He was a young man who wrote jokes in a small apartment in Chicago and he had gone three-hundred-sixty-five days now without filing a tax return. He opened his laptop and launched the tax preparation software. “Santiago, let’s get started on getting you the biggest refund possible!” read a message on the welcome page. But the young man did not want to get started. He wanted to take a long nap.

It was important that the young man get a big refund so that he would have dinero to pay la renta, and el agua, and la electricidad. He did not know why he switched into Spanish when thinking about his financial struggles. Maybe there was something about Spanish that made suffering, el sufrimiento, sound more poetic. “That would explain much about the Latin music industry,” he thought.

The young man went through the tall stack of documents that had been arriving in the mail during the winter. There was the W2 from the day job in Illinois with the kind manager who did not know Santiago sometimes took bathroom breaks to work on his pilot. There was also the W2 from the teaching gig in California that paid so little the young man wondered whether the job was worth the trouble of having to file a California state tax return. Then there were the 1099s for the social content writing in New York, the workshop in Georgia, and the guest lecture in Minnesota, where they had pronounced the young man’s name incorrectly but he had been too tired to correct them. Last, there was the miscellaneous income for the personal pieces he had published that year. He knew he could probably get away with not reporting it, but as a person of color in America, he was too paranoid not to.

Santiago stared at the stack of papers in dismay. “When you earn a living by the pen there are many to whom you must pay taxes,” he thought. He had considered taking his paperwork to one of the many preparadores in the center of town who do people’s taxes for a small fee. But he remembered what his grandfather had always said: “A man must prepare his own taxes.”

“Person. A person must prepare their own taxes,” Santiago had always corrected him.

His grandfather had grown up in a house that did not have electricity and often spoke in outdated and problematic ways. But Santiago had always followed his grandfather’s tax advice. Besides, it was much cheaper to do his taxes himself. He was earning a freelance writer’s income, after all.

The young man fought hard with the glitchy tax software. When he had finally entered his W2 information, the estimated refund quickly grew. It was beginning to look, to Santiago, like it might be the largest refund he had ever received. “Perhaps this is the year I finally finish paying off my préstamos estudiantiles,” he thought as he wrapped up the employment income section.

The sun was setting as the young man entered the earnings from his freelancing gigs. While he typed in the numbers, Santiago saw that the estimated refund was dropping little by little. “It appears as though I have not paid taxes on any of this,” he thought. “Maybe it would be better if I did not report this. After all, who would know?”

“Unless the IRS audits me,” he said aloud. “If the IRS comes, God pity my refund and me.”

The young man knew he did not have a choice. The IRS would get his tax refund and there was nothing he could do to prevent it. He entered the figures from the tall stack of 1099s and watched as the refund gradually dwindled. When he had finished typing, Santiago looked at the refund that had once been so large and saw that he now owed the IRS money. “Perhaps I should not have been a writer,” he thought. “But that was the thing that I was born for.” Santiago’s parents did not agree and often hinted that he should take the LSAT just to “have options.”

The full moon had climbed high into the night sky when the young man finished filling out the returns for the many states—to those he all owed money—and went to file them alongside his federal return. As he was about to press submit, he remembered something.

“Don’t married people usually file their taxes together?”

He had married that year to the only woman he’d met who had not lost patience with being woken up at three in the morning every time he got out of bed to jot down a joke that would be great for Twitter.

“Time to start this tax return all over again,” he thought.

In that moment, the young man remembered another one of his grandfather’s sayings: “(A person) is not made for defeat. A (person) can be destroyed but not defeated.”

“Still,” thought Santiago, as he googled, “how hard is the LSAT?”

“Better to have options.”