What Are Some Ways You Can Make Tax Season a Little Easier?

For many individuals and business owners alike, tax season can be a major stressor right at the beginning of the year.

At Cukierski & Associates, we’ve worked with hundreds of people who are filing for themselves, their family, their business, or their association. We’ve seen firsthand what separates unprepared or stressed-out filers from those who breeze through April with no problems.

The difference? They start early, stay organized, and build systems that work year-round and not just when the deadline is fast approaching.

In this blog, we’ll discuss seven practical ways to make tax season stress-free, regardless of whether this is your first year filing or your fiftieth.

1. Get Organized Before January (Not During April)

The biggest mistake that we’ve seen is filers waiting until March to start looking for receipts. By then, you’re searching through bank statements, digging through your email, and trying to remember everything you had made a “mental note” of.

Start your tax prep for the next year right after you file your return. We recommend creating a filing system to gather all of the documents you need:

• For individuals: W-2s (employers to send to employees by January 31), 1099 forms for freelance work, bank statements, mortgage interest statements (Form 1098), charitable contribution receipts
• For business owners: Prior year’s returns, year-end financial statements, payroll reports, business expense receipts, income records, and invoices

*Note: For the 2025 tax year (filing in 2026), the due date for W-2s is February 2, 2026, since January 31 falls on a Saturday.

Take a picture of receipts the moment you get them and hang on to your bank statements. At the end of each month, sort receipts/charges to make them easily accessible for yourself or to hand everything over to your CPA when they need it.

Good organization isn’t just about efficiency. Our goal is to make tax prep stress free. When you know where everything is, tax season stops feeling like something you must endure and starts to feel a lot more manageable.

Click here for our Tax Planning Checklist.

2. Track Everything Throughout the Year

Block fifteen minutes every Friday (or whatever day works best for you) to log income, classify expenses, and track mileage. When this becomes routine, tax season becomes a matter of printing reports, not trying to recall your entire financial year from memory.

For business expenses, know what’s deductible and keep receipts and documentation for everything: home office expenses, business travel and vehicle costs, advertising and marketing costs, business property rent, utilities, loan interest, and professional services fees.

*Best Practice: If you’re logging mileage, use an app that logs trips automatically. The standard mileage deduction is substantial, but you need accurate records to hand over to the IRS.

3. Know Your Tax Deadlines

What happens when you miss a tax deadline? Missing due dates triggers penalties, which can add up fast. Mark your calendar with every relevant date:

• April 15: Individual returns and any taxes owed are due (or next business day if it falls on a weekend)
• March 15: Partnership and S corporation returns are due (Forms 1065 and 1120-S)
• Quarterly Estimated Taxes (Self-Employed): Typically due January 15, April 15, June 15, and September 15.

Extensions: Form 4868

If you need more time to get your documents together and to file your return, file Form 4868 by April 15 to receive an automatic six-month extension. But it’s important to understand that this extension does not give you more time to pay, it just gives you more time to prepare and file the actual return.

Extensions make the most sense if you’re missing necessary documents or if your tax situation is complex and you need more time to ensure the numbers are accurate.

4. Communicate Clearly (and Early) with Your CPA

While CPAs provide substantial value outside of tax season, the busiest season for any CPA runs from January through April. By March, many tax professionals are all booked up for the tax season.

If you’re looking to hire a CPA, schedule your appointment in January or earlier, especially if you’re a business owner. Early appointments mean more time for strategic tax planning, not just rushing to get everything turned in before the deadline.

Prepare for Your First Meeting with a CPA

When you first meet with a CPA, come prepared with a series of questions:

• What documents do they need?
• What’s their timeline?
• How do they prefer to communicate: email, phone, or their firm’s client portal?
• What expense categories should you track?

Throughout tax season, practice proactive communication. If you’re waiting on a delayed 1099 or discover an error in your records, tell your CPA immediately. Don’t wait until the day before your appointment to mention that your biggest client still hasn’t sent their form.

Find a Local CPA before Tax Season

When you’re looking for a CPA, find someone local who understands your specific state’s tax laws and knows the challenges. That local knowledge matters when it comes to state tools, credits, and planning opportunities specific to your area.

5. Automate What You Can

Manual record keeping can be tedious and is prone to errors. Automation tools save time, reduce mistakes that could trigger IRS penalties, and really help lower your stress level by handling repetitive tasks seamlessly.

Payroll services handle tax-withholding calculations, generate W-2s and 1099s automatically, and file payroll tax forms on schedule. They ensure you have a central location for wage, deduction, and tax payment records. That’s everything your CPA needs for year-end financial reporting.

Other automation practices to consider:

• Receipt-scanning apps that categorize expenses and extract data
• Mileage-tracking apps that log business miles automatically
• Estimated tax payment reminders so you never miss a quarterly deadline

6. Maximize Your Deductions and Credits

Every dollar you don’t claim is money left on the table. While the two terms can often be confused, “tax deductions” lower your taxable income, whereas “tax credits” directly reduce your tax bill. Both matter.

Common small business deductions include:

• Home office expenses: Deduct a portion of mortgage interest, rent, and utilities if you use space exclusively for business
• Business travel: Client meetings, conferences, and work-related trips
• Vehicle costs: Either actual expenses or the standard mileage rate
• Charitable contributions: If made through your business
• Healthcare coverage: Premiums and contributions to employee plans
• Energy-efficient investments: May qualify for credits

But you do need documentation for everything. The IRS doesn’t take your word for it. Keep receipts, maintain detailed records, and document the business purpose of expenses.

Tax credits can be even more beneficial. Certain small businesses qualify for credits related to healthcare coverage or energy-efficient improvements. These reduce your actual tax liability dollar for dollar, not just your taxable income.

Work with a CPA to identify which deductions and credits apply to your specific situation. Tax law changes frequently, and what worked last year might not apply this year. A mid-year meeting or Q4 check-in with your CPA can uncover planning opportunities you might otherwise miss.

7. Take Care of Yourself During Tax Season

We understand why tax season can be stressful for any type of filer. Here are our tips for reducing stress during tax season.

Block time on your calendar specifically for tax tasks

When you set aside dedicated time for gathering documents, reviewing records, or meeting with your accountant, you’re more likely to stay in control instead of feeling overwhelmed by a never-ending to-do list that bleeds into every evening and weekend.

Ask for support when you need it

Lean on your CPA for professional guidance. CPAs will have professional experience working with different kinds of clients and can handle any issues that may arise. If possible, delegate administrative tasks, and if you’re feeling genuinely overwhelmed, that may be a sign that you need to adjust your approach.

Use small stress relievers throughout the day

Five minutes of stretching, listening to music while you organize receipts, or working in a different location can all help break up the monotony and reduce tension. The goal isn’t to eliminate tax season stress entirely. It’s really to keep it at manageable levels so you can think clearly and avoid mistakes that create even more stress later.

*Remember: the organization systems and automation tools we’ve discussed aren’t just about efficiency. They’re also about stress reduction.

Making Tax Season More Manageable

The people who handle tax season well share common habits: they organize documents as they go, they track expenses weekly (not annually), they communicate clearly with their tax professionals, they work with qualified CPAs who answer their questions promptly, and they treat tax planning as a year-round activity—not something that starts in March.

Need help getting ready for tax season? The CPAs at Cukierski & Associates work with individuals and families, businesses, associations, nonprofits, and freelancers across Chicagoland. It’s our goal to make tax planning straightforward and stress free.

Schedule a consultation to discuss your specific situation and how we can help you keep more of what you earn.