Editor’s Note
Last month a few of you wrote back with the same question, so this issue is built around it: why don't the estimated tax "quarters" line up with the actual calendar? It sounds like a small technicality. It is really one of the clearest examples of how timing, not just numbers, drives what you keep.
That is the theme this month. We are halfway through the year, which is the best seat in the house for tax planning. There is still plenty of runway to make real moves before December, and far less pressure than the fourth quarter scramble. The middle of the year is when the smartest adjustments happen quietly.
As always, this is written for both sides of my practice. Whether your income comes from equity or from a business you own, there is something here for you. No jargon, no noise, just what you need.
Matt Curtin, CPA
ON THE CALENDAR
Upcoming Dates to Know
September 15: Q3 Estimated Payment Due
This is the next estimated tax deadline, and the feature below explains why it covers a three month stretch rather than a clean quarter. If your income has been uneven this year, this is the payment to get right.
September 15: Extended Business Return Deadline.
If your partnership or S-Corp filed an extension back in March, this is the final due date. September always feels far away in July and then arrives overnight. If we have not started gathering your documents, now is the time.
Now Through Fall: Mid-Year Projection Window.
The single most useful thing you can do right now is run a real projection of where your year is landing. Every lever in this issue works better once you know your number.
MARKET MINUTE
What’s Happening and What It Means for You
Markets have pushed back into record territory this summer. The S&P 500 finished last week above 7,500 and the Dow closed above 53,000 for the first time, capping the strongest quarter since 2020. The renewed conflict with Iran and the resulting swings in oil prices have kept volatility elevated, and the AI and chip names that led the market wobbled in late June before recovering.
The other big story is that the market for new public offerings has come roaring back. SpaceX completed the largest public offering on record in June, a run of large debuts has followed, and acquisition activity has picked up alongside it. For most of you, the daily moves are noise. What matters is that an active market creates real planning windows, especially if any part of your wealth is tied to company stock. The next section is where that gets specific.
THE PLANNING ANGLE
Why Your Tax "Quarters" Aren't Really Quarters
Here is the answer to the question several of you asked.
The four estimated tax deadlines are April 15, June 15, September 15, and January 15. You would reasonably expect each one to cover three months. They do not. The first payment covers January through March, three months. The second covers only April and May, two months. The third covers June through August, three months. And the last covers September through December, a full four months.
So the "quarters" are really 3, 2, 3, and 4 months long. The dates are set by statute, with the first pinned to the April filing deadline, and the uneven spacing is a quirk of the law rather than anything logical about the calendar.
Why does this matter to you? Because most people take their expected tax bill and divide by four. If your income arrives evenly, that is fine. If it does not, dividing by four either hands the IRS an interest free loan early in the year or leaves you short and facing a penalty. The fix is matching your payments to when the income actually shows up, and there is a method built for exactly that. Here is how it plays out for each of you.
FOR EQUITY COMP PROFESSIONALS
Your Income Is Lumpy. Your Payments Can Be Too.
A vest or an exercise drops a large slug of income into one specific period. If your big RSU tranche landed this summer, it belongs in the September payment, not smeared evenly across a year where the first half was quieter. The annualized income installment method lets you pay tax in step with when you actually earned it, which can erase a penalty or free up cash you would otherwise send in too early.
There is a second lever that is even more useful right now, and it is about withholding. When your RSUs vest, most companies withhold federal tax at 22%. If you are in the 32%, 35%, or 37% bracket, that is not enough, and the gap becomes a surprise bill in April. Here is the part most people miss: withholding is treated by the IRS as paid evenly across the whole year, no matter when it actually leaves your paycheck. That means adjusting your W-4 now, in July, can cover a shortfall from a vest that already happened, as if you had been paying it in all along. There are still enough paychecks left in the year to make it painless. Wait until December and that door narrows fast.
Here is what that looks like in practice. Say a spring vest left you roughly $15,000 short for the year. You could send a large check with your September estimate and hope you sized it right, but the earlier periods would still carry an underpayment penalty because the money showed up late. Instead, raise your paycheck withholding across the paychecks you have left and let it add up to that $15,000. Because the IRS treats withholding as paid evenly all year, it is as if you had been current since January, and the penalty on those earlier periods simply disappears. Same dollars, better timing, cleaner result.
On the market front: new listings are unusually active, from SpaceX in June to a run of large debuts since, and acquisitions are picking up too. If you hold equity or options at a company that could go public or get acquired, the ninety or so days around a lockup expiration are some of the most consequential tax days of your life. Sequencing that sale against the rest of your income is where real money is saved or lost. If that is on your horizon, let's map it before the window opens, not after.
FOR ENTREPRENEURS
Uneven Revenue Deserves Uneven Payments
Most business owners set their estimated payments in April and never touch them again. In a year with steady revenue, that works. In a year with a strong quarter, a slow stretch, or a structural change, the autopilot number is usually wrong in one direction or the other.
The same annualized method equity earners use applies to you. If your revenue is seasonal or simply lumpy, you can pay based on what you have actually earned by each deadline instead of a flat guess. Pair that with the safe harbor rule, which keeps you penalty free as long as you pay in 90% of this year's tax or 100% of last year's (110% if your prior year AGI topped $150,000), and you have real control over both your cash flow and your risk.
Withholding is a quiet lever for you too. If you or your spouse also draw a W-2 paycheck anywhere, bumping that withholding now works the same magic: the IRS treats it as paid evenly all year, so it can shore up a shortfall your estimated payments missed.
And since we are still mid-year, this is the moment to make structural moves count. If a major equipment purchase is on the table, 100% bonus depreciation is back and permanent under the new law, which reshapes both your year end bill and the estimated payments between now and then. And if your business invests in developing products, software, or other domestic research, those costs are fully deductible again in the year you incur them, rather than stretched over five years the way they have been the last few filing seasons. For a research heavy year, that is a real swing. Moves like this land cleanly in July. They get frantic in December.
The bigger structural lever most owners underuse is a retirement plan. A SEP-IRA, a solo 401(k), or for the right profile a defined benefit plan can shelter far more than an IRA ever will, and for a profitable year that deduction moves real money off your tax bill. The catch is timing. Some of these have to be established before December 31 to count for this year, even if you fund them later, so the decision belongs on the summer calendar, not the year end one. If you have had a strong year and no plan in place, this is worth a conversation now while every option is still open.
QUICK HITS
A Few Other Things Worth Knowing
Trump Accounts are live. As of early July, the new tax advantaged accounts for children are open, with a one time $1,000 government seed for kids born between 2025 and 2028. If you have young children, or one on the way, this is worth a look.
High earners, check your 401(k) catch-up. Starting this year, if you earned more than $150,000 last year, your 401(k) catch-up contributions have to go in as Roth rather than pre-tax. It changes the math on your paycheck deferrals, so confirm your plan is set up the way you expect.
A Massachusetts note. For those of you in the Commonwealth, the state runs its own estimated payment schedule and its own 4% surtax on income above roughly one million dollars, indexed each year. In a big equity or sale year, the timing of that income matters at the state level too, not only federal. One more wrinkle worth flagging: Massachusetts does not automatically adopt every new federal deduction, so some of the newer breaks, like bonus depreciation, can look different or arrive later on your state return. Worth confirming both layers before you count on a number.
2026 numbers worth knowing. A few figures that shape planning this year, worth keeping somewhere handy:
401(k) employee contribution limit: $24,500, plus an $8,000 catch-up at age 50 and over
HSA contribution limit: $4,400 for self-only coverage, $8,750 for family coverage
Standard deduction: $32,200 for married couples filing jointly
Annual gift tax exclusion: $19,000 per recipient
Lifetime estate and gift exclusion: $15 million per person
FROM MY DESK
Let's Keep the Conversation Going
If anything here hits close to home, hit reply and tell me. Reader questions are exactly what shaped this issue, and they come straight to me. If you would rather reach me directly, you can always find me at kindledplanning.com.
Looking forward to being in your corner every month.
Matt Curtin, CPA
P.S. Know someone with equity compensation or a business who would find this useful? Forward it their way, and they can subscribe in a few seconds at brief.kindledplanning.com.