Will 2016 be the year we start talking about failure?

“As long as you have not written that article, that speech, that novel, it could still be good.” –Megan McArdle, Why Writers Are The Worst Procrastinators

A lot of writers I know and read have been talking about failure lately, and it’s not even a coincidence. The beginning of 2016 seems to have hit us particularly hard for some reason.

On February 1st, after a particularly unproductive month, I decided to revisit the conditions of what seemed to be 2015’s winning streak. Last January I took a class called 30 Days, 30 Queries, meant to fight the terror of the pitch by forcing each and every one of us to become an idea-generating, pitch-scribbling machine. If you punched them out quickly and cared less about each one, the theory went, you’d inure yourself to the soul-crushing cycle of hope and rejection that’s sent many a freelancer running back to an office job, and instead set yourself on a surefire path to productivity.

I had quite a bit of luck with this course, taught by a smart, kick-ass journalist who’d had more than her fair share of ups and downs and wasn’t afraid to talk about them. I netted some of my best clips, and was even taught the power of perseverance when an essay of mine was finally accepted by Talking Points Memo, after being rejected on spec by the Washington Post and every other outlet I contacted.

I felt as though I’d challenged myself, forced myself to do the work, as the Megan McArdle article in the Atlantic had said, and come out with a growth mindset instead of a fixed mindset, opening up to further challenges and more self improvement as a writer. I was so pleased with myself, I even wrote down 10 lessons I’d learned about being a freelance writer, posting them online on consecutive days as if I had a captive audience, or really anyone who checked my blog regularly besides mom and dad. I was sure this was just the beginning of my long path towards success as a freelancer, so when I mentored younger versions of myself later in life, I could point to this class as the turning point.

Well, it turns out it’s not that easy. I've spent my first two weeks recreating 30 Days, 30 Queries in February 2016 sending out pitch after pitch, only to be met with rejection (1) or silence (14), forcing me to dwell on my failures, question the legitimacy of my small successes and wonder whether I’m at all cut out for the freelance writing lifestyle.

And in case there was any doubt, it is very much a lifestyle. I’m not talking about the ability to wake up late, take midday naps and prepare luxurious meals every night, all because you’re not spending your waking hours rushing to and from an office. I’m not talking about the ability to take a vacation or a day off at any time (something few freelancers are financially equipped to do, but which nevertheless earns us a reputation for being lazy and entitled). I’m talking about the uncertainty, not just financial and professional but psychological, that very few people my age seem to be able to handle. From that same Atlantic article:

Young people are uncomfortable with the unstructured world of work. No wonder so many elite students go into industries with clear boundaries, like finance and consulting.

It took me a while to realize that many of the smartest kids at my high school and college ended up going into finance or becoming lawyers. I could think of a few who’d gone in to more creative feels, but only after they’d added that self-satisfying and somehow worth-affirming MFA to their CVs. Very few had lit out for a career entirely of their own making, because when you build your ideal career from the ground up, there are no bosses, colleagues or mentors to help you along the way.

And that’s the fundamental thing about freelancing. There is no other freelancer out there with your background, your talent (or lack thereof), and your set of goals. If you’re successful, you can look at where you’ve been and feel like everything happened for a reason, everything clicked into place as it should have, and now you’re here and you feel great about it. If you’re unsuccessful, though, it’s very hard to look at the million mixed up pieces you’re juggling and pull out the ones that fit together to make that perfect puzzle image you want to be your life.

If you’re a lawyer and you make partner at a law firm, you have your excellent college grades and LSAT scores to thank for getting into one of the top law schools, once there, the stellar grades, connections and recommendations to thank for getting you into a top law firm and finally, a combination of hard work and luck to thank for getting to partner level. If you’re a doctor or in academia, it is much the same: a lot of where you end up has to do with a professional path that’s been laid out for you.

When you’re a freelancer, there is no map because there is no path.

 A couple of years ago, a successful writer told me, “years from now, you’ll look back on everything you did and you’ll see that it all made sense; it all got you to where you are now.” I thought to myself, “you’re only saying that because you’re successful.”

Indeed, I still can’t shake the feeling that for every successful writer out there claiming to look back on it all with clarity and confidence, there must be a hundred or even a thousand writers for whom it all ends up never making much sense. Much like we never hear about “the folks who believed in the mythical ‘N-rays,’ declared that human beings had forty-eight chromosomes, or saw imaginary canals on Mars,” as Ms. McArdle describes, we also never hear about those people who tried for years to sell a manuscript, applied to that fellowship or grant unsuccessfully, or in my case, sent out a pitch a day for 30 days and never got a yes on even one of them.

The narrative when you’re a freelancer is that everything has to happen for a reason, precisely because you’ve got no one around you to tell you what that reason is. This is why so many of us end up in badly paid content mills, begrudgingly sell an article for a pittance because we just need to publish it somewhere, or still accept “exposure” in lieu of payment. 

“Exposure” is the direct result of that little voice inside of you telling you this might be your big break, admonishing you to say yes at all costs, because you just might look back on your yes five years from now, as the royalty checks pour in and the New York Times and the New Yorker fight over your latest think-piece, and see that it all came down to that little article you wrote for no pay for that little website that could.

So failure to find the right kind of work for your bank account or reputation becomes failure to find the right kind of work to add a rung to your ladder to success. Call it freelancer FOMO, but it is the fear of missing out on that contact with an editor who (surprise!) moves on to a bigger and better publication, that set of eyes from an agent at a publishing house who thinks your piece would be just perfect as a memoir. We crank out more and more work as our quest for quality becomes a struggle for quantity, as we try to cover all our bases, to make sure our work appears everywhere – or at least everywhere our rivals' work has appeared.

I wish I could offer up some inspirational quote or wickedly clever aphorism to end this piece, but not knowing where it ends is, too, the nature of failure. We press on with our pitching and our hustling and our invoice writing and bank account checking in hopes that somehow we’ll have a breakthrough, either mental or professional, and it’ll suddenly all make sense. That someday we won’t have to congratulate people younger than we are or people we once offered advice to, then cry tears of rage and clench our fists with jealousy and fear—no, certainty—that it will never be our turn.

These are all the different kinds of failure no one wants to mention, but if 2016 is the year we finally start talking about them, then I’m ready.

I’ve certainly got enough material to fill a book.