Penny for Her Thoughts

This whiskey-swilling, punctuation-loving, Mad Men-era advertising veteran has tried to retire—really, she has—but ninety-three-year-old Penny Speckter just keeps on chugging.

Penny for Her Thoughts

It’s two days before The General Society of Mechanics & Tradesmen’s annual awards ceremony and Penny Speckter, ninety-three, is drafting a script for the evening’s events. No one’s asked her to—she didn’t need to be asked.

November wind is rolling off the East River as the sun sets, but it’s warm in Peter Cooper Village, the red-bricked Manhattan apartment community on the East Side where Speckter lives. She’s had the same address since January of 1949, when she and her husband moved to New York, the city where they launched their own Mad Men-era ad firm. It’s also where she enrolled in college at age fifty-six, boarded her first plane overseas at sixty-eight, and camped out in her apartment, eating canned food and drinking whiskey sodas, during the blackout that followed Hurricane Sandy.

When we meet at her apartment, Speckter, rosy-haired and smartly dressed with giant red-framed glasses, opens the door and greets me with: “Oh good, you wear a helmet.” She laughs away my offer to remove my shoes and turns on her heel. Her voice and step have infectious bounce and purpose—for anyone, but especially for a ninety-three-year-old. She does sport a “pure Aries” brassy streak that compels her to chastise bike-riding delivery boys for not wearing helmets, or for not sticking conspicuous lights on their handlebars.

Her grit and gusto are earned through curiosity, hard work and six-and-a-half decades in New York. She’s at ease with the hardhats and the executives at The General Society alike, along with the artists, writers and staff at the local trattoria where she eats dinner nearly every night. What Speckter does, she likes—there’s no ill feeling in her shouts to rogue cyclists—and what she doesn’t do, she might try.

Her apartment is filled with heaps of hardbacks; paintings, prints and printing materials; and a dressmaker’s dummy pinned with antique broaches, necklaces and a shiny belt. She traded jewelry once, and shows me a Victorian mourning pin—with actual hair from a deceased nineteenth century woman ornamentally knotted and kept inside the charm as a remembrance.

“Have you ever seen a carousel horse in an apartment?” she asks.

The interrobang.

A small one that’s “the perfect size for a New York apartment” does in fact rear on its hind legs by her desk. She found it while working at her ad agency at Twenty-Sixth Street and Fifth Avenue and kept it in her office before moving it into Peter Cooper Village.

For years Speckter and her husband occupied a second apartment across the hall to house his collection of printing presses. Her husband—a writer, editor, ad man and print and printed-word aficionado—invented the interrobang, which is a question mark-exclamation point combo used to express disbelief or denote a rhetorical question, as in “Who forgot to put the gas in the car?!” But expressed succinctly as: “Who forgot to put the gas in the car‽”

His passion for typography and printing, as well as his rakish humor, are evidenced in a framed poster, next to an interrobang print Speckter discovered in a downtown shop, that reads, in varying fonts:

Post Valentine
Leashed Passions!
Generate Frolic
Bridled Abandon!
Praved Saturnalia,
A veritable Bauch!
Feb.19 8:007P.M.
Host: The Four Penny Press Penny & Martin Speckter

The first two names are famed type designers, while the rest might be one of the most curious invitations ever printed on an in-home press.

Pointing to her husband’s handy work with notable regard for it, Speckter says, “You have to read it; you’ll appreciate it.”

I’d like to appreciate post-“8:007PM” details, but we’re walking out the door, on our way to her trattoria. Midway through my Dewar’s and soda, I forget to ask. I suspect Speckter will remember the evening though, for she recalls events throughout her life with wicked precision.

Speckter, née Penny Bank of Omaha, Nebraska, went to secretarial school and earned her stripes working for the Red Cross during World War II. Of her wartime work, she says: “You form a kind of dedication that stays with you for the rest of your life and translates into everything you do.” She apprenticed with the head of the accounting department, supervised the chapter’s move to roomier digs, and had just been cleared to serve abroad in Europe when she met her future husband, Martin, the week he returned from the service. Love kept the soon-to-be happily married couple stateside. Penny stayed on at the Red Cross while Martin wrote, first for the McCook Daily Gazette and then for the biggest advertising firm in town.

As her husband’s advertising career took off, they relocated frequently so that he could interact directly with clients, and Speckter worked everywhere they went. She was a credit manager in L.A., a bookkeeper for a letter shop in Miami, and the director of the Republican fundraising office during the Dewey-Truman election in Louisville, Ky.

“I remember sitting in a coffee shop at the counter in Louisville when I was twenty-eight and we were new in town and I remember saying to myself, ‘You know, Penny, you can do anything.’”

She’s proven as much. In 1958, Martin pulled her from a fundraising job to keep the books and run the office of the firm he had founded, Speckter Associates, which would promote The Wall Street Journal, Dow Jones News Service and The National Observer through the late sixties. Penny took to the ad industry quickly, and after Martin retired as president in ’69, she ran the show, writing copy, managing accounts and supervising the office help. That means Penny alone (in making the unavoidable Mad Men comparison) played the roles of a Pete Campbell, Joan Harris and Peggy Olson at the real-life Speckter Associates.

While continuing to work in advertising in the mid-seventies, she earned her B.A. in history from Pace University. Martin, by that time retired, would pick her up at the office and chauffeur her to class. Afterwards, they’d spend time in the library if needed, and then eat dinner at the trattoria.

As a graduate student at NYU while in her sixties, Speckter was at the top of her class. She arrived at The General Society while researching her master’s thesis. The institution, founded in 1785, provides tuition-free education in building-related crafts, has the second oldest library in the city, and offers space in its columned, sky-lit midtown building to like-minded nonprofits.

The General Society building is beautiful, and Speckter loves the view of the river from her apartment, but Madison Avenue remains her favorite place in the city. “There’s a mystique about advertising. People were never sure what we did. But nothing happens in the world until a product is sold.” When she was nineteen, Speckter permanently injured her knee performing water safety demonstrations on a surfboard in Little Rock. Now, she says, “The only time my knees don’t hurt is when I’m walking on Madison Avenue.”

Speckter says she retired at eighty-seven, but still works robust hours writing and producing The General Society’s newsletter, chairing its audit committee and serving on its board of governors. She uses a microphone that “looks like a jellyfish” to record board meetings and prepare minutes. The General Society educates and supports the people who build the city she loves. If there’s a gap to fill, Speckter steps in, volunteering time to help the board make a tough decision, or spending an evening writing a script for its annual awards ceremony.

She’s a professional, and protective over what goes in her newsletter. When a burly construction worker pitched a story about his fishing trip as a fall news item, she gave a droll “That ain’t what I’m gonna print,” and they shared a laugh.

Speckter also sees herself as the keeper of the legacy of the interrobang. She planned to write a book about the useful creation, but instead became a contributor to Keith Houston’s 2013 W.W. Norton release Shady Characters: The Secret Life of Punctuation, Symbols, and Other Typographical Marks. While it never was adopted into standard usage the way Martin and Penny dreamed, the interrobang is still available in several fonts in the most recent edition of Microsoft Word.

She takes all of her jobs—volunteer, advisory, or otherwise—seriously with a side of irreverence. She laughs when she calls herself “retired” and considers herself “lucky” to have such an abundance of energy. (That’s as close as she’ll come to giving away the secret to her healthy and productive life.) Other things Speckter describes as lucky: being promoted at the Red Cross, going to college later in life, and always being able to enjoy her work.

While her and her husband’s commitment to their clients in New York long kept her from vacationing, she finally went abroad in 1988, after her husband died, traveling to China. Since then she has visited Thailand, Singapore, Spain, and France.

There are still jobs Speckter hasn’t tried. “You know,” she says, “I’ve always wanted to drive a cherry picker.” Perhaps The General Society will somehow give her a chance.