Interview with Instagram Sensation Caroline Calloway

May 8, 2014 Katja Presnal

Interview with Caroline Calloway

It’s Instagram Travel Thursday, and I have a special treat for you today. I am introducing and interviewing one of the best young storytellers of Instagram.

Meet Caroline Calloway.

I have been following Caroline Calloway’s adventuregrams on Instagram for a while. This 22-year-old Washington DC-native girl hasn’t called The Capital home for years. First, she attended the Phillips Exeter Academy boarding school in New Hampshire, and after graduating in 2010 she spent three years traveling around the world and living in New York City. She left her life in the West Village behind her, and started studying for BA in History of Art at Cambridge University in UK this past fall. Yes, her life is like a great movie, except it isn’t (yet).

While Caroline’s photos are great, it is her storytelling skills that has made her a hit among her over 70,000 followers, whom I think mainly are young girls. There are several very popular Instagramers even with more followers than what Caroline has, but what sets Caroline completely apart: she is a writer and a storyteller, not a photographer. Are her photos good? Sure, of course they are good, but this girl has natural talent for hooking you in, and she leaves you wanting to hear more. She is almost like writing a nonfiction book of her life, a few sentences at the time, and you can’t wait to turn the next page.

Case in point:

nyc taxi cookie

On my last day in New York, I realized from the moment I woke up
that I would be leaving behind an A+ boyfriend. Not only did Josh bring me
breakfast in bed, but he had purchased the kind of sparkly, specifically themed cookies that most 22 year-old boys wouldn’t be caught dead with.
As he sat down on the edge of the bed, he handed me a plate and grinned.
“I called in sick to work this morning so that we can spend the day together.
Today we’re going to do everything you’ve always wanted to do in New York,
starting with–well, you probably already know.”
And he winked.
If my life were a rom com, I would have winked, too, and said something suave and conspiratorial, like “Are you thinking what I’m thinking…?”
Then cue the 80s fun montage.
Instead I just stared at him blankly. “Are there more of these Taxi cookies?” I asked.
“Get dressed,” said Josh. “We’re going on an adventure.”

To Be Continued #adventuregrams
instagram.com/carolinecalloway

Caroline leaves you hanging, and you can’t wait for the next photo to be published to read how the story continues. While she says she hasn’t even thought of online branding, she has done something instinctively that many marketers only wish they knew how to do it. While her world travels, and expensive schools might make her unapproachable, she sees beauty in small things, she is brilliantly funny, and is actually very easily identified with.

instagram photos by caroline calloway | http://instagram.com/carolinecalloway

Interview with Caroline Calloway

Katja: How did you get started on Instagram? And was Instagram really your first platform for telling your story, or were you sharing your stories somewhere else prior starting on Instagram?

Caroline: Believe it or not, but Instagram really was the first place I started telling stories. Of course now that I think about it, that seems wildly impractical. Two years ago if someone had asked me, “Hey, Caroline. How should I share my humorous long-form nonfiction essays with the world?” I definitely would not have said, “OBVIOUSLY THE IMAGE-BASED PLATFORM INSTAGRAM.” But to be fair, the way I tell my stories today was a long time in the making. In fact, if you looked at my posts from this day last year, you’d be shocked at how uninvolved they are–a pretty picture and a joke or two to go with it, nothing more.

But it’s always been my dream to be a writer. Even before I could actually write I used to dictate stories to my Mom on our family’s communal 90s desktop. And so bit by bit, post by post, I started doing what I now always do when I’m in front of a keyboard and screen: writing less than flattering but always honest stories about the exciting things that happen to me.

Katja: Your Instagram stories in all honesty read like an amazing novel, and I can see why so many are addicted to reading and seeing more. I see you as one of the true storytellers on Instagram, and in fact you should have a book deal or movie rights to your story already now – are any of these in the talks? What are your long term goals?

Caroline: I actually don’t have any long-term goals. Just goal. Singular. My dream is, simply, to publish a book. Specifically, a nonfiction essay collection that makes people laugh.

Since starting my blog on Instagram, I’ve actually been contacted by a few literary agents and even an editor at a major publishing house. However, I’m under the strictest of orders not to discuss this until the contracts are signed. So unfortunately that’s really all I can say for now, although please believe me when I say that, for someone who overshares intimate details of her life on the internet daily, the discretion is killing me. Now as for the movie… I’m all for it apart from one problem: I don’t think there are any 22 year-old actresses in Hollywood average-looking enough to play me.

Katja: Do you have any tips for those who want to combine strong storytelling and visual content on Instagram? Some practical tips etc.? Instagram isn’t really the most text-friendly platform, but yet you master the written storytelling on Instagram as well.

Caroline: I think the first and most important thing for anyone who wants to tell their stories on Instagram, is not to get discouraged by other people’s success. There are so many large accounts–accounts way larger than mine–and it’s easy to feel like it doesn’t matter whether or not you slave away on the perfect story. Mathematically, you’ll just never catch up. I know because I feel that way all the time. So my advice is twofold:

1. Don’t think competitively, think creatively.

What can you offer that other people don’t? How can you offer it in a way that’s exciting and fresh and brings value to your readers? And not to sound like a middle school guidance counselor or anything, BUT… What is it about you that makes you special?

2. Write well. And then move on.
There’s a reason I don’t post more than once or twice a day: It takes me that long just to write something I feel good about. However, if I didn’t stop obsessing after a certain point and just move on, I’d never post at all. So find a balance. You need both, because just one is very dangerous.

Katja: Where else we can find you but on Instagram?

Caroline: So glad you asked! On my Facebook page, you can find real-time updates of my adventures as they happen. And on Twitter as Adventuregrams, you can find me trying to brighten your day with jokes. Like, all the time.

Can’t wait to hear more about the book news, but I have a feeling that this is just a beginning for Caroline.

caroline calloway's instagram photos

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Katja Presnal

Katja Presnal shows how to live Nordic inspired life to the fullest and plan your dream life. Katja owns Presnal5 strategic marketing intelligence agency and wants to help marketing professionals to combine a dream career and dream life via freelance work.Katja is an award-winning marketing strategist, and a well-known speaker. Katja has lived in five different countries, and seven states in the USA. Her three children were all born in different countries within three years. When not working or jet-setting the world, Katja is at home cooking big family dinners.She has been featured in NY Times, Glamour, Redbook, Fodor's, Forbes and Woman's Day magazines among many other national and international publications and written for MTV3 and Lifetime TV networks.

Comments (4)

  1. Reeta Laaksonen

    I had to go and check her Insragram account and those stories were really captivating – really make the photos come more alive!

  2. I love this idea! I do think of my pictures as telling a story but haven’t really thought about actually writing the stories in Instagram. Very FUN interview, Katja!!

  3. Actually I never thought about Instagram as a story telling place, but in my work (the one of my real life:), it happened hundred times. Images ARE a story! Thanks to you for offering a new vision to me and to Caroline for her greta photos:)

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