A football team that refuses to look at the scoreboard until the final whistle has already lost the game. It sounds obvious on a football field. Yet every July, I watch smart, driven business owners run their finances the exact same way. They wait until January to ask how the year actually went.
By then, the game is over. The score is locked in. And most of the plays that could have changed the outcome expired months earlier.
Today is July 3rd. That puts us almost exactly at halftime for the 2026 tax year. This is the moment to check the scoreboard, adjust the play calling, and make sure the second half doesn’t undo the good work you did in the first.
The Number Most Owners Never Look At
Here’s a question I ask every client this time of year. What is your actual year-to-date net profit, and what do you project by December 31st?
Most owners can tell me their revenue. Far fewer can tell me their profit. Even fewer have translated that profit into an estimated tax liability. That gap is where the surprises live.
I wrote about this exact blind spot in why your CPA can’t save you in January. A CPA who only sees your numbers after the year closes can only report history. They cannot change it. Mid-year is different. Mid-year, the second half of the year is still unwritten.
So pull your profit and loss statement. Compare it to your projection from January. If you’re running ahead of plan, that’s good news, but it also means your tax bill is likely bigger than you budgeted for. If you’re behind, you may have room to invest, hire, or accelerate expenses before the calendar turns again.
I saw this play out with a client who runs a small landscaping company. His January projection had him at $180,000 in net profit for the year. By late June, he was already tracking toward $240,000, mostly because two commercial contracts came in earlier than expected. Nobody warned him his estimated payments needed to grow along with that number. We caught it in a mid-year review, adjusted his September payment, and increased his retirement contribution to soak up part of the extra income. Without that check-in, he would have walked into January with a tax bill nobody budgeted for.
The Retirement Deadline Everyone Assumes Already Passed
Here’s one that surprises almost every business owner I talk to this time of year. If you filed an extension on your 2025 return, you may still be able to fund a SEP-IRA for the 2025 tax year.
Most people believe retirement contributions for a given tax year die on April 15th, right alongside the filing deadline. For a SEP-IRA, that’s simply not true. The contribution deadline follows your filing deadline, extensions included. If you extended your 2025 personal or business return, you generally have until October 15, 2026 to make that SEP-IRA contribution and have it count for 2025.
For 2025, the SEP-IRA contribution cap was the lesser of 25 percent of compensation or $70,000, with compensation capped at $350,000. That means a profitable year you already closed the books on might still hand you a five or six figure deduction, if you act before the extended deadline arrives.
I covered the mechanics of this account in detail in the SEP-IRA playbook, including who it fits best and where it falls short. Read that if this is new territory for you.
Here’s my honest take. This is one of the few places in the tax code where you get to look backward and still make a forward-looking move. Most deductions require action before December 31st. This one gives you a second chance. I would not waste it.
Why the Solo 401(k) Plays by Different Rules
If you also have a Solo 401(k), don’t assume the same flexibility applies. It doesn’t, and this trips up more owners than you’d expect.
Employee deferrals into a Solo 401(k) had to be made by December 31, 2025 to count for the 2025 tax year. That window closed six months ago. Extensions don’t reopen it. Only the employer profit-sharing portion of a Solo 401(k) follows the extended filing deadline, similar to a SEP-IRA.
I bring this up because I’ve seen owners assume their Solo 401(k) gives them the same October runway as a SEP-IRA. It doesn’t, not entirely. Knowing which piece of which account follows which deadline is exactly the kind of detail that separates a strategist from a form filler. This is also why I generally recommend deciding on your retirement structure well before year-end, not scrambling to figure it out during extension season.
September 15 Is Closer Than It Looks
While you’re thinking about last year, don’t lose sight of this year. Your third quarter estimated tax payment for 2026 is due September 15, 2026. That gives you roughly ten weeks from today.
If your income has grown since you set your estimates back in January, this is exactly the moment to recalculate. Underpaying now means a penalty later, calculated at the federal short-term rate plus three percentage points, compounding the longer it sits unpaid. It’s not catastrophic, but it’s completely avoidable, and avoidable penalties are my least favorite kind of expense.
If your income has fallen instead, recalculating might free up cash you didn’t realize you had. Either direction, guessing is expensive. Checking is free.
I dug deeper into the mechanics of quarterly payments in my article on Q2 estimated taxes, including how retirement contributions can directly shrink what you owe each quarter. The same logic applies heading into September. Every dollar you contribute to a deductible retirement account lowers your taxable income, which lowers your estimated payment, which keeps more cash in your business right now.
This, by the way, is usually the point in a client conversation where someone tells me they will deal with it later. Later is how a manageable adjustment turns into a January scramble. If any of this sounds like your current situation, a short mid-year review is a lot cheaper than a surprise bill next spring.
If You Filed an Extension, You’re on Borrowed Time
Millions of taxpayers file an extension every single year, and there’s nothing wrong with that. If you’re one of them, October 15, 2026 is your true deadline for filing your 2025 return. That date will arrive faster than you think, especially once September’s estimated payment and the usual fall business rush show up on the calendar at the same time.
An extension buys you time to file. It never bought you time to pay. If you owed money on April 15th and haven’t paid it yet, interest has been accruing every single day since then. Waiting until October doesn’t make that number smaller.
Use the months between now and October wisely. Get your bookkeeping finalized. Confirm whether that SEP-IRA contribution I mentioned earlier makes sense for your 2025 numbers. Then file with confidence instead of filing because the deadline forced your hand.
The owners who win at tax season aren’t the ones with the best CPA in April. They’re the ones who checked the scoreboard in July.
Bringing the Mid-Year Check Together
None of these three moves exists in isolation. Your year-to-date profit tells you how much cash flow you have. Your extended 2025 return tells you whether a SEP-IRA contribution still makes sense. Your September estimated payment tells you whether this year’s plan needs adjusting before it’s too late to matter.
Treat July like halftime, not like an afterthought squeezed between summer vacations. Pull your numbers. Compare them to your projections. Decide, deliberately, whether the second half of 2026 needs a different play than the first half did.
I’ve watched clients turn a routine mid-year check into a five figure tax savings, simply because we caught a retirement opportunity or an income shift three months before it would have been too late to act on it. That’s not magic. It’s timing, and timing is something you actually control.
The scoreboard is sitting right there, waiting for someone to check it before the clock runs out on the moves that still work.
I understand why this gets pushed aside. Summer is busy, invoices don’t pause for tax planning, and a spreadsheet review rarely feels urgent until it suddenly is. But the owners who consistently keep more of what they earn treat July the same way a good coach treats halftime. They review the film, they adjust the plan, and they walk back onto the field knowing exactly what needs to happen next. The rest of the field figures it out in January, usually the hard way.
Welcome to the New Age of Accounting. Let’s begin.
P.S. If you found this article helpful, you’ll love my new book S-Corp Mastery: How Smart Business Owners Maximize Tax Savings & Build a Lasting Legacy. It’s now live and available in a sleek, easy-to-read PDF version. Grab your copy here
Chris is the Managing Partner at Weston Tax Associates, a best-selling author, and a renowned tax strategist. With over 20 years of expertise in tax and corporate finance, he simplifies complex tax concepts into actionable strategies that drive business growth. Originally from Sweden, he now lives in Florida with his wife and two sons.
