A collage of illustrations of various helicopters.

Sip On This

How to Walk the Fine Line Between Helping and Hovering

When you love a friend, you want to fix their problems, but is it your job? And how do you tell your well-meaning mom to back off without ruining the holidays?

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Dear Ashley,

I like to think I’m a supportive friend — I’m pretty sure I am — but I also can’t bear to watch people I love step in shit. So here’s the situation: One of my closest friends has decided to take on something she’s terrible at, because she has to, but it’s just not working. She’s a pretty successful artist, and like many artists, she’s taken on a teaching job. But, here’s the thing: She hates teaching. She hates anyone and anything cutting into her studio time. And I get the sense from the way she’s describing her classes that the students hate her. I’m worried she’s not only creating animus and misery for them and herself, but that she’s going to get fired. Is there a way to gently nudge her toward finding another job so that this doesn’t explode in her face? Or do I let her find out the hard way even though it’s unbearable to watch?


Helicopter Friend


Dear Helicopter,

LOL, You’ve named yourself appropriately. I think it’s really sweet how much you care about your friend! It’s almost weird how much. But touching! It sounds like maybe your friend took this teaching job because she needs the money? Art, even when you’re really good at it, tends to not be a consistent way to earn money. I’m assuming she likes to do things like pay rent and buy food, and money does tend to come in helpful for those things. Sometimes no matter how much you hate your job, you just have to keep doing it because of the rent paying and the food buying.

She probably finds it helpful to have a friend to rant to, but that doesn’t necessarily mean she wants you to fix her situation for her. Or even that she wants to fix it. Sometimes people just enjoy complaining! Or is that only me? Ugh, I hate it when people don’t understand how much I enjoy complaining. Maybe teaching is fine, but she feels like she needs to say it sucks because “real artists” aren’t supposed to enjoy teaching. Maybe it’s actually killing her. There’s only one way to find out: ask her!

Tell your friend that you care about her, and she seems dissatisfied at work, and just ask her what she needs from you: a listening ear, a sounding board, help looking for a new job, or figuring out how to make more time for the studio, etc. Don’t assume you know what’s best, find out what she actually wants and needs. Pro-tip: Probably don’t tell her you think she’s terrible at her job and is about to get fired. That is an inside thought. And if it turns out that she’s in a place right now where she has decided she’s going to keep doing a thing that she doesn’t enjoy doing because capitalism, then your job as a friend is just to support her and let her know that you will be there no matter what her job title is.

Anyway, please be my friend. You seem like a very good one.



Dear Ashley,

I love my mom. I’m so thankful to her for everything she’s given me—including life—and we genuinely have a great friendship now that I am an adult human who can take care of herself (mostly). And she remains my biggest cheerleader, which even for a grown kid matters a lot. But the thing is, she’s also trying to be my spokesperson, or agent, or something I never hired her to be. She’s constantly volunteering me for things I have NO INTEREST in doing, and all but assuring her friends, members of her church congregation, long-lost relatives I’ve never met, strangers she meets on the street and strikes up conversation with, that I will “certainly,” “love to” “help out” “in any way.”


Her friend has written a memoir, does she know anyone who can help edit it? “Of course, my daughter would love to!” No.

Her pastor has a book signing, does anyone know how to write a press release to spread the word? “Yes, my daughter can do that!” Technically, I can, but no.

Her neighbor’s son’s girlfriend is opening a restaurant, does anyone know how to get in touch with local media? “Yes, my daughter can review it for the local paper!” I am not even a food critic!

Her cousin’s daughter is applying to college, can I help her with her entrance essay? For fuck’s sake…

I am a writer and editor by trade, skills that I am used to having taken for granted, but not by my mom, the woman who signed checks to pay for the journalism degree I use to keep myself from living in her guest room. She should get this, but alas she does not. How do I tell my mom to stop treating me like free labor for her friends and respect that what I do for a living is not charity work—no, not even for a charity?


Trying Not to Ruin Thanksgiving


Dear Thanksgiving,

This is a toughie! It’s tough because it’s so obvious that your mom’s heart is in the right place. But if she wants you to do all this work then her heart better be in her wallet because you need to get PAID. Show her that Rihanna video! BITCH BETTA HAVE MY MONEY. Just kidding, don’t do that. Unless your mom has a very good sense of humor, that will go very poorly. This is why you shouldn’t come to a comedian for advice.

I think that you are probably right that your mother does this in part because she doesn’t understand the work, and skill that goes into writing. A lot of people don’t. Everyone can write an email, so they figure that you writing an article takes the same level of time and attention that writing an email takes for them. In which case, OF COURSE, you have time to write a quick article for their cousin’s sister’s hairdresser’s dog’s groomer’s girl. But it’s also probably in large part because your mother is super proud of you and wants to show you off. Or maybe she even thinks she’s helping your career by getting you more exposure. Who knows?! No one until you ask her. But there’s probably mostly good intentions there, so keep that in mind when you talk to her. Don’t ruin Thanksgiving!

There are one of two ways to go about this: One is to simply say: “No, I will not do any work for any of your friends. Do not tell them I will, because I won’t.” No is a complete sentence, and you’re well within your rights to just say that.

But it seems like you take pride in your close relationship with your mother, and there is another approach that might actually help deepen that closeness: bring your mother into the process. Sit her down and, without condescending, share with her how much time you spend researching, pitching, re-researching, writing, re-writing, and editing your pieces, and then hounding people for payment because NO ONE EVER FUCKING PAYS WRITERS ON TIME AND IT MAKES NO GODDAMN SENSE WHY I HAVE TO TURN IN MY ARTICLE ON TIME BUT YOU CAN TAKE ANYWHERE BETWEEN THIRTY, NINETY, OR A MILLION DAYS TO PAY ME LIKE MY LANDLORD CAN AFFORD TO JUST FUCKING WAIT AROUND WHILE I SEND YOU MULTIPLE FOLLOW UP EMAILS sorry, I got distracted. Where was I? Oh yeah—share your career goals with your mother. If you tell her your dream job is to write a book about criminal justice reform, she will probably understand why writing a review for her cousin’s housekeeper’s new tapas bar isn’t very helpful for you. I bet she just wants to be included! Also, as long as she’s putting her time into finding you connections anyway, you might as well read her in so she can find relevant ones!

And if she really wants to be involved, recruit her to start sending those payment follow-up emails for you. Then she’ll see how hard being a writer is!

Enjoy your Turkey!


Wait, Keep Sipping! Our new podcast, SOT with Ashley Nicole Black, debuts Oct. 19. Listen to a preview of the star-studded season here, and subscribe NOW. If you have a question for Ashley, write to her via [email protected]

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