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FAVOURITE PROFILE SUBJECTS: Actor Christopher Plummer, tennis ace Bianca Andreescu, Vint “The Father of the Internet” Cerf, singer-songwriter Feist, mystery writer Louise Penny, painter Tony Scherman, Slack CEO Stewart Butterfield.

FAVOURITE PLACES: The Thousand Islands, Dublin, Sydney, Freiburg, Oslo, Berlin, Havana, Riga, Ravello, Baku, St. David’s, the Shetland Islands, the French River, Mendocino County, Buenos Aires.

WHERE I WANT TO GO: Sri Lanka, Mexico City, Athens, Helsinki, Prague, Main Duck Island, Jerusalem — Next Year, Jerusalem?

IF AT FIRST: I grew up outside Toronto — here’s a piece I wrote about my terribly tony, Anglo hometown. Our American mother encouraged her kids to go to the States for undergrad. At Dartmouth College, I reported and edited at the student daily while studying English. Foreign study: Russian language and culture in St. Petersburg.

YOU DON’T SUCCEED: I then followed family tradition and went to law school — back in Toronto, at U of T. For nearly four years, I practiced at a so-called litigation boutique firm in downtown Toronto — mainly libel and slander and freedom of expression. Kudos to those who can make a go of it, but it wasn’t for me. Consolation prize: my piece about leaving the law was nominated for a National Magazine Award. Since leaving the practice, I have co-authored (with Colin H.H. McNairn) two texts on privacy law in Canada. (A link to a review of one).

TRY AGAIN: I started my second career, journalism, by fact-checking for magazines. Then I became an editor (at Saturday Night and Toronto Life), and now I primarily write. I have also worked as a producer at the Canadian Broadcasting Corporation. For five years, I wrote a column on the arts for Toronto Life, profiling painters, playwrights, singers, photographers, a prima ballerina, a potter, a composer (for film), novelists, actors, film-makers and one amazing puppeteer. When transitioning out of law, my play,  Cruel Summer: The Extended Play Remix, was put on at Toronto’s Factory Theatre.

BAY AREA: Since coming to the Bay Area in 2008, I have written for the San Francisco Chronicle and its magazine, San Francisco magazine, Sunset, the Guardian, Wine Enthusiast and the Smithsonian magazine. Travel pieces have recently taken me to Germany, Australia, Argentina, Uruguay, Switzerland, Italy, Monaco, Hawaii, Portland, the Shetland Islands, Grenada, Cuba and all over California. I’ve just taught two classes at Stanford: one on grammar and style in this digital era, another on travel writing.

NOVEL: Over the last five years, I have also worked on a novel in creative writing workshops at Stanford (with Nancy Packer), the Banff Centre and the Bread Loaf Writers’ Conference (with Chang-rae Lee).