The app tracks your feelings over a two-week period, graphing a quantification of what you should do.
By Amy-Willard Cross (Editor, Vitamin W)

If you were wondering about keeping or tossing your boyfriend, Sarah Gray has just the app for you.

Should I Break Up With My Boyfriend is a 99 cent solution to that question. Forget quizzes or boring your friends, this app tracks your feelings over a two-week period. The result is graph which quantifies what you should do — and adds a bit of custom advice. And it’s just the first of her mobile offerings.

Gray developed the original version of the app because she needed it herself – natch – to assess a long-distance relationship. She did leave, but the good news is the next guy was also a geek.

Now they make beautiful code together. Indeed, Gray developed this app with her boyfriend she says, “we’re both programmers, partners in life and business and everything”. Bootstrapping, the duo take programming contracts and advise start ups on tech issues to pay the bills. And they’re gearing up to create more of their own stuff.

Together they run mercuryapp, which is a kind of life-tracking journal—that tracks your mood or how you feel about your job. They also built a program to schedule office hours, Slottd, which supports their technical advising.

Although this Brooklynite turned Chicagoan earned her living programming for a decade with PHP and Ruby, she says, “I just wanted to learn to build an iPhone app – it’s fun and cute and iPhones are everywhere.” But she had to learn objective C. “For the first few weeks, I felt ‘snowblind’, it was slow and it took a couple of months to build.”

As your French teacher said, learning new languages is important, Gray says, “Programming is the new literacy, if you could learn just one language — learn programming, not Spanish or Chinese, it’s everywhere and it provides the understanding of how everything works.” She goes onto say that every business is becoming a technology business, since every single aspect of our lives — from ticket buying to waste streams — is being changed by technology, including the arts. Even poetry.

Just for fun, Gray recently created a program that uses Twitter to read poetry. You input a piece – by T.S. Elliot, Langston Hughes, or your favorite poet – and then watch as the application finds it, word by word, through tweets. “Seeing the poem appear slowly word by word, I felt was watching the poem appear out of nowhere, sometimes it takes a long while to find the word. So it’s like I’m at a game, rooting for the word, come on come on!…”

That Gray would want to put dramatic tension into reading poetry isn’t that surprising when you consider she came to programming from the theatre. Gray started out a theater director, but once someone put a camcorder in her hands, she was hooked on tech. She switched gears and entered an interactive program, ITP, at New York University’s Tisch School of the Arts.

“Technology gave me a whole new language and set of tools, and now I can make projects that are fun and exciting and scratch that creative itch.” Just like the theater. Although there may be more happening in NYC or the West Coast in terms of VCs and investment, Gray says Chicago is a great place to be an entrepreneur.

The digital startup scene is growing: there are loads of people like her who are building, founding, bootstrapping, coding and starting-up. A sign of the scene’s seriousness: the big networking events aren’t cocktails but “Bootstrapping breakfasts.”

Gray says, “I just love making stuff. We’re bootstrapping so we can make more. And I want to move into the future of being able to make money off the products we make.” There is sure to be an app for that… or indeed many apps.

Editor’s note: Got a question for our guest blogger? Leave a message in the comments below.
About the guest blogger: Amy-Willard Cross is the editor of Vitamin W, a platform for news, business and philanthropy. A former editor at national magazines, Cross authored books, written countless articles, features, op-eds and book reviews. Once while working on a documentary, she found an American who had fought with Fidel. Cross wants her daughter to learn how to code because as the pay gap is only 6% for women programmers.