50-for-50 interview: Jean MacDonald, marketing geek rocker

jean macdonald

Jean MacDonald very much resembles her company’s most famous piece of software: you fall for her immediately, but you have no idea how much she’s going to rock your world until you really get to know her. In the few years since we met (after my 100% genuine fangirl fawning over TextExpander), I went from admirer of her good business sense to awestruck by her off-the-charts smarts, unshakeable moral code, and tremendous zest for learning. I blame my slow awakening on myself, of course, just as I blame my slow learning curve with software. But really, she’s far too modest and not nearly tacky enough to toot her own horn about her academic pedigree, her worldly travels, or even her power chords. (Whereas I have made it blatantly obvious that when I say “I can barely play,” I ain’t kidding.) Kind, funny, generous, and one of the most willing sidekicks I’ve ever met, if there is one person who might lure me to the grimly beautiful climate of Portland, Oregon, it’s Jean. Fortunately, she’s showing a growing fondness for certain sunnier parts of the country.

When did you decide to become a writer?

In fifth grade, my best pal Chris Godwin and I created a newspaper for our class at St. Lawrence School. We sat at his house (he owned the typewriter) and typed in our stories on a piece of ditto paper. You know, that two-ply thing that transferred purple wax to the master copy from the sheet with the ink. Since then, I’ve always considered myself a writer.

I have a manuscript in the proverbial drawer, a memoir of my stays in psychiatric hospitals when I was first diagnosed with bipolar disorder in my 30s. It needs reworking, but the subject matter can be so draining for me that I decided to put it aside for now. Instead, I distilled the essence of it into a five-minute Ignite presentation called “The Beginner’s Guide to Psychiatric Hospitalization.”* It allowed me to get the story out there with a mostly-humorous tone, which I’ve found hard to sustain in a 300-page manuscript. ()

Lately, I’ve become interested in songwriting. A couple friends and I formed a band last year, inspired by our experiences at Ladies Rock Camp, a program at the Rock ‘n’ Roll Camp for Girls. We perform original music, and I’ve written two songs so far.

*Inspired by you, dear Colleen, and your amazing Ignite talk in Portland. “You should do this,” you said to me, after finishing your talk. “Do you have a topic?” Thanks for the prompt!

Who was your favorite teacher?

In Florida, a state law required every high school student to take a course called “Americanism versus Communism,” AVC in the local parlance. The teacher I had for the class, Ann Lomery, basically turned it into a Russian history course and made it fascinating. She inspired me to think critically and write rigorously, which is pretty ironic, considering that the state mandated that the teacher “could in not present the Communist system to be in any way superior to the American system of free enterprise.”

For the school newspaper, I did an investigative piece on the AVC requirement, and found out that the law didn’t require that students pass the course, only that they receive 30 hours in instruction about “the evils, fallacies and false doctrines of Communism.” I have to hand it to Phyllis Glassman, our journalism teacher and newspaper advisor, for letting us publish that. The principal forced us to retract it in the next issue, claiming that he interpreted the law to mean that students had to pass AVC.

What do you love to write about?

One of my favorite sources of writing topics (and reading material) is the Readers Write section of The Sun magazine. Each month, they publish several short memoir pieces by readers on a topic that is specific enough to be provocative, but general enough to encourage a broad range of responses. In the current issue, for example, it’s “Paying Attention.” I challenge myself to write something each month, whether I submit it or not. I like to dig up personal stories, often little events that I haven’t thought about in years, and review them with a fresh perspective. (They haven’t published me yet‚Ķ)

What has writing taught you?

Writing is powerful medicine. Getting the bipolar story out of my head and down on paper took a lot of the pain away.

How has writing made you stronger?

When I get stuck writing, I have learned to drop back and examine my intentions and motivations. I get clear with myself, which is always a source of strength for going forward.

If you could go back in time and tell 10-year-old you anything, what would it be?

Don’t lose touch with Chris Godwin when his family moves from Miami to Anchorage in the middle of fifth grade. Don’t inhale the ditto paper fluid.

What are your five favorite books, blogs or things to read?

The Sun Magazine: I love that this magazine exists. Ad-free, publishing some of the most intensely personal fiction, poetry, and non-fiction, along with beautiful black-and-white photography. Once you’re in the habit of reading something with no ads, The New Yorker (I subscribe) feels cluttered and Vanity Fair (occasional guilty pleasure) is nearly unreadable.

Fin-de-Siecle Vienna: Politics and Culture by Carl Schorske
I read this in graduate school, when I was studying late 19th century Russian history. It’s a beautiful read about fascinating cultural figures like Freud, Klimt, and Schnitzler. It was a model for me of how compelling academic history.

Operating Instructions by Anne Lamott
Modestly sub-titled “A Journal of My Son’s First Year,” this is one of the most moving books I’ve read that was also so funny.

Poets In Their Youth by Eileen Simpson
It’s a beautifully-written memoir about the poets John Berryman, Robert Lowell, Randall Jarrell and Delmore Schwartz. Simpson was married to Berryman, and she supported his literary career by taking on typing work. Later, when I read her memoir about her struggle with dyslexia (Reversals), it dawned on me just how hard she had to work to support Berryman and herself. It makes me happy that in later life she was able to write her own books and get them published.

Mysteries: I am a huge fan of the literary mystery genre, primarily British police procedurals. Some of the best writers are women, like P.D. James and Ruth Rendell. These ladies (now 91 and 81 years old respectively) are an inspiration. I wrote a guide to my favorites for Flashlight Worthy Books.

Jean MacDonald is a marketing geek whose company, Smile, makes awesome software for Mac, iPhone and iPad software, like PDFpen and TextExpander. She also serves on the board of the Rock ‘n’ Roll Camp for Girls in Portland and plays guitar with her band Ruby Calling. She likes to think she is the favorite aunt of her niece and two nephews, but the competition is daunting.

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