【Walker (2025)】

My office is Walker (2025)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 dog’s office commute! That would be so awkward. And there’s 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 they’re practically giving away money.

While most people don’t 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:

1. 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 manager’s request for an event your company’s hosting. None of these things cost more than a few dollars. Your bank account will not suffer. You’ll have no trouble paying all of your bills.

But why should you pay for these items? You may not be at company-card level, but that doesn’t 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 it’s a one-time thing, there’s still such a thing as principle. So, take a deep breath before making the purchase and ask your boss if you’ll 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 can’t make a habit of this type of spending.”

2. Declining to contribute to a co-worker’s gift

There’s Jason, going around with the envelope collecting cash from everyone so you can help give his boss, Larry, cigars for his bachelor party. You don’t know Larry well, you don’t work in the same department, and, actually, you didn’t even know he was getting married until now. But Jason’s persistent, “Every dollar helps,” he says with a charming grin.

You consider seeing if you have a single, but then you remember that when you got married, you just got a gift from your team. So instead you say, “Sorry, I have a policy of only contributing to gifts for people on my team.” It’s not about the literal cost—again, we’re back to the principle. If you gave every time someone in your office got married, had a baby, or celebrated a birthday, you’d be broke.

3. Asking for an uneven split

Lunch with your co-worker’s awesome. You’re both delighted that you finally got out of the office and decided to sit down at a real restaurant for a nicer-than-usual meal. You couldn’t help noticing, though, that what your colleague ordered—the steak frites—was nearly eight bucks more than your own meal.

You never go out for lunch though, and what’s a few dollars you feel yourself asking to avoid sounding stingy. On the other hand, why should you pay for her food? Maybe you even chose the burger because you were comfortable with the weekday lunch price tag. This is a situation when having cash comes in handy so you can just offer what you owe. But, if you’re paying with a card, it’s fine to suggest an uneven split. Say, “I am watching my dollars this month! Mind if I just factor in the cost of my meal plus tax and tip, of course? ”

4. Turning down a charity or fundraising request

You give to charity. You, in fact, have one that you really support and have been contributing to for years. Or, you don’t. Either way, when that email from Betsy goes out to the entire company asking for a contribution for the charity race she’s running, you can go right ahead and ignore it.

If Betsy personally hits you up, you can politely decline. Tell a white lie and say that your charity contributions are all spoken for, or just say, “I’m sorry, I can’t right now. Best of luck.” Your money’s your business, and no one needs an explanation on why you aren’t contributing.

5. Following up on money you’re owed

The first time you went for coffee with the co-worker, you didn’t mind treating. “You can get it next time,” you said. The second time came and went, and he didn’t have cash at the cash-only establishment, so you paid again. He promised to “get you back,” but it’s been weeks, and nothing.

You’re reluctant to bring it up because it’s $4 you’re talking about (he, apparently, is partial to the pricier brews), but you’re annoyed every time you think of it, and, frankly, you want your $4. You can buy a small coffee and a donut with it!

Instead of directly asking for the money, suggest a coffee date later in the week. Ping him to remind him that it’s cash-only. Let him buy you the coffee.

There’s probably no world where money won’t cause some anxiety. You don’t want to appear cheap, but you also don’t want to overspend. And you also just don’t want to feel obligated to spend your hard-earned cash. It doesn’t matter if you work in a large or small office or if you have the money or don’t. One thing’s for certain: You manage your money, and with that management role comes power. Use it wisely.