Retirement Planning Roadmap: 9 Key Milestones Starting at Age 50

Even though most people don’t begin serious planning until later, starting at age 50, retirement preparation becomes increasingly important. This article outlines a few things you can do to set yourself up early for a comfortable and secure retirement using a retirement planning checklist as your guide.

Age 50: Catch-Up Contributions Begin

At age 50, you can start making “catch-up” contributions to your retirement accounts. This means you can put extra money into your 401(k), 403(b), or IRA each year. For example, in 2025, people aged 50 or older can contribute an extra $7,500 to their 401(k) on top of the regular limit of $23,500. Those 50 and older can also contribute an extra $1,000 to their IRA on top of the regular $7,000 limit. These contributions are a key item on any “prepare for retirement” checklist, helping boost your savings if you started late or if you just want to save more before retiring.

Age 55: HSA Catch-up Contributions

If you are eligible for a Health Savings Account, you may begin making additional catch-up contributions of $1,000 per year at age 55. This is on top of the regular HSA contribution limits for 2025—$4,300 for individual (self-only) coverage and $8,550 for family coverage. So, for example, a 55-year-old with family coverage can contribute up to $9,550 annually. This tax-advantaged savings option should be considered when building your retirement planning checklist. 

Age 59½: Access to Retirement Funds

Once you reach 59½, you can take money out of your IRA or workplace retirement plans without the 10% penalty. You will still owe regular income taxes on most withdrawals but at this age and beyond you have more flexibility to use your savings as needed. This practice isn’t recommended but it’s an available option if you need it. 

Ages 60–63: Extra Catch-Up Contributions

If you’re 60 to 63, you can make even larger catch-up contributions to 401(k), 403(b), and governmental 457(b) plans. The 2025 “super” catch-up contribution limit is $11,250. This is another chance to boost your nest egg before retiring and should be a priority on your preparing to retire checklist.

Age 62: Early Social Security

You can start receiving Social Security benefits as early as age 62, but your monthly payments will be significantly lower than if you wait until your full retirement age (67 for most people retiring after 2024). Most people benefit from waiting as long as possible. Consider your goals carefully and weigh this choice within your retirement preparation checklist.

Age 65: Medicare Enrollment

Open Enrollment for Medicare, the government health insurance program, begins three months before your 65th birth month. The Open Enrollment period includes your birthday month and the three months before and after it. Even if you’re still working or not ready to retire, you may still need to enroll on time to avoid permanent penalties. This milestone is a standard item in any retirement planning checklist to ensure healthcare needs are addressed. 

Ages 66–67: Full Retirement Age for Social Security

Depending on your birth year, your full retirement age for Social Security is between 66 and 67. If you wait until this age to start benefits, you’ll get your full monthly amount. If you have other income sources to rely on in the early years of retirement, waiting until age 70 can boost your monthly payments and provide some insurance against running out of money later. 

Age 70: Delayed Social Security

Once you reach age 70, your Social Security payments will not increase anymore, so this is often the optimal time to begin collecting your benefits. Evaluating the timing should be a part of your pre-retiree checklist.

Ages 73–75: Required Minimum Distributions (RMDs)

Once you reach age 73 (or 75 if you were born in 1960 or later), you must start taking required minimum distributions (RMDs) from most retirement accounts, like traditional IRAs and 401(k)s. If you don’t take out at least the minimum amount each year, you could face big tax penalties. The RMD rules do not apply to Roth IRAs while the owner is still living.

Other Important Tips

  • Long-term Care Insurance: Consider securing this between ages 50 and 60, which is the optimal window to obtain lower premiums. 
  • Debt Reduction: Aim to pay off your mortgage, home equity loans, and credit card debt before retirement to lower your monthly expenses.
  • Estate Planning: Update your will, trust, power of attorney, and other important documents as you approach retirement. 

Ages 50 to 75 are full of important financial milestones. By knowing what to expect and taking action at each stage, you can build a solid foundation for a secure and enjoyable retirement. As these milestones approach, having a thoughtful plan in place can make a big difference. The CERTIFIED FINANCIAL PLANNER® professionals at Blankinship & Foster specialize in simplifying the complexities of retirement planning in San Diego. Contact us and we’ll partner with you to navigate the road ahead with clarity and confidence.

About Rick Brooks

Rick Brooks, CFA®, CFP® is a partner of Blankinship & Foster LLC and is the firm’s Chief Investment Officer. He is a lead advisor, counseling clients on all aspects of personal financial management. Rick serves on several boards. He is the Chairman of the Board of Girl Scouts San Diego, and also chairs the San Diego Foundation’s Professional Advisor Council. Rick and his family live in Mission Hills. Rick enjoys spending time with his family, theater, cooking, skiing, gaming and reading.

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