Social Security?
If you were born in May 1959, your full retirement age for Social Security purposes is 66 years and 10 months. That means you won’t qualify for your full Social Security benefit until March 2026. You can start claiming benefits as early as age 62, but be aware that it reduces your monthly benefit. Here’s how the numbers generally break down:
- Claiming at 66: Your benefit will be close to, but not quite, the full retirement amount.
- Claiming at FRA (66 and 10 months): You receive 100% of your calculated Social Security benefit.
- Waiting until 70: Your monthly benefit will be roughly 24%-32% higher than your full retirement age benefit due to delayed retirement credits.
In 2025, the average Social Security retirement benefit is approximately $1,976 per month. Your benefit could be considerably higher, potentially $2,500 or more, if you delay it.
Don’t Forget About Medicare

Enrollment typically starts three months before your 65th birthday and extends three months after. Missing your initial enrollment window can result in penalties that permanently increase your premiums. Sign up on time unless you have other qualifying coverage.
Medicare Part A (hospital insurance) is generally premium-free if you paid Medicare taxes while working. However, Medicare Part B (medical insurance) and Part D (prescription drug coverage) do have monthly premiums. In 2025, the standard Part B premium is about $185 per month, but it can be higher for higher-income earners.
You may also want to consider a Medigap (supplemental insurance) policy or a Medicare Advantage Plan. These help with out-of-pocket costs not fully covered by Original Medicare.
Retirement Readiness Checklist
Before deciding when to retire, if you were born in May 1959, it’s a good idea to walk through a retirement readiness checklist. Here are a few things to consider before leaping:
- Assess Your Savings: Have you accumulated enough savings to replace about 70% to 80% of your pre-retirement income? Make sure you understand how much you’ll be able to safely withdraw each year.
- Review Your Social Security Strategy: Determine your full retirement age and the impact of claiming early vs. waiting until 70. Calculate your expected monthly benefits under different scenarios.
- Understand Your Healthcare Coverage: Confirm your Medicare enrollment. Explore whether you need supplemental insurance, a Medicare Advantage Plan or prescription drug coverage.
- Create a Detailed Budget: Estimate your retirement budget, including housing, food, healthcare, travel, hobbies, and unexpected emergencies. Build a realistic monthly and annual spending plan.
- Evaluate Debt: Ideally, you should enter retirement with minimal debt. Pay down high-interest loans and mortgages, if possible, to reduce financial stress later on.
- Plan for Inflation: Make sure your retirement investments and income strategy account for the rising cost of living over time.
- Consider Part-Time Work or Hobbies for Income: If there’s a budget shortfall, consider part-time work or other sources of extra income.
- Consult a Financial Advisor: A professional can help you optimize your retirement income streams, minimize taxes and structure your investment portfolio for both growth and protection.
Taking the time to go through this checklist can help ensure you’re well-prepared for a financially secure and fulfilling retirement.
Bottom Line

If you were born in May 1959, you’re entering a critical stage for retirement decision-making. While you can technically retire at any time you’re financially able, your full Social Security retirement age won’t arrive until early 2026. Affording retirement depends not just on age, but on whether you have sufficient savings, healthcare coverage and an income plan that can last 20 to 30 years.
Tips for Retirement Planning
- Retirement planning is a vital part of making sure your finances line up with your long-term goals. A financial advisor has the expertise to help you navigate this difficult journey. Finding a financial advisor doesn’t have to be hard. SmartAsset’s free tool matches you with vetted financial advisors who serve your area, and you can have a free introductory call with your advisor matches to decide which one you feel is right for you. If you’re ready to find an advisor who can help you achieve your financial goals, get started now.
- Are you saving enough money for retirement? If you’re not sure, consider estimating the amount you may need with a retirement calculator.
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