How to avoid expense-report hell

If work hell exists, then Amanda Larrinaga experienced something like it a couple of years ago.

The start-up consultant from Missoula, Montana, was staring at a gigantic stack of nine months' worth of receipts.

That meant her immediate future was going to be one big expense-report nightmare: scanning, filing and coding; defending claims; and wrestling with maddening reimbursement systems that drove her into fits of expletive-spewing rage.

As the process stretched into days, she felt like she was losing her marbles.

"I cried, I had some wine, I called my mother," remembers Larrinaga, 28. "It was so traumatic."

Larrinaga eventually emerged from expense-report hell but remembers how harrowing it was.

Indeed, the whole process is so despised that 18 percent of employees would agree to take out the company trash if it meant they would never have to file an expense report again, according to a survey of small businesses by expense-management firm Concur. Heck, 10 percent would even agree to scrub the toilets.

That begs the question: Why do people hate it so much? And why are we all so bad at getting it done?

"People in general are overwhelmed by the clerical responsibilities in their life, and that includes expense reports," says Gary Belsky, co-author of the book "Why Smart People Make Big Money Mistakes - and How To Correct Them".

"The irony is that when we are on expense accounts, we tend to buy and spend much more because we think of it as someone else's money," Belsky says, "and that only increases the number of transactions we have to eventually account for."

That in turn increases the number of potential screw-ups. Just think of all the things that can go wrong along the path to reimbursement.

Nearly half of employees say they have lost receipts, for instance, according to the Concur survey. And 36 percent admit to forgetting what expenses are for.

Meanwhile, almost 60 percent fessed up to making mistakes on their expense reports in the previous year, and more than a third of people screwed up five times or more in that time.

So how can we get over our existential dread of expense reports?

FIND AN APP THAT WORKS FOR YOU

Technological advances mean that you have less of an excuse to groan about documentation.

Amanda Larrinaga, for instance, went with a service called Shoeboxed. For her business, Modern Entrepreneur, she just dumps her receipts into an envelope, lets Shoeboxed scan them, and then has her assistant handle the process from there.

Many smartphone apps let you take snapshots of receipts and get the reimbursement process started right away. Expensify is among the most popular, with features like automatically importing credit-card transactions and letting you create and file expense reports right from your phone.

DO IT EVERY WEEK

By putting off expense reports, you are only compounding the problem. "People need to get in the habit of doing their expenses every week for a half-hour or an hour," says Belsky.

It needs to be something you do all the time, like going to the gym or the doctor, he says. "Then, if you don't have corporate expenses to file that week, you get a free hour for yourself."

DELEGATE

If the whole process makes you want to scream, then consider having someone else do it. If you are an executive, that should be easy enough.

"Company founders are often terrible at little details like that, so have an assistant or project manager help support you," says Larrinaga.

But even if you are low on the corporate pecking order, there are still options. Virtual assistants are for hire 24/7 at sites like TaskRabbit. Give potential hires one minor receipt to expense as a test, and if it goes well, then you can start farming it out all the time.

STICK TO CREDIT CARDS

Whip out the plastic whenever possible. That way, if you happen to lose any physical documentation, then a restaurant or hotel, or the credit-card company itself, can usually just dig it back up.

San Francisco entrepreneur David Barrett found that out the hard way. At a previous job, he had taken a 30-day trip to India with five colleagues and ended up filing expense reports for every one of them. That, of course, meant tons of receipts.

"Nearly all the receipts were in cash, scrawled on slips of paper, in a variety of Indian languages," he remembers.

Barrett became so shell-shocked by the whole experience that he left the company and went on to found Expensify. To this day, though, he still sounds emotionally shaken over his first expense-report adventure.

"I expected it to be bad," he says. "But nothing could have prepared me for the sheer horror."