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If you file 1099s directly, the IRS is changing the system you use. The Filing Information Returns Electronically system, known as FIRE, is being retired. The IRS is moving information return filing to the Information Returns Intake System, or IRIS. This change does not need to become a year-end emergency. The key is to understand the dates, choose your filing method, and complete the setup early. I have organized the transition below so you can move from uncertainty to a cle

If you own a business formed in the United States, you have likely heard about Beneficial Ownership Information, or BOI, reporting. The rules have changed several times. Court cases, temporary relief, and interim guidance made the topic difficult to follow. There is now a clearer answer. On August 11, 2026, the Financial Crimes Enforcement Network, or FinCEN, issued a final rule that makes the previous relief permanent. The final rule became effective on August 14, 2026. Unde

If you filed an extension for your 2025 individual tax return, October 15, 2026, is your final federal filing deadline. That date may feel far away. It is not. Fall becomes busy quickly. Client work picks up. Schedules fill. Tax documents get harder to find. Small questions can take longer to resolve. The IRS encourages taxpayers who filed extensions to submit their returns as soon as they have the information they need. I agree. Early filing gives you more time to correct an

A software price change does not need to create a bookkeeping headache. Xero has announced new US subscription prices beginning October 1, 2026. The change applies to all US subscribers, including both new and existing customers. The updated amount will appear on Xero invoices dated October 1 or later. If you use Xero for invoicing, bank reconciliation, reports, or daily bookkeeping, now is a good time to review your plan. You do not need to make a rushed decision. A calm rev

With eight days left until September 15, now is the time to move from planning to completion. This deadline affects several types of small business owners. You may need to: Make your third 2026 estimated tax payment. File an extended 2025 partnership or S corporation return. Provide or review partner and shareholder Schedule K-1 information. Deposit August payroll taxes if you are a monthly depositor. That may sound like a lot. It does not have to feel overwhelming. I recomme

AI bookkeeping tools are moving quickly. They can read invoices. They can categorize transactions. They can match payments to bills. They can draft reconciliations and help organize the month-end close. That is good news for small business owners. Less data entry means more time for customers, sales, and growth. But there is an important question behind the convenience: Who is reviewing the work? I see AI as a helpful assistant. It can handle repetitive tasks and bring order

Tax paperwork can feel heavier than it needs to be. A lender may ask for proof that your taxes are current. A landlord may request tax compliance information before approving a commercial lease. A licensing agency may need confirmation that you have filed and paid your federal taxes. Until now, gathering that proof could mean searching through old notices, requesting transcripts, or making a call to the IRS. The IRS now offers a simpler option. As of August 2026, individuals

If you own an LLC, partnership, LLP, or LLLP, a new Fifth Circuit decision may affect how much of your business income is subject to self-employment tax. On August 12, 2026, the Fifth Circuit issued its revised opinion in K Alain, L.L.L.P. v. Commissioner. The court introduced a new way to evaluate whether a partner qualifies for the limited-partner exception under Internal Revenue Code Section 1402(a)(13). The key question is no longer only: Does this owner have limited liab

If you have been delaying an equipment purchase because bonus depreciation kept changing, you can breathe a little easier. The One Big Beautiful Bill Act (OBBBA) made 100% bonus depreciation permanent for qualifying property acquired and placed in service after January 19, 2025. The previous phase-down schedule is gone. That gives small business owners more room to plan. You do not have to rush a purchase simply because a temporary tax benefit may disappear next year. The rul

If your bookkeeping software bill looks different this month, you are not alone. QuickBooks Online increased prices for its Essentials, Plus, and Advanced plans effective August 1, 2026. The total increase since May has ranged from about 13% to 70%, depending on the plan and the earlier price used for comparison. Simple Start remained at $38 per month. The change does not mean you need to make a rushed decision. I recommend taking a calm, practical approach. First, confirm yo

Tax numbers can feel like a lot to hold in your head. I want to make them easier to use. The figures below are a practical reference for small business owners, entrepreneurs, and employers planning for tax year 2026. These are the numbers generally used for returns filed in 2027. The IRS released its 2026 inflation adjustments under the One Big Beautiful Bill. The update covers more than 60 tax provisions. Use this guide as a starting point. Your business structure, income, e

For years, many small-business owners assumed retirement benefits were too expensive or too complicated. That is changing. According to Gusto’s State of Retirement 2026 research, the share of small businesses offering an active retirement plan grew from about 19% in 2019 to 31% in 2026. An “active” plan is one where at least one employee is contributing. A major reason for this growth is the expanded tax support available through the SECURE 2.0 Act. These credits can reduce t

Year-end payroll does not need to feel overwhelming. A clear checklist can help you prepare accurate Forms W-2 and give your employees the information they need for tax filing. For tax year 2026, there is one important change to understand: Employers must separately report qualified overtime compensation on Form W-2, Box 12, using Code TT. This reporting was optional for 2025. It is required for 2026. I recommend reviewing your payroll setup now. That gives you time to confir

If you still mail your business tax returns, you are adding time and uncertainty to an already busy process. I understand why paper can feel familiar. You print the form, sign it, place it in an envelope, and send it off. Then you wait. You may check your mailbox. You may call the IRS. You may wonder whether your return arrived, whether it was entered correctly, or whether someone needs more information. E-filing removes much of that uncertainty. It gives you a faster process

September 15 is an important date for many small business owners. For individuals and pass-through business owners, it is the due date for the third 2026 estimated tax payment. It is also the extended federal filing deadline for many 2025 partnership and S corporation returns. That may sound like a lot at once. It does not have to be. I recommend treating the next three weeks as a simple countdown. Gather the right records. Review your income. Estimate the payment. Confirm an

Cash flow forecasting can sound complicated. It does not have to be. I use cash flow forecasts to help small-business owners see what is coming before it reaches the bank account. A simple forecast can show when customer payments may arrive, when bills are due, and whether tax payments will create a tight week. The goal is not perfect prediction. The goal is better visibility. With a clear process, you can plan the rest of 2026 with less stress and more confidence. Cash flow

Late August is a helpful time to pause and review your books. The year is more than halfway complete. Q4 is approaching. You still have time to correct small issues before they become year-end problems. I recommend a simple bookkeeping tune-up before September begins. You do not need to rebuild your entire system. You need a clear look at what is working, what needs attention, and what habits will make the rest of the year easier. This checklist focuses on four practical step

Bookkeeping is becoming more automated. That can be good news for a busy business owner. New tools from Intuit and Xero can help with routine tasks such as transaction matching, bank reconciliation, expense categorization, and financial questions. But automation does not remove the need for good judgment. I see these tools as helpful assistants. They can reduce repetitive work. They can help keep your books current. They can also bring possible errors to your attention. Still

If your business accepts payments through Venmo, PayPal, or another payment app, you may have heard about new backup withholding rules. The good news is simple. The IRS has finalized rules that align backup withholding for third-party network transactions with the current Form 1099-K reporting threshold. For most app-based sellers and gig workers, backup withholding generally does not begin unless both of these marks are exceeded: More than $20,000 in payments More than 200 t

Overtime can make a meaningful difference for employees and small business owners. Now, it may also create a new federal tax benefit. The One, Big, Beautiful Bill Act created a deduction for certain qualified overtime compensation. For tax year 2026, eligible taxpayers may deduct up to $12,500 of qualified overtime pay. The limit increases to $25,000 for married couples filing jointly. There is one important detail. For 2026, employers must identify qualified overtime compens