The April 15, 2026 federal tax deadline is less than two weeks away, and the free tax preparation clinic on Penn Avenue in Pittsburgh’s Lawrenceville neighborhood was already packed when I arrived on a Thursday morning in late March. Volunteers from a local VITA (Volunteer Income Tax Assistance) site were working through a backlog of clients — retirees, gig workers, a nursing student with three W-2s. Then there was Randall Chen-Ramirez, 45, sitting in a folding chair near the window, scrolling his phone with the focused expression of someone who had already decided this appointment wouldn’t go well.
He was right to be anxious. But he was wrong about why.
I introduced myself after his session wrapped up. He agreed to talk, mostly, he said, because he was still processing what the volunteer preparer had just told him. “I came in here thinking I owed the government $2,100,” Randall told me, leaning back in the chair. “And now they’re saying I’m getting almost five thousand back. I don’t even know how to feel about that.”
A Six-Figure Income That Doesn’t Feel Like One
On paper, Randall Chen-Ramirez looks financially comfortable. He earns $141,000 annually as a senior marketing manager at a Pittsburgh-based tech startup, a role he’s held since January 2023. He owns a home in the Shadyside neighborhood — a three-bedroom he bought in May 2022 for $487,000 — and he’s engaged to his partner, Marcus, who is currently finishing a graduate degree in education policy at the University of Pittsburgh.
The reality is more complicated. Randall’s mortgage payment runs $3,340 a month, a figure that made more sense when the home’s estimated value was climbing. By early 2026, according to Randall’s own Zillow checks, the property was sitting at roughly $431,000 — about $56,000 below what he paid for it. “I’m not panicking,” he told me carefully, “but I’m also not not panicking.”
The added pressure is a side business Randall has been running since 2019 — a freelance marketing consultancy he operates under an LLC. At its peak in 2022, it brought in roughly $46,000 a year. By 2025, that number had dropped to approximately $18,000, squeezed by clients consolidating their vendors and a market that was leaning harder into in-house teams. The expenses of running the LLC — software subscriptions, a dedicated home office, professional development — hadn’t fallen proportionally.
“The business used to feel like a safety net,” Randall said. “Now it feels like a second mortgage.”
What He Filed Before — and What He Was Missing
For the past several years, Randall had been using a popular tax software platform to file his own returns. He’s not unsophisticated — he understood that his LLC required a Schedule C, that he needed to track mileage and software costs. What he hadn’t done, as the VITA volunteer quickly identified, was properly calculate and claim his home office deduction.
The IRS allows self-employed individuals to deduct expenses for the portion of their home used exclusively and regularly for business, according to IRS Publication 587. Randall has a dedicated room in his Shadyside home — roughly 180 square feet of a 1,400-square-foot house — that he uses solely for his consultancy work. He had never claimed it.
Using the regular method, the VITA volunteer calculated Randall’s deductible home office expenses at approximately $6,200 for 2025 — factoring in his mortgage interest, utilities, and homeowner’s insurance prorated by square footage. Combined with a business loss carryforward from his LLC that had been improperly handled in previous returns, the total adjustments were significant.
The Turning Point: What the Volunteer Found in His Records
Randall had brought a folder of documentation to the clinic — more than most walk-ins, the volunteer told him. That organization ended up being crucial. The preparer was able to reconstruct two years of LLC expense records that Randall had under-reported, identifying approximately $9,400 in legitimate business deductions he had either missed or categorized incorrectly in prior filings.
The VITA preparer also flagged that Randall’s estimated tax payments — which he had been making quarterly through the Electronic Federal Tax Payment System — had been calculated without accounting for his declining LLC income. He had been overpaying estimated taxes relative to what his 2025 income actually required. That overpayment, roughly $1,600, had been sitting with the IRS as a credit.
According to IRS guidance on estimated tax payments, taxpayers can apply overpaid estimates to the following year or request a refund. Randall had done neither — he simply hadn’t known the overpayment existed.
A Refund That Came With Regret
Randall was quiet for a moment after I asked how he felt about the outcome. He didn’t look relieved in the way I expected. He looked tired — the particular exhaustion of someone who has been doing something wrong for long enough that discovering the mistake feels like its own kind of loss.
The VITA volunteer had also mentioned that Randall could potentially file amended returns — Form 1040-X — for tax years 2022 through 2024 to recover some of what he had missed, though the three-year statute of limitations means 2021 would no longer be accessible. According to IRS Form 1040-X guidance, amended returns generally must be filed within three years of the original return’s due date to claim a refund.
Randall said he wasn’t sure he had the energy for that process right now. “Maybe in the summer,” he said. “When things are quieter.” He paused. “Things are never quieter, but maybe in the summer.”
What This Means for High Earners Running Side Businesses
Randall’s situation is not unusual. High earners who also run small businesses occupy a complicated middle ground in the tax system — too financially sophisticated to qualify for many relief programs, but often too busy or too confident in their own filing abilities to catch the errors that accumulate over years. The IRS estimates that millions of small business owners leave legitimate deductions unclaimed each year, though the agency does not publish a specific aggregate dollar figure for missed home office deductions alone.
VITA sites, which are funded in part through the IRS and serve taxpayers who generally earn under $67,000 — Randall qualified because his side business losses brought his effective income calculation for the clinic’s purposes into range — offer free preparation by certified volunteers. The program has been running since 1971. Locating a VITA site near you is possible through the IRS VITA locator tool.
For Randall, the $4,800 refund will go directly toward his mortgage — not a solution, but a temporary exhale. Marcus finishes his degree in May 2027. The plan, such as it is, is to reassess everything once there are two stable incomes in the house again.
When I left the clinic, Randall was still at the table, photographing the completed return on his phone. He looked like a man who had narrowly avoided something — not a disaster, exactly, but the particular exhaustion of a year that had asked too much and given back too little. The refund wouldn’t fix his mortgage, wouldn’t revive his consultancy, wouldn’t compress the years of catching up he and Marcus still faced.
But he walked out with $4,800 he hadn’t walked in with, and a clearer picture of what he owed the years behind him. For a Thursday morning in Pittsburgh, that counted as something.
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