Tax season can be much easier when you know what to gather before you start.

Whether you prepare your own return or work with a tax professional, having the right documents ready can help prevent delays, reduce back-and-forth, and lower the chance that an important source of income or potential deduction gets overlooked.

The exact documents you need will depend on your situation, but this checklist covers many of the items Wisconsin individuals, families, retirees, and business owners should consider gathering before filing their federal and Wisconsin income tax returns.

1. Start With Your Personal Information

Before getting into tax forms, make sure you have the basic information needed for everyone included on your return.

Gather:

• Social Security numbers or taxpayer identification numbers for you, your spouse, and dependents
• Dates of birth
• Current address and contact information
• Bank routing and account numbers for direct deposit or electronic payments
• A copy of your prior-year federal and Wisconsin tax returns
• Identity Protection PINs issued by the IRS, if applicable
• Records of any major changes to your household during the year

Your previous tax return is particularly useful because it provides a starting point for identifying income sources, deductions, credits, and accounts that may appear again this year.

2. Income Documents

Most taxpayers will receive one or more forms reporting income they earned during the year.

Employment Income

Look for:

• Form W-2 from each employer
• Final pay stubs, particularly if you want to verify withholding or retirement contributions

If you changed jobs during the year, remember that you’ll generally receive a separate W-2 from each employer.

Self-Employment and 1099 Income

If you did freelance work, consulting, contract work, or operated a business, gather:

• Forms 1099-NEC
• Forms 1099-K
• Forms 1099-MISC
• Business income records
• Invoices and payment records
• Records of cash or other income that may not appear on a 1099

A common misconception is that income doesn’t need to be reported if you don’t receive a tax form for it. The absence of a 1099 doesn’t necessarily mean the income isn’t taxable.

3. Investment and Savings Accounts

Investment activity can make a tax return considerably more complicated.

Look for:

• Form 1099-INT for interest
• Form 1099-DIV for dividends
• Form 1099-B for investment sales
• Brokerage consolidated tax statements
• Cryptocurrency transaction records
• Cost-basis information for assets sold during the year

If you transferred investments from one brokerage firm to another, double-check that your cost-basis information transferred correctly.

Without accurate cost basis, determining the taxable gain or loss from an investment sale can become difficult.

4. Retirement Income

Retirees and people approaching retirement often have several different sources of taxable income.

Gather documents such as:

• Form 1099-R for IRA, 401(k), pension, and other retirement-plan distributions
• Form SSA-1099 for Social Security benefits
• Records of Roth IRA distributions
• Records of Roth conversions
• Required minimum distribution information
• Pension statements
• Annuity tax documents

Don’t assume all retirement income receives the same tax treatment. The tax consequences can vary significantly depending on the type of account and distribution.

This is also one area where tax preparation and tax planning become very different things. Your tax return tells us what happened last year. Planning can help determine whether withdrawals, Roth conversions, charitable distributions, and other strategies should be handled differently going forward.

5. Health Insurance and Medical Accounts

Depending on your situation, you may need:

• Form 1095-A if you purchased health insurance through the Marketplace
• HSA Forms 1099-SA and 5498-SA
• Records of HSA contributions
• Records of significant unreimbursed medical expenses
• Long-term-care insurance information, when applicable

Marketplace health insurance deserves particular attention because premium tax credits can affect your return.

6. Homeowners and Property Owners

Owning a home doesn’t automatically mean every home-related expense is deductible, but you should still gather the applicable records.

These may include:

• Form 1098 for mortgage interest
• Property-tax records
• Records related to purchasing or selling a home
• Closing statements
• Records of significant home improvements
• Home-office information if you’re self-employed and qualify
• Rental-property income and expense records

Keeping records of major improvements can be especially valuable when you eventually sell a property because certain improvements may affect your home’s cost basis.

7. Business Owners and Self-Employed Workers

If you own a business or earn 1099 income, organization becomes especially important.

In addition to your income records, gather documentation for potential business expenses such as:

• Advertising and marketing
• Business insurance
• Professional fees
• Software and subscriptions
• Office supplies
• Equipment
• Business travel
• Business meals
• Vehicle mileage
• Rent
• Utilities
• Payroll
• Contract labor
• Continuing education
• Retirement-plan contributions
• Health insurance
• Estimated tax payments

You should also have your bookkeeping records reconciled before preparing the return whenever possible.

Don’t Wait Until Tax Season to Think About Business Taxes

For business owners, some of the biggest tax-saving opportunities require action during the tax year, not after December 31.

Entity structure, retirement plans, estimated payments, equipment purchases, payroll, and other decisions can all have tax implications.

That’s why year-round tax planning can be particularly valuable for business owners.

8. Children, Education, and Dependent Expenses

Families may need documentation for several potential tax benefits.

Gather:

• Dependent information
• Childcare provider name, address, and tax identification number
• Childcare expenses
• Form 1098-T for college tuition
• Form 1098-E for student-loan interest
• Scholarship information
• Education expense records
• 529 plan distribution records

If you have a child in college, don’t automatically assume the student should claim education-related tax benefits on their own return. Dependency status and education credits can interact in ways that are worth reviewing before either return is filed.

9. Charitable Giving

If you made charitable contributions during the year, keep appropriate documentation.

That can include:

• Cash contribution receipts
• Written acknowledgments from charities
• Records of donated property
• Qualified charitable distribution records
• Documentation for significant non-cash donations

The tax treatment of charitable giving depends on the type of gift and your individual circumstances.

For retirees in particular, giving directly from an IRA through a qualified charitable distribution (QCD) may have different tax consequences than simply writing a check to a charity.

10. Estimated Tax Payments

Don’t forget taxes you’ve already paid.

Gather records of:

• Federal estimated tax payments
• Wisconsin estimated tax payments
• Prior-year refunds applied toward the current year’s taxes
• Extension payments
• Other tax payments made during the year

This is an easy area for errors if payments aren’t properly recorded.

If you paid quarterly estimates, provide the date and amount of each payment, rather than simply the annual total.

11. Major Life Changes

Some of the most important information you give your tax professional may never appear on a tax document.

Tell your preparer if you:

• Got married or divorced
• Had or adopted a child
• Lost a spouse
• Changed jobs
• Retired
• Started a business
• Sold a business
• Bought or sold a home
• Purchased a rental property
• Moved to or from Wisconsin
• Received an inheritance
• Exercised stock options
• Made a large charitable gift
• Took a significant retirement-account distribution
• Converted money to a Roth IRA

These events can change your tax situation considerably.

12. Your Previous Tax Return

Finally, bring your most recent federal and state tax returns—especially if you’re working with a new tax professional.

A prior return helps provide context about your:

• Filing history
• Dependents
• Carryforward items
• Investment activity
• Business interests
• Retirement accounts
• Deductions
• Tax credits
• Prior tax elections

It also helps your new preparer identify areas that may deserve additional attention.

Tax Preparation Is Only Half the Picture

Gathering all of these documents helps answer an important question:

Did we prepare your tax return correctly?

But there’s another question worth asking:

Could we make next year’s tax situation better?

Once the year ends, many planning opportunities disappear. That’s why we believe taxes shouldn’t only be discussed during tax season.

For example, during the year you may have opportunities to evaluate:

• Tax withholding
• Quarterly estimated payments
• Retirement contributions
• Roth conversions
• Capital gains and losses
• Charitable giving
• Business deductions
• Business entity structure
• Retirement distributions
• Other strategies based on your individual circumstances

Good tax preparation reports what already happened. Good tax planning helps you make informed decisions about what happens next.

Looking for Tax Help in La Crosse?

At La Crosse Tax, we help individuals, families, and business owners with tax preparation and proactive tax planning.

Our goal isn’t simply to get your return filed. We want to help you understand your tax situation and identify issues worth addressing before they become next year’s tax surprises.

Need help preparing your taxes or want to discuss year-round tax planning?