My office is dog-friendly, and luckily I have a friendly dog. While I’d love to bring Odie into the office, there’s no easy way to get him there without driving my car into Manhattan and paying for parking (I generally take the subway). I joked with a co-worker that if everyone in the office gave me 50 cents, I could bring Odie in without it costing me a penny.

But that was a joke. Obviously. I could never ask my colleagues to pay for my dogs office commute! That would be so awkward. And theres nothing worse than an awkward money conversation. Throw a workplace into the mix, and things get even more uncomfortable. In fact, I know people so worried about speaking up that theyre practically giving away money.

While most people dont have to worry about the cost of bringing their dog to work, they do have to navigate tricky situations every day.

Here are five that you should 100% feel more confident dealing with:

51. Asking to expense a low-cost item

You sent a client a package. You buy some stamps to send holiday cards to your most valued customers. You pick up wine on your managers request for an event your company’s hosting. None of these things cost more than a few dollars. Your bank account will not suffer. Youll have no trouble paying all of your bills.

But why should you pay for these items? You may not be at the company-card level, but that doesnt mean that all of the little work-associated costs should fall to you. It can feel funny to expense a 10-pack of stamps, but what if you got in the habit of regularly buying stamps for your company with your own money and never got reimbursed? It would add up.

And, even if its a one-time thing, theres still such a thing as principle. So, take a deep breath before making the purchase and ask your boss if youll be able to expense this. If she says no, then all you have to say, OK, well I guess I can grab it this time, but, unfortunately, I cant make a habit of this type of spending.

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