Tax Season Basics:

What to Expect (and What You Actually Need)

Jan 27, 2026 | 5 min read

Sean Williams

Tax season has a way of feeling more complicated than it needs to be. Between 1099s, Roth conversions, and questions about which forms apply to you, it’s easy to wonder if you’re missing something important.

This quick guide covers the basics—what documents matter, what they mean, and what you need to do as tax season approaches.

Step 1: Gather Your Tax Documents (Don’t File Yet)

Most people’s first instinct is to file as soon as possible. In reality, the smarter move is to gather everything first and wait until the full picture is available.

For investment accounts, that usually means waiting for:

• 1099 forms from custodians
• Any Roth conversion reporting
• Employer and income documents (W-2s, etc.)

Many corrected forms are issued in March, which is why filing later often avoids potential amendments.

What Is a 1099?

This term is thrown around a lot this time of year, but what does it actually mean, and what are all of those letters after it? A 1099 is a tax form that reports income you received outside of a traditional paycheck. Common investment-related 1099s include:

• 1099-DIV – dividends from investments
• 1099-INT – interest income
• 1099-B – sales of investments in taxable accounts
• 1099-R – distributions from retirement accounts, including Roth conversions and rollovers

If you moved or converted retirement money during the year, it’s normal to receive a 1099-R—even if the transaction wasn’t taxable (think: transferring funds from one IRA to another during the year).

What Is Form 8606?

Form 8606 is used to report:

• Roth conversions
• After-tax (non-deductible) IRA contributions
• Basis carried forward in IRAs

This form is critical when Roth conversions are involved. Done correctly, it ensures you’re only taxed on what’s required—and not a dollar more. Done incorrectly, and we have a tax nightmare on our hands 20 years from now.

If you completed a Roth conversion, this form should always be addressed.

Do I Need a Schedule C or Just a 1040?

This depends on how you earn income.

• Form 1040 – Everyone files this. It’s the main individual tax return. It’s how the IRS expects you to calculate what you owe and then penalizes you when you get it wrong. Makes you wish they just told you.
• Schedule C – Only required if you have self-employment or sole-proprietor income (including side income not run through an S-Corp or partnership).

If you’re a W-2 employee or an S-Corp owner receiving payroll, you generally do not file a Schedule C for that income.

When in doubt, this is an easy question for your tax professional—or our team—to clarify.

For more on tax planning, check out our tax planning page

What You Should Do Right Now

Here’s the simple checklist:

1. Watch for 1099s from custodians (often online)
2. Don’t panic if forms arrive at different times
3. Flag any Roth conversions or rollovers
4. Decide who is preparing your return this year
5. Ask questions early—before filing

Tax season doesn’t have to be overwhelming. With the right information, and the right coordination, it becomes a straightforward process instead, albeit a stressful one.

If you have questions or want help deciding next steps, we’re here.