A still of Meryl Streep standing up and Anne Hathaway sitting down in "The Devil Wears Prada" in an office setting.

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Sip On This

20th Century Fox

Are Other People’s Emotions Your Business?

When low self-esteem is sabotaging a job search, and someone else's drama is keeping you up at night, consider this: It's not them, it's you.

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Dear Ashley,

I am in the midst of a career change that has me both scared and excited. I am hoping to pivot out of my current industry and enter a new one, eager to convince my new prospective employers that my skills match their needs. I have been networking, studying these new employers like I have a term paper due on them, and invested in résumé and job coaches to prepare myself for interviews.

The problem is, I’m not getting interviews, and I worry that it’s my lack of confidence that’s holding me back, not my skill set. For this type of career change, I think I need to be 1,000 percent more aggressive than I have ever been on a job pursuit, but I’m not sure how to do that. I am accustomed to sending in an application with a résumé and a letter, sending one polite follow-up email, and that’s it. I know I need to do more. Cold-call the recruiters? Relentlessly email the company? Show up in person? Every time I think about doing something that bold, I start to sweat. I’m terrified of being perceived as pushy or rude. But I know—KNOW—men do this ALL. OF. THE. TIME. How can I be more like them but not—because who needs more men?


Just a Girl, Standing In Front of An Employer, Asking It To Hire Me


Dear A Girl,

Oh man! Reading your letter made me feel like I was transported back in time to last time I was doing a job search. It’s the fucking worst. Here you are, trying to put your best foot forward and impress people while at the same time the very process of looking for a job makes you feel so worthless and ruins your confidence. So I just want to start out by saying, there’s nothing wrong with you. Feeling like your worth and your confidence are based on where you work, and how much you make, is the shitty effect of capitalism and we’ve all been there! So give yourself a break. It sounds like you’re working very hard and doing all the right things!

There’s a good chance that your problem is not your confidence and it’s just that you aren’t as familiar with the industry you’re trying to move into. I know that men tend to be bolder, and reach outside their skill set more, in the jobs that they apply to. So that’s a thing. There’s probably some buzzwords you could include in your application, or some industry connections you could make, that would move your resume closer to the top of the pile. Unfortunately, I’m more of a like emotional advice person, and not like a career advice person (seriously, I write fart jokes about the president for a living—don’t take career advice from me) so for that kind of advice you’ll need to find a real career consultant. So yeah, that’s my advice, ask someone more qualified for advice.

But on the confidence tip… THAT I can help with! I really do think it’s very possible that the reason you’re not getting interviews has nothing to do with your confidence level. Mostly because you aren’t getting interviews, so like… they haven’t met you yet? How would they know how confident you are or aren’t? Unless you’re writing “I’m not very confident” on the top of your resume, they have no way of knowing. I mean, if you’re doing that, stop. But I bet you’re not. So you bringing up your confidence just makes me think that your lack of confidence is bothering YOU. And you’re projecting that on to these potential employers you’ve never even met. So that’s interesting. What can you do with that information? Probably talk to a therapist about it? I deeply apologize that all my advice to you involves you finding another advice person to go to. But I honestly think that whenever we’re projecting that means there’s probably a deeper issue being triggered that therapy can help with.

That being said, the way I work on building my confidence when it needs a lift is by making something. Doing something that I can complete and be proud of always gives my self-esteem a boost. From something as small as cleaning the kitchen, or teaching my dog a new trick, to as big as writing and producing a comedy show, completing something always makes me feel like a rock star! AND GUESS WHAT? That’s also a great way to find a job. OMG, I’m so good at giving advice. I feel very confident in this advice giving right now. See? It’s working.

I think in the modern marketplace the traditional job search may not be working as well as it used to. You should still do it, but you should also take the modern (more confidence building) approach: start doing the job you want and wait for the employer to notice you’re already doing it and then come offer to pay you for it. I don’t know what industry you’re in, and what that would look like for you. But for example, if you want to be a journalist, start writing articles and posting them on Medium and tweeting them out. If you want to be a comedian, start doing live shows and posting the videos and tweeting them out. If you want to be a financial advisor, start offering your friends free financial advice and have them tweet about it if they liked it. If you want to work in the nonprofit sector, plan a fundraiser, take pictures during it, and tweet them out after. If you want to be a teacher, kidnap some kids and take pictures of them holding up that day’s newspaper and tweet them out. That’ll get some attention.

By giving yourself the job you want, you’ll build your confidence because you’ll be doing the thing you want to do without waiting for some all mighty corporate entity to give you permission to do it. Also, you’ll get better at it, people will likely take notice, and then maybe the job will come to you! Or at least you’ll have something to write about when you send those follow-up emails.

Don’t kidnap any kids. That was a joke.



Dear Ashley,

I have a friend who is completely unrealistic about love. She is over the top and wants over-the-top romance and communication around the clock. Her mood is completely determined by men and if someone watched her IG story or commented on another women’s pics. I love her, she’s one of my best friends, but when she’s MADE HERSELF SAD because a boy hasn’t texted back, it’s hard for me to suck it up and validate her feelings. I mean, one of my friend’s had just lost her brother to a terrible accident and then this friend is crying about someone no longer looking at her IG stories. I almost screamed. Did I mention she’s almost 40? Anyway, I don’t know how to tell her all of this without hurting her feelings because she’s sensitive—obviously. I think she could benefit from seeing a therapist but she’s also the type that thinks she’s above therapy. Any advice I do give sounds like a broken record at this point, so I don’t know what to do.


Friend of An Emotional Vampire


Dear Friend,

Man, I wish your friend would write in. I have a lot of advice for her! But I’m not going to type it here, because she didn’t ask me for advice, you did. BUT I HAVE THOUGHTS.

Here’s the thing: your friend’s emotional state is her own. It’s none of your business. Of course you care about your friend, and want what’s best for her, and have an idea of what that is, but you are not the boss of her and you can’t tell her what to feel. You offered advice, and it’s her right to reject it. You’re just frustrating yourself by spending your time trying to tell another human what to feel. That’s just not something you’re in control of.

What you are allowed to do, however, is to set boundaries around how you would like to be treated. And if you don’t want to have any more tearful conversations about boys on Instagram with a grown-ass woman, and LORD KNOWS you are entitled to that want, you have every right to set that boundary. But you need to set it based on what YOU want and need for yourself, not what you want her to do. Because what she does with her free time is, I repeat, not your business. I would say something like this:

“Darling friend who I love ever so dearly, I know I’ve told you that I disapprove of how you deal with relationships with men. I also understand that you’re not interested in my advice about that. So I’m going to respect that, and stop offering you advice on this topic. This is the last conversation we’ll have about it. I’m concerned that the way you ruminate over men is harmful to you. I’m also concerned that by participating in conversations about those ruminations, I’m participating in something I think is harmful. So I’m going to ask you not to have those conversations with me anymore. When you bring it up, I will probably change the subject, or gently remind you that this is no longer a conversation that you and I are going to have. I’m not upset with you. I love you and want the best for you. This is a boundary I need to set for myself. Let’s continue to talk about all the other interesting and important things that are going on in your life.”

Or, you know, phrase it like a human and not like a robot that has spent way too much time in therapy. The important thing to convey is that you no longer want to talk about dudes on the gram, and this conversation is about how you would like to be treated in your relationship with her, and not about you trying to control how she lives her life.

Good luck! I hope you get back to talking about 401ks, or whatever the fuck grown-ups talk about, soon.



Sip On This has BIG NEWS: We’re starting a podcast! Hosted by the hilarious and genuine Ashley Nicole Black, the show will feature a different (shhh, kind of famous) guest each week, and weigh in on life questions from YOU! Write in your questions to [email protected]

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