Cool People: Kerry Winfrey

Kerry Winfrey

I’m so excited to feature Kerry Winfrey as my very first interviewee on this blog! This 27-year-old writer from Columbus, Ohio is at once adorable, funny and witty. She talks about girly, smart, interesting things on her blog Welcome to Ladyville and regularly contributes to other websites, including HelloGiggles. Creative Ladies, one of her regular features on her blog, served as major inspiration for me in starting this new interview series.

How long have you wanted to be a writer?
This sounds like such a cliche, but I’ve pretty much always wanted to be a writer. Writing was always what I was best at in school. It’s what got me the most attention and what I had the most fun doing. I was definitely an “indoor kid,” so I spent most of my time reading stories and then trying to write my own. But as for how long I’ve seriously wanted to be a writer…that’s a little different. I have a bachelor’s in creative writing, but during college and for several years after I had basically no idea what it meant to BE a writer. I didn’t seriously start pursuing writing until a few years ago.

Do your own life experiences impact the work you do, whether that be your HelloGiggles column, other freelancing or writing YA novels? In what ways?
I’ve always been sort of obsessed with love, and that definitely influences the books I write about and the books I want to write. My high school experience, like a lot of people’s, wasn’t so great, and that influences the things I want to write. I want to write something funny that can make a high school girl laugh and take her mind off the fact that she really hates high school. I have a lot of sympathy for teenage girls, and I also feel a real sense of kinship with them. I’m not that far removed from my teenage self—I still have too many feelings and I still feel out of place most of the time. I like writing for and about teenagers because I was so unhappy when I was a teenager, and I hope that something I write will help a young girl feel even the tiniest bit better.

What is your primary motivation for writing?
I think I have two primary motivations. First, I like to connect with people. Sometimes I have a difficult time getting my point across verbally because I’m very shy and I’m a pretty slow thinker, but writing gives me the time to sort through my thoughts before deciding what I want to say. And secondly, I really like to make people laugh. If someone thinks my writing is funny, then that’s just about the best compliment I could get.

Can you tell me a little about what led you to this place in your Creative Lady journey?
I feel like I’m just starting out on my Creative Lady journey, but I guess we all have to start somewhere! I can say, though, that every job or opportunity I’ve had has been the result of deciding to believe in myself and work really hard to become a writer. I didn’t write at ALL for several years after college, and one day I just admitted to myself that I was miserable and I needed to write to be happy. I started really, really small (a few pieces in a local newspaper) and then just kept submitting to any place I could. Once I started writing for HelloGiggles, that opened a lot of new doors. Oh, and blogging the whole time has been a huge help for me—not just because it’s nice to have a lot of work online, but because it’s helped me realize the value of discipline and writing every day. Although I’m proud of the things I’ve done, there are MANY goals I haven’t yet accomplished. I love working towards goals, though.

What are some of your favorite activities to do when you are not writing?
I like to eat A LOT, so cooking and trying new restaurants are my favorite things to do. I love reading, which I think is pretty typical for writers! And I like working on crafts, even though I’m definitely not an expert. I like to sew (I’ve made a couple of pairs of pajama pants, some Christmas stockings, some skirts, and whole lot of half-finished projects) and I love crocheting! Sewing and crocheting are still creative, but they’re totally different from writing–they’re more visual, which is a nice change of pace. I don’t have as much time to do either of those things as I would like, though.

Kerry's crochet project

A crochet project Kerry has been working on ever since she can remember

You recently mentioned on your blog that you finished your first YA novel draft. What can you tell us about the novel? (anything from the synopsis to the process, whatever you’re able to share would be great!)
I don’t like to go into specifics about projects I’m working on (I think Ernest Hemingway once said that you’re not supposed to, and that’s just one of the many things old Ernie and I have in common), but I can say that it’s a romantic comedy. Romantic comedies combine my two favorite things—kissing and jokes—so they’ll probably always be my favorite genre.

What advice would you give a 15-year-old Kerry? I say 15 because I’m guessing that’s the age of most young adult main characters.
Oh, 15 year old Kerry has so much to learn. First I would tell her to give her parents a break. I was very, very mean until I was about 21 and I really regret it. Mostly I’d tell her to stop hating herself so much. At 15, I truly thought I was the lamest, most unloveable person in the world. I think for a lot of people that’s just part of being 15, unfortunately. But I would never have taken any advice because I’ve always hated being told what to do.

Tell me about some cool people who inspire you on a regular basis.
So many! I’m a big, big fan of David Lynch. He’s someone who has a unique creative vision that I enjoy, but more than that, he’s someone who makes creativity a part of his life. His book Catching the Big Fish is a really good explanation of his creative beliefs and processes. Even though some people dismiss him as being pretentious because his work tends to be a little weird, he’s just about the least pretentious person ever in his writing. He seems so kind, generous, and humble—I mean, he used to write every day at Big Boy. Also, he uses his influence to do great things, like help abuse victims and veterans with PTSD get access to transcendental meditation. He’s a good example of an unabashedly creative weirdo who’s still a solidly good person. That seems cool to me.

I really like Miranda July and Carrie Brownstein, too. They both do so many different things and seem to be constantly working. I think about them all the time when I lose motivation. You know, “What would Carrie Brownstein do right now?” The answer is usually not “Feel sad and go to sleep.” Instead it’s, like, “Be a huge badass all the time.”

I also think my family is really cool. They’re all very creative hard workers, and they inspire me all the time. I know everyone thinks their family is the best, but really…mine is the best.

Kerry's family portrait

Kerry’s dad made this portrait of her and her brothers, which she adores

What do you think qualifies someone as a cool person?
I think the most important thing, by far, is being a nice person. Having a good heart. Liking what you like without apologizing for it and not being a snob. Nothing’s less cool than a snob! Encouraging other people instead of tearing them down. And having a killer work ethic is just about the coolest thing there is.

What is your favorite thing about everyday life?
This is a hard question! I like mornings—just having some quiet time, drinking coffee, and thinking about my plans for the day. I also love having meals with my husband, which is something I’m lucky enough to do just about every day! And I love having any chance to laugh, which usually happens when I’m around my family.

Kerry posts regularly on her awesome blog Welcome to Ladyville, and contributes to many websites. Read her YA Fiction column on HelloGiggles here. You can also follow her on Twitter and Tumblr.

I would love to hear what you have to say. Leave me a comment and I'll try to write back soon.

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