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2025 Tax Planning: Critical Deadlines and Document Checklist for Busy Professionals

Writer's picture: Stillwater Business SolutionsStillwater Business Solutions

1040 Tax Return Form From The IRS, an orange clock reminding business owners and W-2 workers of tax deadlines with a pile of money behind the clock

Tax season can feel like a whirlwind, but with the right planning, it doesn't have to be stressful. If you’re already looking ahead to your 2025 taxes, you’ll want to mark the key deadlines on your calendar to avoid penalties and unnecessary headaches. To help you stay on top of things, Stillwater Business Solutions has put together a guide to the most important 2025 tax deadlines for individuals and businesses.

Whether you're filing your personal return, making estimated payments, or managing business taxes, staying organized is the key to a smooth filing season. Here's a breakdown of important tax deadlines on a handy chart that outlines everything at a glance.


2025 Tax Deadlines Chart

Here’s a quick reference chart to help you see all the 2025 tax deadlines at a glance:

Deadline

Taxpayer Type

What’s Due

January 15, 2025

Individuals/Businesses (Self-Employed)

Final 2024 Estimated Tax Payment (Q4)

April 15, 2025

Individuals (Personal Returns)

2024 Individual Tax Returns (Form 1040)

April 15, 2025

Corporations (Business Returns)

2024 Corporate Tax Returns (Form 1120)

June 16, 2025

Individuals/Businesses (Self-Employed)

Estimated Tax Payment (Q2)

September 15, 2025

Individuals/Businesses (Self-Employed)

Estimated Tax Payment (Q3)

October 15, 2025

Individuals (Extended Filing)

Extended Filing Deadline for Individual Returns

October 15, 2025

S Corporations/Partnerships

Extended Filing Deadline for S Corps & Partnerships

January 15, 2026

Individuals/Businesses (Self-Employed)

Final 2025 Estimated Tax Payment (Q4)


Staying organized during tax season is key to avoiding stress and potential errors. This comprehensive checklist helps ensure that you have all the necessary documents before filing your 2025 taxes, whether you’re an individual taxpayer or a business owner. By gathering these documents early, you can avoid last-minute scrambling, reduce the risk of missing valuable deductions or credits, and ultimately streamline the filing process. Many of these tax documents are available digitally. Stillwater Business Solutions offers secure and fully remote tax return solutions for individual and business tax returns.


2025 Tax Document Checklist

Individual Tax Return Checklist

Business Tax Return Checklist

Personal Information

Business Information

- Social Security numbers (SSNs) for you, your spouse, and dependents

- Employer Identification Number (EIN)

- Proof of identity (state-issued ID, driver’s license)

- Legal name of the business, any DBA names


- Business formation documents (LLC, partnership agreement, etc.)

Income Documentation

Income Documentation

- W-2 forms from all employers

- Income Statement (Profit & Loss)

- 1099 forms (1099-INT, 1099-DIV, 1099-MISC, 1099-NEC, etc.)

- 1099 Forms for freelance payments (1099-NEC, 1099-MISC)

- 1099-G (unemployment benefits, state tax refunds)

- Sales records from invoices or POS systems

- 1099-B (Brokerage transactions)

- Bank statements for business accounts

- 1099-R (retirement distributions)




Deductions & Credits

Business Expenses

- Medical expenses (out-of-pocket costs, prescription drugs)

- Receipts for office supplies (paper, printer ink, etc.)

- Charitable donations (receipts, acknowledgment letters)

- Rent or lease payments for business property

- Student loan interest (Form 1098-E)

- Utility bills (phone, internet, electricity)

- Mortgage interest (Form 1098)

- Employee wages (W-2 forms for employees)

- Childcare expenses (Form 2441)

- Contract labor (Form 1099-NEC for contractors)

- Retirement contributions (IRA, 401(k))

- Travel expenses (airfare, lodging, meals)

- State & local taxes (property tax receipts)

- Business-related insurance premiums

- Energy-efficient home improvement credits (solar, EV, etc.)

- Depreciation records for assets like vehicles, equipment, etc.



Other Forms

Tax Forms & Filings

- Last year’s tax return (helpful for reference)

- Form 1120 (Corporate tax return)

- Form 8889 (Health Savings Accounts)

- Form 1065 (Partnership tax return)

- Form 8862 (for EITC or CTC rejections)

- Schedule C (for sole proprietors)


- Form 941 (Employer quarterly payroll tax returns)


- Form 940 (Annual federal unemployment tax return)


- Form 1099 (to report independent contractor payments)


- Payroll records (wages, tips, benefits)



Other Important Records

Other Business Documents

- Form 8889 (Health Savings Accounts)

- Quarterly estimated tax payments records


- Employee benefit records (401(k), health insurance)


Pro Tips for Staying on Track

  1. Set Reminders Early: With so many deadlines, it’s easy to forget. Set calendar reminders a few weeks before each deadline so you have plenty of time to prepare.

  2. Keep Track of Your Payments: If you’re making quarterly payments, make sure to note how much you've already paid and whether you're on track to meet your tax obligations for the year. A seasoned and trusted accountant can help with this.

  3. Consult a Tax Professional: If your tax situation is complex, it’s always a good idea to consult with a tax professional who can help you navigate any issues and ensure you're not missing out on deductions or credits. Stillwater Business Solutions is ready to help you streamline your tax season experience while maximizing your returns.


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