Zack O’Malley Greenburg is the Senior Entertainment Editor at Forbes Magazine. He spearheads all of their coverage of music, movies, and more. But he is also an accomplished author who has written two books, both business biographies of prominent entertainers – books that trace their careers via their moves in the boardroom, as well as onstage. The first was 2011’s Empire State of Mind: How Jay-Z Went from Street Corner to Corner Office, and the second was 2014’s Michael Jackson, Inc.: The Rise, Fall, and Rebirth of a Billion-Dollar Empire. His upcoming book, “a history of the business of hip-hop told through the lens of its three most successful mogul-artists – Dr. Dre, Jay Z and Diddy” – is called THREE KINGS. We called him up to discuss how to balance a demanding job with creative work – or, as he puts it, your main hustle with your side hustle.

Main Hustles and Side Hustles: An Interview With Zack O’Malley Greenburg

Ploymint: With your initial book, did you tell your bosses about it before you started writing it?

Zack O’Malley Greenburg, Senior Entertainment Editor, Forbes: The Jay Z book was kind of unusual in that they [the publishers] came to me to write it, as opposed to the other way around. I already had that pretty much in hand when I went to my boss at the time and I said, I want to work half time for half pay while I work on this book, because it’s my first book and I want to make sure I allocate the proper amount of time to it. They said, that’s nice, but we don’t need half a reporter, so if we do another round of layoffs, you may get laid off – and this was during the doldrums of 2008-2009. But I said, it’s a chance I’m going to have to take. So I started doing the half-time thing. And about a month in, there was a round of layoffs, and they laid me off.

So I spent about a year writing the book – full-time, of course. I had to take on other side hustles to pay the bills, mainly freelancing for a couple other places, including Forbes. When I finished the book, I got a call from another editor at Forbes who said, “We’re looking for a staff writer. Do you want to come back?” I said, “This freelance thing isn’t so bad.” But then they made me a good offer, and I came back. So I like to say, I got laid off for getting a book deal, and then re-hired and promoted for having written a book.

From that, I decided for the next book that I was not going to take any time off, and I worked nights and weekends on it. I also requested twice as much time to do the book as I did for the Jay Z book. So with Jay Z, my first deadline for the first draft was something like six to eight months from when it was requested, and for MJ, I had a year and a half to do it. The benefit was that I was better able to do the nights and weekends thing. The downside was that I was working two jobs for a year and a half, which is a long time.

Ploymint: Did the fact that the books are tied to your day job – they’re about entertainment and they’re about money – cause your bosses to look at them more positively than they might have if they were about an unrelated topic?

Zack O’Malley Greenburg: For sure. When I got the MJ deal, everybody at Forbes was really supportive. Of course, MJ has been on the top of our top-earning dead celebrities list every year since he died. Doing the book helped me get more material for the dead celebs list and for ongoing coverage, and then the ongoing coverage helped get more material for the book. It’s a lot easier to do it this way from my perspective than it is if I was writing a book about, like, gardening, where there’s no overlap. 

Ploymint: Any general advice for people trying to balance creative pursuits with demanding jobs?

Zack O’Malley Greenburg: Totally. I’m a strong believer in the side hustle. The more that your day hustle can connect to your side hustle, the better. But it’s also important to have a day hustle that can work with your side hustle in terms of time. And if your day hustle has some flexibility to it that allows you to do your side hustle, that’s huge as well.

I talk to a lot of people who say they want to write books, and I’m like, “Why don’t you try?” They’re like, “Oh, I’m too busy with my job.” I think if you really want to only write books, you have to start while you still have a job. It’s like if you’re a musician – if you’re Kanye West, you’re working at The Gap and you’re making beats on the side. Whenever that side hustle gets to a certain point, you may be faced with a choice of making the side hustle the main hustle, and I think that’s a great problem to have.