Penny began her career in magazines as a freelance journalist, writing for sports and boating magazines at a time when it was rare for women to cover those topics. In the summer of 1988, a spirited new publication called Cottage Life debuted, and Penny was tapped to write a feature for the inaugural issue about how to buy a windsurfer.
“There’s no doubt about it,” wrote Penny in the opening lines of her first Cottage Life story, “those hot, lazy days of summer are better at the cottage—and best when you can spend most of your time in and around the water.” She still feels that way.
From her modest start as a freelance writer, Penny began to develop and hone the panoply of journalism and leadership skills that she has come to embody today. In 2000, she was named editor-in-chief of Cottage Life, where she quickly earned a reputation as an editor of considerable passion and frequent praise. In her 15-year tenure as editor, the Canadian Society of Magazine Editors named her its Editor of the Year a record four times, while Cottage Life won Magazine of the Year at the National Magazine Awards in 2003 and again in 2014.
“The hallmarks of Penny’s style are conscientiousness, diplomacy, and kindness. There are never any questions she won’t take the time to answer. No matter how tight the deadline, there is always time to adhere to the tight standards she sets for herself and inspires in her colleagues.”
—Cottage Life Media CEO Al Zikovitz
Consistent with the evolving roles of a modern magazine leader, Penny was named brand manager and later vice president of content strategy and development before assuming the mantle of publisher in 2015, succeeding Al Zikovitz. That year, the NMA jury named Cottage Life Canada’s Best Magazine Brand for demonstrating a level of innovation that sets the standard for the industry and represents how a magazine can succeed beyond print with dynamic and thriving extensions.
“As a publisher, Penny has demonstrated her adaptability to changing circumstances and serving readers across multiple platforms. This includes print, digital, television, e-commerce, and live events.”
—D.B. Scott, magazine consultant and publisher of Canadian Magazines
Today, Cottage Life reaches over six million Canadians every year as perhaps the savviest magazine brand in the country.
Beyond the walls of Cottage Life’s old cozy HQ at 54 St. Patrick Street in Toronto, Penny has made an indelible mark on the wider magazine industry as a mentor, teacher, volunteer, and advocate for a stronger magazine community. She was a member of the original Magazines Canada task force that developed the industry’s advertising-editorial guidelines, and has sat on the curriculum development committees of MagsU and MagNet.
“Penny’s insights and thoughtful contributions have always put the interest of readers first. Her calm, cool, and collected demeanor informs her success as an editor and publisher.”
—Patrick Walsh, editor-in-chief, Outdoor Canada
At Ryerson University’s Magazine and Web Publishing Program she taught students the finer points of building a career in magazines. Many colleagues have noted her interest in learning about new talent in the industry and looking for opportunities to mentor others.
“Penny seeks connections for everyone she meets. She sees that if she fosters this talent within our industry, our collective chances at success—at having healthy, thriving Canadian magazines—are so much greater.”
—Jess Ross, multiplatform content director at TVA Publications
All the while, Penny has frequently volunteered her time to sit on panels, juries, and boards of directors (including the NMAF from 2004 to 2010). Currently she serves as president of the International Regional Magazine Association (IRMA), where she has chaired awards committees, led numerous conference sessions, and developed the IRMA Connection initiative to improve communication and learning between members. “Penny is incredibly hard-working and an impressive problem solver who always has time for those who need her help,” says Tara Flint, executive director of IRMA. “She fosters positive discussions and brings out the best in others.”
Last year’s Outstanding Achievement Award winner, Kim Pittaway, sums it up aptly:
“Penny’s career exemplifies the best of what it means to lead a magazine: a deep respect for the audience, a commitment to the highest quality, a desire to innovate, and a dedication to respecting and fostering the talent of those with whom she works.”
For her commendable leadership in every role she has assumed, the NMAF is proud to honour Penny Caldwell with the 40th anniversary Foundation Award for Outstanding Achievement. Penny will receive her award and recognition at the 40th anniversary National Magazine Awards gala on May 26 in Toronto.
Tickets go on sale Thursday April 20 at magazine-awards.com.
The nominees for the 40th anniversary National Magazine Awards will be announced on Thursday April 20.
ABOUT THE OUTSTANDING ACHIEVEMENT AWARD
The NMAF’s most prestigious individual prize is the Foundation Award for Outstanding Achievement, an award that recognizes an individual’s innovation and creativity through contributions to the magazine industry.
The award is open to circulation experts, editors, marketing, sales and promotion professionals, publishers, creators, designers, production managers – in short, to everyone in the industry. It cannot be given posthumously.
The Judging Committee of the National Magazine Awards Foundation will consider the nominations, along with nominations from members of the Committee itself. The Board of the National Magazine Awards Foundation will select the winner.
For more information and previous winners, visit magazine-awards.com/oa.
Photo of Penny Caldwell by Daniel Ehrenworth