The Tax Season Mileage Log: Dave and the Accountant’s Story

The Appointment

Dave shuffled into Maggie’s office, a lopsided stack of receipts and crumpled notes that looked more like a failed art project than proper tax records. He braced himself. This was tradition by now—his annual lecture.

Maggie sat behind her desk, arms crossed, peering over her glasses just like his Spanish teacher in high school when she’d handed him back a test full of red marks. She inhaled deeply, and Dave winced preemptively.

“Dave.” She exhaled. “Do you enjoy doing this to me?”

“Come on, Mags. It’s not that bad.”

She lifted a single gas receipt from the top of the shoebox in his hand with two fingers, shaking her head.

“This is from three years ago.”

“Oh… whoops.”

An Unexpected Turn

He expected the usual speech—how he was leaving money on the table by failing to track his miles, how she had to sort through his chaotic papers for hours, how he could save thousands if he’d just be an adult and use a proper system.

Instead, Maggie sighed, leaned back in her chair, and—smiled? Dave blinked. This was not in the script.

“Okay, what’s going on? You’re supposed to be mad at me right now.”

She gestured toward his stack of chaos. “Just put them down, Dave. It’s fine.”

Fine? She was never fine. She always went on a speech about administrative responsibility, sometimes throwing in exaggerated hand gestures for dramatic effect.

“Mags, I don’t get it. What’s happening?”

The Accountant’s Secret Weapon

Maggie finally grinned. “I gave up, Dave.”

“What do you mean, ‘gave up’? You don’t just ‘give up.’ You’re Maggie. You fight for order in this world.”

“And I found a way to win.” – she said, raising her neatly kempt eyebrows. She tapped her keyboard, pulled up something on her screen, and turned her monitor so he could see the interface.

“MileageWise. What’s that? A new way to judge me?”

She rolled her eyes. “It’s a mileage log software, silly! IRS-proof. Automatic. Makes perfect mileage logs out of existing data. Turns people like you into responsible taxpayers.”

The Invitation

He snorted. “People like me? I’m offended.”

“You should be,” she quipped. “Look, I got tired of sorting through messes like this. So I started using MileageWise to help my clients reconstruct their mileage logs. Some of them even use the mile tracking app.”

“And that means…?”

“It means that next year, you’re walking in here with a neat, IRS-compliant mileage log. Not a pile of  faded receipts and notes covered in coffee stains.”

Dave scratched his head. “I mean, I could try, but you know I’m not exactly good at being consistent with these kinds of things”

“You don’t have to be. The app tracks for you automatically. You just drive, and it logs everything. And when you’re ready, it spits out a report. Minimal effort, no missing deductions, and most importantly—no more speeches from me.”

A New Hope

“Wow.” He sat down, stunned. “So… you’re saying I could save money, avoid the annual Maggie Lecture, and not have to do extra work?”

“Bingo.”

Dave rubbed his chin. “That actually sounds… good.”

“Of course it does. Now get out of my office. See you next year—with a real mileage log.” – she said, with that over-the-glasses look of hers again.

As he walked out, Dave grinned. For the first time ever, tax season didn’t feel like a battle he had already lost.