2017: My Year in Writing

A picture I took in Venice Beach in November, which has nothing to do with this Medium post.

Hi. Does anyone still use this? I’ve always found Medium’s interface pleasant, even if it was a failure as an ads revenue-generating platform. Not everything has to Disrupt, some things can just be good websites. True, it’s probably owned and managed by evil technocrats, but I’ve resigned that if I were to adhere to that level of moral objection I’d have no food to eat, clothes to wear, or teams to root for (Go Knicks and Jets, and all the money I funneled straight to the Trump campaign via tickets, gear, and a cable package!). What do I know.

I’ve seen other writers do this at year’s end, and I think it’s a good way to take stock of one’s work, both for my own benefit and for those who may consider my services in the future. By measure of words and publications I think I had a decent year freelancing, although I struggle to establish a reference point so long as I approach writing with a seriousness closer to “enthusiastic hobby” than “source of income,” and the market for such work continues to shrink.

I don’t feel I’ve earned the right to complain about the debasement of truth and the free press when I mostly write about books and music. By the same token, it’s not for me to bemoan the cruel deaths of outlets I’ve written for and others I’d have liked to write for; so long as I work a nine-to-five the continued narrowing of media hasn’t affected me as much as it has others.

That said, I think an objective appraisal of my own work — and anyone’s! — requires acknowledging that to write, and to think, and to observe and argue is to fly directly in the face of immensely powerful angry rich people who would rather you didn’t do any of those things. I hope that isn’t aggrandizing so much as clear-eyed: I’d love to have written for or Grantland or Gawker by age 27, but guess what.

Looking back at my last year’s output there’s some stuff I’m proud of and other stuff I’m less proud of. I tend to accomplish my actual writing very quickly, but lately I’ve started to second-guess my technique and word choices with an almost manic feverishness. I have a hard time being confident in my words when our use of language is so often just a parroted-back amalgam of everything we’ve already heard and read.

My most immediate resolution is I’d like not only to write more, but to write more broadly; I’ve long aspired to cut my teeth on more reporting and commentary, narrative stuff, opinion pieces, heck, even fiction. Below I’ve assembled a collection of some stuff I published this year, along with random meditations, lessons learned, and recommendations, as if anybody wants those from the likes of me. Cheers to 2018!

On criticism:

I read a lot, although in recent years my diet has constricted somewhat; I seem to gravitate disproportionately to cerebral, contemporary plots and writers who aim for the “literary” shelf, whatever that means. I enjoy reviewing novels although I’m sure some folks would dismiss me as unqualified, having little experience writing fiction myself. This is something I became acutely aware of this year while penning less favorable reviews — I’m in awe of anybody who can write a novel, so when I’m critical I try to focus more on ideas and aesthetics than mechanics.

As An I-95 Kid I always dreamed of writing for , and was thrilled to have my first print review in what would prove to be one of their final weekly editions:

I’ve been contributing semi-frequently to The Awl for two years now, a general-interest non-profit site with a tone and philosophy I’ve always appreciated. Editor Silvia Killingsworth is a one-woman army and somehow also finds time to be an incredibly nice person. My review of Brian Platzer’s was fun to write, and I got a lot off my chest without, I hope, being unfair to the author:

Don Lee’s was one of my favorite reads of the year, and I hope its quietness won’t leave it empty-handed come awards season:

In December I had an amazing opportunity to write a review in ! A million thanks to the legend Ron Charles for letting me write about Webbie and Allen Iverson in the paper of record:

Timing is the most critical factor when pitching book reviews — most outlets nail down their schedules months in advance, and a book that’s a week old might as well be years old as far as most pubs are concerned. Luckily, book publicists are really pleasant and happy to send catalogs and advance galleys. It can be tough to stay informed, though, and I actually do most of my scouting by following writers and critics on Twitter.

In January I wrote a short piece for the on my bedeviled appreciation of David Remnick’s Trump commentary in . I love the because it’s a non-profit and bookish but not too stodgy:

On the music-crit front, I had a nice opportunity to express my conflicted take on Joey Bada$$’s sophomore effort in the . I am super, super bummed the stopped printing and hope their website lives long and prospers.

My J. Cole screed on The Awl was, I think, one of my better pieces of pop criticism, and Silvia’s edits made it worlds better than it would have otherwise been:

I contribute whenever I can to , The Best And Last Rap Blog piloted by benevolent dictator Jeff Weiss. covers great music no one else does, and I’ve exorcised plenty of demons in its pages. also has the best year-end lists in the game. These were my top 25 albums of 2017. These were my 25 favorite rap songs of the year.

On interviewing:

Interviewing is a nuanced skill and one I’m always trying to get better at. Asking strangers about their lives makes me anxious, but I genuinely enjoy talking to people and find a candid interview feature rewarding.

The good folks at Bandcamp let me do a long feature with the incomparable rapper O.C., which was a thrill. Bandcamp is producing fantastic editorial work — I’ve learned tons about jazz, world music, and indie releases through their Guides and Daily content — and their team is amazing to work with. It’s meaningful for me to contribute to a platform I believe in; they’re fighting the good fight in trying to compensate musicians for their work in the streaming world.

I also interviewed a few novelists I deeply admire. Writers are easy interviews in a sense because they’re so thoughtful and well-spoken, but they’re also intimidating for the same reasons. B.G. Firmani was incredibly generous in my interview:

In the spring I interviewed Darcie Wilder about her debut novel for Magazine, and really enjoyed getting the chance to pick her brilliant mind.

A writer-friend told me recently that he doesn’t write questions before an interview, but instead just goes in knowing the general topics he’d like to discuss to better keep the conversation spontaneous and organic. I wish I had that confidence, but I write my questions in a notebook that I bring along after agonizing over sequencing. For in-person interviews I record on my iPhone, for phone interviews I record my call on a laptop.

I try to begin as conversationally as possible, because I find that the best way to make both myself and my subject comfortable is establishing relatability. O.C. and I probably don’t have a ton in common, but we love a lot of the same music — we spent hours talking about arcane 1990s rap records. Firmani and I had fairly similar backgrounds despite our gulf in age and experience, which shaped both my questions and her answers. Short of that, my foremost recommendation for interviewing artists is to first display a personal interest in their work. For me that’s easy because I rarely take assignments or interview people I hate, but I’m often surprised how much displaying mere familiarity with my subjects’ work makes them open up.

I find background research easy, albeit time-consuming. If my subject’s been interviewed before, I read those, and watch available YouTube clips to pick up on mannerisms. It’s tempting to cut answers short or talk over a long-winded response, but don’t — you can’t put words in your subject’s mouth, and if you asked the question you need to live with the answer. I look my subject in the eye as much as possible, even if I’m taking notes or fiddling with my recording device. When he’s finished giving an answer, I wait a beat before asking another question to make sure he’s satisfied. Pay for drinks/food if you’re comfortable doing so.

On profile features, and writing for disappearing publications:

I selfishly enjoy writing profiles because it’s a green light for me to use my interview subject’s words in service of my argument as to what his/her work is/means. The market for profiles has severely diminished over the past few years because now that artists have a multitude of digital means with which to easily and succinctly convey their PR, “access journalism” isn’t really a thing anymore. Seriously, how many exclusive artist profiles do you remember reading in 2017?

Last year let me write a giant feature on a rap group that means more to me than to virtually anyone else, which needless to say was my biggest challenge as the writer. This March, I did a feature on Brooklyn rapper Your Old Droog.

For this piece, the timing was both a hook and a challenge. A widely accepted premise of music journalism, which I don’t agree with, is that artists have A Moment upon which their careers hinge. Supposing that premise, Droog’s has probably passed. What I was hoping to convey here was the strangeness that an artist as great as Your Old Droog, due to some combination of his race, voice, and narrative, is still seen as something of a novelty despite dues paid and a fantastic catalog. I hope I haven’t contributed to that narrative, and that, in any event, he gets to continue making the great music he wants to make. I’m deeply appreciative to the multiple editors who lent their wisdom and hatchets to this piece — knows better than anyone how this type of piece should read, and I think that of the remaining flagship music pubs, they do the best job of balancing insight with passion.

One of the tragedies of the year in journalism was the death of alt-weeklies. Since the advent of and internet porn, most proud municipal weeklies had to settle with being edgy-but-not--edgy, so their target audience basically became graying cool-dads who still have a weed guy in their phone contacts and can spend a few minutes reading about what’s going on in the world of hippity-hop over their coffee. Their full decline is worthy of a thesis and not this already overlong Medium post, but suffice to say there was plenty of self-immolation and external factors involved, as detailed in this excellent piece by Gustavo Arellano. In any event, this all really sucks, because alt-weeklies were the last bastion for investigative reporting, municipal journalism, leftist editorials, and arts writing, and they delivered news and ideas in a voice that sounded like it was actually written and edited by human beings.

Like the Gawker and Gothamist sites immediately before it, died a cruel and puzzling death, murdered by disingenuous libertarians who purchased it from the latest syndicate which tried and failed to pump money out of the historic title. Again I’m afraid that 2017’s mass murder of hallowed outlets isn’t my story to tell, but I find myself despondent nonetheless; the and were, for me, proud pubs I could reliably approach for freelance work. Now they are no longer, and I don’t see anything filling their void.

I always felt privileged to write for the ’s music section, the more so because I’ve spent a grand total of four days of my life in Southern California. Andy Hermann is a great editor who gave a home to some of my favorite pieces which I can’t imagine living anywhere else. In October I caught up with R&B star Eamon upon the release of his first record in a decade:

The ’s short profile style has been largely phased out at larger pubs, who probably reason that social media breaks that caliber of artist nowadays, but I found alt-weeklies essential in featuring working-class musicians outside the major-label machine. After stumbling upon his album and enjoying it for months, I tracked down producer Anthony “L’s” Cruz to discuss it. The format allowed for coverage of his engineering and recording techniques, which I expect most outlets would shy away from.

tl;dr, R.I.P. alt-weeklies/save alt-weeklies.

On pitching:

Start with your back foot on the rubber, your throwing and gloved hand together at chest level. Jokes!

I still do a lot of cold pitches. I miss a lot more than I hit, but the hits have generally been good opportunities and provided a foot in the door for future work. If I don’t hear back within a week or so, I follow up once if it’s a piece I’m really itching to write and I think it’s a good fit. Most editors I’ve worked with admit to being absolutely buried in pitches, so at risk of seeming thirsty most don’t get offended by a polite follow-up.

If I’m aiming high or pitching pubs I’ve never worked with before, I think it’s kosher to pitch multiple simultaneously — if it’s a long shot anyway, what do you have to lose? I provide a short introduction with my 3–4 best recent bylines. They have the same internet you do, so no need to tell your life’s story. Shorter pitches are preferable, but if you need space to convey your idea or qualifications don’t agonize over word count.

When I land a pitch, I offer a deadline I know I’ll be able to keep, assuming it’s not super time-sensitive and my editor doesn’t establish a hard deadline. My attitude is that, since I’m asking for work, I’m more or less at the mercy of my editor in matters of compensation, but make sure you’ve reached an agreement before you get started writing. Negotiating within reason is fine, but if you feel you’re being low-balled, and that’s a deal-breaker, you should probably go somewhere else — editors have budgets and would pay you more if they could.

I’m a member of the Study Hall Patreon group, which has been a massively helpful resource for help formulating pitch ideas. For $8 a month they have a newsletter, message board, contact lists, and a direct line to the best freelancers doing it. Highly recommended!

On promoting your shit:

I dunno, man. I tweet my pieces, which can help you find readers if you have some nice writer-friends who will share them, but you risk annoying people by tweeting the same shit over and over. I have a few hundred followers and can’t figure out how to get more without making a fool of myself on the internet, which I think I do enough of already.

I keep an archive at this site, which breaks every couple of weeks. I have a Contently too, which is probably redundant.

On freelancing, as a hobby and/or a job:

Like anyone else, I’d love to be a full-time features writer for the or or wherever else still has giant expense accounts and trim Ivy League assistants in pencil skirts, but there are like four of those jobs in the entire world and to chase one would be to condemn myself to a harsh existence. I value stability to a fault, so for now part-time freelancing is ideal for me. I get to write what I want when I want to, and have never taken on work I didn’t feel good about. Even as a hobby, it’s something I find rewarding enough that I feel comfortable making certain sacrifices to pursue it.

For anyone considering freelancing full-time, my advice is, don’t. Don’t let me kill your dreams — if you’re really good and really driven, it may work out for you — but based on my average per-word rate this year (not an ideal metric for this exercise, but a pragmatic one), I’d need to publish about twenty features a month to break even living with (multiple!) roommates in New York City. And even if I could crank out a piece a day without direly compromising quality (I couldn’t), there’s not nearly that much work to go around. If I pitched even editors I have good relationships with that frequently, they’d tell me to take a hike and maybe recommend therapy. To scrape by I imagine I’d find myself doing shoddy work and/or taking on jobs I don’t feel great about. ‘90s child that I am, I hope that the going rate for my professional services will increase in proportion to my knowledge and experience. An egalitarian freelance economy doesn’t work that way.

I hope any brave full-timers who stumble upon this Medium post won’t feel I’m undermining their work. It’s unfortunate there are so few writing gigs, and all the more so because of how quickly the market shift occurred. Since childhood we’ve been led to believe that literary expression is a higher calling valued by society, which doesn’t appear to be true anymore.

This is very jarring. I consider the countless years I spent honing a five-paragraph essay (which isn’t even a thing outside of public school classrooms) to help my schools angle for government funding. Turns out this wasn’t great prep for the job force, and our economy and a lot of smart people are worse off for it. Sure literacy and being able to think critically are helpful skills to have, but I know plenty of people who make tons of money who read at a fifth-grade level and can barely write an email. The humanities are not in-demand or well-compensated skills on their own.

I hope the transitional period in which we find ourselves in an aberration. Anybody working in media needs to have faith that we’ll return to the days in which the free press was a profitable enterprise, despite the fact that after two decades nobody has a damn clue how to make money off online media. But cynic that I am, I’m quietly worried that recent history — annual subscriptions, full-page ads, glossy foldout spreads — was the aberration. What if it’s not the supply that’s flawed (inopportune platforms, conveyances, and/or revenue strategies) so much as the fact that, due to people getting poorer or dumber, there isn’t a demand for written ideation anymore?

So as much as I really enjoy writing — and in moments like this of dark lucidity I suspect it’s just another thing that was beaten into me over the course of an American education — it’s better, for me at least, to pursue it as a low-stakes, high-reward hobby. I find comfort in working out my thoughts on a keyboard that I don’t derive from more passive recreation. And if you’d do me the honor of allowing me to contribute to your esteemed pub in 2018, I live at ptosiello at gmail!



writer, on good days. NYC. @tosiello

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