How to Make Tax Season Less Painful (Yes, Really)

Tips for Getting Organized and Working with Your Accountant

Tax season is back—cue the collective groan. But it doesn’t have to be a stressful, last-minute scramble. A little preparation and some strategic help from your accountant can make filing your 2024 taxes surprisingly painless (or at least less miserable). The key is to stay organized, communicate early, and let your accountant do the heavy lifting.

Here’s how to make this tax season as smooth as possible—and maybe even avoid those dreaded “we need to talk” emails from your accountant.

Organize and Provide Comprehensive Financial Records

Your accountant can’t work magic without the right information. Get ahead by gathering and organizing your financial records early, including:

• Income records – W-2s, 1099s, rental income, and side gig earnings.
• Investment details – Interest, dividends, capital gains, and losses.
• Deductions and credits – Mortgage interest, medical expenses, charitable donations, and student loan interest.
• Business financials – If you’re self-employed, pull together receipts, invoices, and expense reports.
• Retirement contributions – Statements for 401(k), IRA, and HSA contributions.
  

Handing your accountant a neatly organized file (instead of a pile of crumpled receipts) sets them up to maximize your deductions and catch any issues early.

Reconcile Accounts Before Meeting with Your Accountant

Think of this step as tidying up before a houseguest arrives—except the houseguest is your accountant, and they’re about to see all your financial mess. Before you hand over your documents, make sure your records are accurate and consistent:

• Match Financial Statements – Check that bank and credit card statements line up with your records.
• Confirm Investment Transactions – Ensure all buys, sells, and dividends are recorded correctly.
• Check Business Expenses – Make sure expenses are categorized properly (no, that dinner with your friend probably isn’t a “business meeting”).
• Verify Retirement Contributions – Confirm that contributions and withdrawals match official statements.
  

Getting this sorted ahead of time means fewer back-and-forth communications—and fewer headaches for everyone involved.

Talk to Your Accountant Early (and Often)

Your accountant isn’t a mind reader. Schedule a meeting early in the tax season to go over:

• Tax Law Changes – Find out if any new regulations affect your return.
• Major Life Changes – Marriage, divorce, new house, new baby—anything big in your life probably impacts your taxes.
• Estimated Payments – Review any estimated tax payments you made during the year to make sure they were properly applied.
  

Staying ahead of the game gives your accountant more time to troubleshoot and optimize your return.

Use Secure Tools to Share Documents and Sign Forms

Accountants love efficiency, and secure digital tools make their job easier:

• Secure Portals – Upload sensitive documents to your accountant’s secure system instead of emailing them.
• Digital Organizers – If your accountant sends you a tax organizer, using it can help them catch everything.
• E-Signatures – Most accountants now use electronic signature tools, which speed up the process and reduce paper waste.
  

It’s faster, safer, and keeps you from having to dig through the junk drawer for a pen.

Make Sure Your Accountant Files Electronically and Uses Direct Deposit

Let your accountant handle the actual filing process—just confirm they’re filing electronically and setting up direct deposit for any refund:

• Electronic Filing – Reduces the chance of errors and speeds up processing.
• Direct Deposit – Refunds arrive faster and more securely when they’re deposited directly into your account.
• Payment Arrangements – If you owe money, your accountant can help you set up automatic payments to avoid penalties.
  

This isn’t the place to DIY—let the pros handle it.

Double-Check Before You Sign

Don’t hit “approve” without giving your return a once-over:

• Personal Details – Names, Social Security numbers, and account numbers should be accurate.
• Income and Deductions – Confirm that all your income and deductions are included.
• Credits and Adjustments – Make sure you’ve claimed all available credits, including those for childcare, education, and energy-efficient upgrades.
  

If something looks off, ask. Better to catch it now than explain it to the IRS later.

Plan for Next Year (Yes, Already)

Once you’ve filed, take a moment to breathe—then start thinking about next year:

• Max Out Retirement Contributions – Talk to your accountant about adjusting your contributions to reduce taxable income.
• Review Your Withholding – If you owed a lot (or got a huge refund), it might be time to tweak your W-4.
• Track Expenses Better – If recordkeeping was a pain this year, look into an expense-tracking app or tool.
  

A little strategic planning now means a smoother tax season next year.

Setting Yourself Up for Tax Success

Tax season doesn’t have to be painful. Working with your accountant early, staying organized, and using the right tools can turn a stressful chore into a manageable task. Plus, the better prepared you are, the more money you might save—and that’s always worth it.