My interview with Tim Herrera for his Freelancing With Tim newsletter
“We’re all in this together. America Runs on Dunkin. Please don’t ask us whether or not employees get sick leave during the pandemic.”
A while back, Tim Herrera asked if he could interview me for his Freelancing With Tim newsletter. Naturally, I said yes, and today, he posted it:
Additionally, tonight at 5pm ET, I’m joining Tim for one of his Zoom panels. We’ll be talking about newsletters, how to start them, how to grow them, etc. More info on that here.
Here are a few choice excerpts from my interview with Tim (he is the bold, I am the… uh… not-bolded). Click over to his page for the full thing.
1. I love your newsletter, The Present Age! Where did you get the idea for it, and can you tell me a little about how you got it off the ground?
Thank you! So, the general idea for the project — I wasn’t sure at the time whether it would be a blog, book, podcast, newsletter, or something else entirely — started taking form in summer 2020. The pandemic was raging, the presidential campaigns were, uh ... also raging, and my take on the world at the time was basically, “Well, this all sucks.”
Remember all those commercials that would be like, “In these unprecedented times …” or put on some sort of emphasis on how “we’re all in this together”? I thought that maybe I could riff on that a little, thinking about how if “we’re all in this together,” we’re sure as hell not acting like it. Plus, the “this” that we were all supposedly together in was not exactly the same. A multimillionaire celebrity spending the early covid months cooped up in a 20,000-square-foot mansion is different from my experience of being stuck in a 1,200-square-foot apartment or that of others who had to be frontline workers, risking it all in those days when we didn’t really even know that much about the virus. These slogans came off less as the inspirational lines companies presented them as, and instead, to me, at least, seemed more like cynical cash-grabs. Like “We’re all in this together. America Runs on Dunkin. Please don’t ask us whether or not employees get sick leave during the pandemic.”
The other notion, that we were living in “unprecedented times,” was more interesting to me, and it’s what guided me in the idea for The Present Age. There are so many lessons to be taken from the past if you want to look for them. During the fall of 2020, I started digging through old newspaper archives to see what parallels were out there from past pandemics. The 1918 flu pandemic was an obvious example, and I found a bunch of old newspaper clippings from the time with headlines like “Flu Hurts Thanksgiving,” about public officials urging people to be careful about holiday gatherings, or “Flu Cops Are Given Orders; Policemen Must Wear Flu Masks,” about the reluctance of police officers to cover their faces. Those were both very 2020-2021 stories if you swap out “flu” with “covid.” The more time went on, the more I realized that we were living in totally normal times — or at least as normal as they’ve ever been.
And that’s when I started thinking about Søren Kierkegaard, whose 1846 pamphlet, “The Present Age: On the Death of Rebellion,” could have just as easily been written in 1918 or 1995 or 2020. Kierkegaard worried a lot about the role of mass media in society. “A revolutionary age is an age of action; ours is the age of advertisement and publicity. Nothing ever happens, but there is immediate publicity about it.” I could go on and on about this, but the idea for my project was to create something that illustrated an understanding of society as being both tied to the present moment and rooted in history. Same as it ever was, essentially.
So that bounced around a bit in my head for a few months. After the presidential election, I was looking forward to taking some time to just unwind after 2.5 years of non-stop work monitoring and writing about political media at Media Matters for America, a progressive media watchdog organization. And then the usually calm post-election period was, well, anything but. Lawsuits, Rudy Giuliani standing on stage looking like he was leaking gravy from his hair, “the Kraken,” QAnon, the Jan. 6 insurrection, and a bunch of other things I’m probably forgetting — having to wade through the way the press covered all of that, especially in the world of right-wing media, took a major toll on my mental and physical health. So I started thinking about how I could turn The Present Age into something real.
My options boiled down to starting something at Patreon, Twitter’s Revue, Facebook’s then-unnamed newsletter tool, or Substack. I ruled Twitter and Facebook out because both of those companies have a big tendency to acquire products only to shut them down rather abruptly (R.I.P. Vine!), and I’ve just never liked the way Patreon looks as a writing platform. That left me with Substack, which, while I had a lot of hang-ups about it (I detailed those on the first post of my newsletter), it made the most sense to me, especially given that platform’s rapid growth at the time.
I quit my job at Media Matters and launched The Present Age on June 7, 2021.
2. Writing a regular newsletter is a ton of effort. What is your process like for generating ideas and keeping a regular cadence?
Oh man, you’re not kidding. I’m definitely doing more work writing this newsletter than I was at Media Matters. I think part of it is that the focus at my old job was somewhat narrow: Pay attention to what’s happening in the world of right-wing media, analyze it, and offer my own insights on it. In starting my own newsletter, I didn’t have, well … any of those constraints. This is both a gift and a curse, to be sure.
I try to break my work down to three parts, which represent the three posts I aim for each week (on occasion I’ll only send two and sometimes I’ll send four in a week). The first is to find something newsy, something people are discussing on Twitter or making headlines in the news that week. I try to make this the most researched (and usually longest) piece of the week.
The second is an interview with someone I find interesting. I usually release those as both podcasts and transcripts on Wednesdays, though I put new episodes of those on hold until the new year.
And then the third piece for the week is usually a relatively short post that ties the first two together.
I think the week of Oct. 11 is a great example of this. On the 11th, I wrote something about the controversial Dave Chappelle Netflix special that had social media on fire for a few days at that point. The big criticism being leveled out there was that some people thought Chappelle’s set was transphobic, and others would roll their eyes and defend him on the grounds that he was speaking unspeakable truths. My slightly more nuanced than average take on the topic seemed to resonate with people on both sides of that issue, which was a relief as I’d prepared for the internet to throw virtual tomatoes at me over it.
Two days later, I published an interview I did with singer/songwriter Nick Lutsko about his music, the attention he’s gotten on Twitter with some of his more comedic songs, and trying to find the line between Nick Lutsko the character (extremely sweaty on camera, has a backstory involving a cast of characters I can’t even begin to start listing, makes jokes) and Nick Lutsko the musician. Was one more authentic than the other? Which one was the “real” him? Are we who we appear to be on the internet? Those sorts of questions. I’m such a huge fan of his work, and that was one of my favorite interviews (up there with the interview I did with Joe Galbo, the man behind the U.S. Consumer Product Safety Commission’s wonderfully bizarre social media accounts).
And then two days after that, I wrote an essay about my fascination with technology, mixed reality, identity, and a really weird Fox show called “Alter Ego.” The thread between the three is this sort of philosophical “What does it mean to be?” question. Each of the three pieces stand on their own, but together they (hopefully) create a coherent series that others can riff off of either for their own work or just … life, generally. Different weeks mean different questions to think about, and thankfully, there’s no shortage of topics to take on.
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4. You focus a lot on writing about the media. How did you develop that as a sort of “beat”? And would you recommend independent journalists have a “beat,” or not?
I’ve been something of a news junkie since I was 7 years old. I used to wake up, go downstairs, turn on the TV, and watch all of the local news broadcasts. Yes, all of them. On a given day I’d catch whatever the local NBC station had on at 6am, click over to ABC at 6:30, watch CBS at 7, Fox at 7:30. Whenever my parents would come downstairs, I’d just rattle off a totally incomprehensible jumble of stories and numbers that I didn’t even understand. It’d be like, “Traffic on the Edens is 17 minutes from such and such street to whatever boulevard, Greg Maddux threw a shutout for the Cubs on 92 pitches, it’s going to be 67 degrees with a low of 50 and partly cloudy, and next week starts the Taste of Chicago!” My poor bleary-eyed parents … They were eventually like, “We need to talk about you getting up and watching so much TV,” and from then on I was supposed to stay in my room until at least 7am.
I was … a lot.
But this made working for Media Matters such a great fit for me. I never stopped caring about the news, the press, media, generally. Newspapers, TV, internet, radio, I absorbed it all. And a lot of the time, I’d share my opinions online. Getting offered a job to basically do what I’d been doing for my entire life for free was perfect. I think part of my obsession with media has to do with its power. Speaking generally (as simplifying things as “the press” or “the media” as though they’re singular entities rather than just a description of the intersection of technology and communication around current events), I’m fascinated by the decision-making processes that go into determining which stories get heard and which ones get buried. These decisions affect every aspect of our lives.
I guess this is a really long way of saying that I think if you’re going to have a “beat” as an independent writer or journalist, it helps if it’s something you’re really passionate about. Some of the most successful Substacks I see are centered around extremely niche topics. What I’ve tried to do is to start broad and narrow my focus a bit more with time, learning from my audience and understanding what matters to me. The great thing about being independent is that you can chart your own course. If you care about knitting or making tiny model ships in bottles or Minor League Baseball or any other just-barely-outside-the-mainstream(-at-least-when-it-comes-to-journalism) topic, there’s no reason not to give it a shot. Maybe an audience exists for what you want to do. Maybe it doesn’t. There’s only one way to find out.
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7. Being independent/freelance is a tough business. What advice would you give to someone who is newly independent or at the start of their freelance career?
Try not to get discouraged and don’t take rejection personally. You’re going to get rejections. You’re going to send a lot of emails that don’t even get a response. You can’t take it personally or it’ll drive you mad. I say that as someone who absolutely has gotten discouraged and has taken rejections personally. It’s easier said than done, but if you want to succeed, it’s something you need to work on.
Oh, and keep a spreadsheet of the pitches you send out. Not only will this be important when it comes to actually making sure you get paid, but it can help you keep track of what different editors at different outlets are looking for.
8. Last, for you personally: What’s one or two things you wish you had known at the start of your career?
Don’t sell your personal story to any media outlet for a few hundred dollars. This is probably more of a 2013 problem than a 2021 or 2022 problem, but it remains true. Every once in a while, I think about those old xoJane “It Happened to Me” posts where someone would put their actual name next to headlines like “It Happened to Me: I Farted in My Tattoo Artist’s Face While Getting My First Tattoo” or “It Happened to Me: I Walked 10 Blocks with a Used Menstrual Pad Stuck to My Shoulder” or, well, you get the idea. While I’m glad I never put anything on the internet that embarrassing, there are definitely instances where I wish I would have just said “No thanks.”
As always, thanks for reading. Back to regularly-scheduled programming tomorrow!
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