The first time Deshawn Parker checked the IRS Where’s My Refund portal, he was sitting on a folding chair in his studio apartment in Detroit, a half-eaten burrito going cold on the table beside him. He had filed his 2024 taxes in early February 2025, and he was certain — absolutely certain — that money was coming back to him. He had barely scraped by all year. Surely the government owed him something.
The portal did not agree.
From the Warehouse to the Waiting Game
When I sat down with Deshawn Parker at a coffee shop near his apartment on East Jefferson Avenue, he looked like someone who had recently survived something — which, in a financial sense, he had. He is 27, sharp-eyed, and the kind of person who talks with his hands when the subject matters to him. Tax season, he made clear, mattered to him now in ways it never had before.
Deshawn left a steady warehouse logistics job in early 2024, walking away from a $38,000 annual salary and, critically, an employer who withheld payroll taxes on his behalf every two weeks. He had been doing freelance graphic design on the side for years — brand kits, social media packages, the occasional album cover — and decided the time had come to go all in.
The first quarter of freelancing went well. He cleared roughly $4,200 in March alone — more than he had ever made in a single month. He told me he felt invincible. He upgraded his monitor setup, bought a new iPad Pro, and did not set aside a dollar for estimated quarterly taxes. The IRS self-employed tax center lays out the quarterly payment schedule clearly, but Deshawn had never read it.
“I thought taxes were something you dealt with in April,” he told me, rubbing the back of his neck. “I didn’t understand that the whole system assumes somebody is already taking money out of your check every two weeks. When that stops, you’re on your own. Nobody tells you that when you quit.”
The Year Everything Compounded
Income for Deshawn in 2024 was erratic in the way that freelance income often is — feast and famine cycling without warning. His strongest months brought in $3,800 to $4,500. His worst months — particularly August and November — barely cleared $800. His total net freelance income for the year came to approximately $27,400, a significant drop from his warehouse salary but still enough to generate a meaningful tax liability.
Then came October. Deshawn was rushed to the emergency room with acute appendicitis. The appendectomy and two-night hospital stay produced a bill of $18,200. He had no employer-sponsored health insurance — he had been meaning to enroll in a Marketplace plan through HealthCare.gov since leaving his job, but kept putting it off. He negotiated the hospital’s chargemaster bill down to $14,000, then missed the payment window while chasing invoices from three different clients who were running late.
“The hospital sent it to collections before I even knew what was happening,” Deshawn told me. “I thought I had 90 days. It was 60. That one mistake knocked my credit score from about 680 down to somewhere around 530. I checked my credit report and just sat there.”
What the IRS Portal Actually Showed Him
Deshawn filed his 2024 federal return using tax preparation software in early February 2025. He used Schedule C to report his freelance income and, for the first time, encountered Schedule SE — the form used to calculate self-employment tax. The software did the math automatically. He owed $3,869.
There was no refund. There was a balance due.
According to the IRS Topic 554, self-employed individuals must pay 15.3% in self-employment tax on net earnings — 12.4% for Social Security and 2.9% for Medicare. On Deshawn’s $27,400 in net income, that alone came to roughly $4,192 before any deductions. The software did catch the deduction for half of the self-employment tax, which trimmed the overall liability, but not enough to eliminate it.
He had also missed all four 2024 estimated quarterly payment deadlines — April 15, June 17, September 16, and January 15, 2025 — which added a small underpayment penalty to his total. The IRS calculates this penalty using Form 2210, and while it rarely amounts to hundreds of dollars for a taxpayer at Deshawn’s income level, it stung on top of everything else.
The Turning Point: Setting Up a Payment Plan
Deshawn could not pay $3,869 in a lump sum by the April 15, 2025 deadline. He was carrying the medical debt, his credit cards were nearly maxed, and he was in the middle of a slow client month. What he did next, he told me, was the first financially deliberate thing he had done since leaving his warehouse job.
He went to the IRS Online Account portal and applied for an installment agreement — specifically, a short-term payment plan, which the IRS offers to taxpayers who owe less than $100,000 and can pay within 180 days. There is no setup fee for short-term plans requested online. He was approved within minutes.
As Deshawn explained to me, the process was less intimidating than he had feared. The IRS website walked him through eligibility, and he did not have to speak with anyone by phone. Interest continued to accrue at the federal short-term rate plus 3 percentage points — a detail he acknowledged reading only after the agreement was already in place.
“I just assumed the IRS was going to make it as hard as possible,” he said. “But the online system was actually straightforward. That surprised me. I thought I’d be on hold for six hours.”
Where Things Stand Now
When I spoke with Deshawn in late March 2026, he had made all five installment payments on his 2024 tax bill. The IRS balance was cleared. His credit score, still damaged by the medical collection, sat around 548 — an improvement of roughly 18 points from its lowest point, mostly from on-time payments on a secured card he opened specifically to rebuild his history.
The medical debt remains. He told me he had contacted the collections agency twice to attempt a pay-for-delete negotiation, with mixed results. The account shows on his Experian and TransUnion reports. He is still without health insurance, though he told me he had finally pulled up the HealthCare.gov Marketplace and was close to pulling the trigger on a plan.
His freelance income in 2025 totaled roughly $34,000 — up from the prior year. He made three out of four estimated quarterly payments on time and missed the September deadline by nine days, resulting in a small penalty he expects to show up when he files his 2025 return this spring. He has already started setting aside 25% of every client payment into a separate savings account he labeled, somewhat grimly, “IRS first.”
The design work continues. He landed a recurring contract with a Detroit-based clothing brand in January that pays $1,200 a month in retainer fees. It is not quite the warehouse salary he walked away from, but it is consistent in a way that changes how he plans.
Deshawn Parker’s story does not have a triumphant final chapter yet. The credit damage from the medical collection will likely take another year or two to fade. The 2025 tax return is still pending. What he has, at 27, is a much clearer map of the terrain — the kind of map that costs something to acquire.
Before I left the coffee shop, he said one more thing that I keep coming back to. “Nobody fails at freelance taxes because they’re stupid,” he told me. “They fail because the system assumes someone already explained it to them. Nobody explained it to me.”
Related: A $14K Medical Debt Went to Collections Before This Detroit Freelancer Knew He Had Options
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