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Plus: what uneven income does to your estimated tax penalty, and the paperwork that follows a house across state lines.
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Good morning! Every Saturday, we open the mailbag, pour some strong coffee, and tackle the tax questions keeping America awake at 2 a.m.
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Here are this week’s topics:
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💼 Two jobs, one W-4, and a formula that only knows about one of them.
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📉 Your income doesn’t arrive on a schedule. The IRS still wants a number every quarter.
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🗺️ Owning property in one state and living in another comes with paperwork you didn’t order.
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Filing Made Simple
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💼 Your new W-4 thinks you’ve worked there since January.
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I started a new job mid-year and my withholding seems off. How do I fill out the new W-4 correctly?
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Your instinct is right, and here’s why it happens: withholding tables assume your new paycheck is your only income for the whole year. They don’t know you already earned money — and had tax withheld — at your last job. That gap is usually why your new paycheck looks like it’s withholding too little.
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👉 Check whether this applies to you
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The fix lives in one specific part of the form: Step 2, “Multiple Jobs or Spouse Works.” It only matters if you (or a spouse) had more than one job this year. You have three ways to fill it out, in order of effort:
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Check the box in 2(c) if you have exactly two jobs total that pay about the same. Fastest option, but can under-withhold if the two paychecks are far apart in size.
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Use the Multiple Jobs Worksheet on page 3 of the form and do the math by hand.
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Run the IRS Tax Withholding Estimator — the most accurate option. Enter pay stubs from both jobs, including what’s already been withheld this year, and it tells you the exact extra amount to add in Step 4(c).
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One more thing to watch: Step 3 (dependents and credits) should only be filled out once, at whichever job pays more. Filling it out at both jobs claims the same credit twice — and the IRS will ask for the difference back at tax time.
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Skipping Step 2 is the single most common reason two-job households end up owing money they didn’t expect. It’s not a mistake on your part — it’s a form that’s never met your other paycheck.
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⚙️ THE TAXSTACHE TOOLKIT
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Pick wrong and you’re redoing this math every paycheck until April. Pick right and you never think about it again.
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PRESENTED BY GROUNDFLOOR
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Our most popular investment is over 90% full: 9.5% fixed, 6-month note
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Here’s what’s happening with the Groundfloor Bond Note: It’s nearly sold out and on pace to close before its September 3rd deadline. Lock in a 9.5% fixed annualized return over a defined 6-month term — short enough to keep your options open, long enough to build wealth. Once the offering fills, it’s gone. Groundfloor has a 100% repayment track record on Notes since launching them in 2018. Accredited investors – invest now while space remains.
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Tax Strategies
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📉 Your income is unpredictable. The IRS’s math isn’t.
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My income varies a lot month to month. Is there a way to avoid the underpayment penalty on estimated taxes?
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Yes, and it depends on what kind of “varies” you’re dealing with.
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The easy version: pay 100% of last year’s total tax (110% if your prior-year AGI was over $150,000), split evenly across the four due dates. The IRS doesn’t check when your income actually showed up — just whether you hit the flat number each quarter. A slow March and a huge October are irrelevant.
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👉 See which one actually applies to you
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The real fix, for genuinely erratic income — a seasonal business, a big client payment in Q3 — is the annualized income installment method (Schedule AI, Form 2210). It bases your required payment on what you actually earned by each due date, instead of assuming your tax liability is spread evenly across all four quarters — the way a gym membership bills you the same amount whether you showed up twenty times that month or not at all. It requires real bookkeeping, so most freelancers only need it if their income is dramatically uneven year to year.
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One more thing: owe less than $1,000 after withholding and credits, and none of this applies. The IRS has decided you’re not worth the paperwork — the nicest thing it says to you all year.
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⚙️ THE TAXSTACHE TOOLKIT
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The wrong pick means overpaying all year or getting hit with a penalty for guessing. Thirty seconds tells you which one you actually need — and does the math for you.
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THE BUSINESS EDITION
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Every Thursday, we go to work.
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The TaxStache Business Edition breaks down the tax and finance topics that actually matter to business owners, from quick intros to in-depth dives. Plus, book, podcast, and video recs to keep you sharp.
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If you own a business (or you’re building one), this one’s for you.
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Would you like to receive our Thursday Business Edition?
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Filing Made Simple
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🗺️ Owning the house is fine. Renting it out is a paperwork trigger.
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My property is in a different state than where I live. Do I have to file taxes in both states?
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It depends on what that property is doing for you, not just where it sits. The IRS and your state’s revenue department are not interested in your real estate portfolio as a concept. They’re interested in whether it’s making you money.
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Owning vacant property, or a personal vacation home you never rent out, generally doesn’t create a state income tax filing requirement in the property’s state. States tax income, not real estate ownership — property taxes are a separate, local matter, and they show up in your mailbox with or without anyone’s permission.
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👉 See exactly what your state requires
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Rental income changes the answer. If you’re renting the place out, that income is sourced to the state where the property is located, and most states with an income tax require a nonresident return reporting it — even though you’ve personally never voted there. Meanwhile, your home state generally taxes your full income no matter where it was earned, which means that same rental income also shows up on your resident return. Two states, one Airbnb listing, two forms with your name on them.
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That sounds like double taxation, and without a fix, it would be. Your home state almost certainly offers a credit for taxes paid to another state, claimed on your resident return, which offsets the tax you already paid to the property’s state. You still file two returns; you just don’t pay twice on the same dollars, which is about as close to a consolation prize as the tax code offers.
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Selling the property works the same way. A gain on the sale is sourced to the state where the property sits, so expect a nonresident return in the year of sale, plus the credit on your resident return.
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A few outs worth checking: if the property is in a state with no income tax at all (Florida, Texas, Washington, and a handful of others), there’s nothing to file there regardless of rental activity — one of the only times “no state income tax” pays off for someone who doesn’t even live there. And reciprocity agreements — which let some neighboring states skip dual filing — almost always apply to wages, not real estate income, so don’t count on one bailing you out here.
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THE TAXSTACHE TOOLKIT
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Get this wrong and you’re either skipping a filing you owed or doing paperwork nobody asked for. Two questions settles it.
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