Small Wonders: Paying taxes on the American Dream

April 05, 2013|By Patrick Caneday | By Patrick Caneday

I'm pretty diligent when it comes to my taxes. And by diligent, I mean that in November, I make an appointment for February with my tax guy, which is unlike those co-workers in your office asking around in April if anyone knows a good accountant. That's like trying to get face-value Super Bowl tickets on game day.

To coin an overused phrase, a good accountant is like a good pair of shoes: The best ones give you comfort for the long haul and are worth the cash outlay. Bad ones may look nice for the price, but are painful and need replacing too soon.

Diligent also doesn't mean organized. Not unless stuffing receipts into an over-packed folder from January 1 to December 31 makes me organized.

On Groundhog's Day each year, I pull the mummified remains from the drawer and carefully unfold shriveled receipts into their own piles: utilities, phone, entertainment, business expenses, toiletries.


I then condense that information down to a spreadsheet with categories like "stuff & things" and "Misc. ice-cream-related expenses" in preparation for my exam by the "Proctologist of Personal Finance." A session that goes something like this:

I wrote a column about my dogs. Can I deduct vet and grooming fees?


How about dog food?


Cat food?

"Do you own a cat?"


"Then no."

Going over numbers with your accountant is like playing Keno. Pick a series of numbers then wait for someone to tell you whether you picked the right ones. The odds you'll win are about as good as those in Keno. I just wish my accountant's office had an all-you-can-eat buffet or a depressing bar.

Can buying Girl Scout cookies be considered charitable giving?


Trying to figure out how much to have withheld from your paycheck throughout the year is yet another effort in futility. I'm married and have two children. So logically, one would think that my bride and I should each claim "Married - 1." Safe bet, right?

Foolishly trusting that method a few years back led to a nifty payment plan to give even more hard-earned cash to our state and federal governments. I've never understood why they add interest charges, setup and late fees to the installment payments of those who obviously don't have enough expendable cash to begin with.

But I guess the extra booty is needed to fund Congress-folks' private jets to vacation homes and better pensions and medical benefits for life than you or I will ever be lucky enough to get.

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