What Individuals Need to Do Before Tax Season Starts

Tax season is approaching faster than you think. The IRS opens e-filing for individual returns on Monday, January 26, 2026, which means now is the time to get organized, not March when you’re scrambling to find last year’s return.

Preparing early doesn’t just make tax filing smoother. It gives you time to gather missing forms, understand how life changes affect your return, and make informed decisions about whether to file yourself or work with a professional. Waiting until the last minute means rushed preparation, missed deductions, and unnecessary stress.

Whether you had a baby, bought a house, changed jobs, or experienced other major life events in 2025, those changes likely affect your tax return. The more complex your situation, the more important early preparation becomes.

Here’s your pre-season checklist to get tax-ready before the filing rush begins.

1. Gather Your Documents

This is priority number one. You can’t file accurately if you don’t have all your documents.

Income Documents (due by January 31, 2026):

W-2 forms - Wage and tax statement from every employer you worked for in 2025
- Tips and overtime earners: Check for any additional supplements or documentation from your employer about tip income or overtime pay under the new OBBBA provisions
- Save your final paystub - Helpful for verifying W-2 accuracy and documenting year-end totals
1099 forms - Various types depending on your income sources:
- 1099-NEC (nonemployee compensation, contractor work, side hustles)
- 1099-MISC (miscellaneous income, rent if you’re a landlord)
- 1099-INT (interest income from banks, savings accounts)
- 1099-DIV (dividend income from investments)
- 1099-B (proceeds from broker transactions, stock sales) - Note: Brokerage firms often don’t send these until mid-February or even mid-March, so plan accordingly
- 1099-G (unemployment compensation, state tax refunds)
- 1099-K (payment processor transactions if over threshold)
- 1099-R (retirement account distributions)
Form 1095-A - Health insurance marketplace statement (if you used healthcare.gov or MNsure)
Schedule K-1 - Partnership or S-corporation income (if you own part of a business)
Prior year tax return - Reference for carryovers, estimated payments, and comparison

Deduction Documentation:

Charitable contributions - Receipts for cash donations, written acknowledgment for $250+
Medical expenses - If significant (must exceed 7.5% of AGI to deduct)
Mortgage interest - Form 1098 from your lender
Student loan interest - Form 1098-E from your loan servicer
American-made vehicle loan interest - Form 1098 from auto lender (new OBBBA deduction for qualifying vehicles purchased in 2025)
Property tax records - Assessment statements, payment receipts
State and local taxes - Payment confirmations (SALT cap is now $40,000)
Business expenses - Receipts if self-employed or have side hustle (home office, supplies, mileage)

Life Change Documentation:

New baby or adoption - Social Security number, childcare provider EIN and address
Marketplace health insurance - Form 1095-A (premium tax credit reconciliation)
Education expenses - Form 1098-T (tuition statement), receipts for qualified expenses
Home purchase - Closing disclosure, Form 1098 (mortgage interest)
Retirement account contributions - IRA contribution receipts, 401(k) statements
Moving expenses - Only if active duty military

Why this matters: The IRS receives copies of all W-2s, 1099s, and other information returns. If you don’t report income that they know about, expect a notice. Better to gather everything upfront than to amend your return later.

2. Why Preparing Early Matters

Most people think about taxes in March. Smart taxpayers think about them in January. The difference isn’t just timing. It’s the quality of your tax filing and the stress level you experience getting there.

When you start preparing now, you give yourself breathing room. Employers and payers have until January 31 to send W-2s and 1099s, which means if you haven’t received something by early February, you still have two months before the April 15 deadline to track it down. Compare that to realizing you’re missing a form on April 10 when you’re frantically trying to file.

Early preparation also means you can catch errors before they become problems. If your W-2 shows the wrong withholding amount or a 1099 reports income that doesn’t match your records, you need time to get corrected forms issued. Discovering these issues in March leaves you scrambling. Discovering them in February gives you time to fix them properly.

Some tax-saving strategies can still be implemented even after the year ends. You can make IRA contributions until April 15 that count for the previous tax year. You can contribute to an HSA if you’re eligible. But you need time to evaluate whether these moves make sense for your situation, not rush into them the week before filing because you heard they might save money.

If you decide professional help makes sense for your situation, tax preparers book up fast. Calling in January gets you scheduled at a time that works for both of you. Calling in March means either waiting until after the rush or being squeezed in at the last minute when the preparer is juggling dozens of other returns.

Tax filing doesn’t have to be stressful. Preparing early turns it into a manageable task you can tackle methodically. And if you’re expecting a refund, why wait? E-filing with direct deposit typically means you’ll have your refund in 2-3 weeks. Filing in February beats filing in April.

The people who prepare early are the ones who file accurately, maximize legitimate deductions, and start the year with confidence. The people who wait until March are the ones dealing with extensions, penalties, and unnecessary tax bills. Which group would you rather be in?

3. Choose Your Filing Method

You have three main options for filing your tax return. The right choice depends on your situation’s complexity and your comfort level with tax concepts.

Self-preparation software works well for straightforward situations. If you have W-2 income only (no side hustles, rental property, or business income), you’re taking the standard deduction instead of itemizing, and you haven’t experienced major life changes like marriage, divorce, or buying a home, software can handle your return just fine.

The appeal of software is clear: it’s cost-effective, you can file on your own schedule, and e-filing with direct deposit is built right in. Interview-style questions guide you through the process step by step. But there are limitations. Software provides limited guidance on complex situations, there’s no one to represent you if you’re audited later, and the software doesn’t know what questions to ask about YOUR specific situation. The upsells can add up quickly, and ultimately you’re responsible if something goes wrong.

Professional tax preparers make sense when your situation gets more complicated. If you’re going through your first year with a significant life change (marriage, divorce, new baby, home purchase, job change), dealing with self-employment or side hustle income, or managing investment income from stocks, real estate, or cryptocurrency, professional help often pays for itself. The same goes if you have multi-state income, you’re on the fence about itemizing deductions, you received an IRS notice last year, or you simply value strategic tax planning instead of just filing a compliance return.

When choosing a professional, look for credentials. Enrolled Agents (EAs), CPAs, and tax attorneys all have representation rights before the IRS and are held to professional standards. You want someone who specializes in situations like yours, is available year-round (not just during filing season), and has a clear fee structure based on complexity rather than a percentage of your refund. (For detailed credential comparison, see our post: Understanding Tax Preparer Credentials: Why It Matters Who Handles Your Taxes)

The benefits of professional help go beyond just getting the return filed. You get expertise and experience, representation rights if issues arise with the IRS, strategic planning for the following year, and someone to call if you receive an IRS notice. Yes, it costs more than DIY software, and you need to schedule appointments and provide information. Quality varies by preparer, so credentials help but aren’t everything. But for complex situations, the investment typically pays for itself through deductions you wouldn’t have known about and mistakes you avoid.

Paper filing is rarely recommended anymore. Processing is slower (weeks instead of days), you don’t get immediate confirmation of receipt, math errors are more common, and refunds take 6-8 weeks instead of 2-3 weeks for e-filing. The only time paper filing makes sense is when you have specific forms not eligible for e-filing (rare) or special circumstances that require it.

The bottom line: most people should e-file, either through software or a professional. The real question is whether your situation is straightforward enough for DIY or would benefit from professional guidance.

4. Understand Your Deadlines

Missing tax deadlines triggers penalties and interest, so it’s worth understanding what’s actually due when.

The big deadline is April 15, 2026. That’s when your Form 1040 and all applicable schedules are due. If you owe tax, payment is also due April 15. This is the one everyone knows, even if they don’t always act on it until the last minute.

Before that, January 31, 2026 is the deadline for employers to provide W-2s to employees and 1099-NEC forms to contractors. If you haven’t received these by mid-February, it’s time to contact the issuer directly.

If you need more time to file, you can submit Form 4868 to extend your filing deadline to October 15, 2026. Here’s the critical part that trips people up: filing an extension extends the filing deadline, NOT the payment deadline. If you owe tax, you still must pay by April 15 to avoid interest and penalties. The extension just gives you six more months to file the paperwork.

Extensions make sense when you’re missing information or forms (especially in complicated situations), your return is complex and requires more time to prepare properly, life circumstances are preventing timely filing, or you’re waiting on K-1s from partnerships or S-corps (these often arrive frustratingly late). Extensions don’t help if you owe tax but can’t pay it (you’ll owe interest either way) or if you’re just procrastinating (in which case, prepare now instead).

If you have income not subject to withholding (self-employment, rental property, investments), you may owe quarterly estimated payments. The deadlines are April 15, June 15, September 15, and January 15 of the following year. Miss these, and you could face underpayment penalties even if you pay your full tax bill by April.

The penalties for missing deadlines add up fast. Late filing costs you 5% of unpaid taxes per month, up to 25%. Late payment is 0.5% of unpaid taxes per month. And interest compounds daily on unpaid balances, currently around 8% annual rate. If you’re getting a refund, there’s no penalty for filing late, but why wait? File early, get your refund sooner.

Mark your calendar now. April 15 comes faster than you think. Preparing in January means filing in February or March, long before deadline stress hits.

5. What to Do If Forms Are Missing

It’s mid-February, and you still haven’t received a W-2 from your former employer. Or a 1099 you expected never arrived. This happens more often than you’d think, and there’s a process to handle it.

Start by contacting the issuer directly before February 14. Call or email your former employer, client, or payer to verify they have your correct mailing address and ask them to re-send the form. Many can email you a copy immediately, solving the problem on the spot.

If that doesn’t work, wait until February 14 before contacting the IRS. The IRS won’t help with missing W-2s until mid-February because the deadline for issuers is January 31, and they want to give employers a two-week grace period after the deadline before escalating.

After February 14, you can call the IRS at 800-829-1040 to report the missing form. They’ll contact the employer on your behalf. You’ll need to provide the employer’s name, address, phone number, EIN, your employment dates, and an estimate of your wages.

If you’ve contacted both the employer and the IRS and still don’t have your W-2 by filing time, you can use Form 4852 (Substitute for Form W-2) as a last resort. Use your final pay stub to estimate wages and withholding, attach the form to your return, and file. This is much better than not reporting the income at all.

Here’s why you can’t just skip unreported income: The IRS receives copies of every W-2 and 1099 issued. They run a matching program that compares what employers report to what you report. If you omit income that shows up in the IRS system, you’ll get a notice (CP2000) proposing additional tax, penalties, and interest. It’s always better to report using the best available information (Form 4852) than to omit income entirely.

If the actual W-2 arrives after you’ve filed with Form 4852 and the numbers are different, you’ll need to file Form 1040-X (amended return). If you receive a corrected form (W-2c or 1099-corrected) after filing, you’ll need to amend only if the correction changes your tax liability. Minor corrections that don’t affect your tax don’t require amendment.

The best defense against missing forms is tracking them proactively. Create a checklist of expected forms based on how many jobs you had, what bank accounts you have, which investments you own, and any side income sources. Cross them off as they arrive. This makes it easy to spot what’s missing before deadline pressure hits.

Don’t let a missing form stop you from filing on time. Form 4852 exists for exactly this situation.

6. Life Changes That Affect Your Taxes

Major life events often have significant tax implications. If any of these happened to you in 2025, they’ll affect your return in ways that might surprise you.

Marriage changes your filing status and usually saves you money, but there are decisions to make. Most couples benefit from filing jointly because of lower tax rates and access to more credits and deductions. Filing separately makes sense in rare cases, like when one spouse has large medical expenses or needs to protect income-driven student loan repayment amounts. If you changed your name, you must update it with Social Security before filing. Your name on the return must match Social Security Administration records, or the IRS will reject your e-filed return. Combined income also affects tax brackets, credit phaseouts, and Medicare premium calculations. You’ll need both spouses’ W-2s and 1099s, prior year returns if this is your first joint return, and documentation if your name changed.

Divorce complicates your filing status and dependent claiming. Your final year as a married couple, you can file jointly or separately. After that, you’re single or potentially head of household. Alimony rules depend on when you divorced: pre-2019 divorces mean alimony is deductible for the payer and taxable for the recipient, but post-2018 divorces mean alimony is NOT deductible and NOT taxable. Custody agreements determine who claims children, and only one parent can claim the Child Tax Credit for each child. Property settlements are generally not taxable, but they affect your basis in assets. If retirement accounts are being divided, you must use a QDRO (Qualified Domestic Relations Order) to avoid taxes and penalties. Gather your divorce decree or separation agreement, documentation of any alimony paid or received, and the custody agreement regarding dependents.

Having a baby or adopting opens up valuable tax benefits. The Child Tax Credit, dependent care credit, and adoption credit can all reduce your tax bill significantly. If you’re unmarried, you may now qualify for Head of Household filing status. Don’t forget employer benefits like dependent care FSA contributions. You absolutely need the child’s Social Security number to claim any of these benefits, plus the childcare provider’s name, address, and EIN if you’re claiming the dependent care credit. For adoptions, gather your adoption expenses and finalization documents.

Buying a home is when the itemizing vs. standard deduction decision becomes important. Mortgage interest is deductible if you itemize, and property tax is deductible but falls under the SALT cap. First-time homebuyers may qualify for state credits (Minnesota has first-time homebuyer programs worth investigating). If you made energy-efficient improvements like installing heat pumps, solar panels, or new windows, these may qualify for federal credits. The key question is whether your mortgage interest plus property taxes plus other itemized deductions exceed the standard deduction. You’ll need Form 1098 (mortgage interest statement), your closing disclosure showing property taxes and points paid, and receipts for any energy-efficient improvements.

Changing jobs means tracking multiple income sources and handling retirement accounts carefully. You’ll receive W-2s from every employer you worked for during the year, even if you only worked there briefly. If you rolled over a 401(k) to an IRA or new employer plan, this must be done correctly to avoid taxes. Moving expenses are only deductible for active duty military since TCJA eliminated the deduction for most taxpayers. Unemployment compensation is fully taxable, which often surprises people. Signing bonuses are taxable compensation and often under-withheld, potentially leaving you with a tax bill. Gather W-2s from every employer, Form 1099-R for any retirement distributions or rollovers, and Form 1099-G if you received unemployment compensation.

Retirement introduces Required Minimum Distributions and Social Security taxation. Once you turn 73, you must begin taking RMDs from traditional retirement accounts. Social Security benefits become partially taxable. Up to 85% of your benefits may be taxable depending on your other income. Pension and 401(k) withdrawals are fully taxable ordinary income. Your income also affects Medicare premiums (IRMAA), where higher income means higher premiums based on your tax return from two years ago. If you’re under 59½ and taking early withdrawals, expect a 10% penalty unless an exception applies. You’ll need Form SSA-1099 (Social Security benefits), 1099-R forms (retirement distributions), and Form 1095-B or 1095-C (health coverage).

If you experienced any major life change in 2025, consider professional help. These situations have nuances that software may not catch, and mistakes can be costly.

7. When to Seek Professional Help

Some tax situations are straightforward. Others benefit from professional expertise. The trick is knowing which category you’re in.

Your situation is probably straightforward if you have W-2 income only (one job, one employer, one state), you’re taking the standard deduction instead of itemizing, you have no dependents or a simple dependent situation, you experienced no major life changes in 2025, you have no investments beyond a savings account, and your situation is basically the same as last year. For these situations, quality tax software like FreeTaxUSA, TurboTax, or H&R Block often works fine.

Professional help starts making sense when complexity enters the picture. If you’re going through your first year with a significant life change (marriage, divorce, new baby, adoption, first home purchase, job change with retirement account rollover, moving to a new state, or retirement), the nuances of how these events affect your taxes can be tricky. Software might get you to the right answer, but a professional can explain why it’s the right answer and help you plan for next year.

Income complexity is another sign you might benefit from professional guidance. Self-employment or side hustle income means dealing with Schedule C. Rental property income means Schedule E. Investment income beyond simple savings account interest (stock sales, cryptocurrency, K-1s from partnerships) adds layers of complexity. If you worked in multiple states or moved mid-year, you’re dealing with multi-state tax returns, which get complicated fast. Even unemployment compensation combined with other income can create tax surprises if you’re not prepared.

Itemizing deductions is where many people wonder whether professional help is worth it. If you have significant medical expenses (over 7.5% of your income), large charitable contributions, or mortgage interest plus property taxes that might exceed the standard deduction, you want to make sure you’re making the right choice. The decision between itemizing and taking the standard deduction can swing your tax bill by hundreds or thousands of dollars, and a professional can run both scenarios to show you which saves more.

Prior year issues are a clear signal to seek help. If you received an IRS notice or were audited, owe back taxes or are on a payment plan, didn’t file a prior year return and need to catch up, or made estimated payments and need help calculating next year’s requirements, professional assistance can prevent problems from getting worse.

Finally, if you value strategic planning beyond just filing a compliance return, professional help offers real value. Planning for next year’s retirement contributions, estimated payments, and withholding adjustments can save you far more than the preparer’s fee. Representation rights if you’re audited provide peace of mind. And having a professional signature on your return means someone credentialed has reviewed it.

Professional help costs vary by situation, but it often pays for itself. The deductions and credits you didn’t know about, the costly mistakes you avoid, and the strategic planning that saves tax in future years typically outweigh the preparer’s fee. And peace of mind is valuable too.

The right preparer should hold credentials (EA, CPA, or Attorney—see our Tax Preparer Credentials guide for details), specialize in situations like yours, explain things clearly in plain English, be available year-round instead of just during filing season, and sign your return with their PTIN.

Don’t choose a preparer based solely on price. Choose based on credentials, experience with your situation, and communication style. The cheapest option often costs more in the long run if they miss deductions or make errors.

8. Digital Organization Best Practices

Paper receipts fade. Files get lost. Digital organization keeps your tax documents safe and accessible for years, and it’s easier to set up than most people think.

Start with scanning. You want digital copies of all paper receipts (charitable donations, medical expenses, business expenses), tax forms (W-2s, 1099s, even though digital copies are often available), supporting documentation (mortgage closing statements, adoption papers, medical invoices), and prior year tax returns. Yes, it’s tedious the first time you do it, but once you’re current, maintaining it takes minutes per month.

File naming matters more than you’d expect. Use a consistent, searchable format like YYYY-MM-DD_Category_Description.pdf. For example, 2025-12-15_Charitable_Church_Donation.pdf or 2025-01-28_Income_W2_ABC_Company.pdf. This format sorts chronologically and makes finding specific documents easy. Three years from now, you’ll thank yourself for being this organized.

Create a simple folder structure that mirrors how tax returns are organized: a main folder for each year, with subfolders for Income (W-2s, 1099s, Other Income), Deductions (Charitable, Medical, Mortgage Interest, Property Tax), Filed Return, and Supporting Documents. Keep it consistent year to year so you always know where to look.

For cloud storage, pick one service and stick with it. Google Drive has a generous free tier and good search functionality. Dropbox offers reliable sync and a solid mobile app. OneDrive integrates well if you’re in the Microsoft ecosystem. Honestly, consistency matters more than which service you choose. Don’t scatter your tax documents across multiple platforms.

Security matters because tax documents contain sensitive personal information. Use strong, unique passwords for your tax storage accounts. Enable two-factor authentication for that extra security layer. Most cloud services offer built-in encryption for sensitive folders. And never email tax documents unencrypted. Use secure file sharing links or password-protected PDFs instead.

Follow the 3-2-1 backup rule: keep three copies of important documents, on two different media types (cloud plus external hard drive), with one offsite backup (cloud counts as offsite). This protects you against hard drive failure, ransomware, and accidental deletion.

Retention guidelines are straightforward. Keep filed tax returns and supporting documents for at least three years, which is the typical IRS audit period. Six years is better for returns with substantial underreporting (25%+ unreported income) and basis documentation for investments. Some documents should be kept permanently: home purchase documents (you need the basis when you sell), retirement account contribution records (especially Roth basis), and business formation documents. Prior year returns can be replaced once you file the current year.

Digital organization takes maybe 30 minutes to set up initially, but it saves hours during tax season every year. Scan documents as you go throughout the year, and filing becomes simple document gathering instead of frantic searching through boxes and drawers.

The Bottom Line

Tax season preparation isn’t just about filing on time. It’s about having complete information, making informed decisions, and avoiding costly mistakes.

The checklist:

✅ Gather all income documents (W-2s, 1099s, K-1s, prior year return)
✅ Collect deduction receipts (charitable, medical, mortgage interest, property tax)
✅ Review prior year return (carryovers, estimated payments, comparison)
✅ Choose filing method (software for straightforward, professional for complex)
✅ Understand deadlines (April 15, extension options with Form 4868)
✅ Handle missing forms (Form 4852 if needed, don’t skip income)
✅ Document life changes (marriage, divorce, home purchase, job change, retirement)
✅ Organize digitally (scan receipts, name consistently, back up in multiple locations)

Why preparing now matters:

Catch and fix errors before they become IRS notices
Gather missing forms without deadline pressure
Make informed filing method decisions (DIY vs. professional)
Get on tax professional’s calendar before filing rush
Identify tax-saving opportunities while time remains (IRA contributions, withholding adjustments)
Start the year with accurate records and peace of mind
Avoid last-minute stress, rushed decisions, and extension scrambling

The difference between smooth filing and stressful filing:

People who prepare in January:

File accurately in February or early March
Maximize legitimate deductions and credits
Get refunds quickly (if expecting one)
Have time for strategic planning conversations
Start the year confident and organized

People who wait until March:

Scramble to find documents
Rush decisions about complex situations
Miss tax-saving opportunities
File extensions out of necessity, not choice
Carry stress through April

Which approach sounds better?

Start now. Your future self will thank you.

Need Help Navigating Your Tax Situation?

Tax filing doesn’t have to be stressful or complicated. At JCT Tax Solutions, I help individuals prepare accurate returns, maximize deductions, and plan strategically for the year ahead.

Whether your situation is straightforward or complex, I’m here to make tax season less overwhelming.

Tax Preparation Services

Individual tax return preparation:

Form 1040 and all applicable schedules
Multi-state filing for individuals working across state lines
Complex income situations (self-employment, rental property, investments)
Itemized deduction optimization (when it saves money vs. standard deduction)
Life change guidance (marriage, divorce, home purchase, job changes, retirement)

Strategic tax planning:

Minimize tax liability through legitimate strategies
Retirement contribution planning (IRA, 401(k), Roth conversions)
Estimated payment calculations (avoid underpayment penalties)
Withholding adjustments for next year
Year-ahead projections and planning

Problem resolution:

Prior year amendments (Form 1040-X)
Missing form assistance (Form 4852)
IRS notice response and resolution
Back tax return preparation (catch-up filing)

Year-round support:

Not just filing season availability
Questions answered throughout the year
Planning conversations when decisions matter
Proactive communication about tax law changes

What Makes JCT Tax Solutions Different

Enrolled Agent credential:

Passed comprehensive 3-part IRS examination covering individual and business taxation
Unlimited representation rights before the IRS (audits, appeals, collections)
Required continuing education (16+ hours annually) to stay current on tax law
Federally licensed to practice in all 50 states

Personalized service:

Every situation is different, and your tax preparer should understand YOUR specific circumstances
Clear explanations in plain English (no jargon or confusing tax-speak)
Time to understand your situation and goals
Recommendations tailored to you, not one-size-fits-all advice

Focus on education:

You should understand your return, not just sign it
Explanations of why certain strategies work (or don’t) for your situation
Empowerment to make informed decisions
Transparent process from start to finish

Professional peace of mind:

Accurate preparation based on complete information
Signature of credentialed professional on your return
Someone to call if you receive IRS correspondence
Representation rights if audit or issues arise

Ready to Get Started?

Tax season is approaching. Whether you need help with a straightforward W-2 return or a complex situation involving life changes and multiple income sources, JCT Tax Solutions is here to make the process smoother.

Contact JCT Tax Solutions to schedule a consultation. Let’s discuss your tax situation and create a plan to file accurately and confidently.

Serving individuals and families in Minnesota and nationwide (EAs can practice in all 50 states).

Disclaimer: This blog post provides general information about individual tax preparation and should not be construed as tax advice for your specific situation. Tax laws and regulations are subject to change. For personalized tax advice, please consult with a qualified tax professional.