looking for rejection

+ a new york workshop!!

Cecily Brown, Rainy Day Women, 2007

dear bear,

i recently graduated college and am faced with soul-crushing anxiety about jobs and career that i've been trying to keep at bay for the past few years. i'm infinitely lucky that i've found what i love to do (and am quite good at, i think?) but that just leaves me with anxiety about how to do the best i can in my career. i know what my goal/desired position is for the short term, but it seems so hard - impossible even - to get my foot into that door. i apply to things, get to nearly the final stage, then am turned away for things beyond my control. i have a job i don't love, in a field i don't love, with what seems like little to no room to grow into the direction i want. i guess my question is: how do i combat this uncertainty and fear? how do i move forward when it feels like i know exactly what i want, but i don't know if/when i'll be able to get it? more broadly: how do i know what to do *at all*??

Hi Bear,

Your question couldn’t have come at a better time. Ever since the workshop Rishi and I hosted last month, I have been “on one” (as S describes it). The workshop was about conflict, and facilitating it made me understand my own fear of conflict in a deeper way than ever before. All my life I have been so afraid of speaking my mind!! Why? Because I might make people feel bad. And what would happen if I made people feel bad? Well, they might not Love Me Anymore, and I’d be a Bad Person. So you see, my fear of conflict is really tied up in shame, and also really tied up in a fear of Rejection. (If you’re close to me and have noticed that I’ve been… really willing to initiate conflict lately… blame the workshop.)

Maybe you’ve heard of Ask Culture vs Guess Culture. People who belong to Ask Culture feel able to ask for whatever they want, but they know they might get a no. People who belong to Guess Culture only ask when they’re verrry sure the answer is yes. As you might tell from the paragraph above, I have historically been a Big Time Member of Guess Culture. Maybe it’s because of my parents. Maybe it’s because I’m Chinese-Canadian. Maybe it’s because I’m a girl. Or maybe it’s just because I’m a coward. But I really do not enjoy asking for things and getting a No!!! It just makes me feel so terrible about myself. Like, let’s say I apply for something, and don’t get it. I historically would take it so personally—like, they saw into my Soul and decided I Wasn’t Worthy and I am now being Punished for Wanting Something I Don’t Deserve. Which is, now that I’m spelling it out like this, really quite a self-absorbed way to think—I’m making everything about Me and My Own Worthiness. But I think it’s actually very common! It is extremely normal to have a Terrible relationship with rejection.

All this to say that I have been in your position exactly—I have something I really want, and then I apply to a position or maybe even five, and then I make it to the final stage, and then bam—I get the NO. Or maybe I don’t even get the NO, I just get no response. And then I sort of crumple in on myself and feel dejected and undeserving.

But the thing I’ve been really leaning into lately is—what would it feel like to believe that the NOs are good? That the NOs are a way to getting to the yes? What would it feel like to actually Enjoy getting a no?

Now, despite being a big time member of Guess Culture, I do have experience Asking for things. I worked on a startup and I now am an Internet writer and I just generally have had an unorthodox career path. So I’m no stranger to a cold emails and asking for strange favors. And I actually do know that sometimes what it takes to get to a Yes is to just ask a lot of people. Of course sometimes that means iterating your approach—like, maybe you need to adjust how you’re asking, or you could do something to make yourself a stronger candidate. And of course incorporating some of Guess Culture and asking people who are way more likely to say yes is important. But if you’ve ever been in a situation where you’ve actually asked a ton of people, say 100, and 10 of them say yes and 90 of them say no, you understand the value of just pushing through it. Sometimes the raw persistence is just what it takes.

But MAN it’s so hard being persistent when you have shame around every no!! When you take rejection so personally that you’re psychologically debilitated by it. When I look back at my life now, I’m just like, I wish I did more asking!!! There are so many situations where I truly wish I’d had the courage to get 50 NOs before giving up. Everything from submitting poetry to raising money to applying for various things.

And it’s like—my life now is literally enabled by Asking. I ask people to pay for my writing so I can make a living. I ask nice people like you to submit questions so I can write my advice column. I share links to these posts on Twitter and Ask people to click on it so they discover my work. This is all quite challenging for someone who can be so intimidated by ordering at a restaurant that I’ve been accused of using a “shy little mouse voice” while talking to servers. But it is also so incredibly fulfilling to put yourself out there in that way—to say, hey, I believe in myself, and I’m asking you for this thing, and it’s actually totally okay if you say no. But it would be so so cool if you said yes.

There is no penalty for asking. You can apply to the same thing 10 times and no one’s gonna get mad at you. You can advertise something on the Internet and even if 99% of people think it’s dumb, 1% might think it’s really cool. You are always doing things for the one person who will give you the yes. And often one yes is enough. I’ve been trying to reframe my relationship with rejection from avoiding it to literally looking for rejection—going out there and risking the NOs. I’ve been doing it in really silly ways, like trying to buy an staff-only hoodie at my favorite grocery store and walking into restaurants when there are no reservations available, but also in meaningful ways like proposing writing collaborations and meeting new people. It’s so fun! I can’t believe I’ve been running away from it for so long.

When I look back to my younger self, I see that I was obsessed with getting permission. I really wanted someone to tell me what to do and reassure me that it was okay. Like, yes, you should work on this company. Or yes, you’re allowed to be a writer. And I think some people do find someone like that, a mentor who gives them permission, and they benefit a ton. But personally I had to realize that no one really cares what I do and that’s both scary and freeing. It’s scary because it’s all on you but it’s freeing because there are no rules. You’re allowed to do literally anything you want as long as you don’t break the law or hurt anyone else. Permission doesn’t really exist in the way you might imagine it to because no one is in charge of your life except for you. You don’t have to sit on the sidelines, guessing where it’s okay to jump in. You can just start doing things.

Bear, you asked me what you should do, but you sound like you know what you want to do! If you’re fortunate enough to know what you want, it’s just about trying different paths to get there. I think you should pursue the thing you want with a demented level of persistence (coupled with careful analysis of how to best achieve your goal). Jam your foot in the door!! Kick it down!! Be willing to ask 17 times or 177. And sit with the extreme discomfort and uncertainty and fear of not knowing that you’ll get what you want. The discomfort is a gift. Being able to endure the discomfort is what will make you the person you want to be.

This is a perfect segue into announcing that Rishi and I are going to do another workshop on June 22, in New York, and it will be focused on… you guessed it… rejection. The workshops are an opportunity to discuss and confront your relationship with something you’re afraid of but also trying to embrace. We’ve received feedback from many participants post-workshop that they’ve been able to initiate conversations that they were really worried about having. I can personally assure you that facilitating the workshops has helped me enormously. It’s from 10 AM to 5 PM with long breaks and ample opportunity to chat. And then some very intense roleplaying sessions. Lunch will be provided. And if you register in the next seven days you’ll get $75 off :)