I am obsessed with being at the edge. I’m constantly chasing what’s next in technology, media, and in my own career. The only problem is: No one knows where the edge is, not even me.
The first time I encountered this feeling was in high school, when I started contributing to a regular feature in the San Francisco Chronicle called “Two Cents,” in which readers sounded off on a topic in the news in a “man-on-the-street” interview format.
The trick, I quickly figured out, was that the Chronicle didn’t actually go out and interview people, but instead emailed out a question to a pre-vetted list of readers who would respond with a sentence or two of their opinion.
I learned to game this system of attention: I discovered that if I just said something minorly controversial, I was guaranteed publication. Using this knowledge, I appeared in the paper all the time. My parents’ friends would exclaim: “You got stopped on the street AGAIN!?”
This first brush with local fame was great for inflating my ego, but not for actually teaching me to delve deeply into finding out what I truly believed. It did, however, give me a real sense that something as simple as email could be wielded as a tool to change things.
I continued exploring this relatively new online universe in college — circa 2006 — where I saw the opportunity the web could bring to college life, and started a hyper-local blog covering our campus in Middlebury, Vermont. The college newspaper published just once a week, and missed out on anything happening in real time. I knew I could outperform the paper by reaching students faster and more efficiently than anyone else on campus.
I learned two things from my entrepreneurial endeavor that would stick with me throughout my career: Testing things out — and learning from that experimentation — was at the heart of every process, and not needing anyone’s permission to publish equaled total freedom.
My blog led to my first professional newsroom job: as the first-ever social media intern at National Public Radio. I mainly moderated web comments, a decidedly unglamorous task, but one I treasured for the chance to get to know the NPR community.
I now tell everyone that they should start their journalism career in content moderation, because you get an intimate sense of who your readers or listeners are, what they care about, and why. It also helps you develop a sense of responsibility for the journalism being produced.
When I started at The Washington Post in 2010, I felt as though I had joined an organization at war with itself, as it had recently merged its print and digital newsrooms. I was so naive that I literally had to ask which team I was on. This naivete extended to me having to be told the name of the man who was sitting at my assigned desk on my first day, as I did not recognize him. His name was Bob Woodward, and he was only pretending to occupy my seat as he was starring in a commercial being filmed for the new Washington Post iPad app.
I had entered that newsroom — where I would remain for more than a decade — obsessed with the coming tsunami of mobile phones and social media. Although they were nascent technologies at the time, that was how I consumed the internet — loading mobile web pages on a slow Motorola Droid X smartphone. I used Instagram in its early days when it was still a blurry photo-sharing app, and Twitter when it was still referred to as “microblogging.” Thinking back, I chuckle with nostalgia, but at the time, it was exhilarating.
The growing pains of early digital adaptations made for widespread newsroom uneasiness dotted with occasional breakthroughs. For example, when I was assigned to help the Post’s federal government reporting team and offered to assist a colleague who was searching for a source in an obscure federal department, I got a response along the lines of: “Knock yourself out, kid.”
I ran a series of callouts — a kind of online/social media request for sources — and, sure enough, found a reader who had worked in this obscure government department. I found the person’s phone number from a print subscriber record, and the reporter was able to make contact, weaving the interview into a Page 1 story.
I will never forget the power of that lesson: Our readers were not merely consumers of our product but also potential sources. It was exhilarating to feel I had discovered the precise edge where the editorial and the business sides met.
I rose to become a manager during the Marty Baron era of the Post. [Former Executive Editor] Baron was clear about his newsroom priorities: one, to produce the best journalism, and two, rapid digital progress.
On the latter goal, I got to pitch Post owner Jeff Bezos on my strategy to build out an editorial experiments team that would rapidly expand the Post’s presence on new social platforms and reach new audiences. Bezos, the founder of Amazon and one of the richest men in the world, read my proposal and gave it the green light.
Also during my time at the Post, I got to interview hundreds of candidates and hire nearly 90 people for jobs — from general assignment reporting to social media — over the span of this national growth era from 2013 to 2018. Many of my hires were among the youngest on staff.
I was young myself and, at 29, among the youngest department heads in the Post’s history. I tried to be thoughtful about how I carried and conducted myself, not only to show respect, but to be respected by sage editors twice my age.
During the pandemic, I joined Axios, a newsroom rapidly expanding its local offerings from three to 30 cities in just over a year. There, I learned the value of speed: Everything needed to have been done yesterday. But working in that atmosphere, where there was a willingness to change everything on a dime, helped rewire my brain for the media era we’re living in now. The pace of change keeps accelerating, even for those, like me, who are accustomed to it.
In the past, balancing on “the edge” in my career meant never letting myself get particularly comfortable or settled. My career successes were predicated on the idea that I was always working myself out of a job, in order to pursue the next new thing.
Because if you stand still, even for a moment, you’re no longer teetering on the edge. And yet, how do you know you’re on an edge at all, if you never go over?
