June 23rd, 2026
By Margaret Allen
PRESENTED BY Crowne Point Tax & Wealth Counsel
THIS WEEK
The Quiet Deadline That Just Cost the Other 30% of Freelancers
The headline tax deadline most people circle is April. The expensive one was this week. Second-quarter estimated tax payments were due June 16, and the IRS does not send a reminder — it sends a penalty, currently set at 6% annualized on whatever you underpaid this quarter.
For a freelancer or small business owner who owes $5,000 quarterly and misses the date by a month, that is roughly $25 quietly added to next April’s bill — for one missed week. The wider point is that estimated taxes are how the IRS forces self-employed income to look like W-2 income. Salaried employees pay as they earn. Everyone else has to send the payment themselves, four times a year, with no email reminder.
The trap most freelancers fall into is treating April 15 as “the” tax deadline. It is not. It is the date to settle up — but the IRS expects taxes to be paid throughout the year. Miss a quarterly payment, and the underpayment penalty starts accruing daily from that day forward, no matter how big or small your final refund ends up being.
That is the version of a money mistake that is easy to make and easy to avoid: the deadline passes in silence, but the interest charges show up at filing time.
The good news is that the rule for staying penalty-free is simple. If you pay at least 100% of last year’s total tax — 110% if your AGI was over $150,000 — across four equal installments, you generally avoid the underpayment penalty regardless of what this year looks like. Set it up once, and the worry disappears.
Before next quarter’s deadline on September 15, check three things:
Do you owe this year? If you expect to owe $1,000 or more in federal tax after withholding, the IRS expects quarterly payments. The threshold has not changed in years and catches new self-employed earners off guard.
Are your installments equal? The IRS calculates penalties quarter-by-quarter. Pay $0 in Q1 and Q2 and overpay in Q4, and you still owe penalty on the early underpayments — even if your year-end total is perfect.
Is your withholding off? If you also have W-2 income, increasing withholding mid-year is treated as if it had been paid evenly through the year — a clean way to make up a missed quarterly payment without the penalty math.
A missed estimated payment is one of the rare money mistakes the IRS lets you fully fix the day you catch it. Pay it now, eat the small interest, and move on.
ALSO THIS WEEK
Why Your Savings Rate May Get Better Before It Gets Worse
For the first time in a year, the Fed conversation has shifted from when the next cut arrives to whether the next move is a hike. Kevin Warsh chaired his first rate-setting meeting as Chair this week, with market odds overwhelmingly favoring a hold at 3.50%–3.75% — but a meaningful share of traders now expect at least a quarter-point increase by October.
For savers, that is a quiet good story. After months of high-yield accounts drifting downward, the bias is starting to flip. Top accounts have actually edged up this month: Pibank now leads NerdWallet’s list at 4.40% APY, with Vio Bank, Climate First, and Peak Bank tied at 4.01%.
The good news is that the gap between a great account and a forgettable one is still wide. The national savings average is still stuck at about 0.38%, while top accounts pay more than ten times that. A short-term CD at 4.10% from a major issuer locks in today’s yield through next year — useful if you believe the next move is up but not certain.
If you have cash sitting at a big-four bank earning under 1%, the gap to a top high-yield account is now over 350 basis points. On $25,000, that is roughly $900 a year you are voluntarily skipping. The macro picture is uncertain, but the personal one is not: an idle dollar in a 0.38% account is a tax you are paying to your own bank.
The move this week is the same as last month: check your current APY, compare against today’s top high-yield savings accounts, and decide whether convenience is still worth what it is costing you.
QUICK HIT
The 110% Rule Most High-Earners Forget
If your adjusted gross income on last year’s return was over $150,000, the IRS bumps the safe-harbor estimated tax rule from 100% to 110%.
Translation: to avoid a penalty without doing real math, you need to pay at least 110% of last year’s total federal tax across four equal quarterly payments. Miss this by a small margin and the 6% annualized interest penalty starts ticking from the missed quarter forward.
This is a quirk that punishes people who had a great year. A bonus or a one-off windfall last year likely pushed your AGI over the threshold, even if this year’s income is back to normal. The IRS does not care about that — it cares about last year’s total tax.
The fix is mechanical: pull last year’s Form 1040 line 24, multiply by 1.1, divide by four, and set up the four payments as automatic withdrawals on the IRS Direct Pay page. Done in ten minutes, peace of mind for a year.
THE BOTTOM LINE
Three Mid-Year Money Checks Before the Quarter Closes
The middle of June is the cleanest checkpoint of the year — half the calendar gone, far enough from January to know whether the goals stuck, far enough from December to fix what didn’t.
Start with tax. If you owe quarterly tax, this week was the deadline; if you don’t, take 60 seconds to confirm your W-2 withholding has not drifted off-target since January. A missed quarterly payment is cheap to fix today and expensive to ignore until April.
Then check your cash. With Fed direction uncertain, idle savings is the single most-fixable money leak in most households. If your savings APY is below 3.5%, the gap to a top high-yield account is real money, not a rounding error.
Last, the spending the budget stopped tracking. Half the year is enough to catch the subscription, the auto-renew, and the convenience charge that quietly cost more than the line item suggests.
None of this is glamorous, but the people who keep more of their money tend to do the boring check now rather than the urgent fix later. The mid-year reset is not about doing more — it is about catching the few things that compound if ignored.
Pay the deadline. Check the rate. Cut the leak. That is how more of your year stays yours.
That’s the week. See you next issue.
Margaret Allen
Editor-in-Chief
Smrtt Money
P.S. Tax season doesn't wait — and neither do the rules. The sooner you have a strategy in place, the more you keep. Book your free 30-minute session here.