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Writer's pictureKevinGuarino

How to Estimate (and Pay) Your Taxes During Retirement

Navigating taxes in retirement can be a headache, especially when we're accustomed to the simplicity of payroll deductions during our working years. We all want to make sure that we can enjoy as much of our assets as possible, rather than Uncle Sam. With some foresight and understanding of the tax rules, you can manage your tax obligations smoothly. 

Avoid Overpaying

Understanding the Safe Harbor Rule 

One of the best ways to avoid IRS penalties for underpaying taxes throughout the year is by adhering to the Safe Harbor Rule. This rule provides three ways to meet your tax payment obligations: 

  1. Pay 90% of your estimated taxes for the current year. 

  1. Ensure your tax payments are within $1,000 of your total tax liability for the year. 

  1. Pay 100% of your total tax liability from the previous year. 

These options offer flexibility and a clear target for tax payments, helping you stay on the IRS's good side. 


Types of Retirement Income and Their Tax Implications 

Different sources of retirement income have varying effects on your tax liability. Let’s break them down: 


Social Security 

Up to 85% of your Social Security benefits may be taxable, depending on your income level. To simplify things, you can request the Social Security Administration to withhold taxes from your benefits by completing IRS Form W-4V. 


Traditional IRAs 

Withdrawals from traditional IRAs are fully taxable as ordinary income at the federal level. Most custodians allow you to set up withholding from these distributions, helping to manage your tax payments efficiently. (Just ask) 


Roth IRAs 

These are easy. Qualified withdrawals from Roth IRAs are tax-free, making them a valuable tool in tax planning during retirement. 


Brokerage Accounts 

The taxable events in brokerage accounts include dividends, interest, and capital gains. These are taxed differently: 

  • Dividends and Interest: Taxed as ordinary income. 

  • Capital Gains: Taxed based on how long you've held the asset. Gains on assets held for more than a year are taxed at long-term capital gains rates, which are typically lower than ordinary income rates. 

Income Streams

Withholding taxes from these types of accounts can be tricky. You may need to make estimated tax payments quarterly (April, June, September, and January of the following year) via the IRS website. 


Average vs. Marginal Tax Rate 

The difference between your average tax rate and your marginal tax rate is surprisingly overlooked quite often. Your marginal tax rate is the rate applied to your last dollar of income, while your average tax rate is your total tax paid divided by your total income. For instance, if your total income places you in the 22% tax bracket, only the income above the previous bracket's threshold is taxed at 22%, not your entire income. In most cases, your average tax rate, therefore what you should be withholding, is much much lower.  


Additional Considerations for Estimated Tax Payments 

Certain events in retirement might require additional estimated tax payments to avoid penalties: 

  • Roth Conversions: Converting a traditional IRA to a Roth IRA can incur significant tax liabilities. This maneuver, while potentially beneficial for long-term tax planning, requires careful timing and a thorough understanding of the immediate and future tax consequences. Consulting with a tax advisor before making any conversions can save you from unexpected tax burdens. 

  • Selling Property: Capital gains from property sales can impact your tax bill. The sale of a primary residence, a vacation home, or other real estate investments can trigger substantial capital gains taxes. Familiarize yourself with the IRS rules on capital gains exclusions for primary residences, and consider the tax implications of selling at different times. 

  • Harvesting Capital Gains: Realizing gains from investments can also lead to higher tax liabilities. This strategy involves selling investments to take advantage of lower tax rates on capital gains. While this can be a smart tax move, it must be balanced with the potential tax hit and the overall impact on your investment portfolio. 

Take steps today

Action Steps 

  1. Review Your Income Sources: Understand the tax implications of each. 

  2. Calculate Your Estimated Taxes: Use the Safe Harbor Rule as a guide. 

  3. Set Up Withholding or Make Quarterly Payments: Choose the most convenient method to pay your taxes on time. 

  4. Plan for Additional Tax Events: Stay aware of any actions that might trigger extra tax liabilities. 


Retirement should be a time of relaxation and enjoyment, not stress over taxes. That’s where we come in. Our retirement income planning services are designed to help you navigate these waters without a second thought. Let’s work together to ensure your money stays in your pocket and out of Uncle Sam’s. Reach out to us today to schedule a consultation and secure your financial future. 




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