
For more than three decades, James Whittington traveled the world as a financial analyst for international commercial real estate companies, building an impressive career and collecting stories along the way.
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But it wasn’t until the St. Charles man began working in semi-retirement as a tax preparer that he stumbled upon the richest narratives of all.
In the course of 90-minute appointments, Whittington has talked to thousands of people from all walks of life – doctors, engineers, teachers, gig and truck drivers, business owners, veterans, immigrants, caregivers, government employees, students looking ahead and retirees looking back.
The list of clients ranged from multi-millionaires to those struggling to stay above water. But what stayed with Whittington the most were not their job titles or incomes. It was their situations, their personalities, and the narratives they candidly shared about their careers, their personal lives, their ambitions, challenges, disappointments and hopes.
“You think (filing taxes) is just a bureaucratic obligation. But I wasn’t just preparing tax returns,” he told me. “I was listening to the heartbeat of everyday people.”
Over the years Whittington scribbled notes from those he helped at his St. Charles and Geneva H&R Block offices or via phone for TurboTax. Encouraged by his family, he thought about putting their stories into a collection as a primer for training seasonal tax preparers. But as the manuscript took shape, he realized it had become something larger.
In May he published “Taxing Revelations: A Window into America’s Annual Civic Ritual,” with chapters and subtitles that reveal the rich mosaic which makes up our local humanity.
Examples include the perfectionists, the anxious, the procrastinators, the line-crossers, the know-it-alls and the know-nothings. There’s also the yuppies, the day traders, the crypto guys, the injured spouses, the same sex couples, the paper marriages, the elderly widow, the gamblers, the prize winners, the job-hoppers, the religious, the spiritual and the lonely.
Some of the stories are humorous: Like the family with three small children who “appear to have consumed sugar as a pre-game ritual,” the mom who could not get her young brood to use their “quiet voices” and the laser-focused dad who lost all the tension in his shoulders once he realized he was getting a refund.
Some are touching, such as the 95-year-old man who rode a bike 12 miles one-way for his March appointment – not because he wanted the exercise but because he had no other means of transportation.
Others are more poignant, like the quiet, middle-aged man who brought a single W-2 issued through a halfway-house work program and cared deeply about the $20 refund he would get.
“There was a posture of caution” about him, Whittington wrote, “as if he were navigating a world that had already judged him.”
These vignettes all include Whittington’s reflections and observations that come from a man who obviously paid as much attention to those sitting in the chair across from his desk as the documents they brought to him.
“Over time,” he wrote, “I stopped seeing numbers on a page and began seeing people, each one navigating their own unique path through life, doing the best they could with what they knew, what they had and what they believed.”
“Taxing Revelations,” which is available on Amazon and at Town House Books in St. Charles, is an easy read. But don’t mistake its simplicity for lack of depth. Whittington might be a numbers guy but he’s also an excellent writer whose genuine affection and respect for people is revealed in every page.
That’s what gives this book so much heart.
Like most of us with more than a few tax filings under our belts, Whittington has seen plenty of change over the years. One of the most troubling, he told me, was how companies went from “personnel departments where it was personal” to human resource departments – “like we were a lump of coal and part of a machine.”
More than ever, particularly with the onset of AI, he continued, our identities are simply data points, “tied to numbers that keep us from embracing our humanity.
“That’s what these stories try to tell.”