7 For Seven: 7 Questions For ... Mike Hilleary

"How I do what I do as a freelance writer has taken a lot of perseverance, patience, and an overwhelming willingness to be rejected time and time again by editors."

mike with passion pit pink

Every second and fourth Friday of the month, Brady Gerber’s “7 For Seven” interviews writers talking about writing. This week’s guest is Mike Hilleary. Mike is a freelance music and culture writer who has written for such national publications and websites as GQ, Vanity Fair, Pitchfork, FLOOD, Under the Radar, Paste, Filter, Interview, Alarm, and various alt-weeklies. He lives in Northern Virginia. And Mike wants you to check out … his new book out this month! On the Record: Music Journalists on Their Lives, Craft, and CareersRead this interview on your browser.

Twitter: @mikehilleary

Instagram: @mikehilleary


Tell us: What (all) do you do? Bonus points if you show us how you got to where you are today.

I assume a lot of different roles depending on the time and day of the week, but all of them involve some form of writing. For my nine-to-five day job, I serve as an editor and writer for an organization called the American Medical Group Association, which represents large integrated health systems across the country. It involves a lot of writing feature stories; writing, editing, and assembling newsletters; summarizing various presentations and webinars covering industry best practices, trends, and educational insights; and doing a little bit of marketing content. When I am not tapped into that role, I enjoy a modest career as a freelance music and culture journalist where over the years I’ve made inroads with a number of national publications such as Pitchfork, SPIN, GQ, Vanity Fair, Paste, FLOOD, Under the Radar, and others.

As of this month, I can also call myself a published author, having spent the past several years working on and developing my first book, On the Record: Music Journalists on Their Lives, Craft, and Careers, which I feel is an attempt to makes sense of a profession I am incredibly passionate about, yet constantly at odds with.

How I got to where I am now – where I can make a living and make a little money on the side doing what I love – is an incredibly long and unlikely to be repeated by anyone else if they were looking for a career blueprint (god help them if they were). I started off getting into journalism when my creative writing class in high school filled up too quickly and I was stuck registering for an intro to journalism class, an elective course I had almost zero interest in. In a weird twist of events, the class inevitably led me to join a troupe of high schoolers who helped contribute and produce a weekly youth insert publication found in my local newspaper. As someone who was really starting to figure out his musical tastes at the same time, I got into reviewing concerts and interviewing fairly notable musical artists at the time.

Looking back I was incredibly lucky. I know a lot of these acts (or at least their publicists) wouldn’t have given a sixteen-year-old kid the time of day if I was simply writing and reporting for a high school newspaper. When I got to college I started ingesting all kinds of new music and reading “indie” focused music magazines like Paste and Filter and Magnet and just knew what I wanted to do with my life.

After completing a summer internship with Paste my senior year the reality of being a working music journalist hit me hard – really hard. I survived by moving in with my girlfriend (now wife). While she made a legitimate salary, I continued to struggle to find work, taking unpaid assignments to build my experience and portfolio of clips. For a brief time I worked as a substitute teacher to make what little money I could (and repeatedly get asked where my hall pass was). Moving to Richmond, VA, I had a moment of luck landing a gig as the Calendar Editor for the city’s alt-weekly Style. The job didn’t pay much, and I was more or less a perma-lancer with no benefits, but it entrenched me in the arts and culture coverage of a metropolitan city, where I contributed small write-ups and listings on musical and theater performances, art gallery openings, and noteworthy cultural events.

As much as I loved working at Style there just wasn’t anywhere for me to advance without being in my perma-lance role for a long time, and it just wasn’t sustainable. After a brief couple of years living in New Jersey where I tried finding work in New York City, my wife and I eventually returned back to Virginia, this time just outside of Washington D.C. where I found contract work writing for the American College of Cardiology. This led to another contract job with the American Medical Group Association, where I’ve had steady work ever since. Of course, throughout all of these career ups and downs, I continued to pursue music journalism. I’ve written for Under the Radar for years (and even made some part-time income for a while writing news stories for the publication’s website), contributed to Filter and its successor publication FLOOD, contributed to Paste and Interview. It’s oddly enough only been within the last several years that I’ve made some serious strides in pitching bigger publications and contributing to places like Pitchfork, SPIN, GQ, and Vanity Fair. I started working developing On the Record in the last few months of 2015, conducting my first interview in November of that year.

Over the course of my career, I’ve experienced a hell of a lot of doubt about my ability and worth as a writer. I’m incredibly insecure about it to this day. Because of my other responsibilities with my family and my day job I produce probably seven to nine pieces in a year. Not exactly the kind of output that really puts you on anybody’s radar. I touch on this a little in the introduction to my book, but when I was interviewing all these fantastic music journalists I became increasingly overwhelmed by the stature of their accomplishments relative to my own, which I really struggled to reconcile for a while. It’s really easy in this business – particularly in the age of the internet and social media where you can see everything by everyone – to feel like what you’re doing doesn’t measure up. Constantly comparing yourself to others is an absolute killer of confidence. And while it’s still difficult for me to resist that urge all the time, I’ve gotten a lot better at redirecting my focus. Where was I as a writer a year ago? Where was I as a writer five years ago? I’m only getting better. I will only be better as I move forward. The trajectory of my career is mine and mine alone, and I don’t regret where it’s been and where it’s going.

Walk us through a typical day.

While my pre-COVID days looked a little different and involved a much longer commute time, my days have had some small sense of normalcy lately. After waking up, depending on if my kids are dressed or not, I’ll pry them off their morning cartoons or movie and get their clothes on and their teeth brushed. A few mornings out of the week I’ll then go run a couple of miles or walk for an extended period of time to listen to a podcast. After I come back and get cleaned up I’ll make myself a coffee and get to work. This typically involves sending out a lot of emails, usually sending pitches, follow-up on pitches, or some form of correspondence with a publicist about scheduling an interview with an artist. Typically my kids would be at their respective school or daycare, but because of COVID, that’s kind of been thrown out the window of late. Luckily my wife and I managed to find them a nanny to help through the summer days to keep them occupied and to assist with distance learning when school kicks into gear.

After completing my freelance activities I try to turn my attention to my day job workload, which involves a lot of write-ups and summaries related to presentations and webinars hosted by members of the medical association I work for. I’ll also do the occasional original feature piece for the association’s flagship publication Group Practice Journal. There was a bit of a learning curve at first when I first came on making sense of some of the inner workings of our convoluted healthcare industry, but it’s certainly been rewarding writing about something other than music. When the workday is done, dinner is fixed, and the kids are put to bed. If I have a feature to write I take advantage of the last few hours before turning in to write (my wife works a lot of overtime with her job, so we often set up shop on the couch and just enjoy each other’s company typing away in silence).

The order of all of these things can certainly get mixed up from time to time but I think this fills the primary events of my average day.

Describe more about how you work; how do you do what you do?

As a parent, the question of how I work and how I do what I do just generally involves a lot of time management, working in the crevices of free time available to me when I’m not focusing on my day job or trying to take care of two little boys. How I do what I do as a freelance writer has taken a lot of perseverance, patience, and an overwhelming willingness to be rejected time and time again by editors.

What’s your trick for when you’re feeling stuck?

When I was younger I had a tendency of always getting stuck writing – particularly at the beginning of an assignment. I was very linear in my approach. I always had to begin from point A (the introduction) and work my way to point B (the conclusion). What made it particularly difficult was that I was such a stickler for getting the introduction just right. The lines and phrasing had to be perfect – or at least my version of perfect. And when I couldn’t translate what was going on in my head to the page I made myself miserable.

It took many years for me to get comfortable enough to move around the story, even if it doesn’t actually exist on the page yet. I know the beats of the story I want to tell, the quotes from an interview I want to utilize to propel the narrative. Now if I get stuck developing that opening scene or introduction I leave it behind and move somewhere else. It could be the middle somewhere. It could be at the very end and my very last line. That willingness to move around within a story has really helped me as a writer. Sometimes working on the middle or the end of a story provides the very inspiration or idea for how I should write the beginning of the story.

List some of your notable influences, past and present: writers, books, works of art, your heroes, anything and anyone that has inspired you. Also: The best article you read recently?

I think one of the benefits of working and developing my book On the Record, was that I was able to interview and talk with so many incredible music journalists. Everyone who is featured in the book has in some way, large or small, had an impact on me over the last several years. Whether I was talking with someone like Chuck Klosterman or Rob Sheffield who I followed and admired since I was in college, or discovering new voices and perspectives like Maria Sherman or Hanif Abdurraqib, I really feel like I’ve become so much stronger as a writer since I began the undertaking of making this book. I encourage everyone to read their works.

Mike has such great insight to share - I’m glad we could make this work. This interview is possible because of subscribers. Thank you for following! Other ways you can support 7 for Seven: Tip for coffee (so I have fuel to edit everything) and share this dang thing. But the most helpful thing you can do is:


Advice time: What’s a piece of wisdom that you wish you first heard when you were starting out?

While I certainly wouldn’t change the trajectory my life has taken as a result of the choices I’ve made, looking back if I had the opportunity to speak to my past self as I was entering college I would have tried to persuade myself to study something a little more applicable in the real world, definitely something with computers, coding or web production, etc. Nothing would have stopped me from writing on the side even if I chose something practical to pursue. I’ve never met anyone where they got a job in journalism because they studied it in school. They got their jobs in journalism because they just wrote and built a voice and perspective that got them noticed or just plain hustled freelancing behind their ideas.

That’s another thing I wished I learned starting out: how to pitch. You can be a great writer, but if you don’t have the know-how of actually selling an idea, delivering a concise paragraph to an editor that convinces them to run with that idea, you’re going to struggle. And even when you get really good at pitching, be prepared for rejection. A lot. It’s a numbers game. You just have to keep plugging away.

“Art”: What the heck is it?

Art is self-expression. It’s anything that allows you, the individual, the ability to channel what you feel, outward, which can then be interpreted and internalized by others, creating a whole new catalyst of emotions. Not to get too existential, but it’s a dialogue, a constant transference of inspiration. Art begets art.

BONUS: Cats or dogs?

I enjoy dogs. I grew up with dogs. But cats all the way. I appreciate their self-sufficiency. I also appreciate that with cats, their personalities don’t immediately bend towards submission. If a cat gives you affection, you’ve earned it.

BONUS BONUS: Pick a piece of writing that you're proud of and walk us through how it was done: How you got the idea, how you confirmed it was going to happen, drafting the piece, editing it, and publishing it?

For a few years, I lived in New Jersey just outside of New York City. During that time, while I struggled to find full-time work, being so close to my favorite place in the world offered some incredible opportunities as a freelance music journalist. During the summer of 2012, songwriter Michael Angelakos was set to release his sophomore album as Passion Pit. While I was familiar with the band and enjoyed songs like “Sleepyhead” and “Moth’s Wings” from the group’s debut album Manners, it was the band’s new single “Take a Walk” that really sold me wanting to interview Angelakos in the lead-up to Gossamer.

Writing for a publication like Under the Radar my editor Mark Redfern more or less sends out a mass email that says, ‘Here’s a bunch of artists with albums coming out that we could potentially interview for our next issue. Who would you like to talk to?’ Having written for the magazine for years at that point, the more experienced/veteran writers usually get first dibs, and I was all in with Passion Pit. In the days leading up to the interview, as I listened to a copy of Gossamer, I read over the press release, and it made me nervous. There were all these allusions and hints that something really bad happened to Angelakos over the course of making the record with references to alcohol and depression. I suddenly realized this wasn’t going to be a casual kind of chat and really had to prepare myself for some difficult questions. Luckily we were going to do the interview in person.

On a ridiculously hot summer day, I met Angelakos at Bryant Park. He wasn’t exactly in the best mood having just got out of an interview with NPR where he felt the host interviewer had been really rude in his questioning. I tried to ease into the conversation as best I could, but before I knew what was going on my second or third question started grappling with some of the things I had read in the press release. I wasn’t sure what I expected to get out of him, but he was suddenly so matter-of-fact and honest and confessed to being bipolar, and that Gossamer retraced the aftermath of a terrible phase he endured and relationships he compromised and hurt as a result. Needless to say, I was not expecting this kind of confession, and it really threw me off my prepared line of questioning. As someone who has his own share of mental health issues, dealing with depression and anxiety, all I could do was talk about my own struggles and try to find some common ground with him. By the time the interview was over Angelakos admitted to feeling in a better mood after the disastrous NPR session.

The piece I was assigned was just supposed to a small print feature somewhere between 500-800 words. Given how unprepared I was for the turn the interview wound up taking, I didn’t know how to approach the story in the way it needed to be properly handled. It felt like I would have done a disservice to Angelakos if I tried condensing what we had talked about (and had really only scratched the surface) and tried to fit it all of into such a pitiful word count. While I made references to Angelakos being hospitalized and going through a difficult emotional period and how it influenced Gossamer I made the conscious decision not to use the word bipolar or mental health or mental illness. While I was writing my article Pitchfork wound up publishing their big exclusive digital cover story revealing Angelakos’ struggles with bipolar disorder. Obviously, with my story being for print, mine came out much later. Looking back at the piece I wrote it still reads pretty well.

This strangely enough wasn’t the end, however. As 2008 came to a close Under the Radar was gearing up for its review of the past year. I approached my editor to see if I could revisit the Passion Pit story to give it a proper telling, one that could also examine the aftermath of Angelakos opening up about his condition and really dig into his full history dealing with the illness. With my new story approved I reached out to Angelakos’ people for another interview. At this point, Angelakos was on tour and while he was totally game for talking again, he didn’t feel comfortable talking to me over the phone – so he had his label foot the bill to fly me out to his location on the road. Within no time at all, I found myself on a plane heading for Royal Oak, MI, just outside of Detroit. I joined Angelakos on his tour bus and for several hours before his headlining show we just talked and talked and talked covering so much territory. It was the most rock journalist experience of my life, and it’s never been topped. The resulting story I was able to write is still one of my favorites from my career.    

Other favorites include the time I wandered around a Richmond cemetery with Lucy Dacus, interviewed The National in the Hudson Valley, and Tegan and Sara in New York City, hell even Phoebe Bridgers over Zoom. Pretty much anytime I can be face-to-face with a subject, it just gives me the ability as a writer to elevate the story, the narrative I’m trying to create. That is my honest-to-god favorite thing about writing: recreating a moment for a reader, giving them a sense that they were there with me when something unique occurred with an artist. It’s incredibly difficult to do that with just a conversation over the phone.

Photo Credit: Wendy Lynch Redfern

This is one of two monthly interviews with writers talking about writing, from Brady Gerber’s “7 For Seven.” All cartoons by Brady Gerber. Sign up for the newsletter here.