The IRS deadline for 2025 tax returns falls on April 15, 2026 — and for millions of self-employed workers, the weeks leading up to it carry a particular kind of dread. Not the ordinary anxiety of paperwork, but the stomach-dropping fear of a bill you didn’t budget for. Claudette Fulton knows that feeling well.
Claudette reached out to American Relief in late February, about six weeks before the filing deadline. She had read a piece I wrote last fall about gig workers who unknowingly overpay the IRS by missing self-employment deductions, and she told me the headline had stopped her cold. “I read it on my phone between rides,” she said. “I kept thinking, that’s me. That’s exactly me.”
We spoke over two sessions — once by phone and once at a coffee shop in South Minneapolis, a few blocks from where she parks between airport runs. Claudette is 47, married, and has a teenager who will be applying to colleges this fall. She has driven for Uber full-time for four years, logging somewhere north of 40,000 miles annually across the Twin Cities metro. By most measures, she is doing well financially. But the tax picture, she told me, has been quietly unraveling for years.
A Good Income That Didn’t Feel Like One
On paper, Claudette’s household income looks solid. She grossed approximately $76,400 driving for Uber in 2025. Her husband works in IT project management and earns a comparable salary. Together, they’re firmly in what most people would call comfortable territory. But comfortable, she told me, doesn’t account for everything pulling at the edges.
There is $42,000 remaining on a graduate school student loan from a communications degree she completed at 38 — a degree she pursued with the intention of moving into media consulting, a plan that stalled when the industry contracted. There is the persistent shortfall from her husband’s ex-partner, who has not paid child support consistently in over two years, leaving a gap of roughly $8,400 in unpaid obligations according to documents Claudette shared with me. And there is the looming reality of college costs for their son, who has his eye on engineering programs that run $35,000 to $55,000 per year.
“We’re not broke,” Claudette said, carefully. “But we’re not ahead either. Every time I think we’re getting traction, something costs more than we planned.”
The $6,800 tax bill arrived after she filed her 2024 return — processed in early 2025 — and it hit at the worst possible moment, right as her husband’s hours were temporarily cut during a project transition. She paid it, she said, but she paid it by drawing down money she had been slowly accumulating in a brokerage account intended for retirement. “I cried about it,” she told me, then paused. “I don’t usually tell people that. I don’t really talk about any of this.”
What She Didn’t Know She Could Deduct
When I asked Claudette how she had been handling her taxes, she described a process that will sound familiar to many gig workers: she received a 1099-K from Uber each January, added the number to her filing software, and paid whatever the program calculated. She had taken a mileage deduction in prior years but had not been tracking it carefully. She had not opened a retirement account in her own name.
According to the IRS, self-employed individuals can deduct the employer-equivalent portion of their self-employment tax when calculating adjusted gross income — a deduction that reduces taxable income, not just the tax owed. For someone at Claudette’s income level, that deduction alone can be worth several hundred dollars. She had not been claiming it.
The standard mileage rate for 2025 was set at 70 cents per mile by the IRS. At 40,000 miles driven per year, a fully documented mileage deduction could reduce her reported business income by $28,000 — a number that visibly surprised her when I walked through the math. “Wait,” she said, setting down her coffee. “Twenty-eight thousand dollars off the top?”
The deduction she was leaving on the table extended beyond mileage. As a self-employed worker, Claudette is also eligible to deduct a portion of her cell phone use for business purposes, car washes and detailing, certain insurance costs, and potentially a home office if she uses a dedicated space for trip planning and recordkeeping. She had claimed none of these.
The Retirement Gap She’s Racing Against
The part of our conversation that stayed with me longest was not the missed deductions — it was what Claudette said about retirement. She is 47. Her husband has a 401(k) through his employer. She has nothing equivalent in her own name, partly because gig platform workers don’t receive employer-sponsored retirement benefits, and partly because she had never investigated what was available to her independently.
“I think about it at, like, two in the morning,” she said. “I’m almost fifty. My husband has his thing. What do I have?”
For self-employed individuals, the IRS allows contributions to a SEP-IRA of up to 25% of net self-employment income, with a maximum of $70,000 for 2025. Beyond the retirement benefit, those contributions are tax-deductible — meaning they reduce the adjusted gross income on which federal taxes are calculated. For someone in Claudette’s bracket, maximizing a SEP-IRA contribution in a strong earnings year could reduce her taxable income by tens of thousands of dollars while simultaneously building a retirement cushion she currently lacks.
Claudette told me she had not spoken with a tax professional in several years. She filed using consumer software and considered herself reasonably organized. But as she described her situation across our two conversations, the picture that emerged was of someone who had been working very hard while systematically underutilizing the tax infrastructure built — however imperfectly — for people in her exact position.
The College Question Hanging Over Everything
Her son turns 18 this summer. He’s a strong student with an interest in civil engineering, and Claudette spoke about him with unmistakable pride — though the pride was always edged with worry about what comes next financially. His college years will likely overlap with the years she most needs to accelerate retirement savings. Both feel urgent. Neither feels affordable.
When I mentioned the American Opportunity Tax Credit to Claudette, she said she vaguely remembered seeing it in her filing software but had assumed her household income disqualified them. Given that her and her husband’s combined income likely pushes past the phase-out range, she may be correct — but the interaction between that combined income and potential deductions is exactly the kind of calculation that benefits from professional review.
“I feel like I should know more than I do,” she said quietly. “I have a graduate degree. I run a business, essentially. And I still feel completely lost when it comes to this stuff. That’s embarrassing to admit.”
It didn’t strike me as embarrassing. The U.S. tax code runs to thousands of pages. The self-employment provisions alone involve overlapping deductions, credits, quarterly estimated payment requirements, and retirement contribution rules that interact in ways no filing software fully explains. What Claudette described — a capable, educated person who fell through the gaps — is not an exception. It’s a pattern.
Where She Stands Now
By the time we finished our second conversation, Claudette had already made one concrete change: she had scheduled an appointment with a CPA who specializes in gig economy filers. She found the referral through a Minneapolis-area small business resource center. The appointment was set for mid-March, giving her time to gather mileage logs — which she began tracking meticulously starting January 1, 2026 — and documentation of other business expenses.
She had also contacted the Minnesota Department of Human Services about the child support enforcement process, which she said she had been hesitant to pursue formally out of concern for conflict. A caseworker walked her through the state’s income withholding procedures, which can compel payment directly from a non-paying parent’s wages or other income. According to the federal Office of Child Support Services, state enforcement agencies collected approximately $32.9 billion in child support payments nationally in fiscal year 2023 — but only for families who were actively engaged in the enforcement process.
The retirement account remains open. She has not yet opened a SEP-IRA, though she said she intended to discuss it with her CPA. The student loans, for now, continue accruing interest at 6.8% annually — a figure she tracks with grim awareness.
When I asked Claudette what she wished she had done differently, she didn’t hesitate. “I wish I had asked for help sooner,” she said. “I kept thinking I had to figure it out myself because asking for help meant admitting I didn’t have it together. And that felt like failing.” She looked out the window for a moment. “It wasn’t failing. It was just being proud about the wrong thing.”
I left that coffee shop thinking about how many people are sitting in versions of Claudette’s position right now — earning real money, working hard, and still bleeding quietly from a dozen financial pressure points they’ve never fully mapped out. The April 15 deadline is close. For Claudette, this year’s filing will be the first one in four years where she walks in prepared.
Related: She Retired from USPS at 33 With a Spine Condition — Then Her Health Insurance Bill Hit $612 a Month
Related: His $4,200 Tax Refund Was Seized Over a Loan He Cosigned — And He Never Saw It Coming
Leave a Reply