The Power of Asking

Colton Underwood, sixth-string tight end for the Oakland Raiders, was “just asking a girl on a date.” He had no idea that his video invitation to Olympic gold medal gymnast Aly Raisman would go viral. More importantly, he had no idea whether she’d say yes.

But you know what? He knows now. Because he asked.

Asking is powerful. It can also be terrifying. I briefly tried to start my own business with one of those skincare companies that mostly market their products through intimate house parties. The products were good and the company was good, but I was not good, because I hated asking (and I especially hated follow-up asking – when does it cross the line into nagging?).

In an effort to be kind, people who knew me personally would kick the can down the road, promising to reorder next month or to host a party in the spring. I learned to translate these responses the same way I interpret a “Maybe” RSVP to a Facebook event:

Yeah, that ain’t happening.

And yet, unbelievably, some of the biggest asks of my life have been answered, and even exceeded, by people who had no obligation to give me the time of day. I went out for drinks with my favorite author, and you know how I did it? By asking him on Twitter.

It was the day before the Boston Book Festival. While I planned to attend the full event, there was really only one person there who I wanted to see, one reason I had cordoned off an entire Saturday to, essentially, go to class: Scott Westerfeld, author of Uglies, Afterworlds, Midnighters, Peeps, and Leviathan, and my idol since, oh, probably 2005 or so, when I’d bought a copy of his book So Yesterday on vacation with my family and swallowed it whole on the car ride home.

Scott was slated to take part in a panel discussion with two or three other young adult fantasy authors sometime in the afternoon, and there was going to be a book signing after that. So the day was going to be a win no matter what. But I had been to enough meet-and-greets with bands to know that, at that sort of thing, you basically get your autograph (or your photograph – rarely both) and then you leave.

I had so much to say to Scott. I had so much to ask about. Which one question would I have time to ask as he scribbled his name on the title page of my copy of Goliath? You can’t really start with, “So you’re the greatest and I want to be you when I grow up can you tell me how to do that?”

No, I needed more time. I needed to talk to him at length. So I sent him a message.

And for some reason, he responded.

And that’s how, less than twenty-four hours later, I wound up at an exclusive, authors-only cocktail hour with my idol.


That cocktail hour honestly might have saved my writing career. It had been an absolutely harrowing morning, during which a panel of agents, who were supposed to give me advice on the first page of my manuscript, instead laughed at my submission and made me feel like I should just forget about that whole being-a-writer thing.

Scott put an end to that thinking real fast. “You have to find your people,” he said. “Those weren’t your people.”

He was right. My submission had showed an argument between a demon and his host just after the demon forced the host to kill somebody against his will. Gripping, right? Not to this panel. Their favorite piece had something to do with a crack in a wall. But like, that crack had seen shit, you know?

They weren’t my people. I am not ever going to write a story about a crack in a wall, unless Narnia or something is on the other side of it, and that panel would’ve liked the crack-in-the-wall piece a lot less if it had ended with the characters finding Narnia.

That’s fine. There are deeply passionate readers and writers of literary fiction. They love the genre and do good work. But I’m not one of them, and if Scott Westerfeld hadn’t pointed it out to me that day, I might have just given up instead.

Thank God I’d been brazen enough to ask.

Asking has gotten me through the door with other favorite authors and musicians. It has turned networking events into paying gigs. As a journalist, it has gotten me interviews with people I never would have met and opened doors I never would have thought to knock at.

In 2013, when I asked my church if I could paint over the depressing beige walls in our basement with lime green and invite a bunch of teenagers to play music and board games there, I had no idea that the community we started would survive three years and continue growing bigger than ever, with new people in new places and new ideas taking shape all the time.

Sometimes it feels like I have no right to ask for these things. Believe me, I can hear how crazy I sound. Do I deserve the good things that come to me any more than the next person? Absolutely not. We all deserve good things. We all deserve to see at least one of our crazy fantasies become, against all odds, reality.

The only difference is that I asked.

This post originally appeared on the Odyssey Online.


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