Asking for What You Want


Me asking people to give me money.

The past week, I’ve attended a few different events centered around women entrepreneurs. The events were great and excellent opportunities to network and learn. But as usually happens when you attend events centered around a specific topic, you start to see recurring themes. Time and time again, I heard the point raised that women need to be better at speaking up and asking for what they want.

It’s not a new point – from Sheryl Sandberg talking about it in her book “Lean In” to it being a common issue raised at conferences or panels. To be fair, it probably is something many women might need to work on. But to be clear, women not being vocal enough isn’t the real problem or the reason why women get a negligible share of VC funding and so few board seats (although that’s a different post).

I can’t say that I can completely relate – as I’m not the kind of person who feels that I have to wait permission to speak or that I can’t ask for what I want. As one of my former editors can likely attest, in every weekly performance meeting, I used to ask for a raise. (While, I did not get one every week, I did get a few.) As an entrepreneur, you sometimes encounter really great folks who say, “Is there any way I can help you?” And recently I having been saying, “Yes, I need money.” They do not just cut you checks on the spot, but several have helped by making introductions that can get me closer to folks who cut checks.

As I’ve been hearing people both say that women need to get better at asking for what they want and other women saying they have a hard time asking, I started reflecting on why I didn’t seem to feel that way. (If you know my mother, you can probably guess why.)

I remember being in second grade when an adult said to me, “Didn’t anyone ever tell you children should be seen and not heard?”

I had been asking questions about something or other. I have always asked a lot of questions.

“Yes,” I replied. “But my mom says that’s stupid and that I have as much right to talk as anyone else.” (If you know my mother, that probably does not surprise you at all.)

The look on the person’s face is probably what has embedded that moment in my memory.

Needless to say, my entire life, I have always felt that I had the right to speak my opinion and/or ask questions. As I’ve grown older, I have come to see that not everyone feels that way. So often, I hear people lamenting, “I really wanted to say something, but…” or “What I wanted to ask was…” I know people who have gone years at a job not asking for a raise or promotion because they didn’t feel comfortable asking for what they wanted.

kids with cookies and cereal all over the bed

Here my children have learned the key to getting all the Oreos you want is just to ask… Ask Grandpa, that is.

My belief that I always had the right to speak is probably why I was able to be a journalist for some many years as it’s a job that literally centers around asking random strangers questions. I’m not saying it’s always easy. I don’t really enjoy the fundraising and sales processes of a running a startup – there are few things less fun than having to ask people for money, knowing most of them are going to say no.

But I’m also a believer in you don’t get things unless you ask – whether it’s money or sales or information. It’s an important skill, one that I’m working to make sure my children possess.

“I can’t speak my voice,” my 3-year-old told me recently. He wanted his dad to give him an apple, but wanted me to ask for him.

“I’ll come with you to ask him, but you have to ask,” I said.

If he can’t ask his dad for something, how on earth will he ever ask anyone else?

One of my many proud parenting moments came when my oldest daughter was not quite 5-years old. We were at the American Girl Doll Store in New York City, and she had some specific overpriced doll outfit that she wanted for her birthday. Like most preschoolers, her preference was to have me ask for things for her. But that day, we walked into the store, and she walked right up to the clerk on her own with a level of confidence I did not know she possessed and asked for what she was looking for. I was so surprised/impressed that I ended up somehow agreeing to pay $10 to get her dolls’ ears pierced on top of the rollerskating outfit we bought. But that moment stuck with me, because it showed me that if there was something she really wanted, she wasn’t going to be hesitant to ask – even if it meant pushing herself outside her comfort zone.

Of course, I have gotten many dirty looks from my daughters – and have suffered through several meltdowns over – making them ask for things. But it’s worth it for them to learn if you want something you have to ask for it and that no else is going to ask for you. (That doesn’t always mean you’ll get what you want, but again, that is a whole other post as well.) And while they might think that I’m mean and unreasonable, I know firsthand that being able to “speak your voice,” will get you a lot further in life than you might think.

You know what else will get you further in life? Math skills. Check out our games that teach those skills here.


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