Small Wonders: Paying taxes on the American Dream

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.

Or you could try to figure out in advance how much to pay by using the handy worksheet on your W-4 form, a mathematical exercise even the most seasoned CPA fears. No matter what amounts and number of dependents you enter in lines 4 through 4,386, you're told you still need to pay more.

How about wine? Can I deduct wine?

"Did you buy it as a business gift?"

No. As a medical expense.

"Then no."

And if you're lucky enough to get the annual bonus check back from the "Tooth Fairy of Taxation," it's not for saving. It's for injecting back into the economy for the betterment of something called the GNP by taking a trip to Hawaii or some other high-tax state.

Am I sounding a little bitter?


Like so many of you, we are a two-income family where both parents work at good, stable, full-time jobs, by necessity, not choice, since we live in an overpriced region. Property values are skyrocketing again. Housing Bubble 2.0 is here. And with a new pool of renters walking away from foreclosed homes, so is the rental market.

The more you succeed, the more you're punished. And I'm not talking about millionaires who can afford to pay people to stash their money in the mattresses of sheltered accounts and tax loopholes.

I'm talking about middle-class Americans just paying the bills, keeping food on the table and perhaps trying to enjoy some of the fruits that are supposed to come with the American Dream.

Sniff out every tax deduction like a wild boar hunting for truffles. Fight your way up the salary ladder and into a tax bracket that sees you putting more money into the government abyss while prohibiting you from saving for that home that is the last gasp of the tax write-off.

Work hard so you can pay more and have less is the motto of the middle class.

But if you're still looking for a good tax guy, I know one. He might be able to get you in next year.


PATRICK CANEDAY has left the building. Reach him at Read his ramblings at

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