Understanding major financial deadlines is essential for everyone, it can make a world of difference in financial health. Knowing what numbers to focus on and when certain deadlines hit can keep your finances in check, ensure tax efficiency, and safeguard your wealth for years to come.

This guide will walk you through important financial numbers and deadlines, how they affect your money, and why paying attention to them matters more than you might think.

Why Do Financial Numbers Matter?

Let’s start with the basics. Your financial numbers:

• such as net worth, 
• retirement savings milestones, 
• tax deadlines, 
• and more—are the foundation for managing your wealth. Understanding and managing these figures help you make informed decisions, avoid unnecessary penalties, and plan for the future.

Let’s consider this, someone that’s very hands on with their finances, but even they were caught off guard with an unexpected tax penalty. They missed a quarterly estimated payment, which added late fees. 

If they’d been more aware of key dates, they could have avoided this entirely. The takeaway? Even financially concise individuals can benefit from better organization and tracking.

For more on how inflation impacts your financial numbers, check out How Does Inflation Affect My Daily Life?

Tracking Your Net Worth

What Is Net Worth?

Your net worth is the value of everything you own (your assets) minus what you owe (your liabilities). For high net worth individuals, this number provides a snapshot of your overall financial health. 

It helps you understand if your wealth is growing or shrinking over time and is an essential part of estate planning and wealth management.

Tracking your net worth allows you to:

• Measure your financial progress.
• Make adjustments to your investments or savings plans.
• Plan for major life events like retirement or wealth transfers.

Key Action: Calculate Your Net Worth Regularly

Start by adding up your assets,

• homes, 
• investments, 
• retirement accounts, etc.
• and subtract your liabilities, 
• like mortgages, 
• loans, 
• or any other debts. 

Reassess this number at least once a year to ensure you’re on track. Also, if you would like to calculate your net worth visit the following page for a net worth calculator.

If you need a refresher on investment principles, take a look at 7 Investing Principles You Should Know.

Retirement Savings Milestones

The Importance of RMDs

Once you hit age 73, you’re required to start taking Required Minimum Distributions (RMDs) from your retirement accounts. The key date here is April 1st of the year following your 73rd birthday. 

Missing an RMD can result in a hefty penalty—25% of the amount you should have withdrawn!

For example, a retiree who didn’t realize they had to take RMDs and ended up with a $10,000 penalty because they missed the deadline. This underscores why it’s so important to work with a planner who can help you track these dates.

For more detailed strategies around RMDs, check out What Factors Impact My Required Minimum Distributions?

Maximizing Contributions

For high earners, making the maximum allowable contributions to retirement accounts each year is a key strategy. As of 2025, you can contribute up to $7,500 annually to an IRA if you’re 50 or older. 

The deadline to make contributions for the previous tax year is April 15. Maximizing these contributions reduces your taxable income now while allowing for more tax-deferred growth in the future.

For more tax-saving strategies, visit Maximizing Your After-Tax Returns: Advanced Strategies for High Earners.

Key Tax Deadlines and Estimated Payments

Quarterly Estimated Tax Payments

High-income earners often have income from various sources,

• investments, 
• businesses, 
• Real estate
• and consulting work that isn’t subject to traditional withholding. 

If that sounds familiar, quarterly estimated tax payments are critical for you. Missing these payments can result in penalties, so mark your calendar for April 15, June 15, September 15, and January 15.

A business owner I worked with once missed an estimated payment because they didn’t realize their income had pushed them into a higher tax bracket. The penalties and interest added up fast. After that, we set up automatic reminders to ensure all future payments were made on time.

Filing Your Taxes

The main tax filing deadline is April 15, but if you need more time, you can file for an extension until October 15. While an extension gives you more time to file, it doesn’t extend the payment deadline. If you owe taxes, you still need to pay by April 15 to avoid penalties.

For more on the tax numbers to keep an eye on, read Important Tax and Financial Numbers for 2025.

Business Tax Deadlines

For Business Owners

If you’re a high earner with your own business, there are several additional key dates to track:

• January 31: Deadline to issue Forms W-2 and 1099.
• March 15: Tax filing deadline for S-Corporations and partnerships.
• April 15: Deadline for sole proprietors and single-member LLCs.
• September 15: Deadline for third-quarter estimated payments.

Miss any of these deadlines, and you could face stiff fines and penalties from the IRS.

Learn more about how to avoid financial mistakes as a business owner in Common Mistakes to Avoid When Saving: A Guide for High Net Worth Individuals.

Medicare and Health Insurance Deadlines

Key Medicare Dates

As you approach age 65, it’s time to think about Medicare. If you don’t enroll during the initial period, which starts three months before and ends three months after your 65th birthday, you could face higher premiums down the line. Here are the dates to remember:

• January 1 – March 31: General Enrollment Period for Medicare Parts A & B.
• October 15 – December 7: Annual Enrollment Period for existing Medicare enrollees.

Health Insurance Marketplace

For those under 65 who are purchasing insurance through the marketplace, open enrollment typically runs from November 1 to December 15 for coverage starting the next year.

Charitable Giving and Gifting

Gifting Limits

The IRS allows you to gift up to $19,000 per person annually without incurring gift taxes. If you plan to make substantial gifts, the deadline is December 31 to ensure they count for the current tax year.

Making tax-efficient gifts can reduce your taxable estate, which is particularly important for high net worth individuals concerned about estate taxes.

For more on charitable contributions and wealth management, visit The Secret Strategies the High Net Worth Use to Maximize Wealth in Uncertain Times.

Planning for Education Expenses

FAFSA Deadlines

If you’re helping to fund your children’s or grandchildren’s education, knowing the FAFSA deadlines is key. The form opens on December 1, and the final filing deadline for the prior academic year is June 30.

529 plans can be a tax-efficient way to save for education. If you’re still wondering how to prioritize this in your overall financial plan, check out What’s the Right Strategy for Funding My Child’s Education?.

What’s Next – Final Thoughts: Stay Organized, Stay On Top

The key to managing wealth is staying organized and aware of key financial dates and numbers. Missing one of these dates can result in penalties, lost opportunities, or added stress. 

Take control of your finances by marking these dates on your calendar and working with a Certified Financial Planner to ensure you never miss a beat.

If you’re ready to take your financial organization to the next level, I recommend reading Organize Your Financial Life, which provides actionable steps to help you stay on track year-round.

By staying informed and organized, you can protect your wealth, minimize your tax liability, and achieve long-term financial success.

Key Financial Dates to Remember

To help you stay organized, here’s a list of important financial dates:

For Individuals:

• January 1: Start of the tax year and General Enrollment for Medicare Parts A & B.
• January 15: Q4 estimated tax payment deadline for the prior year.
• January 31: Income tax return deadline to avoid late penalties for unpaid Q4 estimates.
• February 15: Deadline for updating your W-4 if claiming a tax exemption.
• March 31: End of General Enrollment for Medicare Parts A & B and Medicare Advantage.
• April 1: Required Minimum Distribution (RMD) deadline for those turning 72.
• April 15: Income tax return filing deadline, Q1 estimated tax payment due, and last day to contribute to an IRA or HSA for the prior year.
• June 15: Q2 estimated tax payment deadline.
• June 30: FAFSA filing deadline for the prior academic year.
• September 15: Q3 estimated tax payment deadline.
• September 30: Deadline for identifying designated beneficiaries of retirement accounts.
• October 1: Start of Q4.
• October 15: Extended tax return filing deadline and start of Medicare Open Enrollment.
• November 1: Start of Health Insurance Marketplace Open Enrollment.
• December 7: End of Medicare Open Enrollment.
• December 15: Health Insurance Marketplace deadline for coverage to begin on January 1 of the next year.
• December 31: Deadline for completing RMDs, gifts, and other year-end financial tasks.

For Business Owners:

• January 31: Deadline for issuing Forms 1099 and W-2.
• March 15: S-corporation and partnership tax return deadline.
• April 15: Filing deadline for sole proprietors, LLCs, and C-corporations; Q1 estimated tax payment due.
• June 15: Q2 estimated tax payment deadline.
• September 15: Q3 estimated tax payment deadline and extended tax return filing deadline for S-corporations and partnerships.
• October 15: Extended tax return filing deadline for sole proprietors and LLCs.
• December 15: Q4 estimated tax payment deadline for C-corporations.
• December 31: End of tax year.