How I Learned To Ask For What I Want

September 5, 2019  |  
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I wasn’t taught to ask for what I want. Unfortunately, that just wasn’t the case for me. My mom was a sweet but submissive and demure woman who mostly told me to “be a good girl.” She did not teach me to be a nasty woman. She did not teach me to be a boss. She taught me to do what I was told, and to be pleasant. So, from a young age, my motto was, “Just don’t cause any trouble.” Naturally, that didn’t help me in my career. Only the troublemakers—those willing to kick up a fuss and perhaps make others a bit uncomfortable—get anything great done. So for a long time, I didn’t ask for what I wanted. In fact, while I looked around at others getting what I wanted (while I didn’t get it), I still just took comfort in the fact that at least I wasn’t annoying/aggressive/overly-assertive. But you know what? One day, that stopped providing me much consolation and I just wanted what I wanted. So I had to get comfortable with asking for it. Here are some shifts in perspective that helped me do that.

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I do my research

First I’d like to get one thing straight: I don’t just ask for every single thing that looks appealing to me. I make calculated, well researched asks. And part of the way I do that is by having a mentor. If an opportunity catches my attention, I ask my mentor—who is well beyond having already conquered that milestone and others—if I’m ready and if it would be appropriate for me to go after it. We all want to jump from level one to level 10, and don’t often realize we are trying to skip levels two through nine, and the tastemakers or authorities in our industry see that, and find it silly. You can often only ask for something once, so make sure you’re ready when you do.

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It’s the only way anything happens

I eventually accepted that, while once in a blue moon, when I’m very lucky, somebody just thinks of me on her own for an opportunity and reaches out to me. But that will likely only account for about one to two percent of the things I get in life. The rest I’ll have to ask for. It’s very rare somebody just reaches out and offers an opportunity on her own. The people who get stuff asked for it. I ditched my pride around wanting people to reach out to me. It ain’t gonna happen (usually).

asking for what you want at work

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Somebody else will ask

If I don’t ask, somebody else will ask. And it could be (and often is) someone far less qualified. And she’ll get it, because she asked. I got tired of watching people who deserved something less than I do, have that thing, all because they asked.

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The person I’m asking is used to it

I used to worry so much about being a bother—about being seen as a nuisance to the person I’m asking for the favor. But you know what? Anybody who is in the position to give out favors is used to being asked. A lot of people ask them, every day. So I won’t stand out as particularly obnoxious. I’m one of many.

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I alone can’t protect her from the hassle

More on that last point, I alone cannot save this person from being hit up for favors every day. All I do by not asking is rob myself of an opportunity. But that person who I was going to ask for something, she’s still being bothered by others, every day. I didn’t spare her of that trouble by being quiet. I just screwed myself.

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She’s an adult; she can just say no

I also reminded myself that I cannot waste time worrying about putting people in an uncomfortable situation. Anyone I ask for an opportunity is an adult who is fully capable of (or should be) just saying no if they want to. If they say yes, I can’t worry that it’s only because they were uncomfortable saying no. That’s not my problem.

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And getting a “No” won’t kill me

Another important step was learning that getting a No will not kill me. It’ll hurt for a moment. But it won’t kill me. Nothing is actually taken from me when I get a No. I just don’t get the thing I wanted, but I don’t lose anything.

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In fact, a “Yes” will be embedded in “No’s”

Furthermore, I had to accept that the few Yes’s I’m going to get in this life will be embedded in hundreds of No’s. Any greatly successful person will tell you that they were rejected and failed so many times before they had their big wins. And there was no way they were going to get to the wins without suffering the losses. You have to take the bad with the good.

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Nobody hears about the rejections

This is another little talk I had to have with my pride. I had to remind myself that nobody outside of myself and the person I ask knows about this No. It’s doesn’t tarnish my reputation to get a No. Nobody really thinks about or knows about that.

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They just know when you get a “Yes”

The only thing outsiders remember or even notice is the Yes. We all know about the teams our favorite sports stars have played on, but we don’t know about the ones from which they were rejected. We know about the TV competitions our favorite singers thrived on, but we don’t know about the ones that wouldn’t even give them an audition.

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Well, I protect myself, too

I also give myself a bit of emotional insurance by doing this: when I’m applying for something/going after something, I don’t tell people. I only tell them if I get a Yes. I don’t tell my friends and family that I have applied to a job that I haven’t gotten yet. I just call them up if I get it. That way, if I don’t get it, I don’t have to tell them I didn’t get it. They didn’t even know I was up for it.

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If someone doesn’t like it, screw ‘em

I want people to like me and sometimes that’s a weakness. It certainly was when it came to asking for what I wanted. I worried that somebody who I’d been on great terms with would suddenly dislike me because I asked for something. But you know what? If someone dislikes me because I advocate for myself, I don’t want that person in my life. That means that person only liked me when I was weak.

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People usually respect it

Typically, people respect someone who asks for what she wants. Even if their answer is No, they still respect that you speak up for yourself. They remember that. Sometimes they keep you in mind for other things in the future.

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Sometimes, I get a different “Yes”

Sometimes, when I ask for something, I’m surprised to find that I don’t get exactly what I wanted, but I get something else—something I didn’t know I wanted or needed. I ask someone for an opportunity and they say, “I can’t give you this, but I actually think you’d be great for this other thing.” That never would have happened if I hadn’t just asked for the first thing.

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I skip the thinking phase

If I know I want something and have done the appropriate research a-la slide one, then I just ask. I have trained myself to skip the phase of doubting myself and thinking of all of the reasons the person will say no. That’s a useless phase. That’s wasted energy and time. It goes want: research: ask.

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