A Friday Chat on When You Should Ask

And what do we really want, anyway?

ESTER: “If you have to ask, the answer is no.” Pretty grim advice, huh?

NICOLE: What happened to “it doesn’t hurt to ask?” I’ve kind of found that advice to be untrue in practice, though. It often does hurt to ask. Probably because if you have to ask, the answer is no.

ESTER: Well, in my experience, it really depends. One time, as I wrote about for the site, I was approached about a consulting gig and offered the same rate that I’d received the previous time. I asked whether there was any flexibility in the rate, and instead of simply saying no, the clients withdrew the offer altogether. I asked, and I lost the gig. That stung. But I’ve also had other experiences where I asked for something — more money, more flexibility, the ability to work from home — and gotten it without any kind of fuss. In fact, I feel like that’s usually what happens: by the time I’m ready to ask for something, the person on the other end is like, “Duh, we expected you to demand this a while ago.”

NICOLE: Maybe you can tell by the relationship. Whether the person you’re asking feels like they have all the power, or whether they’re willing to have a conversation with you. There are some people I have no problem asking, especially now that I am more established in my career. When I had no leverage, whether in a workplace or an interpersonal relationship, and I was asking because I was unhappy with some part of the relationship, I was terrified. Also, the answer was often no.

This also ties in to the entitlement thing and the spoiled thing, which you wrote about earlier this week: if the person you’re asking sees you as acting entitled, that’s going to affect the response to the request.

“Spoiled” Isn’t Actually A Thing You Can Be

ESTER: Maybe! Honestly though I don’t know. I have a friend who can come off as pretty entitled: she makes lots of requests — of friends, of strangers, of institutions — because she is very comfortable asking for what she wants, and what’s amazing is that she usually gets what she wants. (Is it actually amazing? Or is it THE SECRET??) Anyway I end up just kind of marveling, and a little envious, too. There are certain people, I feel like, who the universe actually rewards for asking without apology, without self-consciousness even. I’m not sure I could get away with it; but maybe I could, and I’m holding myself back? You can’t be afraid to hear “no,” that’s for sure.

NICOLE: I’m a lot better at asking for what I need than I used to be, because I have more options if I hear “no.” Hearing no doesn’t mean I lose the assignment that would pay my rent, as it were. But I also hear a lot fewer nos, now. For whatever reason my value is at the point where people are willing to accommodate me. Wow, that sounds presumptuous — another word like “entitled” and “spoiled!”

But I want to compare this to a time where I was called entitled for asking: I was working as a counselor at this fine arts camp, and all of the other counselors had single rooms (we were living in a dorm, not in tents or cabins), and two counselors had been asked to share a room. I brought this up with the person in charge, not in a public forum or anything but in a one-on-one, asking if that was something that could change. I was told that I was acting entitled, even though I was asking for the same thing everyone else got. I was also a young worker with not a lot of experience.

ESTER: Ugh. Older people love telling people they’re acting “entitled.” Older people act entitled all the time too, maybe more often; they’re usually just senior enough to get away with it. But yeah, if you’ve demonstrated your value, and especially if you have demonstrated that you are irreplaceable, your smallest whims will be attended to. When I spent the day as a pitch-woman for Progressive this week, I was the TALENT, which was a very strange feeling: everyone in the studio was there for and around me. At one point, after, like, my 15th interview, I started to feel dizzy under all the lights and my head hurt and I asked if maybe someone had some Tylenol? Just like that, the pills appeared. I laughed a little and said, “Wow, I guess I should ask for more things?” I was being rhetorical, but a voice in my ear, immediately, said, “Sure! Ask for more things!”

I need that voice in my ear more often.

NICOLE: So what would you ask for? I feel like this is the other difficult question. Is it more money? More time to complete work? Do I ask my landlord if he can replace the nasty-looking caulk in my bathroom? I’m happy with my compensation, I can meet my deadlines no problem, and my landlord already told me — before I asked — that if he redid my bathroom he’d raise my rent. What do we ask for?

ESTER: I don’t think one should ask for things just for the sake of asking for things. But I think at least occasionally asking for what you want, especially if you can be precise, is not just good practice for when it’s really important; it may actually mean you’re more likely to get exactly what you want. You, Nicole, are not a high-maintenance person. You’re accommodating, you’re flexible. But even you can probably think of one or two things you’d like from someone. Some responsibility you’d like someone else to take on, some freedom you’d like to take advantage of.

NICOLE: I have been told I’m high-maintenance at least as often as I’ve been told I’m entitled — which was a lot, especially when I was young!!!

But sure, okay, here’s an example of a time when I could have asked but didn’t: this week I met with a new CPA, and she asked if I could meet at a certain time, and I said “yes” instead of suggesting a time that would have been better. Which was not that big of a deal overall, because I was able to rearrange some stuff and it worked out fine. But I didn’t ask.

ESTER: Likewise, Ben is often telling me to ask him to take on more of the Second Shift stuff, things that I instinctively and silently take on that are usually related to the kids. I know I’m MS. FEMINISM around these parts but in my own head I still sometimes feel as though it’s my responsibility as the mother-wife to make sure there’s always milk in the fridge, or that the doctors’ appointments are calendared, or whatever. It drives Ben crazy and the added stress can make me crazy too — or at least it keeps me closer to the edge than I need to be. But my father never did any of that stuff and it’s hard to remember that my own partner is different than my mother’s was, and that the person I married is actually happy to take on his fair share.

NICOLE: Those are the kinds of people we need to find, both in our work and in our personal lives: the ones who are happy to take on their fair share. (I have never met Ben, but I know from your descriptions that he is amazing.)

ESTER: Aw, you’d like him! I hope he’s reading this and blushing. The thing is, I think most people in our lives probably want to treat us fairly and help us feel less stressed. Most people like saying, “Yes,” especially to people who are important to them. I mean, I like saying “Yes!” It’s fun to say “Yes!”

That said, what does your Labor Day weekend look like? Can you incorporate a little extra “Yes” or asking for something you want into it?

NICOLE: I already said yes to a friend who needed some volunteer help — I’m going to be teaching people how to play a new tabletop game at PAX this weekend. I can’t tell you how good it felt to say yes. It was like I could give someone something useful! Plus I get to hang out with friends and teach people how to play this game:

Illimat is Unveiled Witness or Participate 47.6110° N, 122.3324° W 2457633.500000- 2457636.500000 1200-1700

 — @illimat

What about you?

ESTER: I’m going to be among family all weekend down in North Carolina, where we’re celebrating a centennial. I imagine there will be many opportunities for me to ask for help. I pledge to take advantage of at least one of them. And to say “Yes” to at least one fun, stress-relieving thing.

NICOLE: Labor Day is about asking for what you need, after all.

ESTER: Happy Labor Day!!

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