How I Got That Job(s)

Every now and then I get asked to explain how I ended up with the career I have, and it’s been happening a lot lately, so I thought I’d write it up. (The more general and frequent inquiries come from students, and the more specific ones from other journalists.) 

CHARACTER SUGGESTS PLOT

I can’t really speak to any specific planning that gets you from wherever you are now to whichever thing I do that seems appealing, because I’m not much of a long term planner. But there are some throughlines in most of the things I’ve done and here they are: 

• I care a lot about justice and fairness and that underlies a lot of my topical interests, which heavily center around power imbalances, class, money, public policy, and of course, the gleeful skewering of people with influence who make the world worse. 
• I’m bad at a lot of things, reasonably good at a few, and above average at two or three. I enjoy a lot of things I’m bad at, and don’t like some of the things that I’m good at. But I enjoy AND am good at writing** so I have always gravitated to jobs where I use writing in some material way. (I am, however, a horrendous copyeditor. Pretty good structural and line editor, but will absolutely miss that semi-colon.)
• I have an entrepreneurial streak and ADHD, which means that I like working on different things and doing lots of different jobs, and will work to avoid tedium more than I work to avoid pain. An investor I used to work for once told me my pain tolerance–by which he meant tolerance for risk and uncertainty–was higher than that of anyone he’d ever worked with. (He said it with both admiration and concern.) I told him I preferred difficulty, messiness, and uncertainty to boredom. I love working in startups, unsurprisingly. 

I can only speak for myself, but I think it’s easier to work out what a career path might look like if you know these essential things about yourself: what speaks to your values, what you’re good at or would like to be good at, and what kind of work you’re suited for temperamentally. (For students: you may have to learn some of that by trying different things and learning from experience what you do and don’t want.) 

In fiction writing, it’s axiomatic that character suggests plot, that who the character is will determine what they do and how they make choices. To some extent, that will happen to you whether you intend it or not, so better to know yourself as well as you can from the get-go. 

SPECIFICS ABOUT NOT HAVING A REAL PLAN and DOING THINGS ANYWAY

I’ll work backwards. I got the New York Times opinion writing contract because I’d written for the New York Times as a freelancer a lot. (What’s a lot? 20 times maybe?) I asked my agent how you get a contract there, and she told me, “you write for them a lot.” I asked my editors and they said, “you write for us a lot.” In order to write for them a lot, you also have to pitch them a lot, and get a lot of rejections, and just keep doing it while also doing whatever job is paying your bills now. 

I’d also written columns for their direct competitor, The Washington Post, for a few years prior and editors were familiar with my work. That helped. I was never on contract at the WaPo, but I had a good relationship with my editor, and pitched a lot, and eventually they came to me with ideas. I had written columns before, and had been a columnist at Fast Company and then Fortune in my late 20s, where I was writing about tech, finance, and economics. In the intervening years I worked in progressive politics, so it helped that I could write knowledgeably about several different things. There are advantages to being a specialist, but being a generalist has always worked better for me personally. I can pinch hit on a variety of different beats. 

I’m sure there are columnists who just write whatever they want, but I have never had one of those jobs. I have to pitch my columns. Occasionally, an editor comes to me with an idea. As such, most of what I pitch never gets assigned, and that is where my high tolerance for pain is helpful. It also means that I have to have other jobs to make ends meet. 

One of those jobs is co-hosting Slate Money. I got that job because I’d been a finance and econ writer before (Fortune, Fast Company), had started a Wall Street site in my 20s called Dealbreaker, and before I went into media, I worked as an equity analyst for an investment firm. That is a fairly laborious route to a podcast. I got the Fortune gig because the website was successful, and starting a media property from scratch isn’t a normal route to a columnist gig either. There are easier ways! 

I do media and startup consulting as well because I have to pay the rent and keep my kid in Takis and Pokemon cards. But I enjoy it because it scratches my entrepreneurial itch, and once again, I had to be successful at digital media in a public way before anyone would hire me to help them do it. Most of my consulting work comes via word of mouth from people who’ve worked with me before and found me tolerable and competent enough to want to work with me again. (I’m not going to go into how the consulting works here because it’s a whole other thing, but maybe in a future post.)

I also did some political consulting to progressive candidates and organizations after I tried unsuccessfully to raise money for a political media property that would be a kind of lefty version of Breitbart/The Federalist/etc, the openly right wing digital properties that DNGAF about whether anyone thinks they’re biased. A lot of the work was at the intersection of politics and digital media, and my business partner was a friend who’s a pollster. I especially liked working with candidates and orgs who were interested in problems of inequality and criminal justice reform. As a result, I ended up writing a lot about politics as well.

Before that was my last full time institutional job: I was editor-in-chief of The New York Observer. My boss was Jared Kushner. (I wrote about him here.) I met Jared in 2006 shortly after he bought the newspaper when I was still running the Wall Street site and thought we could work with The Observer. So years later when Jared was looking for someone to push the newspaper in a more digital direction he hired me, because of Dealbreaker, and also … Gawker. 

I had worked at New York Magazine for a while, and got that job because an editor there liked what I was writing at Gawker, which Nick Denton and I started in 2002. I got the Gawker job–”job” in scare quotes because it was Nick writing me a check for $1200 a month--because Nick and I were hanging out 24/7 socially and we both had blogs and one day he told me he wanted to launch a commercial blog about New York City (unheard of at the time) and asked me if I wanted to write it. 

In almost all of these cases, I had to demonstrate that I could do something well for little or no money before anyone would pay me to do it. I wanted to write about Wall Street when I went to New York Magazine but they knew me as the Gawker writer (pop culture, celebrities, etc.) and so I had to leave and start a Wall Street site to prove I could actually write competently about it. Maybe at some point in my career I won’t have to prove myself first, but I’m 49 and it hasn’t happened yet. 

Before that I was employee number 7 in an early social network, and later an equity analyst. I had no professional writing experience, and had to go out and write a lot in public via Gawker (with no editor) to demonstrate competence. 

THIS IS THE HARD WAY TO DO THINGS!!! (BUT IT WORKS) 

So what might be useful here for you? 

If you want to do a kind of writing (or anything else) that you haven’t done professionally, it helps to demonstrate publicly that you know how to do it. Sometimes that means assigning yourself something and putting it on your website so that when you pitch you can point to it as “the kind of thing” you want to do. It's evidence of your competence.

Get used to rejection and pitching, especially in this media environment. There are Pulitzer winners who are out of work right now, and this is just a hard industry to survive in. Find a part time gig to support your real work if you have to. I know many critically acclaimed novelists and independent journalists who still derive much of their income from marketing work, or some other day job. But keep trying. If you want to write for The New York Times Opinion section, pitch The New York Times Opinion section. A lot. Rack up rejections, and keep pitching. If there’s something that’s really important to you and no one assigns it, write it anyway and publish it yourself. 

Know thyself. When people ask what being a journalist or a columnist or any kind of deadline-driven writer is like, I tell them it’s like having a term paper imminently due--all of the time. If that sounds miserable to you, you may want to find another mode of self expression for your ideas. 

Follow your values. That’s how you may end up working on disparate things but in a fulfilling way. Note that I am not saying follow your passion. If you have the financial security to do that, by all means, do that too, but know what kind of work will sustain you if the job doesn’t pay enough, if your boss sucks, if the industry is in shambles, etc. Meaning will get you through the hard times. 

I don’t know that I have much career advice beyond that because I’m fairly certain that for most media people the trajectory is something like, high school newspaper to college newspaper to internship to actual media org and then advancement along a predictable ladder in a linear way. I didn’t even check the first box. (We didn’t even have a newspaper, man.)

I’m writing this mostly so I can send it along with specific answers to questions to students who email me but maybe some of you will find pieces of it useful too. 

** Like many women, I’ve been socialized to put a thousand qualifiers in front of any statement like “I’m an above average writer”, but I think I can reasonably say I’m good at writing without implying that I’m The Best of All Time and wildly delusional about my capabilities and limitations. Plus, lots of people write professionally while being genuinely bad at it. Look at Stephen Miller!

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Now back to our regularly scheduled programming of me writing about things that I care about that are not me. 

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Admin note: I’m now offering opinion writing and personal essay workshops for $100 if you just want to participate in the workshop and not get the one-on-one coaching after. I hope this makes the workshops more accessible to more people. I enjoy teaching them! 

As always, thanks for reading!

Elizabeth