Fail more, and fail often

If you're batting .1000, you're not aiming high enough

via Dall-E

In my recent workshop on pitching, an attendee asked a question that struck me. It was something along the lines of, 

Why bother pitching [x publication] if I already know they’re going to say no?

First, setting aside the fact that there’s no way to actually know if a publication is going to reject your pitch, it kind of misses the point. Sure, rejection is a fact of life, but for us freelancers, if we’re being rejected, it means we’re aiming high, but it also means we’re not settling. Anchor clients are wonderful and we should all have them, but the goal of any profession is to continually work to improve your craft. Freelancing is no different. 

If you’re not failing often, you’re not aiming high enough.

This is all a long way of saying: Go pitch The New Yorker or The Washington Post. The worst that can happen is they say no, which is simply an impetus to move on to the next publication on your pitch list.

I was inspired to write this newsletter after coming across an excellent post on Study Hall headlined “How to bring a killed story back to life” (which, coincidentally, is an idea I’ve been kicking around forever and was expertly written by Hannah Docter-Loeb). It basically boiled down to an idea I both sincerely believe in and talk about on pretty much every workshop: A “no” from one editor is not a “no” to the idea.

There are a million reasons editors decline ideas, and shockingly few of those reasons are about the idea itself. 

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Ignore imposter syndrome. As freelancers, it’s easy to take rejection as a personal failing, as if we’re not good enough to make it. This is a common thought! I have gone through that emotion countless times, as I’m sure every person reading this newsletter has as well, whether it’s pitching a top publication or tackling a project my stupid brain “knows” I can’t do. But whenever I find myself spiraling down that (misguided) rabbit hole, I think back to my years as a commissioning editor at NYT. 

I can tell you firsthand: Don’t assume your pitch, story idea, or concept was shot down because it’s bad. Of course, sometimes those things just don’t work, but many, many times, the reason I would turn down an idea, story form, project, or something else wasn’t because I didn’t like it. It was very often for reasons completely unrelated to it, and, if I’m being honest, sometimes the decision was simply out of my hands.

We need to take the high shots and reach. I hate myself for referencing this awful, embarrassing cliché, but it really does ring true: Shoot for the moon. Even if you miss, you'll land among the stars. Cringe as that saying is, it’s something we all should keep in mind. 

So write the longform feature you’ve obsessed over time and again, dive into that investigation you’ve been avoiding because it feels intimidating, or start that other line of income you don’t feel fully qualified for. As we’ve all learned, it’s nonsense to apply to only jobs you’re 100% qualified for, because that just means is you’re not stretching and growing. The same philosophy applies to freelancing at every step of the process.

Now go forth, and write stories beyond your abilities, pitch places where you never thought you’d be published, and revel in rejection. If you’re stretching and failing, it means you’re on the right track.

Okay bye ily!

-Tim ❤️

Oh, a few other things …

• I offer one-on-one coaching! Need help developing an idea or sharpening one you already have? Or want to talk about careers and building your freelance business? I gotchu! Book a one-on-one coaching session to talk about pitch reviews, story development, editing, and anything else you might need help with.

• Get a pitch commissioned recently? I want to see it! I’d love to feature you and your #pitchesthatsold in an upcoming series examining great pitches that resulted in stories. Let’s see ’em!

• I’m now doing Q&A posts in the newsletter to answer all of your questions, comments, and thoughts about freelancing and journalism in general. Drop any and all questions in the comments section below this post or email me at tim@freelancingwithtim.com, and I may feature it in a future newsletter. Let’s hear it!