Tax season may be over for many people, but May is actually one of the best times to get organized for the year ahead. Whether you filed your return already, filed an extension, started a business, changed jobs, or had a major life change, a quick midyear tax review can help prevent surprises later.
At Coastal Tax, we work with individuals, families, and small businesses across Rockland and the South Shore to make the tax process clearer, more secure, and easier to manage. Here are five smart steps to consider before summer gets busy.
1. Review your tax withholding
If you owed more than expected this year, received a much smaller refund, changed jobs, got married, had a child, bought a home, started a side business, or began receiving retirement income, your withholding may need a second look.
The IRS offers a Tax Withholding Estimator that can help employees and retirees review whether enough federal tax is being withheld during the year. A withholding checkup can help reduce the chance of owing unexpectedly when the next filing season arrives.
2. Check whether estimated tax payments apply to you
Estimated tax payments are common for self-employed individuals, business owners, landlords, investors, retirees, and others who receive income without enough tax withholding.
For federal estimated taxes, the IRS generally uses quarterly payment periods, with the next 2026 estimated tax due date falling on June 15 for income earned from April 1 through May 31. Massachusetts taxpayers can also make estimated tax payments electronically through MassTaxConnect.
If you had a balance due last year or your income has changed, now is a good time to review whether your estimates still make sense.
3. Do not ignore an extension
An extension gives you more time to file, but it does not give you more time to pay. The IRS explains that taxpayers who receive an extension still need to pay any tax owed by the original filing deadline to help avoid penalties and interest.
If your return is on extension, use the next few months wisely. Gather missing documents, review business income and expenses, confirm estimated payments, and respond quickly if your tax preparer asks for additional information.
Waiting until October can create stress, rushed decisions, and fewer options if something needs to be corrected.
4. Clean up your records while the year is still fresh
Good records make tax preparation easier and can also help you make better decisions during the year.
For individuals, this may include keeping track of charitable donations, real estate tax bills, medical expenses, education forms, investment activity, and major life changes.
For business owners, this may include reconciling bank accounts, organizing receipts, reviewing payroll records, saving loan statements, tracking mileage, and separating personal and business expenses.
If your bookkeeping is behind, May and June are better times to fix it than December or next March.
5. Make sure your tax office has your current information
If your address, phone number, email, filing status, dependents, business activity, payroll provider, bank account, or ownership structure changed, your tax preparer should know before filing season begins.
At Coastal Tax, we use secure document sharing, electronic signatures, and client intake tools to help keep information organized. Updating your information early helps reduce delays and keeps the process moving smoothly when it is time to prepare your return.
Final thoughts
A little planning now can make next tax season much easier. Reviewing withholding, estimated payments, extensions, and records before summer gives you more control and fewer surprises.
Coastal Tax is accepting new individual and business clients. To get started, visit our website and complete the new client intake form.
