Knowing important financial dates are essential to both long term and near term financial planning. Preparing for this financial landscape gets more complex as your years increase. 

Whether it’s planning for retirement, claiming Social Security, or managing taxes, certain milestones come with crucial decisions. Understanding these key dates can help you maximize your benefits, avoid penalties, and create a more secure financial future.

In this guide, we’ll address common questions about important milestone dates that every financial conscience person needs to know. Let’s explore the most critical dates and what you should be doing at each point in your financial journey.

1. Social Security and Early Retirement (Ages 62-70)

When Can I Start Claiming Social Security?

You can begin claiming Social Security as early as age 62. However, this comes with a caveat: your monthly benefits will be reduced by about 25-30% if you take social security early. 

Also, keep in mind that your spouse’s benefit is reduced by 30% to 35% if social security is taken early. The Full Retirement Age (FRA) is between 66 and 67, depending on your birth year. 

If you want to maximize your benefits, delaying until age 70 is ideal, as it increases your payout by 8% each year past Full Retirement Age for those born after 1943. This brings up the critical decision:

• claim early or delay? 

This insight on key financial numbers can help you understand how your claiming strategy can impact long-term finances.

What Is Full Retirement Age (FRA)?

Full Retirement Age refers to the age at which you’re eligible to receive 100% of your Social Security benefits. If you were born between 1943 and 1954, your FRA is 66. For those born after 1960, the FRA is 67. 

Between these years, your FRA adjusts incrementally. Knowing your FRA is crucial. 

It affects not only your retirement benefits but also the spousal and survivor benefits that may be relevant in certain situations.

2. Medicare Enrollment (Age 65)

When Do I Qualify for Medicare?

Medicare eligibility begins at age 65. You can enroll three months before your 65th birthday, which starts your Initial Enrollment Period (IEP). 

Missing this enrollment period could lead to late fees that increase your premiums for life, so mark this date in your calendar. Many clients ask me, “Do I need Medicare if I have private insurance?” 

In most cases, enrolling in Medicare even if you have employer coverage is beneficial. However, you might want to check with your benefits administrator for more specifics on how Medicare will integrate with your existing coverage.

Pro Tip: Don’t miss out on exploring strategies to protect your wealth from unforeseen risks, including healthcare costs.

How Does My HSA Change After Age 65?

Once you turn 65, you can withdraw from your Health Savings Account (HSA) for non-medical expenses without incurring the 20% penalty. 

However, you will still owe taxes on these distributions. This flexibility is useful for covering a wide range of retirement expenses beyond healthcare.

3. Retirement Account Milestones (Ages 50-75)

When Can I Make Catch-Up Contributions?

Starting at age 50, you can make catch up contributions to various retirement accounts, such as 401(k)s, 403(b)s, and IRAs. For high earners, this is an excellent opportunity to turbocharge your retirement savings. 

In 2025, individuals over 50 can contribute an additional $500 to an IRA (Total of $7,500 to an Traditional IRA), on top of the contributions you can make to your workplace retirement plans.

Currently at the time of this writing (2025) there is an additional catch up contribution for those aged 60 to 63 of total contribution amount of $11,250.

If you’re playing catch-up with your retirement savings, this additional contribution space is your best friend. You may also want to explore 7 budgeting tips for non-budgeters to ensure you’re maximizing every opportunity to save.

When Do Required Minimum Distributions (RMDs) Begin?

If you were born before 1960, RMDs start at age 73. For those born in 1960 or later, RMDs don’t kick in until age 75. These mandatory withdrawals from your tax-deferred accounts (like IRAs and 401(k)s) can significantly impact your taxable income in retirement.

Missing an RMD comes with a steep penalty 25% of the required amount. So, make sure to plan carefully. To dive deeper into RMD strategies, check out my insight on important tax and financial numbers for 2025.

Can I Withdraw from My IRA Without Penalties?

At age 59½, you can withdraw from your IRA without the 10% early distribution penalty. However, keep in mind that withdrawals are still subject to income tax. 

This is a key date for those who want to access their retirement savings early for expenses like home renovations or starting a business.

4. Maximizing Social Security and Charitable Giving (Ages 60-70+)

When Do I Reach Maximum Social Security Benefits?

You’ll reach your maximum Social Security benefit at age 70. Every year you delay claiming past your FRA, your benefit increases by 8%. 

This could be a significant boost to your income in retirement, especially when factoring in spousal benefits. As someone who has worked with countless retirees, I’ve seen the immense value of waiting. 

A client of mine once told me that waiting until 70 was the best decision they made because it provided a higher level of financial security. If you’re concerned about inflation reducing the purchasing power of your Social Security benefits, take a look at inflation strategies for financial resilience.

Can I Make Tax-Free Charitable Donations?

At age 70½, you can begin making Qualified Charitable Distributions (QCDs) from your IRA. These donations are not subject to federal income tax and can also count toward your RMD. 

This is a fantastic strategy for high earners who want to support their favorite causes while reducing their taxable income.

5. Special Considerations for High Earners

How Do These Important Financial Dates Affect My Tax Planning?

Strategic timing of withdrawals from retirement accounts and Social Security can significantly impact your tax bracket. One strategy to consider is Roth conversions, which allow you to move money from a tax-deferred account to a Roth IRA, where it can grow tax-free.

I recently had a conversation with a client who was concerned about how receiving social security would push them into a higher tax bracket. By incorporating various tax strategies into their retirement plan, we are able to manage and efficently spread out their tax liability over several years, reducing their overall tax bill.

What Should I Consider for Estate Planning?

As you approach these milestones, it’s critical to keep your estate plan up to date. If you haven’t reviewed your beneficiary designations in a while, now is the time. 

Life changes like marriage, divorce, or the birth of grandchildren can all impact your estate planning needs. Also, do not forget about your income in retirement, and playing for loved ones after passing.

Check out 7 steps to evaluate your lump sum pension options for more insight into planning for these significant life events.

What’s Next: Staying Ahead of Key Milestone Dates

Understanding and preparing for these critical milestone dates can make a significant difference in your retirement planning. Whether it’s ensuring you’re claiming Social Security at the right time or making tax-efficient charitable contributions, each of these dates carries weight.

By planning ahead and working with a financial planner, you can navigate these milestones with confidence. If you’re ready to dive deeper into your financial journey, explore our insights page for more articles and resources.

Questions about the important financial dates, and/or you would like to receive the list of dates in a one page document? Let’s talk and I will send you the document via email.

FAQ: Important Financial Dates for High Earners and High Net Worth Individuals

Q1: When can I start claiming Social Security?

A: You can begin claiming Social Security as early as age 62. However, your monthly benefits will be reduced by about 25-30%, and your spouse’s benefit is also affected. To receive full benefits, you’ll need to wait until your Full Retirement Age (FRA), which is between 66 and 67 depending on your birth year.

Q2: What is Full Retirement Age (FRA)?

A: FRA is the age when you can receive 100% of your Social Security benefits. If you were born between 1943 and 1954, your FRA is 66. For those born in 1960 or later, it is 67. Your FRA also impacts spousal and survivor benefits.

Q3: When do I qualify for Medicare?

A: Medicare eligibility begins at age 65. You should enroll during your Initial Enrollment Period, which starts three months before your 65th birthday, to avoid lifetime penalties.

Q4: How does my Health Savings Account (HSA) change after age 65?

A: After age 65, you can withdraw HSA funds for non-medical expenses without a 20% penalty. However, you will still owe taxes on those distributions.

Q5: When can I make catch-up contributions to my retirement accounts?

A: Starting at age 50, you can make catch-up contributions to accounts like 401(k)s, 403(b)s, and IRAs. For 2025, individuals over 50 can contribute an additional $500 to their IRA, and those aged 60-63 can contribute an additional $11,250.

Q6: When do Required Minimum Distributions (RMDs) begin?

A: RMDs start at age 73 for those born before 1960, and at age 75 for those born in 1960 or later. Missing an RMD comes with a 25% penalty of the required amount.

Q7: Can I withdraw from my IRA without penalties before RMDs start?

A: Yes, at age 59½, you can withdraw from your IRA without incurring the 10% early withdrawal penalty. However, these withdrawals are still subject to income tax.

Q8: When do I reach maximum Social Security benefits?

A: You’ll reach your maximum Social Security benefit at age 70. Delaying your claim past Full Retirement Age (FRA) increases your benefits by 8% per year.

Q9: Can I make tax-free charitable donations from my retirement accounts?

A: Yes, starting at age 70½, you can make Qualified Charitable Distributions (QCDs) from your IRA. These are not subject to federal income tax and can count toward your RMD.

Q10: How do these milestone dates affect my tax planning?

A: Strategic timing of Social Security and retirement account withdrawals can impact your tax bracket. Roth conversions are one method to manage tax liability by moving funds to a Roth IRA, where they can grow tax-free.

Q11: What should I consider for estate planning as I approach these milestones?

A: Ensure your estate plan and beneficiary designations are up to date, especially after significant life changes like marriage, divorce, or the birth of grandchildren. Keeping your plan current can help preserve wealth for your loved ones.For more detailed information, visit our insights page, or contact me to receive a one-page document summarizing these important dates.