Old Boys at Career Day - Jonathan Kay '85

Keynote speaker Jonathan Kay ’85 had a rather unorthodox bit of advice for students at Career Day on April 30. His message: “Relax a little bit.”

High school is not the time in life to focus too specifically on the question of what job you want, he said. Instead, he suggested, “Think about what makes you special.” Long-term career success rests on finding a good match between your job and your personality type.

It was only after he had graduated from McGill with degrees in engineering, economics and Japanese language, and had earned a law degree at Yale that he found the career he loved, as Comments Page Editor for the National Post.

Over the years he has met many smart people with bad careers who have picked job they are not well suited for. To avoid this, he said, “Be a student of yourself.”

He advised students to ask themselves: “How does my brain work? Do I work better individually or in groups? Am I a people person? Do I like to work with ideas? Languages?

“I studied Japanese for three years before I realized I’m not good at languages,” he confessed.

Working on the National Post editorial board requires him to collaborate with four or five other people to write unsigned editorials. Everyone else who was on the team when he started has left because they were unsuited for teamwork. One has become a freelance author; another a researcher.

Even when he was a student at Selwyn House he could tell what his classmates were going to do in life, Jonathan said. He knew that Kai McCall would be an artist, that Jacob Richler would be a writer. “These guys have it easy,” Jonathan said. “They have great passions that manifest themselves early in life.” For the rest of us, finding career happiness is a matter of trial and error.

How does a young person know which job is right for him? If you have your eye on a particular profession, talk to someone in that profession who is happy and ask yourself: “Am I like him?”

Jonathan told of a colleague during his days as a tax lawyer who could be found working in his office at 11 pm Friday night, simply because he loved his work. “I want to get a job where I like my work as much as he does,” Jonathan said to himself.

Jonathan eventually realized that he loved the practice of writing. If you’re not sure how much you love a profession, ask yourself: “Is it something I would do for free?”

Flexibility is essential in the modern working world, Jonathan says. The days of keeping the same job throughout your working life are over, which means that long-term career success requires strategic thinking.

“In 10 years, newspapers won’t exist,” he predicts. However, if one keeps up with technology, other media opportunities may open up. “There’s always going to be a market for news and provocative opinion.”

In the end, though, success in any career comes down to results and relationships, Jonathan said. “If people don’t like you they won’t want to do business with you. “The last person you want to be is the guy who, when his name comes up on your call display you think, ‘I don’t want to talk to that guy.’”

Jonathan’s final piece of advice was something he called the “Sunday night test.”

When trying to decide whether a job is right for you, don’t judge by how you feel about it on Friday. Judge it by how you feel on Sunday night. If you’re dreading going back to work the next morning, you’re not in the right job.