It Always Hurts to Ask

I don’t like to ask for favors — but you probably won’t guess that from how often I ask for favors. In the past 24 hours, I’ve asked a friend to take photos for my train tour press kit, cold called an event space about using their venue for a book event, asked a handful of other authors to donate their time to that event, asked to crash in the D.C. apartment of a co-worker I knew a decade ago, and emailed friends (and a few strangers) for help finding contacts for my New York book signing. And that’s not even all, I just feel like this paragraph is getting boring.


People say, “It never hurts to ask.” That’s silly. Of course it hurts to ask — if it didn’t hurt, we’d probably do it more easily. It can hurt to ask if the person you’re asking feels used and it damages your relationship. It can hurt to ask because you might get no for an answer, and (for me at least) the real no hurts more than the theoretical one. Even at the best of times, when you get what you asked for, it’s hard to admit that you need someone and to put yourself in the vulnerable position of feeling grateful and/or indebted to another person.


I read Amanda Palmer’s The Art of Asking at the close of my Kickstarter campaign, and it was incredibly encouraging, inspiring and comforting. She really bravely exposes her fears and insecurities, and reading about the similarity of her struggles to mine (even though she operates on a much bigger scale) was so helpful to me. I’m hoping to write a little review of her book soon, but it also got me thinking about my own strategies for asking. I certainly don’t ask perfectly, but here’s how I’ve tried to ask for favors for my shop (Church Street Coffee & Books) and for my book (The Localist) — and I guess for the rest of my life, too.


Carrie Rollwagen’s Art of Asking


Make it easy to say no


This can certainly be counter-productive, because people actually do say no, but I think it’s important, partly because this is how I want to be asked. (Oh, and I get asked to do favors a whole lot, too — it’s a two-way street.) The people you’re probably asking for favors are talented and giving and in-demand already, and that means they’re most likely stressed and stretched a lot of the time. I think it’s only right to help people feel comfortable telling me that they’re too busy or I’m asking too much, or even just that they don’t feel like helping at the moment. I want them to know our relationship is still intact no matter how they respond. (In order to do this, though, you really do have to be willing to let it go if they can’t help.)


Shrink the favor if possible


Especially when asking for professional favors (videography, graphic design work, web development, photography — all of which I’ve asked for with The Localist), ask what you can do to help. When Seth Newell shot my Localist book Kickstarter video for me, I wrote the script, arranged for locations, did the propping and ordered food for the shoot without his help — not because I didn’t want it, but because he was already doing me a huge favor by showing up and shooting, so it was my responsibility to do as much as I possibly could beforehand and not make a gigantic favor even bigger. Only asking for what you really need is key, particularly when you’re asking creative professionals to donate skills they usually get paid for. (This applies to revisions, too — keep them to an absolute minimum. For some reason, pro bono clients are usually the pickiest, which is kind of the definition of adding insult to injury — and understand that asking someone to donate time that they usually get paid for is kind of an injury.)

Be grateful


It’s kind of stupid that I even have to write this, but because I give out a lot of favors, too, I know that a lot of people miss it. Being grateful means saying thank you (and probably following up with an email thanks as well), but it also means buying lunch or coffee or drinks for your friend while they’re helping you. (It’s a small expense, and it shows that you understand they’re doing you a favor and are doing what you can to acknowledge it.) It means asking the best way to give them credit — Morgan Trinker’s shooting photos for me today, and I’ll be asking her if she wants a photo credit, where she wants me to direct potential clients, and how she wants to be tagged on social media (oh, and you should totally follow Morgan on Instagram because she’s awesome). It also means being as accommodating as possible to the schedule and preferences of the person helping you — work around them, don’t make them work around you.


I’m not saying these tips are going to make asking easier; asking is still hard for me every single time. But trying my best to honor the help that other people are giving me does make it feel a little better, and they seem to appreciate it, too. The Localist book couldn’t have happened without the support of so many people, including all my Kickstarter backers (thanks, guys!), and this train tour I’m trying to put together has already been saved over and over by friends, booksellers across the country, and strangers who are generous with their time and ideas. Does it hurt to ask? Definitely. But the best things in life usually hurt a little bit, too.


Carrie Rollwagen is author of The Localist: Think Independent, Buy Local and Reclaim the American Dream. Find her on Instagram, Facebook and Twitter @crollwagen.

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