Author: Philip DiMartino

  • How much can I give my kids before the IRS cares?

    How much can I give my kids before the IRS cares?

    Americans are sitting on an estimated $124 trillion they plan to leave behind someday.

    A lot of families are starting to ask whether to hand some of it over now instead of waiting.

    Good news: you can give away more than you probably think without filing a thing.

    What this means for you

    • Give up to $19,000 per person in 2026 with no form to file and no tax owed.
    • Married couples can double that to $38,000 per recipient, no filing required.
    • Paying tuition or medical bills directly to the institution skips the limit entirely.

    How much can I gift my kids tax-free?

    The IRS calls this the annual gift tax exclusion.

    For 2026, it’s $19,000 per recipient, per giver, every year.

    Give your son $19,000 and your daughter $19,000 in the same year, and neither gift touches anyone’s taxes.

    Married couples can combine exclusions and give $38,000 to one person without filing anything.

    Go over that number and you don’t automatically owe tax. You just report it on a gift tax return, which quietly reduces your much larger lifetime exemption instead of triggering a bill today.

    What do people get wrong about gifting?

    1. Assuming any gift over a small amount means a tax bill. It almost never does, since you’d have to burn through your full lifetime exemption first.
    2. Treating gifting as all or nothing. You can give a little now under the exclusion and still leave the rest inside your estate plan.
    3. Gifting cash when stock would do more. Handing appreciated stock to someone in a lower tax bracket than you can sidestep capital gains tax you’d otherwise owe.

    If you’re not sure how a gift this size fits your overall return, our tax planning team can run the numbers with you before you sign anything.

    What are the 2026 gift limits?

    Gift type 2026 limit Filing required?
    Cash or assets, single giver $19,000 per recipient No, if under the limit
    Cash or assets, married couple $38,000 per recipient No, if under the limit
    Tuition or medical bills, paid directly to the institution No limit No
    Gift above the annual exclusion Any amount Yes, gift tax return, reduces lifetime exemption

    What should you actually do?

    1. Cover your own expenses first. Make sure your retirement and long-term care costs are funded before you give anything away.
    2. Use the $19,000 exclusion for straightforward cash or account gifts to kids, grandkids or anyone else.
    3. Pay tuition or medical bills directly to the school or hospital when you can, since that money skips the limit with zero paperwork.
    4. Hand over appreciated stock, not cash, when the recipient sits in a lower tax bracket than you.
    5. Check the five-year Medicaid look-back before gifting anything if long-term care might be in your future.

    Who doesn’t need to worry about this?

    If you don’t have money beyond what you’ll need for your own retirement, none of this applies yet. Fund your own future first.

    If you might need Medicaid to help pay for long-term care within the next five years, gifting now can disqualify you from benefits later. Talk to an elder law attorney before you give anything away.

    And if your estate is nowhere near the lifetime exemption, you don’t need to track any of this closely. The annual exclusion is a convenience here, not a requirement.

    Philip’s take

    I rank this the same way every time someone asks.

    Your own security comes first, full stop. After that, the $19,000 annual exclusion is the easiest move on the table, since it costs you nothing to use.

    Direct tuition and medical payments come next, because they skip the limit with no paperwork at all.

    Appreciated stock gifts rank below that, useful but situational. A trust with strings attached only makes sense if you want control over how the money gets used after it leaves your hands. Our tax education hub has more on how gifts fit into a broader estate plan.

    Giving while you’re alive can be smart, generous and tax efficient, all at once.

    It just can’t come before your own security.

  • Florida boat sales tax: the $18,000 cap, repairs and the 6-month rule

    Florida boat sales tax: the $18,000 cap, repairs and the 6-month rule

    Florida caps the sales tax on a boat. Whether you buy a center console or a 100-foot motor yacht, the most you pay on the purchase is $18,000. Repairs have a cap of their own, and boats bought out of state or by nonresidents follow separate rules.

    The cap is generous, but the rules around it are strict, and most expensive mistakes happen before the boat is delivered. Here is how it works in 2026.

    What this means for you

    • Florida sales or use tax on the purchase of a boat is capped at $18,000, including any county surtax.
    • Each repair done in Florida has its own cap of $60,000 in tax.
    • A boat bought out of state and brought to Florida within six months can owe Florida use tax, with credit for sales tax already paid to another state.
    • Nonresidents can buy in Florida without paying Florida tax only if the boat leaves on time and the paperwork is in order.
    • Buying from a private seller or through an LLC does not avoid the tax.

    How the $18,000 cap works

    Florida’s sales tax rate is 6%, plus a discretionary sales surtax set by each county. On the sale of a boat, the surtax applies only to the first $5,000 of the price, and the total tax on the sale or use of a boat cannot exceed $18,000, surtax included.

    At 6%, the state tax alone reaches the cap at a price of $300,000. Above that, the tax stays at $18,000.

    Purchase price Tax at 6% plus a 1% county surtax Tax you pay
    $80,000 $4,800 + $50 $4,850
    $150,000 $9,000 + $50 $9,050
    $250,000 $15,000 + $50 $15,050
    $400,000 $24,000 + $50 $18,000 (capped)
    $2,000,000 $120,000 + $50 $18,000 (capped)

    Surtax rates differ by county, so your exact figure below the cap depends on where the boat is delivered or registered.

    Trade-ins. When you trade in a boat to a registered dealer or broker as part of the same purchase, tax is calculated on the price after the trade-in allowance.

    Private sales. Buying from a private seller is still taxable. The buyer pays the use tax when titling and registering the boat with the county tax collector.

    Repairs have their own $60,000 cap

    Repairs to a boat in Florida, including parts and labor, are generally taxable, and the tax on each repair is capped at $60,000. At 6%, that cap is reached at $1 million of work.

    The cap applies per repair, not per year or per boat. For a large refit, how the work is scoped and invoiced affects the tax you pay, and you need documents that support it if the Department of Revenue asks later.

    Bought your boat outside Florida?

    Florida use tax applies to a boat bought elsewhere and brought into the state for use here. The key is timing.

    • Used outside Florida for six months or more first: Florida generally presumes the boat was not bought for use in Florida, and use tax does not apply.
    • Brought in within six months of purchase: Florida use tax can apply, up to the same $18,000 cap.
    • Tax already paid to another state is credited against Florida use tax, so you only owe any difference.

    Some boats, such as those that require a saltwater fishing license, follow a different schedule, so check the rules for your boat before relying on the six-month presumption.

    Nonresidents buying in Florida

    A nonresident can buy a boat from a Florida dealer or broker without paying Florida tax, but only by meeting the removal rules.

    Boat size What the rule requires
    Under 5 net tons Remove the boat from Florida within 10 days of purchase, or place it directly into a repair facility under its own deadline
    5 net tons or more A Department of Revenue decal allows the boat to stay 90 days. An extension decal, obtained within 60 days of purchase for $425, adds 90 more days, for 180 in total

    The dealer files the buyer’s affidavit with the Department of Revenue within 30 days of the sale. The buyer must then prove the boat left Florida and register it in another state or country within 90 days. If the boat stays too long or the proof is missing, Florida use tax becomes due, along with penalties.

    Charters change the picture

    Chartering a boat in Florida is not automatically taxable or exempt. It depends on how the charter is structured.

    • A bareboat charter, where the customer takes control of the boat, is generally taxable as a rental.
    • A charter where the owner supplies the captain and crew and keeps control of the vessel can be treated differently, and some fishing charters and transportation-only trips are exempt.
    • Party boats and head boats that charge per person are generally taxable as admissions.

    If you plan to charter your boat, the charter agreement and how it is priced matter as much as the income itself. Charters also raise federal income tax questions, which we cover on our marine and yacht page.

    Common questions

    Does buying the boat through an LLC avoid Florida sales tax?

    No. An LLC can be useful for liability and privacy, but the purchase is taxed the same way. The LLC also needs its own records to be worth having.

    I live in Florida and bought a boat in a state with no sales tax. What do I owe?

    If the boat comes to Florida within six months of purchase, you will generally owe Florida use tax, up to $18,000, because there is no tax from the other state to credit.

    Is the sales tax on a boat deductible on my federal return?

    If you itemize, Florida residents can deduct sales tax instead of state income tax, and the tax on a boat can generally be included. The deduction is subject to the federal limit on state and local taxes, so whether it helps depends on the rest of your return.

    Does a broker or dealer collect the tax?

    Yes. Boat brokers in Florida must register as dealers and collect the tax on sales they handle. On a private sale, the buyer pays it at the tax collector’s office.

    Philip’s take

    The $18,000 cap gets all the attention, but the expensive problems come from timing and paperwork: a boat that arrives in Florida a few weeks too early, a nonresident decal that lapses, or a refit invoiced in a way that cannot support the repair cap. All of those are cheap to get right before delivery and expensive to fix afterward.

    If you are buying, selling or chartering a boat, Get My CPA Quote for a fixed fee in writing, or Book 30 Minutes With Philip. You can also see how we work with yacht owners and marine businesses.

    Sources: Florida Statutes sections 212.05, 212.06 and 212.09; Florida Department of Revenue brochures GT-800005 and GT-800006 and Tax Information Publications 10A01-07, 15A01-07 and 24A01-10R; Florida Administrative Code Rule 12A-1.071. This article is general information, not advice for your situation. How the rules apply depends on the details of your purchase, your residency and how the boat is used.

  • Your 1099-K doesn’t match your income. Here’s what to do

    Your 1099-K doesn’t match your income. Here’s what to do

    Tax forms from platforms and brands rarely add up to what you actually earned. The total on your 1099s can be thousands of dollars more than your real income, and every so often it comes in lower.

    Both cases are fixable. What matters is that your return tells the same story as your records, because the IRS compares the forms it receives against what you file.

    What this means for you

    • A 1099-K shows the gross amount that went through the platform, before refunds, fees or anything else comes out.
    • The same brand payment can show up on two forms. Report it once and keep the proof.
    • Getting no form does not make income tax-free. Income is taxable whether or not a form shows up.
    • Reconcile your forms to your deposits before you file, not after a notice arrives.

    Why your 1099-K doesn’t match your income

    A Form 1099-K comes from a payment platform or processor, such as a payment app, a checkout processor for your merch or digital products, or a marketplace. It reports the gross amount of payments you received through it. The IRS instructions define that gross amount as the total without regard to adjustments for credits, discounts, fees, refunds or shipping.

    That is why the number is often higher than what reached your bank account. Your income for tax purposes still starts from that gross figure. The refunds and fees are then subtracted on the return rather than left out.

    A Form 1099-NEC is different. It comes from a brand or agency that paid you directly for your services, usually by bank transfer or check.

    Who has to send you one in 2026

    Form Who sends it Federal reporting threshold
    1099-K Payment apps, processors, marketplaces More than $20,000 and more than 200 transactions in the year
    1099-NEC Brands and agencies paying you directly $2,000 or more for payments made in 2026

    The 1099-K threshold went back to $20,000 and 200 transactions under the One Big Beautiful Bill Act, replacing the much lower thresholds that had been scheduled. That does not change what is taxable. A platform can still send you a 1099-K below the threshold, and some states have lower thresholds of their own.

    What people get wrong

    1. They report the 1099-K as their profit. It is a gross figure. Refunds, chargebacks and platform fees belong on the return too. Leave them off and you overpay.
    2. They add up every form and report the total. If a brand paid you through a payment app and also sent a 1099-NEC, the same money is on two forms. IRS instructions say card and payment app transactions belong only on the 1099-K, not on a 1099-NEC, but some brands send both anyway.
    3. They only report what shows up on a form. Brand deals under the reporting threshold, direct payments and small platform payouts are all still income. The form is a reporting requirement for the payer, not a test of whether you owe tax.
    4. They run personal money through a business account. Friends paying you back for a trip as “goods and services,” or selling your old camera on the same account, can land on a 1099-K and look like business income.

    A worked example

    Say you are a creator whose forms for the year look like this:

    • A 1099-K from your merch and digital product checkout: $28,400. That total includes $900 you refunded and $1,100 in processing fees.
    • A 1099-K from a payment app: $14,000. That includes a $6,000 payment from Brand A and $1,200 friends sent you for a shared trip.
    • A 1099-NEC from Brand A: $6,000, the same payment already on the payment app form.
    • A 1099-NEC from Brand B, paid by bank transfer: $9,000.
    Item Amount
    Total of all forms $57,400
    Less: Brand A payment counted twice ($6,000)
    Less: friends reimbursing a trip, not income ($1,200)
    Business gross receipts $50,200
    Less: refunds (returns and allowances) ($900)
    Less: processing fees (an expense) ($1,100)
    Before your other business expenses $48,200

    Adding up every form would overstate income by $9,200 before any other deductions. For someone paying self-employment tax plus federal income tax, that difference is real money.

    How to fix a 1099-K that is wrong or double counted

    1. Pull every form and every deposit. List each 1099-K and 1099-NEC next to your bank and platform payout records for the same year.
    2. Match each brand payment to one form. Where a payment sits on both a 1099-K and a 1099-NEC, keep the invoice, the payment record and both forms together.
    3. Ask for a correction. The contact information for whoever issued the form is in its upper left corner. Ask a brand to void a 1099-NEC for a payment it made through a payment app, and ask a platform to correct a 1099-K that includes personal transfers.
    4. Don’t wait on a corrected form to file. The IRS says to file on time and correct the error on your return. Amounts that were never income, like a friend paying you back, are reported and then backed out on Schedule 1 so they net to zero.
    5. Report business income on Schedule C. Gross receipts go on line 1, refunds on line 2 and platform fees on line 10. Your records should show exactly how the forms tie to those numbers.
    6. Separate accounts going forward. A dedicated business account and a business profile on each payment app keep personal money off your 1099-K in the first place.

    If you skip the reconciliation, the usual result is an IRS notice called a CP2000, proposing tax on the difference between your forms and your return. It is answerable with records, but it is much easier to never get one.

    Who this does not apply to

    • Creators paid entirely through one platform that sends a single, accurate form, with no refunds or fees to account for.
    • Payments you received as an employee on a W-2, which follow different rules.
    • Gifted products and free trips, which do not usually appear on a 1099-K but can still be taxable. That is its own topic.

    Common questions

    I didn’t get a 1099-K this year. Do I still report that income?

    Yes. The IRS says plainly that income is taxable whether or not you receive the form. The higher threshold means fewer forms, not less income to report.

    My 1099-K includes personal payments. Do I pay tax on them?

    No, as long as they really are personal, like a friend repaying you for dinner or a shared trip. You report the amount and back it out so it nets to zero, and you keep records showing what it was. Selling a personal item at a loss is handled the same way. The loss is not deductible, but it is not income either.

    A brand sent me a 1099-NEC and I was also paid through a payment app. Which one is right?

    The payment belongs on the 1099-K. Report the income once, ask the brand to correct its form, and keep the documents together in case the IRS asks.

    Does Florida care about any of this?

    Florida has no personal income tax, so this is a federal issue for Florida creators. If you live in another state, your state may have its own, lower 1099-K threshold.

    Philip’s take

    The biggest mistake here is doing the math in the wrong direction. Creators often start from what landed in the bank and hope it lines up with the forms. It works better to start from the forms, then show each step down to your real income. When you do that before you file, a mismatch is a line on a worksheet. When you do it after a notice, it is a letter with a deadline.

    Once your income is steady, it is also worth seeing whether an S corp election makes sense for you, or run your numbers in our S corp calculator for creators.

    If you want this done for your own forms, Get My CPA Quote for a fixed fee in writing, or Book 30 Minutes With Philip. You can also see how we work with content creators.

    This article is general information, not advice for your situation. How a specific payment should be reported depends on what it was for and how it was paid.

  • S corp election for content creators: when it actually pays

    S corp election for content creators: when it actually pays

    Once creator income gets steady, someone will tell you to become an S corp. The pitch is simple: pay yourself a salary, take the rest as profit, and skip self-employment tax on that profit.

    The pitch is not wrong, but it leaves things out. The election also shrinks one of your deductions, turns you into an employer, and adds a second tax return. Here is the full math using 2026 numbers, including the income tax effect that usually gets left out.

    What this means for you

    • An S corp can lower your total tax once profit is steady, usually somewhere above $80,000 to $100,000 a year as a rough rule of thumb.
    • The payroll tax you save is not the same as what you keep. Part of it comes back as higher income tax.
    • You will be running payroll for yourself, on a schedule, with the filings that come with it.
    • Brand deal income has its own rules for the 20% business income deduction once your income is high enough.

    What an S corp election actually changes

    As a sole proprietor or single-member LLC, your net profit is subject to self-employment tax: 15.3 percent on 92.35 percent of it, with the 12.4 percent Social Security portion capped at $184,500 of earnings in 2026. Nobody withholds it, so paying it is on you.

    With an S corp, the business pays you a salary through payroll. Social Security and Medicare apply to that salary the same way they would for any employee, split between you and the company. Whatever profit is left after your salary passes through to your personal return without self-employment tax. That gap is where the savings come from.

    The trade-off is that you become an employer. That means regular payroll runs, W-2s, federal payroll filings, federal and Florida unemployment tax, and a separate Form 1120-S every March.

    What people get wrong

    1. They count only the payroll tax savings. An S corp salary reduces your qualified business income, which shrinks your 20% deduction. You also lose the deduction for half of self-employment tax. Both push income tax up.
    2. They set the salary too low. The IRS expects reasonable pay for the work you do before you take profit out. There is no safe percentage. Paying yourself $15,000 on $200,000 of profit is the kind of pattern that draws scrutiny, and when distributions are reclassified as wages, back payroll taxes and penalties follow.
    3. They elect in a spike year. One viral quarter is not steady income. If profit falls back, you are left running payroll on a business that no longer needs it, and after revoking the election you generally cannot elect again for five years without IRS consent.
    4. They miss how brand deals are treated. Fees for endorsing products, licensing your name or likeness, and paid appearances are specified service income under the qualified business income rules. Below $201,750 of taxable income for single filers, or $403,500 joint, that does not matter. Above it, the deduction on that income phases out, and if those fees are 10 percent or more of your gross receipts the whole business can be treated the same way. Above the threshold the deduction is also limited by W-2 wages paid, which is one place an S corp salary helps.
    5. They pay health insurance the wrong way. For an owner of more than 2 percent, premiums the company pays or reimburses go on your W-2 to stay deductible. Paid from a personal account with nothing run through the company, the deduction is generally lost.
    6. They treat the company account as their own. Platform payouts, brand payments and merch revenue belong to the business. Personal spending from that account turns into distributions or wages you did not plan for, and it makes the books hard to defend.

    The numbers

    One creator with $120,000 of profit, filing single in Florida for 2026 with the standard deduction and no other income. In the S corp version they pay themselves a $60,000 salary. Figures are rounded to the dollar.

    Sole proprietor S corp, $60,000 salary
    Self-employment tax, or payroll taxes including federal and Florida unemployment tax $16,955 $9,411
    Federal income tax $11,506 $14,081
    Total $28,461 $23,492
    Difference before payroll and tax prep costs $4,969 less

    The S corp saves $7,544 in payroll taxes, and $2,575 of that comes back as federal income tax. Subtract what you pay to run payroll and file a corporate return, and the real savings are smaller again. At lower profit, or with a higher salary, they can get close to zero.

    The steps

    1. Confirm the profit is steady. Look at the last twelve months and what is already contracted for the next six, not your best quarter.
    2. Form an entity if you do not have one. A sole proprietor cannot elect S corp status directly. Most creators form a Florida LLC through Sunbiz.
    3. Set a salary you can defend. Base it on what the work would cost to hire out, and write down how you got there.
    4. File Form 2553 on time. It is due within two months and fifteen days of the start of the tax year the election applies to. For a business that already exists on January 1, that is March 15.
    5. Set up payroll before the first payday. That includes federal payroll filings and a Florida reemployment tax account.
    6. Separate the money. A business bank account, reconciled monthly, with platform payouts matched to your 1099s.
    7. Plan distributions and estimates together. Salary withholding covers part of your tax. Profit that passes through may still need quarterly estimated payments.

    Who this does not apply to

    • Creators whose profit is well under the $80,000 to $100,000 range, where payroll and the extra return take a large share of the savings.
    • Anyone whose big year came from one campaign or one viral moment.
    • Creators living outside Florida, where state tax can change the result. The federal math above still applies, but your state has to be part of the calculation.

    Common questions

    Do I need an LLC before I can be an S corp?

    You need an entity. Most creators form a Florida LLC and then file Form 2553 with the IRS. The LLC stays an LLC under Florida law and is taxed as an S corp federally.

    How much salary should I pay myself?

    Enough to be defensible as pay for the work you actually do. The IRS looks at factors like your role, time spent, what comparable work costs, and what the business earns. There is no fixed percentage, and half of profit is not a rule.

    Is it too late to elect for this year?

    For a business that existed on January 1, the deadline was March 15. If you are forming a new LLC now, its first tax year starts on the day it is formed, so the two months and fifteen days run from that date. If a deadline has passed, late election relief is available when you intended to be an S corp from the start, reported consistently with that, and file within three years and 75 days with a reasonable cause statement. A late election also means no payroll was run for those months, so planning for the next start date is often cleaner.

    Does Florida tax my S corp?

    Florida has no personal income tax, and an S corp generally does not owe Florida corporate income tax unless it has built-in gains or excess passive income, which is rare for a creator business. Your company will owe Florida reemployment tax on the first $7,000 of your wages each year. New employers start at 2.7 percent, which is $189, and the rate is recalculated after the first ten quarters.

    Run your own numbers. Our S corp calculator for content creators shows the payroll tax you save, the income tax that comes back and what is left at your profit, using 2026 rates.

    Philip’s take

    The S corp is a good tool for the right creator in the right year, and a costly habit for everyone else. The question is not whether it saves payroll tax. At a sensible salary it usually does. The question is whether it saves more than it costs once the income tax, the payroll and the second return are counted, and whether your income will still be there next year to justify it.

    If you want your own numbers instead of an example, Get My CPA Quote for a fixed fee in writing, or Book 30 Minutes With Philip. You can also see how we work with content creators.

    This article is general information, not advice for your situation. The right salary and the right year to elect depend on your actual numbers.

  • The tax penalty that hits you even if you pay in full

    The tax penalty that hits you even if you pay in full

    The IRS does not wait until April to see if you paid enough. It checks four times a year, and it can charge a penalty for any quarter where you came up short.

    Paying your full tax bill by December 31 does not undo that. The shortfall from June already happened, and the penalty for it does not disappear just because you caught up later.

    What this means for you

    • Missing one estimated tax deadline creates a penalty for that quarter, even if you pay in full by December.
    • Freelance, rental, side business, investment, and consulting income with no withholding usually means you owe estimated payments each quarter.
    • There is a safe harbor that protects you even in a big year, and it is based on last year’s return, a number you already have.
    • Set calendar reminders for January 15, April 15, June 15, and September 15 right now.

    What are estimated taxes, actually?

    Most employees never think about this because their employer sends tax money to the IRS out of every paycheck. That is withholding, and it happens automatically.

    Estimated taxes exist for income where nobody is withholding anything on your behalf.

    That includes freelance or contract income, rental income, side business profit, investment gains, and consulting fees. If any of that applies to you, the IRS expects you to send in your own payments, four times a year, roughly matching what you earned in that period.

    What people get wrong

    1. They think a year end catch-up payment fixes everything. It does not. The underpayment penalty is charged per quarter, so a late payment in December does not erase a penalty from a quarter you missed in June.
    2. They assume any withholding at all means they are covered. A part-time job with a W-2 does not offset a large rental profit or a big consulting invoice if nobody is withholding tax on that side income.
    3. They wait until they see the total tax bill at filing time. By then, three or four quarters have already passed, and each one is judged on its own.

    The numbers

    These are the four payments and the dates they fall due. The periods are not equal lengths, which catches people out. Missing any one of them can trigger a penalty tied to that specific period, not the year as a whole.

    Payment Covers income earned Due date
    1st payment January to March April 15
    2nd payment April and May June 15
    3rd payment June to August September 15
    4th payment September to December January 15 of the following year

    Note the last one. The payment that closes out a tax year is not due until the middle of January in the next one, which is why January 15 shows up on a calendar of reminders alongside the other three.

    The shortcut most people miss

    You do not actually have to predict this year correctly. There is a safe harbor, and if you land inside it you are generally protected from the underpayment penalty even if the year turns out much bigger than you expected.

    You are inside it if your payments across those four dates add up to the smaller of these two amounts:

    • 90 percent of this year’s total tax. Accurate, but it requires forecasting a year that has not finished yet.
    • 100 percent of last year’s total tax, or 110 percent if your adjusted gross income last year was above $150,000, or above $75,000 if you file married filing separately.

    The second one is the useful one, because it is a number that already exists. One clarification that trips people up: it means the total tax line on last year’s return, not the check you wrote in April. Those are two different figures, and the one you want is usually much larger.

    Take that total, apply 100 or 110 percent depending on which side of the income threshold you were on, divide by four, and pay that on each date. A consultant who lands an unusually large project in August is then not punished for failing to see it coming.

    The steps

    1. Set a calendar reminder today for January 15, April 15, June 15, and September 15. These repeat every year.
    2. List every income source with no withholding: freelance work, rental income, side business profit, investment gains, consulting fees.
    3. Pull last year’s return and find the total tax line. That is your safe harbor number. Divide it by four.
    4. Pay that amount on each of the four dates, and keep a record of the date and amount in case a period is ever questioned.
    5. If your income changes a lot during the year, call your preparer mid-year rather than waiting until filing season to adjust.

    Who this does not apply to

    If you are a W-2 employee with no significant outside income, your employer’s withholding is probably already covering you. This is not aimed at you.

    It also does not apply if your only extra income is small and already covered by adjusting your W-4 withholding instead of making separate payments. Some people prefer to handle it that way, and that is a legitimate option to discuss with whoever preps your return.

    Philip’s take

    Of the two ways to cover extra income, quarterly estimated payments or adjusted W-4 withholding, I usually rank estimated payments first for anyone with irregular income like freelance work or rental profit, because the amount owed changes period to period and a fixed withholding adjustment cannot flex with it.

    And I would rather see someone use the prior year safe harbor than try to forecast. Forecasting is where the penalties come from. Last year’s number is already sitting on a return you filed.

    A calendar reminder costs nothing. A missed period costs you a penalty you cannot undo later, no matter how much you pay by December.

    This week, open your phone calendar and set those four reminders: January 15, April 15, June 15, September 15.

    If you are not sure whether your income needs estimated payments or a withholding adjustment, our office is glad to help you figure out which one fits.

    This article is general information, not tax advice for your particular situation. Rules change and individual facts matter. Talk to a CPA before acting on anything here.