4 min

How My First Boss Taught Me How to “Work Happy”

How My First Boss Taught Me How to “Work Happy”

I was lucky that my first boss turned out to be the ultimate mentor. He not only taught me to embrace all types of media, but he also inspired me to turn my weaknesses into strengths — and to enjoy every day of work.

My first job straight out of college was reporting for a Renaissance man of business journalism, Andy Serwer, now editor-in-chief at Yahoo Finance. It was 2000 and Fortune Magazine hired me the same week the market peaked. I started, a sort of apprentice to Andy, after the market had begun its steep descent. The rise of digital content was about to kick off an unprecedented transformation of the media business, and the subject we covered was headed for a roller coaster, between the market crash, 9/11, and the rise of a new digital economy.

Through this transformation of the business landscape, and the format in which we were reporting, as editor-at-large Andy was doing it all: writing cover stories and a twice-monthly column in the magazine, plus a daily digital column that was a kind of early blog. Called “Street Life,” it wrapped up the highlights of the market action that day. On top of that he also appeared nearly daily on CNN, commenting on all things business.

At 21, I was the youngest reporter Fortune had ever hired, and my job was to help Andy with any and all reporting — interviews, research, etc… — he needed, while also writing the shorter articles in the front and back of the magazine. The storied halls of the Time Inc. building, filled with industry legends, like Carol Loomis, were a far cry from the dingy offices of my college newspaper. I was excited. And terrified.

With a different kind of boss, I would have read plenty of SEC filings and done plenty of interviews with analysts. And I did all that with Andy. I also observed how to ask questions, listen and follow up. But with a different boss I would have always been watching from the outside, constantly anxious of intruding or getting something wrong.

What made me so lucky — and made Andy such a good mentor — was the fact that he brought me into his process. Part of it was practicality: the more I understood how he thought and what he was looking for, the better I could help him. If I understood what business narrative he was trying to follow in a cover story on the Rolling Stones, or what disruptive potential he saw in Ben Affleck and Chris Moore’s “Project Greenlight,” I could better come up with secondary interviews, or a source for estimating revenue from concert ticket sales. Plus, I learned more.

Perhaps most important: despite being in a high-pressure cutthroat environment, Andy took the time to treat me with the kindness and generosity with which he would have wanted anyone to treat his two daughters. When he was overwhelmed with writing cover stories, he asked me to fill in for him writing his daily digital column about the markets. He said I was doing him a favor, but he was giving me a huge opportunity, which taught me to track market action and write on a tight deadline.

Andy deserves credit for my nine-year career in TV: When I was asked to appear on CNN to talk about an article I had written on the billions lost in the market crash, I blanched, insecure about appearing as a kid talking about weighty economic issues. He insisted I get over myself, and get out there. And he pushed me to seize the opportunity when CNN Headline News invited me to come on three days a week.

What I found most striking about my mentor in the six years we worked together at Fortune Magazine is that he could find the fun in any of it: not just an interview with the Rolling Stones’ business manager or an hour on the phone listening to Carl Icahn rant, but also a deep dive into Oracle’s competitive landscape. When I’m teased for getting all fired up about something that sounds dry — like the Cable TV show — I think about what I learned from Andy about how to work. Relish it.

1) Face your fears and overcompensate:

As a Type-A personality with no experience in the world of business news — and like many college grads — I was afraid of messing up. I hadn’t studied finance and expected to lean more toward the light lifestyle-oriented pieces in the front of the magazine. But the fact that I was afraid of writing an investing article? That was all the more reason I should “lean in” to what scared me the most. None of this was rocket science, Andy stressed, so at his insistence I asked for some tutorials from the intimidating and impressive Carol Loomis, who between Fortune 500 cover stories wrote Berkshire Hathaway annual reports.

Because I started off so insecure about my abilities to write an investing article, I overcompensated by beefing up my knowledge of balance sheets and ability to read SEC filings. And it paid off big-time: I became more comfortable tearing through capital expenditures and 10-Qs than my colleagues who had started off with a more general level of financial literacy. I could pitch and write investing articles with ease, and instead of balking at the heavy numbers, I could enjoy it.

2) Relax 

I felt lucky to have landed a reporting job at Fortune straight out of school and was very much aware of how much I had to learn, and terrified about screwing up. But all that energy I expended only worrying about asking the right questions in an interview or how to buttonhole a CEO, was just wasted energy, Andy explained. That brain power and time would be much better expended crafting a lede, or thinking about a different anecdote to end with. Anxiety = waste of time.


Business journalism is neither heart surgery, nor rocket science. No lives are at stake. It’s a job that entails asking interesting people questions, reading stuff to learn things, and writing to piece a puzzle together. It’s not everyone’s cup of tea, and yes, there are deadlines, office politics, and pressure, but if you’re into the whole asking/reading/writing thing, it’s a pretty sweet gig. Andy reminded me that work was not a drag — I was, and am, very lucky to be in this world.

Andy sought out fun: those cover stories on the Rolling Stones and Ben Affleck and Matt Damon were definitely his idea. And he inserted his personality — and the fun he was having — into his cover profiles of Bill Gates and Larry Ellison. People wanted to work for, and with, Andy because he was having fun.

Author: Julia Boorstin
Julia is a report for CNBC covering Media, Social Media, Entertainment & Start Ups.

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