Tax Planning · Jacksonville, FL
7 Tax Changes Jacksonville Small Business Owners Need to Act On in 2026
By Remi Matteo · Matteo Bookkeeping · Jacksonville, FL
TL;DR
- Several deduction rules, write-off limits, and reporting thresholds changed for 2026.
- Most small business owners won't find out until their tax bill is higher than expected.
- Knowing what changed lets you plan now instead of catching up later.
Tax law in 2026 looks different enough from prior years that small business owners in Jacksonville and Duval County who are not paying attention will feel it at filing time. Most will not find out until the bill is higher than expected. Here are the seven areas you need to have on your radar right now.
Bonus depreciation has dropped significantly
A few years ago you could write off 100% of a piece of equipment the year you bought it. That percentage has been phasing down under the Tax Cuts and Jobs Act and is now a fraction of what it was in 2021. If you are planning to buy a truck, trailer, or expensive tools this year, how you structure that purchase matters more than it used to. Timing and method of depreciation can swing your tax bill by thousands of dollars.
The 20% pass-through deduction is easy to miss
If you operate as a sole proprietor, LLC, or S-Corp, you may qualify for a deduction on up to 20% of your qualified business income. There are income limits, phase-outs, and W-2 wage tests that affect whether you get the full deduction. Most small business owners either do not know they qualify or do not have their books set up in a way that supports claiming it correctly.
Underpaying quarterly taxes is getting more expensive
If you are self-employed or taking distributions from an S-Corp, you owe estimated taxes four times a year. Penalties for underpayment have increased. The safe harbor rules can protect you from a penalty even if you end up owing more at filing, but only if you are paying the right amount each quarter. That calculation requires knowing what you actually made, which requires current, accurate books.
Digital payment reporting is catching small businesses off guard
If clients pay you via Venmo, PayPal, Cash App, or similar platforms, you may receive a 1099-K for those payments. Reporting thresholds for these platforms have changed, and many Jacksonville small businesses are seeing 1099-Ks for the first time. That income needs to match what you reported. If your books are not tracking digital payments separately, you are creating a mismatch problem that is tedious to explain later.
Vehicle and mileage deductions still require documentation
The IRS standard mileage rate changes every year, and choosing between actual vehicle expenses and the standard mileage rate can produce very different deduction amounts depending on your vehicle and how much you drive for work. Either method requires contemporaneous records. A mileage log you reconstruct in April is not documentation. Most small business owners skip this entirely and leave a real deduction sitting on the table.
Retirement contributions are one of the most underused deductions
If you are a solo operator or small business owner, a SEP IRA or Solo 401(k) lets you deduct a significant chunk of your income before you pay tax on it. Contributions can be made up until your tax filing deadline and still count for the prior year. Most trades owners skip this entirely because no one brought it up. It is one of the cleanest legal tax reductions available and requires no complex restructuring to use.
Your entity structure might be costing you real money
Operating as a sole proprietor when your net profit crosses a certain threshold means you are paying self-employment tax on income an S-Corp owner would not. The crossover point depends on your revenue, your expenses, and what a reasonable salary looks like for your type of work. It is not the right move for every business, but if you have never looked at the math, you might be paying more than you should every single year.
Free Resource
2026 Small Business Tax Planning Checklist
A one-page checklist of what every Jacksonville small business should have in place before tax season. Print it, go through it, and find the gaps.
Get the ChecklistWhat to do with this information
These are not things that resolve themselves. Every one of them requires either a decision, a record, or a conversation with someone who knows your numbers. If you are not sure where you stand on any of them, a 15-minute strategy session is the fastest way to find out. No prep required. Just show up and we will go through what applies to your specific situation.
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