2025 Tax Calendar: The Tax Tool Every U.S. Small Business Owner Needs

It’s year end, fireworks are going off in the distance, and you’re reflecting on everything you and your business accomplished over the last 12 months. Then you wake up the next morning and it’s the start of tax season.

January to April is commonly known as “tax season” by business owners and CPAs. This is because it’s jam packed with deadlines. With 1099s, payroll forms, and federal tax returns, this four month span can leave you stressed with the feeling that there’s always something to do.

To ensure you’re always on top of what needs to be done, we compiled the key deadlines with some tips on what to do in between them.

Be ready for every federal tax deadline

Small business owners everywhere are faced with the consistent challenge of managing tax obligations without getting overwhelmed. A comprehensive tax calendar can serve as the solution, transforming complex tax requirements into clear, manageable guidelines that help you stay on top of critical financial deadlines and requirements.

To be IRS ready, you’ll need to get your financial reporting for the year up-to-date. But if you’re struggling to figure out what to prioritize, this calendar will help. With clear information and visual prompts for action, you’ll know what to take care of and when it needs to be done by. No more planning or strategizing, just doing.

By providing strategic guidance throughout the year, a tax prep calendar like ours becomes more than just a scheduling tool. It's a critical resource that helps you anticipate important dates, prepare necessary documentation, and make informed financial decisions that can potentially save your business time, money, and unnecessary stress.

What is a tax calendar?

A tax calendar is a comprehensive roadmap that guides small business owners through the complex landscape of tax obligations and deadlines. Unlike a standard calendar, a tax calendar is a strategic planning tool that highlights critical financial dates, tax filing requirements, and important milestones throughout the year. It offers a more proactive approach to managing your business's tax responsibilities, helping you stay organized, avoid penalties, and maintain financial compliance.

Why small business owners need a calendar for tax prep

Every small business owner knows that taxes can be confusing and that staying consistent with the IRS’s federal tax schedule on top of all the other business obligations can be overwhelming. That's where a well-designed tax preparation calendar can come in handy, as it can transform this challenge into a manageable process. 

Here's what a tax prep calendar can do for you:

• Avoid costly penalties: Missing tax deadlines can result in significant financial penalties and unnecessary stress. A tax calendar ensures you never miss a critical filing date or payment deadline.
• Improve financial planning: By understanding upcoming tax obligations, you can better manage cash flow, set aside appropriate funds, and make strategic financial decisions throughout the year.
• Reduce tax season stress: Instead of scrambling at the last minute, a tax calendar allows you to prepare methodically, reducing anxiety and potential errors in your tax filing.
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Understanding the federal tax schedule

The federal tax schedule is an official, structured timeline of tax-related events and deadlines set by the Internal Revenue Service. While some dates remain consistent year to year, it's crucial to stay updated on the specific deadlines for the 2025 tax year—and each year, thereafter. 

Here are some key dates and considerations for tax season:

• Estimated Tax Payment Deadlines:
  • April 15, 2025 (first quarter)
  • June 15, 2025 (second quarter)
  • September 15, 2025 (third quarter)
  • January 15, 2026 (fourth quarter)
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• Income Tax Filing Deadlines:
  • Partnerships and S corps: March 17, 2025 (for calendar year filers)‍
  • Sole props and C corps: April 15, 2025 (for calendar year filers)
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• Extension Request Deadlines: October 15, 2025 (for those filing an extension)
  • Partnerships and S corps: September 15, 2025 (for calendar year filers)‍‍
  • Sole props and C corps: October 15, 2025 (for calendar year filers)
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If a deadline falls on a weekend or legal holiday, the due date shifts to the next business day.

It’s important to note that these dates are subject to change, especially in extraordinary circumstances like federally declared disaster areas or global events. Always verify the most current information directly with the IRS or a qualified tax professional. 

How to use Bench Accounting's tax prep calendar

Bench's tax prep calendar is a simplified approach to tax deadline management. It’s designed to completely streamline the way small businesses like you navigate their annual tax responsibilities. 

Unlike traditional calendars that simply mark dates, our comprehensive tool is organized in a way that can easily walk you through the world of tax preparation, offering insights, warnings, and actionable steps throughout the year. It focuses on the most critical tax-related months and moments that can make or break your financial compliance and includes essential resources so you have everything you need right at your fingertips.

Here's an overview of how our tax prep calendar works and provides invaluable support:

A. Monthly tax responsibility breakdown

Each critical tax month in our tax prep calendar is carefully broken down into specified sections that provide:

• Critical deadline highlights: A clear, concise overview of the most important tax-related dates for that specific month
• Actionable guidance: Detailed, step-by-step instructions on what actions you need to take to maintain tax compliance, request forms, and file for extensions or specific types of tax forms
• Proactive preparation strategies: Insights and recommendations also have dedicated sections to help you stay ahead of your tax obligations

B. Comprehensive monthly guidance

Our calendar provides explicit guidance regarding critical decisions you’ll need to make about tax filing deadlines and extensions. 

Using the month of March as an example, the calendar dedicates an entire section to S corporations and other types of partnerships, specifying approaching deadlines and what to expect based on the decision you make. 

Let’s say you were interested in filing an extension for your S corp business. Here’s a quick overview of what the calendar offers regarding information and guidance:

• Deadline details:
  • Specific deadline for applying for tax filing extensions
  • New potential tax filing dates if the extension is granted
  • A comprehensive explanation of the extension process
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• What to expect:
  • Detailed information about the implications of filing an extension
  • Potential impact on your business's financial planning
  • Strategies for managing cash flow during the extension period
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• Direct resources:
  • Clickable links to official IRS forms and websites
  • Guidance on how to properly complete extension requests
  • Contact information for additional support

C. Other helpful resources

For each month in our tax prep calendar, we provide additional resources which include:

• In-depth guides about specific tax forms and explanations of tax requirements for different business structures
• Practical tax tips on strategies for efficient bookkeeping, reducing tax liability, and insights into potential tax deductions and credits
• Comprehensive links and references to specific IRS resources and other helpful tax tools and educational materials
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Navigating your entire tax year with Bench Accounting

We’ve designed our tax calculator to be more than just a list – it's a comprehensive document that helps to:

• Break down complex tax requirements into manageable steps
• Provide year-round support by offering  guidance and resources throughout the entire tax year
• Empower small business owners like you by providing the knowledge and tools to confidently manage your tax responsibilities
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Our calendar transforms tax preparation from a dreaded annual chore into a strategic, manageable process. We help you stay compliant, minimize stress, and focus on what truly matters – growing your business.

Just fill out the form above and you’ll receive your tax calendar in seconds. Our team of expert bookkeepers is also here to help transform your tax experience. Get started with Bench today and take advantage of our 100% tax-deductible bookkeeping and income tax accounting services!

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