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Estimated taxes apply to income not subject to withholding, including self-employment, investment, and rental income. Learn when these payments are required, deadlines to note, and tips to avoid penalties.
Blog Post
by Nathan Brickley, CPA

Why You Might Need to Pay Estimated Taxes: A Guide for the Self-Employed and Investors

Financial Planning
Tax Planning
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Notice: The content of this post is over two years old, information may not be up to date.

Many people rely on paycheck withholding to manage their tax obligations, but if you're self-employed, receive investment income, or earn income from sources that don’t withhold taxes, you may need to make estimated tax payments to avoid penalties. Here’s what you need to know.

What Are Estimated Taxes?

Estimated taxes are quarterly payments made to cover income not subject to automatic withholding—such as self-employment earnings, investment income, rental income, and alimony. The IRS requires taxes to be paid as income is earned, so these payments help prevent a hefty bill or penalties at tax time.

Who Needs to Pay Estimated Taxes?

You might need to pay estimated taxes if you expect to owe $1,000 or more in federal taxes after withholding and credits. Common scenarios include:

  • Self-Employed or Freelance Income: Taxes aren’t withheld, so you’re responsible for paying income and self-employment taxes (Social Security and Medicare).
  • Investment Income: Dividends, interest, and capital gains often require estimated payments.
  • Rental Income: Landlords must pay taxes on rental earnings without automatic withholding.
  • Other Non-Wage Income: This includes alimony (for pre-2019 agreements), prizes, and royalties.
  • High Earners: Even with paycheck withholding, those with bonuses or significant non-wage income may need to pay quarterly.
  • Restricted Stock Units (RSUs): Default withholding on RSU vesting may be insufficient for higher tax brackets.

How to Calculate Estimated Taxes

Determining your estimated taxes requires projecting your annual income, deductions, and credits. At Brickley Wealth, we offer comprehensive tax projections to help calculate your liability and determine accurate quarterly payments.

When Are Payments Due?

Estimated taxes are paid quarterly:

  • April 15
  • June 15
  • September 15
  • January 15 (of the following year)

If the due date falls on a weekend or holiday, the deadline moves to the next business day. Missing a payment can lead to penalties and interest charges.

Avoiding Penalties

To avoid penalties for Federal, you must pay at least:

  • 90% of your current year’s tax liability, or
  • 100% of last year’s liability (110% for high earners with adjusted gross income over $150,000).

If you meet specific safe harbor provisions or your total tax bill is under $1,000, penalties may not apply.

Alternatives to Estimated Payments

Prefer to avoid making estimated payments? Consider these options:

  1. Increase Withholding: Adjust your W-4 with your employer to cover additional tax.
  2. Leverage Deductions and Credits: Maximize retirement contributions, HSAs, or charitable donations to lower your tax liability.

Stay Ahead of Your Taxes

Paying estimated taxes is crucial for anyone earning income not subject to withholding. Consulting with a CPA can simplify the process, help you avoid surprises, and keep your finances on track. At Brickley Wealth, we’re here to guide you. Let us help you calculate payments, manage your tax strategy, and reduce stress when tax season rolls around.

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Brickley Wealth Management is a Registered Investment Adviser*. Advisory services are only offered to clients or prospective clients where Brickley Wealth Management and its representatives are properly licensed or exempt from licensure. The information throughout this website is solely for informational purposes. The content is developed from sources believed to provide accurate information, and we conduct reasonable due diligence review however, the information contained throughout this website is subject to change without notice and is not free from error. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. Readers should conduct their own review and exercise judgment prior to investing and should carefully consider their own investment objectives and not rely on any post, chart, graph or marketing piece to make a decision. No investment or tax advice may be rendered by Brickley Wealth Management or Brickley & Company unless a client service agreement is in place. We are not providing any personalized investment advice through this website. Please consult your investment, tax, or legal advisor for assistance regarding your individual situation. Brickley Wealth Management does not provide legal advice, and nothing in this website shall be construed as legal advice. For more information on our firm and our advisers, please see the latest Form ADV and Part 2 Brochures and our Client Relationship Summary https://adviserinfo.sec.gov/firm/summary/287487. For a copy of our Privacy Notice, please go here.

*Please note that the term "registered investment adviser" and description of our firm and/or our associates as "registered" does not imply a certain level of skill or training.

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Key Financial Terms 
Related to this Post:

This is some text inside of a div block.

Adjusted Gross Income (AGI)

Adjusted Gross Income, your total income minus certain deductions. Used to determine eligibility for tax deductions and credits.
This is some text inside of a div block.

Quarterly Tax Estimates

Periodic tax payments made by self-employed individuals or those with significant non-wage income.
This is some text inside of a div block.

Restricted Stock Unit (RSU)

Restricted Stock Unit, a form of employee compensation involving company stock that vests over time.
This is some text inside of a div block.

Tax Bracket

Income range used to determine the tax rate applied to your income. The higher your income, the higher the tax rate.
This is some text inside of a div block.

Tax Credit

A dollar-for-dollar reduction of your tax liability. Can be refundable or nonrefundable.

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Contact@brickleywealth.com
(650) 638-0111

Brickley Wealth Management is a Registered Investment Adviser*. Advisory services are only offered to clients or prospective clients where Brickley Wealth Management and its representatives are properly licensed or exempt from licensure. The information throughout this website is solely for informational purposes. The content is developed from sources believed to provide accurate information, and we conduct reasonable due diligence review however, the information contained throughout this website is subject to change without notice and is not free from error. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. Readers should conduct their own review and exercise judgment prior to investing and should carefully consider their own investment objectives and not rely on any post, chart, graph or marketing piece to make a decision. No investment or tax advice may be rendered by Brickley Wealth Management or Brickley & Company unless a client service agreement is in place. We are not providing any personalized investment advice through this website. Please consult your investment, tax, or legal advisor for assistance regarding your individual situation. Brickley Wealth Management does not provide legal advice, and nothing in this website shall be construed as legal advice. For more information on our firm and our advisers, please see the latest Form ADV and Part 2 Brochures and our Client Relationship Summary https://adviserinfo.sec.gov/firm/summary/287487. For a copy of our Privacy Notice, please go here.

*Please note that the term "registered investment adviser" and description of our firm and/or our associates as "registered" does not imply a certain level of skill or training.

2020 Brickley Wealth Management. All rights reserved.
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