16 Painful Truths About Freelancing

I'll_Cry_If_I_Want_ToToday is my six year freelance anniversary. For the past couple of years, I’ve paused to offer a reflection of sorts. Two years ago, I wrote about 20 things I learned the hard way. Last year I wrote about avoiding the trap of focusing on pay at the risk of quality, integrity, or personal goals.

Although this past year has been incredible in many ways, and I wouldn’t trade my job for the world, I’d be lying if I didn’t say that a lot of things about freelancing that just plain suck.

We all know about the great things: interviewing amazing people, writing posts that expose corruption or highlight the best of human nature, making an impact in the world, having a flexible schedule, and making good money doing work you love. But aside from minor quibbles, there’s a whole underbelly of hard stuff people don’t often talk about.

The only way around is through, but since it’s my party and I’ll cry (and swear) if I want to, I decided not to sugarcoat any of the hard but instead to sing it from the rooftops. So here’s a glimpse of some of the suck that you’ll want to be aware of before diving headfirst into freelancing, or ones you might relate to if you’ve been freelancing for a while.

Being a journalist won’t magically give you access.

For every person who will only talk to you (or a small handful of reporters), there’ll be a few who’ll dodge your calls or pretend they’re out of town or pull a no-show or turn off their porch lights just so you’ll think they are not home.

And then there are the people at conferences who will make a beeline towards you or anyone else with a media badge loudly proclaim that they don’t talk to the media, even if you didn’t try to talk to them at all. (Pro tip: taking cabs from your hotel/crash pad to the conference rather than getting on a shuttle or bus is expensive, but sometimes worth it for sanity’s sake.)

Sadly, the people you really want to talk to may not feel the same way, and the people who really want to talk to you are usually PR people who you don’t want to talk to at all, creating some sort of weird media love triangle. Or something.

Speaking of PR people…

You’ll get so inundated with PR pitches that you’ll want to scream. Screaming won’t help. Neither does responding, because most won’t take no for an answer, so now you have three pitches and six follow-ups to delete instead of just one pitch and six follow-ups. I try to deal with this by using SaneBox and setting up filters and having multiple email addresses and funneling pitches through Muck Rack, but you can still hear muffled screams coming from my general vicinity.

People will be dismissive and distrustful.

Most people (sources, editors, you name it) will ignore your calls and emails.You’ll get a great story but your source will back out at the last second before an interview and give it to another writer instead. You would’ve told it better, but the world will never know… Someone will listen to terrible advice on some podcast and decide to only do interviews over email…which will kill your interview. You’ll build trust but as soon as you can get one source there’ll be one you can’t get who you’ll want even more because human nature. The best solution is to find an editor with great contacts (good luck with that!) or to pick up Buddhism and renounce desire.

People will blame you for things outside of your control.

People will do interviews with you and break their own university’s conflict of interest policy (unbeknownst to you) and blame you when they get in trouble. That guy you know who gives workshops to journalists but seems to despise them probably didn’t find errors in the article you wrote so instead decided he’ll publicly share his opinions of a headline you didn’t write. Editors will introduce errors into your work, leaving you to choose between throwing them under the bus and protecting your professional reputation. More often than not, they’ll completely ignore your urgent emails about adding a correction…

Editors will kill or neuter your best stories.

You’ll have amazing editors that make your work shine, and you’ll fire all the sucky editors, but some of the amazing ones will sometimes do sucky things. You’ll write about NGOs working on human trafficking issues in Thailand and your editor will sit on the story for months and then kill it because she decided the person she asked you to interview, the person who gave up her life and moved across the world, “isn’t compelling enough.” And since you actually cared deeply about the piece, getting paid for unpublished work won’t be any consolation.

When a PR flack complains about an entirely accurate story, that editor who you thought had your back will lose his backboon and capitulate to insane demands quicker than you can say “conflict of interest.” There’ll be very little you can do. Freelancers are expendable, after all.

Editors will even ask you to send questions in advance when interviewing administration officials so that the state, with all of its resources, has all the time in the world to properly spin their answers. Up next: no blog post needed, just an Instagram photo of the government’s talking points… no wonder media folks are worried about robots taking their jobs.

You’ll fuck up.

Your editors will ask you to cover topics you don’t know on tight deadlines. You’ll fact check as much as you can and get things wrong sometimes anyway because you’ve got a blind spot and won’t double-check stuff you think you know. You’ll have to write corrections (or worse, send an editor corrections and be summarily ignored) and it’ll suck. They say fighters are only as good as their last fight. Writers are only as good as their most error-riddled post. I’ve seen entire industries turn on journalists with 15, 20+ years of experience because of a single error they immediately corrected. The sad part about fucking up is that it’s not always easy to learn from your mistake, because you can build resistance to these tactics and find new ways to fuck up that you haven’t accounted for in your new time-consuming strategy.

You’ll waste a lot of time because you’ll think you may have fucked up, when you hadn’t.

You’ll get vague criticism and go down the Google rabbit hole and then realize that there is debate within an industry on the way a term is used, but the way you picked is the more accepted one. +1 for wasting time realizing that you were pretty much right all along, I guess. If only you could bill for those hours.

Your worst posts will do the best.

The dumb post you dashed off on no sleep, fueled by sugar and caffeine, will get tons and tons of traffic because of a gimmicky headline and reference to porn or pop culture (that you may not have even written). The smart post about internet kill switches will go almost entirely unread.

You’ll want to blame this on site readers, but even in your own social networks, a cute new profile pic will be far more popular than that column you spent 15 hours on. You know some people are reading because they’re whining about something or other in all caps in the comments, but you’ll pretend they are bots because the possibility that they are representative of your readers is too depressing for words.

Everything will be unfair.

The writer who has no command of spelling or grammar and isn’t great at factual accuracy either will somehow start writing for glossy mags you can’t break into. Writers at the same sites you write for will scoop you (no wonder they wouldn’t share contacts when the editor asked). You’ll turn down countless trips and dinners and events and beers because of a stringent conflict of interest policy, and then your assigning editor will write about that same free trip you declined. Your favorite sources will think you’re batshit insane because you insist on buying your own drink, leading to so many awkward moments that you’ll want to switch to copywriting, where the perks flow freely.

But it’s not just COI that’s at stake. Your colleagues will get basic factual information wrong, casually dox people for page views, or find other creative ways to destroy people’s lives, and nobody will bat an eye. Your heroes will follow them (and not you) on social media and publicize their other work (and not yours).

Of course nobody will know own about all the (similar…not to mention lucrative) stories you turned down for ethical reasons. Nobody gives a shit about your ethics. Nobody will even notice your ethics. Nobody sees the stories you can’t publish because they might be inaccurate or because a source backs out or because publishing would be problematic for various reasons.

Oh yeah, and that person you’re ghostwriting for will get invited to speak about the post you wrote on a radio show with your favorite actor of all time who he’s never even heard of. It’s the freelance version of someone repeating your idea in a meeting, except you agreed to ghost, so you can only blame yourself.

You’ll get opportunities you can’t take.

Because who is going to cover your hotel and airfare to give that unpaid keynote or host that unpaid panel? Per diem? What were you thinking? You’re not even on staff.

Not to mention all the stories you lost because a site said yes and then changed their mind before a contract was signed, but after you could still pitch the time-sensitive idea to the other sites that originally expressed interest.

You will realize that freelancing is incredibly lonely.

I’m a huge extrovert, and though I have no trouble finding events to attend and making friends, there’s something about working with a group of people toward a common goal that I miss. Long gone are the days of work parties or happy hours. As a freelancer, I’m lucky if I can get more than a few sentences in an email from an editor. I have a handful of freelancer friends and we support each other and work through work drama, share leads, and take turns listening to each other vent. I go to cafes and co-working spaces and work parties. Even still, but most of the day is filled with dead silence. Add to that the fact that you typically have to email everyone multiple times to even get a response and even the most stable, well-adjusted freelancer might start to feel radioactive.

You’ll get limited feedback, and the feedback will probably make you feel shitty most of the time.

Since your editors don’t really give you feedback, you’ll instead be rewarded with…reading the comments, peaking at responses on Reddit or social media, and dealing with emails. The nicer feedback won’t tell you how to improve, and the other ones won’t be constructive either. Even if you go above and beyond and spend hours fact-checking the accuracy of claims until you’re proud as hell of a finished product, someone you actually like and respect at your favorite non-profit will tell you she wasn’t a fan because it didn’t include some favorite pet peeves & she didn’t like the order of suggestions given. You won’t make corrections since there’s nothing to correct, but this comment will probably cancel out all of the positive feedback you actually did get. But typically all you can hope for is that sigh of relief when nobody comments at all (or they just argue with each other).

No good deed will go unpunished.

Your future pay will hinge on that post you over-delivered on because you cared about the subject, but your sweat and tears won’t be reflected in the page views. You’ll stick up for other writers an editor is screwing over, and learn months later about how they retaliated—in a way that has negative career repercussions.

Continuing ed is a motherfucker.

As a freelancer, nobody is really invested in your long-term career except for you, so you have to be your own freelance hero. For me that means taking lots and lots of online classes or learning new things. I’ve set out to learn everything from programming languages to visual design to cryptography. Unfortunately, the courses are either easy/boring or pretty frickin’ hard and I don’t have the same level of support that someone working with other people at the same publication would have. (No afterhours study groups for me!) Nor is it obvious what will be useful a month or a year or five years from now. I have never believed in certainty anyway, but the support systems and group learning situations that non-freelance positions can bring have their own benefits.

You won’t even know what metrics editors are judging you by.

Sure, you can check WhoSharedMyLink.com, but you probably won’t have access to page view data or know how your work stacks up. And since nobody talks to you about it, you can’t offer feedback about all the reasons a post may have done well (or not). Because a lot of the time it’s the topic, or the image, or the SEO keywords used, or the headline. But metrics are a whole ‘nother ball game for obsessives, where no number will ever live up to your own expectations.

The good feelings don’t last.

Even if you write a dream post for a dream site, the buzz will only last a few hours to a few days. After the initial thrill, you’ll get depressed about how you’ll never be able to repeat the feat, or find some way to discount the experience. And if your goal is to make an impact on the world, there may not even be a good metric you can use to judge whether you’re doing that.

So what’s the verdict?

I’m not trying to talk people out of freelancing. I’m just pointing out that it’s not a bowl of cherries. Chances are that if you quit your job and start freelancing, you won’t be able to interview everyone you write, even if you work for Bigshot Magazine. That people will often be upset at you for reasons outside of your control. That editors won’t always improve your work and will sometimes destroy it (or worse, capitulate to brands or governments). You won’t always get things right. People maybe think you’re wrong even if you do get things right. The amount of energy you put into a post, or the gravity of the topic, is not what will get you traffic. Hard work won’t always pay off. Having high standards will make things harder for you, not easier. You won’t be getting a lot of feedback or even talking to editors for more than a few minutes. You’ll be lonely. You’ll probably cry a lot. And you won’t appreciate your own success as much as you should.

But this isn’t the end of the story.

I’ve been busy brainstorming ways to move past this, which may start with working fewer hours and coming up with new goals/metrics that are meaningful to me, and balancing heavy-hitting work with stuff that’s less exhausting, including a bit of brand work I’m doing. Here’s hoping next year I’ll have a more positive outlook to share.

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