Wealthsimple is a whole new kind of investing service. This is the latest installment of our "Dear Ms. Etiquette" series, where our columnist untangles the issues that happen when people and money get together. This week, we have a guest Ms. Etiquette — well, he's actually a Mr. Etiquette.

Dear Guest Mr. Etiquette:

So I got a new job that comes with an expense account of $1000 a month. Coworkers tell me I can use it however I like – it’s seen as part of the compensation package here. But it feels wrong. Tell me what to do!

Sincerely, Can I Expense This Lunch?

Dear Ms. Free Lunch:

First of all, congratulations! I remember what it’s like to start a new job. I began my career as an editor in glossy magazines at the end of the last century — and thank you for not doing the math. At that point I was paid roughly what would get an employer reported to Amnesty International. But there was a surprise perk that no one mentioned in HR. One of my duties was to prepare expense reports for my boss, and take them down to the company cashier, who turned those flimsy forms into crisp new tens, twenties, and hundreds before my ever-widening eyes. About a week after I started, my boss looked up as she was signing a stack of what were called petty cash vouchers (perfect name – sounds just like petty theft) and said, “I know we don’t pay you much. Feel free to take cabs or cars if you need to, and submit your meals. I’ll sign for them.”

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I learned that the culture of my glamour-industry company allowed people to live a slightly fancier (in some cases much fancier) lifestyle than their salary might allow. (One day, looking for a pen — that’s a stick with ink that writers used to use — I discovered about 3 months of un-deposited paychecks stuffed in a coworker’s desk. That was a kick in the head.) In my problem at hand, though, I had no idea what “submit your meals” meant – a $3.75 Cold Cut Combo from Subway? A $400 tasting menu? So I discreetly asked around. “Just keep it under a hundred bucks a pop and no one will raise an eyebrow,” said a trustworthy colleague, who actually cashed her paychecks to, you know, pay the rent and stuff. “Oh, and here’s a book of vouchers for cars.” Predictably, I started with $20 take-out but soon graduated to restaurant fare. There were a lot of $98 dinners in the ensuing months. (Somehow, those two dollars under the unspoken limit made me feel as virtuous as St. Francis eating bugs.) And not all of them were work-related. I thought it was an OK thing to do – or that’s what I told myself. Like many people in media, even as I advanced in that world, my salary was never commensurate with folks from lots of other industries.

Before we go much further, let’s get the obvious out of the way. Is it okay to fudge your expenses? To give yourself perks? And lie about it when there is no express consent that this is how things are done? The answer is no. If your company has profit sharing, it’s no because it effectively reduces your and your coworkers’ bonus possibilities (inflated expenses mean deflated profits, and less to share). It’s no because it’s stealing and lying, and I hope it’s still true that stealing and lying are bad. And then there’s this, from a senior executive in finance: “It’s always been pretty clear. The guidelines are written down, and they’re unambiguous. If you cheat, you will be caught by a routine audit. If you’re caught, you can be reprimanded or fired.” That would be another no.

But let’s address your particular question, which is, I think, a little trickier: is it right to use your expense account for the express purposes of your own pleasure if it’s, either explicitly or implicitly, ok with the company? It still happens. One sector where it seems to happen a lot is tech start-ups — places that are still swimming in investors’ cash and have to create a desirable work culture from nothing. If you’re trying to hype a billion dollar idea, you can’t take people to a food cart. “Start-ups try to look as shiny as possible so they spend a ton of money on perks,” says Ignacio Ramirez, a PR consultant who works in the tech field. “It’s part of the game to look sexier, as you’re going for new rounds of funding. The appearance is everything.” In Silicon Valley, that means gridlock of company-leased Teslas, regular 8pm reservations at Quince, the best passes at Web Summit, and so on.

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Of course none of that can be had for $1,000 a month, which your company (quite generously, I might add) provides. But you should be aware that besides that money, what your company is entrusting you with is a certain responsibility, and they might well take note of how you spend it — what your inner compass tells you is appropriate. “It may sound obvious, but regulations come from the organization, and ethics come from the individual,” says Steve Ketterer, a marketing consultant who has worked for Big Pharma. “You can tell a lot about an employee if you give them freedom, and see how they set guidelines for themselves.” In short, just because they won’t tell you how to spend it doesn’t mean they don’t care.

The very best advice for anyone on this topic is to know exactly what your company’s policy is and to follow it to a T. Pushing the boundaries is just asking for trouble. In the political sphere, where lavish perks are charged to taxpayers, expense abuse is radioactive. Just ask Tom Price, Steve Mnuchin, or Ryan Zinke. My favorite example is former Congressman from Illinois and abs model Aaron Schock, who had his congressional office decorated to resemble the library of “Downton Abbey.” Schock was indicted on 24 counts last year. His trial is scheduled for January, 2018. Fingers crossed that they have a good gym at the penitentiary and his office goes to the Smithsonian.

But here’s what I think about using your expense account as a personal perk. I happen to have some experience with the permissively padded expense account. And I think there’s a price to pay even if you will never, ever get caught or disciplined. First, profligacy wounds me to my Connecticut Yankee core. I was taught that, no matter who is paying, frugality is a virtue, and the reverse is vulgar — or vaguely European. So I felt gross the whole time I was supposedly enjoying myself on the largess of the company. Second, I got used to it. Regular pricey dinners with friends and loved ones seemed like a basic employment benefit. Is it Wednesday? We’ll need a bottle of champagne to celebrate. Traveling for work? Let’s throw a party in the hotel suite. I came to think I lived in a tax bracket that I really, truly did not live in. In general I think that entitlement is a bad look – especially if, as is often the case, it’s entitlement you can’t maintain on your own.

When I was doing these things, I would console myself with moral relativism. I wasn’t taking advantage nearly as much as others did, I reasoned, weakly. I never altered or faked a receipt, because, though it was commonly done, that really felt like stealing. But I was no angel. The tipping point came when I charged a $250 massage to my room on a business trip to Los Angeles for a photo shoot, knowing the entire bill would be covered. The fact that I still have a twinge of shame about it decades later shows how worthwhile that bit of indulgence was.

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And I have to admit something: it was a relief of sorts when expense accounts were slashed, or eliminated, at the company where I worked. It was easier. It felt better to not be lying about who I was having dinner with – or about how the photo shoot crew needed massages. Functioning with more ethical clarity was a benefit that is worth paying for – even if you’re paying for it with those Wednesday night bottles of champagne you no longer get to drink.

There are better ways to do well than riding your expenses up the income ladder. I’m not saying you shouldn’t enjoy your monthly stipend while it lasts. But you should realize it may come with a price, even if that price isn’t always clear. And if you feel you are abusing your expense account to get back at a company that doesn’t treat you right, you’re doing it wrong. If you ever feel you are underpaid, or unfairly treated, you should ask for a raise or find a new job rather than spend your time trying to find creative ways to pilfer from the company. It’s not worth it. Just like my $250 massage.

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