The Tax-Prep Document Checklist

The hardest part of tax season usually isn’t the return. It’s the scavenger hunt that comes before it. This is the companion to my downloadable document checklist: a way to see, in one place, roughly what you’ll be gathering so nothing turns up missing at the last minute. Think of it as a menu, not a homework assignment. You only need the sections that sound like your life.

What does almost everyone need to gather first?

A few things show up on nearly every return, so start here. You’ll want a photo ID and Social Security numbers (or ITINs) for yourself, your spouse, and anyone you claim as a dependent. Pull last year’s tax return if you have it. It’s the fastest way for me to spot something that carried over or got missed. Add your bank’s routing and account numbers if you want a refund deposited or a balance paid directly. If you moved, got married or divorced, had a baby, or started drawing Social Security or a pension during the year, jot that down too. Those “life stuff” changes drive more of your return than most people expect.

What if my household is mostly W-2 income?

For a straightforward wage-earning household, the pile is friendlier than you think. Gather every W-2 from every employer you and your spouse held during the year. Add any 1099-INT or 1099-DIV forms from banks and credit unions, plus a 1098 if you paid mortgage interest. If your kids are in daycare or after-school care, collect the provider’s total and their tax ID. Tuition (Form 1098-T), student loan interest (1098-E), and records of any estimated payments you made all belong here. If you itemize, or aren’t sure whether you should, keep records of property taxes, charitable giving, and out-of-pocket medical costs. When we talk, I’ll tell you honestly whether itemizing beats the standard deduction for you, so you’re not saving receipts for nothing.

What do I add if I’m self-employed or freelancing?

Self-employment is where good records pay off the most. Pull together your income first: 1099-NEC and 1099-K forms, plus your own tally of anything paid to you that didn’t come with a form (yes, that still counts). Then gather the expenses, the numbers that lower what you owe. Think supplies, software, phone and internet used for work, professional fees, business insurance, and mileage if you drive for the business. If you work from home, note the square footage of your workspace and the home’s total. Collect records of any health insurance you bought yourself and any retirement contributions you made, like a SEP-IRA or Solo 401(k). If you already sent in quarterly estimated payments, bring those dates and amounts.

What do I need if I own a rental property?

Rentals have their own short stack. Start with total rent collected for the year, then the costs against it: mortgage interest, property taxes, insurance, repairs, management fees, utilities you covered, and HOA dues. Keep receipts for anything you bought or improved on the property. A new roof or appliance is treated differently than a plumbing repair, and I’ll sort out which is which. If this is the property’s first year as a rental, I’ll also need what you originally paid for it and the date it went into service, so depreciation is set up correctly from the start.

What about investments and brokerage accounts?

For taxable investment accounts, the key form is the 1099-B (usually bundled into a consolidated 1099 with your interest and dividends). It reports what you sold and what it cost you. If your brokerage didn’t track the cost basis for older shares, dig up your original purchase records. That number is what keeps you from overpaying on a sale. Add any 1099-DIV for dividends, K-1s from partnerships or S-corps you have a stake in, and records of cryptocurrency sales or trades if you dabbled there. Retirement account activity matters too: a 1099-R for distributions, or your contribution confirmations for a traditional or Roth IRA.

When should I start gathering all this?

Earlier than feels necessary. Most of these forms are legally required to reach you by the end of January, so a good rhythm is to open a folder (paper or digital) in early February and drop things in as they arrive. Come our appointment, you upload it all through the secure portal in one go, and we’re not chasing a stray W-2 in April. The checklist download organizes this by your exact situation so you can tick boxes instead of guessing.

If you’d rather not sort your pile alone, that’s the whole point of the intro call. Book a free 15-minute conversation and tell me what your year looked like, whether that was a job change, a side gig, or a first rental, and I’ll tell you precisely which of these sections apply to you, so you gather once and gather right.