That Boston-to-New-York thing: When a music writer makes the move

Photo by James Joiner

[dropcap]I[/dropcap]t’s pretty simple: when the time comes to decide if you’re going to re-sign the lease to your apartment, you either do or you don’t. You say nothing will change, or you make the decision to leave. This wasn’t the case for me a year ago, when I quit my job at DigBoston and packed up my perfect tiny apartment with the yellow walls and beautiful woodwork in Davis Square. The month leading up to the deadline was one of the most stressful to date in my adult life, and that basic yes-or-no question — Should I stay or should I go? — was one that brought little relief once I answered it by putting pen to paper and admitting that I was yet another member of the Boston music community who was leaving it for New York City.

The Boston vs. New York thing is a tired, predictable and fruitless argument that pops up in all walks of life between Port Authority and North Station, but for Bostonian creative-types especially, it’s a perpetual back-and-forth that comes up whenever things aren’t going the way you want them to with your passionate pursuits. Talk to any disillusioned Boston musician and they’ll tell you that if you want to land a record deal, or actually go somewhere with your band, the accepted plan-of-action, more often than not, is to flee the city as soon as you can afford to do so and head to the nearest global capital, which in our case is New York City.

“Be a big fish in a small pond!” gets a snappy “You’ll never know until you try” retort; “We can play every night in New York!” is met with a “But we’re comfortable and can sell out shows with our fanbase at home” excuse. New York is bigger and tougher and more competitive and rewards those with the talent and indefatigable drive in spades, sometimes; Boston is smaller and forces folks to get creative with a more intimate scene and a network of venues they can build their career at. There are pros and cons to living in both cities or leaving one for the other, but bands, frequently, associate a move to New York with trying to “make it” — and for us music journalists, it’s a Do or Don’t that floats out of the ether every time we hit a rough patch in our careers.


When I left Boston, I wasn’t unhappy there, but I wasn’t content, either. The deal, up until recently, was that the music/A&E staff at Boston’s publications climbed up a ladder if they were any good: if you started at the Herald or the Metro, you’d eventually go to the Dig or Phoenix, and then ultimately to the Globe, Boston Magazine, etc. etc. Michael Brodeur did that, nearly to the letter — he was the A&E Editor at DigBoston, he moved on to the Phoenix, and currently runs the A&E section at the Globe. Luke O’Neil was a Dig editor and now freelances for pretty much everybody. Vanyaland founder Michael Marotta was at the Herald before becoming the Phoenix’s music editor, and Chris Faraone spent time at both alt-weeklies. My point — do excuse the name-dropping — is that the ceiling in Boston was very visible to me. Quite frankly, it wasn’t that there was nowhere to go; it was that there was nowhere to grow, as everyone holding down the fort at their respective publications was doing kick-ass work.

I loved my time at the Dig and am incredibly proud of my colleagues and the work I did while running my section of the book and its digital foil, but two years of concerts and countless interviews and radio spots and movie screenings and absolutely ridiculous festival showcases flew by, and I got to thinking: what if I blink, and I’m exactly where I’m at three years from now? Or five? What if I hit my wall?

Yes, my job was great. But the fact that I wasn’t writing the kind of pieces I wanted to — DigBoston capped its features at 600 words when I left it, a meager fraction of the standard long-form word counts accepted by other publications — didn’t outweigh the perks of staying, and so I hit a roadblock. Either stay in Boston and wait for something to change while running the Dig’s A&E section and ramping up my freelancing, or move to New York, shake shit up, try my luck in the most ferocious job market on the planet and see where I wind up.


I started freelancing for a few national magazines and sites to get my name out there, and when my management company asked me if I wanted to sign on to keep my Davis studio for another year in June, I knew I couldn’t. I needed to do something to yoink me out of my creative funk, and the only option that seemed drastic enough to do the trick was a move to New York City.

I gave my notice to Dig Founder/Publisher Jeff Lawrence over beers at Foley’s (aka the Dig’s official watering hole) last July, and I sniffled and hiccupped my way through the incidentals chat — the one where we decided when my last day would be, how I’d approach my sign-off, etc. — like a child, because the idea of leaving home was no longer a maybe I will/maybe I won’t kind of thing. I knew Jeff would be supportive and that leaving the Dig and my friends there would be difficult, but I hadn’t prepared for the weight of my departure would hold personally, especially considering the fact that the Dig is where I grew as an editor and a writer and a member of the Boston music scene.

At some point in my tenure as the Dig’s A&E Editor I picked up the nickname Hilary Fucking Hughes, or HFH, for short, and this rabble-rousing alter-ego in rock that followed me around felt like it was no longer relevant. Without the Dig and the Boston music scene, I wasn’t HFH anymore — I’d outgrown her — and I was kind of okay with that, given the fact that “pulling an HFH” often involved getting kicked out of the Hard Rock Café (never again) or ending up in the Middle East’s green room cracking terrible jokes in front of one of the biggest bands in the country. That doesn’t mean that it felt good -— change doesn’t have to, when it’s necessary — and it doesn’t mean I was ready for it, either, but away I went.

So, HFH lost the middle initial, became plain ol’ Hilary Hughes again and moved to Brooklyn. To say that the change was fucking brutal would be an understatement, though it mostly had to do with a barrage of personal turmoil at the time — someone very close to me died suddenly, my housing situation went to shit and the relationship I was in seemingly disintegrated overnight.


Making the switch from full-time editorial to full-time freelancing was a bumpy transition as well, in that I was writing tons but had to triple the number of pitches I was sending out in order to meet a quota I set before myself each month. I’d go to shows, either to review them or interview bands as I always did, except this time, I never, ever saw friends at them, either in the crowd or at the door or behind the bar — I felt like the new kid on the first day of school who was wearing a dumb sweater her mom picked out, and the only way to shake it off was to embrace the loneliness and remind myself that it would be temporary.

I moved into a 17×19 apartment I couldn’t afford in Boerum Hill because it was the only thing available that wasn’t littered with belly-up roaches in a non-stabby neighborhood, and the unforgiving, unavoidable realities (and price tags) of life in New York nearly paralyzed me. “I left my apartment and my job and my friends and my coffee shop and my family for this. I left my permanent house list spots and my haunts and my favorites venues for this. I don’t even know what ‘this’ is yet, and I left everything I’ve built for myself for THIS”: that’s the mantra that ran through my head for the first three months while I tried to get my shit together, and that’s when I got why there’s a very strong argument for staying in Boston to make your art — if it ain’t broke, don’t fix it, and if it ain’t the best, still, it could be worse. And I wasn’t entirely sure if life in New York felt worse or not.

After a bit, things turned around: I pitched relentlessly, had a couple of pieces killed, freaked out about it, scored a few new freelancing gigs and checked off a box on the career bucket list when I wrote my first web feature for The Village Voice in October. I made new industry friends in New York and eventually stopped hitting shows alone, and when the door guy at the Mercury Lounge recognized me on a weeknight from a set the week before, I could’ve hugged him, I was that happy to feel like a regular again.

Coincidentally, I’ve gotten a lot of work covering some big music events in Boston lately, and the irony of that — writing the kind of stories I want to write, for both national and Bostonian publications — isn’t lost on me now that I don’t live there anymore. I found my routine and adapted to the perpetual, bipolar rejection/elation dance that comes with being told you know nothing about music or you’re a natural tastemaker by a variety of people day in and day out. I threw myself into my writing, and though my new, astronomical rent and my new, astronomical workload rarely played nice and resulted in financially breaking even on a monthly basis, I was getting there.


The risk of leaving behind a good, comfortable thing (my work and life in Boston’s music scene) for the unknown (New York and the extreme highs and lows that come with its opportunities in journalism) was starting to pay off. I may write less than I want to every month and the glossy print features that pay bank may be few and far between, but I’m doing what I set out to do — I’m a music journalist who’s actively working and living in New York — and sometimes, doing just that in its most basic form is enough to remind you of why you made the move in the first place.

I got an email from my management company asking if I was going to re-sign the lease on my shoebox studio in Boerum Hill, and without hesitation, I said I would — I’m doing okay here, but I’m nowhere near where I want to be and I can’t leave this place before I know I’ve exhausted every shot at the dream. New York has a way of doing that to you — of making you feel like the textbook example of a failure if you think about calling it quits before retreating and giving your music or your writing or your art a shot somewhere else — and I’ve fallen victim to it like thousands of writers and musicians before me.

HFH may be over and out, and that’s okay, because her writing’s a thing of the past, too. The reason why I feel compelled to share all of this is because I know that people will disagree with what I have to say, and I want to get the conversation going about it, because we music writers aren’t all too different from the talents we’re fortunate enough to write about when it comes down to the sacrifices we make to try our hand at living the dream—and especially when it comes to that Boston and New York thing none of us can escape. When I left the Dig, I said that Boston is a place where people come to “cultivate their genius” in my final Letter from the Editor, and I meant it. New York is where you’re forced to defend that pursuit every 60 seconds, and I’m grateful that that hustle exists in order to keep musicians, artists and the folks who write about them on their toes between the two cities.

So if you’re thinking about it — if you’re thinking of leaving your second homes of Cambridge, Somerville, Allston and JP for the stages of Bushwick, Astoria, or the Lower East Side, do it before you’re ready. Sometimes you need a landlord breathing down your neck to force you into taking a leap without the faith. And sometimes you need to work yourself to the bone and come face-to-face with a muse you never saw coming in order to redefine the faith you have in yourself.