The Art of the Ask

One thing I hugely admire about Naomi-my-internet-crush (aka Itty Biz) is the way she totally asks for things. “Huh. What type of things does she ask for?”, you ask. Well, pretty much anything she wants. It’s fantastic.

It’s not just the way she asks for what she wants since I’m also in mind-melting awe of the way she gets it … but that’s another part of the equation altogether. Actually, it’s so far out of the equation, it might not even be up on the same chalkboard.

The thing I’m thinking about right now though is how Naomi sums up her philosophy/outlook/whatever in such a completely different way than I would. For her it’s basically all about “If you don’t ask, you don’t get … so I’m asking.”

The concept — especially the way she freaking lives by it — rocks my world. Talk about applying your philosophy to real life. Love it. Want it.

Thing is, the phrasing just isn’t working for me. And here’s why.

Don’t ask = don’t get? Always? Not doing it for me. Too many minuses in it. Too many rules.

I can almost feel a subconscious block downloading into my brain. And it’s coming from a (potentially problematic) assumption that’s hiding out in the equation — of the kind that linguist Suzette Haden Elgin would call a stowaway.

“Don’t ask = don’t get” is really an If-Then equation that doesn’t necessarily always have to be true.

Don’t get me wrong. Asking is absolutely a skill worth honing. Asking people for stuff. Also asking yourself for stuff. All of it. Whether you want to take it on as a conscious life practice or you just want to land some schwag, totally worth your while master the Art of the Ask.

So I’m just going to institute a teensy edit into the phrasing. From here on out — for me, anyway — the don’t-ask-don’t-get rule will be known as: “Ask and what the heck, who knows, you might even receive.

Actually, forget the receiving part. That’s not the point.

Way before you even want to think about the receiving, know that it’s the ask that’s important. Like I said, it’s a skill. And one that we (all of us, but especially us chicks we ladies) don’t always work on because it is tied up in a lot of scary. There are so many what-ifs that come along with the ask. Like:

What if I get rejected and laughed out of town? What if this person I like / respect feels awkward and uncomfortable and stops liking / respecting me? What if they say yes but secretly resent me? What if I lose all the confidence I’ve ever had and go slink under a rock and never come out?

Yeah, the what-ifs make asking really hard. The thing that’s helped me the most with learning how to ask is a concept I picked up from Mikelann Valterra from the Women’s Earning Institute in Seattle.

Here it is. The ask is the win. Even better, it’s the first win.

Which means …? Well, for starters, it means you mentally agree to shift your definition of winning.


“Success means one thing only: I ask for the thing and I get the thing. If I don’t get it, I’m a big ole failure who should be pelted with tomatoes.”


“Whoah, I totally worked on my pattern and asked for the thing! Right on.”

That’s what the first win means. You asked. You pat yourself on the back for doing something which is (potentially) hard and scary. Then, if you get the thing, it’s the second win. But either way you have one thing to be proud of.

But wait, isn’t that kinda lame? Also: what should I do?

I’ll be honest here. When I met this concept for the first time, my initial reaction was an annoyed eye-roll from my inner-perfectionist.

C’mon, everyone knows you can’t trick yourself into thinking you don’t suck just because of some motivational lollipop. A win? But then I thought about it some more and realized, no, I can get used to giving myself credit for asking. Asking is a pretty big deal for me and working on feeling okay with it is a legitimate practice.

So nice reframe, Mikelann. Thanks.

Alright, so if the ask is everything (and I’m telling you it is), how are you supposed to do it? I think entire books have been written on this stuff, but here are a few examples. What to do, what not to do, and (bonus) what can happen when you don’t linguistically trip yourself up with a limiting if-then premise.

Examples of doing this asking thing *right*

You know how I met Naomi-my-internet-crush (aka Itty Biz)?

She emailed me and said, sweet, flattering things about me and my website. And my duck. I responded in kind. Then she said, “You know when your mother says ‘If you don’t ask, you don’t get'” and then came out with an ask. It was a legitimate ask and it didn’t violate my principles or my duck (horrors!) so I said, sure. And then we became friends. She asked and she got it.

You know how I migrated my enormous website to wordpress?

I asked Nathan Bowers who is a WordPress Consultant, for crying out loud, if I could ask him some questions. It felt a little like going out on a chutzpah limb but we’re Twitter pals and I decided that as long as I gave him an easy out, I could do it. And then he told me what I needed to know and then some.

And all he wanted in return was one tiny piece of advice which I was 100% happy to give and which apparently was all like, knock-yer-socks-off-ariffic. Or something. All I know is 1. he said I was a “super dynamo of helper-ocity”, and 2. don’t go bug him — hire him and give him lots of monies because he totally deserves it. Yeah, that’s right. Find your own Ask!

Anyway, these are both examples of Possible Situation #1: you ask, you get.

Examples of getting this asking thing *wrong*

You can’t really ask wrong. Well, you can, but in general the wrong way to do it is by not asking.

This awesome woman I know, Penny Hoff, decided to self-publish a book of her writing, called Fitness Rants For The Chronologically Enriched. Penny is a yoga/fitness instructor with a seriously great, very wry sense of humor and her writing is motivational, but totally not preachy (read: the rare kind that doesn’t get on my nerves).

Anyway, she self-published without asking anyone for advice because (I think that’s why, unvalidated theory here) she didn’t want to bug people.

And the book ended up being unbelievably expensive. $42.50, in fact. Per book. So even if she was willing to not make any profit at all and just break even, she was going to have be the best saleswoman in the world to move these things.

I know at least five people we know in common she could have asked about this, including me, but she didn’t and I don’t blame her for that because I do stuff like that all the time. Asking is hard. And awkward. And scary. That’s practically the whole point of this post.

$42.50 per book. Ugh. And that’s your example for Possible Situation #2: you don’t ask, you don’t get.

For the win: Examples of doing it wrong and still *winning*

The better you get at asking, the better you get at being able to receive help and support. Which is one of the hardest things there is.

Luckily, you can feel better now about the depressing example above because I’m an exceptionally nice person. Well, I have my moments. Even though she didn’t ask, I sent her some suggestions for different ways to give people more while actually making money from the book so as not to feel like she was scamming people. Because she’s not like that.

And then sent her straight to Booklocker where she was able to republish her book for 42% less. Go Booklocker. If Booklocker were a car, it would run on integrity.

This is an example of Possible Situation #3: “you don’t ask, but you still get”.

Ha! You didn’t ask, but you got it anyway.The best thing about Possible Situation #3 is that it’s like a finger in the eye to that crotchety old “you don’t ask, you don’t get” rule.

It turns it around and morphs it into something more like this: (said in old lady voice with yiddish accent): “Okay, so you didn’t ask. Is it a crime you didn’t ask? Too bad for you, bigshot, because you’re going to get what you want anyway, whether you asked for it or not, alright? Good. Good? Good.”

Okay, this post is already way longer than it was in my head. So I’m going to stop writing now. But I would love it if you would go out and ask for something. Even something really small. Start where it doesn’t feel impossible. Maybe you’ll get it. Maybe you won’t. But you’ll get better at asking.

[Bonus practice for people like me who can easily think about this kind of thing all day: Since there are probably other If/Then equations that you live by that could be messing with your game, any ideas as to what they might be?]

The Fluent Self