Like Throwing Darts in the Dark? That's Freelancing

Share:Tweet about this on TwitterShare on FacebookShare on LinkedInShare on Google+Pin on PinterestShare on Tumblr
Freelancer Cheryl Sternman Rule. She's learned how to throw darts that hit the target. (Photo by Paulette Philpot)

When I was a magazine editor, I wondered why freelance writers couldn’t figure out what I wanted. I rejected 95 percent of pitches.

Now that I’m on the other side, I see how difficult it is when you’re an independent writer, on the outside looking in.

At the recent Book Passage conference on Travel, Photography and Food Writing, food writer Cheryl Sternman Rule spoke about why pitching to publications is such an anxiety-producing process. What she said resonated with me, so I asked her to share it:

“As a freelancer since 2004, I’ve spent years both pitching and avoiding pitching,” explains Cheryl. “For me, pitching seems like a dark art. There’s black magic about it that often makes me feel like I’m throwing darts in the dark.

“Editors have editorial calendars, or ideas in their heads for what they’d like to cover. We writers are not often privy to this information. So we shoot story ideas out like darts and hope they’ll hit some mysterious, shrouded target. It’s a tough game to play, psychologically.”

That’s exactly right. You keep throwing until you strike the target, even when you get no feedback. You need a thick skin to be a freelance writer, not to mention an ability to see in the dark.

Meanwhile, Cheryl started a food blog. “If I come up with a good idea, I develop it immediately, put my own spin on it, and take it in any direction. The lights are bright, I can see the target, and I can hit it dead-on. It’s a tonic for the frustrations of freelance life, a life I love but whose secret handshake can be awfully difficult to master.”

Now she throws a few less darts, because editors she’s worked with are likely to assign more stories to her. “Over the years I’ve worked with a slew of editors with whom I have ongoing relationships. And while I still accept and seek writing assignments, I pitch less often.”

Like Cheryl, if you have tons of good ideas and you keep throwing darts at the same target — politely and professionally — sooner or later an editor will respond. A lot of writers give up without practicing their throw long enough, because it’s hard to keep going. Silence feels a lot like rejection.

Or they give up without trying a different dart. If you’ve only got one story idea, and pitch it without success, it’s time to move on and try several more ideas.You do have tons of ideas, right? Because the more darts you throw, the easier it will be to hit the bull’s eye.


  1. says

    What a great piece. You know that for me pitching really is akin to the dark arts and I just can’t get to a comfortable place about it. So I choose avoidance. Not the best plan if I want to get anywhere with freelancing. Time to pull out those darts and start throwing, I guess…

  2. says

    I do some freelance work, but it’s not enough for me to be able to quit my day job. I’d love to get most (if not all) of my income from freelancing someday and it’s good to hear about how people deal with the ups and downs. Getting freelance work can be a tough process but the rewards are sweet!

    • diannejacob says

      Very few people make a living as full-time freelance writers, so you’re not alone. I must say, it’s a pleasure when the magazine arrives and you see your name in print, I must agree!

  3. says

    I can sooo relate to the metaphor of throwing darts in the dark and know it can be difficult keep throwing sometimes – that’s when avoidance starts to look like an option. Still, nothing ventured, nothing gained – so we just keep on aiming for that shrouded target.

  4. says

    Really true article. I find the best way is to build a relationship with the editor and pitch all ideas, dumb or clever. You can pitch 10 ideas at once and hope the editor likes a couple of them.

    • diannejacob says

      Well, you hope none of them are dumb, at least! Ten at once is a lot. But that way there has to be at least one that works.

  5. says

    Leah you artfully touched on my question. How many ideas should I load into each dart? I don’t want to seem scattered, yet sending one idea per email seems a little bit like spamming. Though I have kept trying with one editor and she picked-up a second idea a year later – lesson learned!

    My biggest problem is not ideas or darts… but editors to shoot them to!



    • says

      Leah and Laura, I agree with Dianne here. I don’t think you want to pitch 10 ideas. Think about 2 or 3 ideas that suit the publication, and the department within that publication you can see your story fitting into, and fine-tune those so they sparkle. I think 3 well-composed ideas will get you an editor’s attention.

      Of course, whether that attention turns into a story assignment depends on a whole host of factors, some of which may be very transparent. Others may be mysterious. (Tip: Wear your decoder ring.)

  6. says

    Great photo; the scarf and the artichoke; perfect match. i bought your book to learn how to express myself about food on my simple blog. I am not out to make a living at this….much too old, but it is a great hobby; keeps me out of trouble and keeps my brain active. Really enjoy following your blog and get an insight on how the younger generation load their darts.

    • diannejacob says

      Thanks Rita. I imagine the photo of Cheryl works well for her upcoming book, Ripe.

      It’s strange to me to think of freelance writing as a hobby. I suppose it’s true financially because the pay does not match the effort, but on the other hand, it’s not like quilting or doing tai chi!

  7. says

    As a freelance playwright, one has to finish a play and then pitch it to theatres and publishers. You cannot send “an idea’ for a play. A lot of second-guessing goes on and you can toil for nothing. The play can win awards and it doesn’t mean there will be a market (production). For me, the most frustrating thing is when the quality product lies dormant while the silly play gets done again and again.

    I love the analogy of “throwing darts in the dark.” I will take that with me as I write.

    • diannejacob says

      A lot of writers send an idea as a query. Its clear that they haven’t fleshed out what the story is about because they haven’t thought it through. As you might imagine, those kinds of queries don’t get anywhere either.

      I suppose writing a play is more like writing a novel, short story, or memoir. For those, you have to write the whole thing first, because it’s all about whether you can tell a story.

  8. says

    To me, the most important factor is your relationship with the editor. You can get a lot of writing opportunities if you develop a rapport and act more like an employee than a freelancer (available for spur of the moment gigs, flexible, helpful,etc.). It’s tough but possible.

    • diannejacob says

      Absolutely. But that relationship comes after you’ve successfully hit the bull’s eye a couple of times. So you still need the good aim.

  9. says

    This comment is actually to Rita. Age is irrelevant to what you do, as long as you enjoy it and get out of it what you intended to get out of it. Saying all that, you should not eliminate right from the outset the potential of making a living out of things you like to do. When someone reads your article, it does not contain your birth certificate; although they may guess that you are not 20+ by the way you write from life experience.

    Rita, not long ago I was where you are ’96 obsessed with my age because I looked around the blogosphere and all I saw is young smiling faces. And you know who got me out of this defeatist behavior? Diane Jacob. If for nothing else, only for this taking her coaching program was a worthwhile experience and time and money well spent. I guess we all need someone like Dianne to direct us to follow our dream and not letting something as minor as age to interfere with it. BTW I am not Dianne’s affiliate, just a satisfied, “young at heart” student.

    • diannejacob says

      Well thank you, Jayne. You’ve come a long way since starting your blog. But you are not making a living as a writer either, just like Leah. Does that mean it’s a hobby? I don’t think so.

  10. says

    Your piece is not only filled with pertinent information, it is timely. I write a weekly food column in a community publication in addition to my food blog. My aspiration is to freelance, also. I have been shopping for a suit of armor that I will need to wear as I begin the process of pitching ideas to editors. Your book, and this article, provides the encouragement I need to just get out there and do it. Ok, world….ready or not, here I come!

  11. says

    I stopped trying to write professionally when I realized I was no longer at the top of my game as a writer. Three years out of the professional arena and you start to find that you’re a little less than top notch.

    It wasn’t until I began blogging last year that I slowly started getting back to writing. I moved into the current blog and have taken the past 6 months to truly hone in my writing style and what specifically I write about. Things change every so often but I do believe I have improved greatly in the year since I started.

    As for freelancing? It would be nice to try again but I don’t think I quite there just yet. It’s hard work doing both pitching and the writing itself. I feel it’s best to wait until I know I am 100% ready and capable before taking a handful of darts and tossing recklessly or even not so recklessly.

    • diannejacob says

      You are never going to be 100 percent ready, Kim. You just have to decide to do it anyway.

      You don’t have to, by the way, unless you plan to write a book. In that case it will help you enormously to show published work on the topic of your book, outside of your blog.

  12. says

    My image is not so much darts but those metal spikes (pitons) that rock climbers use to achieve toe-holds and slowly work their way up to the top of the mountain. I agree with Rose: it’s all about building a relationship with the editor. Twice I started by pitching the smallest item in a magazine and then worked my way up to features and columns, once the editors saw that I delivered good stories on time. Writers often want to start by pitching features. I’d say start at the bottom – there are more inviting crevices for toe-holds to get a good start. (Now I just have to follow my own advice for a national magazine). Meanwhile, blogging is a good outlet and place to try out new ideas. Good luck, all.

    • diannejacob says

      That is good advice, Anna. You did not start out trying to get a feature in Saveur. And look how well you’re doing, with regular features in a city magazine. It’s all because you got a toe-hold and worked your way into the editor’s confidence.

  13. says

    Well, you hit the points Dianne! I am not thick skinned by nature (is anyone?), so I need to make a big effort not to take things personally and not to be discouraged. The fear of rejection can really hold you back! I think it might have been a few years (!) before I got up the nerve to query a certain editor. One way of coping with unknown outcomes is to try to control them by feeling rejected in advance–a terrible strategy!! It is totally immobilizing. It is also not based in reality!

    I was actually shocked and quite pleased when she agreed to ‘try me out.’ Now when she calls me or assigns me something, it feels great; but more than that, it is a lesson in persistence and bravado. Both are needed. You can build a thick skin by persisting. Then, if an editor gets to know you and you learn about the publication, it becomes much easier to hit the target. I am still trying to expand from that one publication, and am finding I come up against the same ol’ stuff over and over. That’s when I need to say ‘hi there, old friend, you can sit in the back seat for this particular trip’ and plunge ahead.

    No matter how much we all might know this, it is good to be reminded of it (thanks Dianne) and to understand that it is a shared experience. Keep on keepin’ on! :)

    • diannejacob says

      You are so right, Sally. Nobody likes to admit how paralyzing it is to be rejected, or how hard it is to even get up the guts to try. You are working on your thick skin. Keep telling yourself that you’ve succeeded with one editor, so there’s another one out there who will appreciate you.

  14. Christina says


    I would love some tips on how to throw darts in general :) I’ve been reading “The Writer’s Digest Guide to Query Letters” to get up to speed on formalities, but I really have enjoyed your comments on things that are trending (or not trending!) in food writing. Cheryl Sternman Rule commented that editors have a specific niche they’re looking to fill and freelancers are often not privy to that information. I’m wondering why there isn’t better communication between these two groups. Wouldn’t editors much rather see 100 pitches that hover somewhere near the bull’s-eye, rather than 95 that pierce pinholes into the surrounding wall and 5 that barely make it onto the board? Or does it make it that much easier for editors to pick a submission if the pool is smaller?

    I know that there are guides out there like Writer’s Market guide that help writers navigate where to submit various types of pieces, but it would be awesome for an additionally comprehensive guide on specific interests to submit pitches for. I’m not super active on Twitter, so maybe I’m missing tweets from editors throwing out ideas they’re looking for? Any thoughts on how to close the gap beyond not giving up and building a relationship with an editor? That’s great advice, and I’m working on building my own network at the beginning of my writing career. Especially with book publishing, if you scan the shelves you’re looking at ideas that are 1-2 (or more!) years old. It would be helpful to know how to see a wave! :)

    As usual, your blog is wonderfully helpful and I look forward to every post! :) You’re mentoring a new generation of writers! :)


    • diannejacob says

      That is a big subject, Christina. I did try to cover it in the freelancing chapter of Will Write for Food.

      Basically, editors have their own ideas of what to cover, and they look to writers to fill in, or — in the best circumstances — to sniff out stories they don’t know about but want to cover. Editors don’t write down their strategy very often. They don’t throw ideas out on Twitter. Even if you can find writer’s guidelines, they are quite general. Of that 100 percent, maybe 20 percent are in the ballpark. The rest come from people who really don’t know how to pitch successfully. They need the Writer’s Digest Guide but are probably never going to read it.

      The best way to figure out the right story is to read the magazine closely to figure out what they like to cover. And then figure out the angle they use, which makes them different. A piece in Prevention will not read the same as a piece in San Francisco magazine, even if it’s on the same subject.

      Re building a relationship with an editor, you can do that after you get your foot in the door. And the way to get your foot in the door is with a pitch that’s right for the magazine, newsletter, or website.

  15. says

    My first job out of college was in sales, and I became really immune to rejection. Ironically, with this career, which is my truest passion, it’s different. It’s personal. And, the rejection stings like no other. But, as many of you have said, nothing ventured, nothing gained. In the midst of it all, I try to remind myself that people are incredibly busy and a lack of reply doesn’t always equal a lack of interest. Persistence (and solid, creative ideas) are key.

  16. says

    I’ve reached the point where I’d rather be pummeled with rejection responses than endure the dreaded and painfully common CRICKETS AND TUMBLEWEEDS that tweet and blow through my inbox so often after launching a pitch. It’s frustrating and exhausting to sit and wait and wonder and wait and waffle about resending or repurposing elsewhere after working hard to craft a solid, professional pitch. An acknowledgement, even if it’s “thanks but no thanks” would feel like a win.

    Some people may argue that if there is no response from an editor, it means either a) your pitch was no good OR b) the editor is not interested or can’t find a spot for your work. But on more than one occasion, I’ve pitched a polished idea that was greeted by radio silence, and then some time later (in a recent case, YEARS later) that same pitch was acknowledged, appreciated, accepted, even lauded. This experience makes me wary of assuming rejection (even if I feel certain of it). When does waiting become wasting time?

    It’s a tough psychological game, as Cheryl says.

    (Thanks, Dianne and Cheryl for more discussion!)

    • diannejacob says

      Hmm. When does waiting become a waste of time? Good question. After 2 weeks, follow up politely. Hearing nothing after 2 weeks longer, move on. This is why you’ve got to have lots of ideas. If you’re really invested in one, radio silence is devastating.

      • Tara Mataraza Desmond says

        I wouldn’t say it’s “devastating” to me. I keep right on with it, since it’s what I do. But it is frustrating. Yup, true that the name of the game is LOTS OF IDEAS, but we also have to spend considerable time honing our pitches for quality. After we have, getting no response either way is enough to make us grumble a little… and to fuel the feeling of playing darts in the dark… which isn’t really much fun.

        • diannejacob says

          Yeah, I understand. So if it isn’t much fun, why do it? Is it because when you do hit the target, it’s worth the frustration?

          • Tara Mataraza Desmond says

            Sure, in part. Getting a bite is fantastic, a relief, a motivator, a validator and all the rest. But I’ve also come to accept that this is the way freelancing goes. I’m grateful for the relationships I’ve managed to build with editors who now assign me recurring work without my having to go through the dark arts darts, but I’m also always on a mission to break into new markets and work with new editors. That quest is mostly preceded by this frustrating work of breaking through. I don’t think I’m alone in saying that part isn’t much fun, am I?

          • diannejacob says

            Definitely not. How about if we say it’s a challenge? That makes the process of finding new markets slightly more motivating.

        • says

          I know what Tara is talking about. . Sending out queries and never receiving acknowledgement is really dispiriting. Isn’t there a code of “editor etiquette”? A simple, “no thanks” would do.

          • diannejacob says

            In the old days, pre email, editors could answer every query. Writers had to mail a query on letterhead and include photocopies of clips. It was an effort.

            Now, anyone can approach an editor through email, without thinking through the story. In their defense, I believe editors are overwhelmed, and the delete key makes their job bearable.

            That being said, established writers should get a few words of reply. It’s not fair to lump everyone into the same group. Sure, there’s a 95 percent rejection rate, but probably 10 to 15 percent of that 95 percent got pretty close.

    • says

      Once more Dianne, you’ve brought up a most valuable topic ! Thank you! Great comments. Excellent advice. Recently retired, I had my very first article published and paid for by a magazine in Beirut Lebanon. I sent them the article in Dec.2010 and it was published in August 2011. It took 8 months for the editor to respond to my two other pitches and request articles. What did I learn from this? Just keep sending them out and don’t look back until I hear from them.
      I’m learning so much from all the comments. Thank you.

      • diannejacob says

        Eight months! I’ve never heard that before. It made me laugh. Still, you were patient and waited. Congratulations!

  17. says

    Yes, pitching can definitely be frustrating. You MUST be persistent. Give your pitch three weeks. If the editor hasn’t contacted you, send a polite email asking her if she’s had a chance to look at it. No news is sometimes good news – It could mean that the editor likes your idea but needs to wait until her editorial meeting to get it approved.

    There are two ways to go about pitching:
    1. Have an idea that you’re in love with, then find the right publication for it
    2. Have a publication that you love, then pitch any and all ideas that you think will fit their needs.
    I tend to use #2 most often, and with the most success.

    • diannejacob says

      Thanks Laurie. You said to wait 3 weeks, I said 2. Both are good.

      Re your ways to go about it, I like No. 2 better also. I saw a ton of No. 1s that I rejected as an editor, because the authors couldn’t make a good enough argument for why my magazine was a good fit. I think they just sent the same article idea around to a whole bunch of publications. It was easy to tell.

  18. says

    To Dianne,

    You are right. I am not making a living from my blog, but I’d like to think that I am working toward that direction (Aside from enjoying the outlet). Rome was not built one day, blogs, particularly in the food area take time to build up. I just started guest blogging, and I am in the process of changing the design of the site. I am patient, even though I should be wanting to rush things, before I am at the stage where I will not be able to use my hands at all due to my ever progressing health condition (but there is a voice activated software)

    Basically, I just thought to encourage Rita (and actually we lost communication, because at one point I got in touch with her when I saw her favorite singers to be Elvis and Neil Diamond) not to hold back anything because of her age. Isn’t that what you told me when I expressed concern about my age as a “newbie” blogger among the mostly 20 or 30 plus writers?

    • diannejacob says

      Yes I did encourage you, Jayne, and I’m pleased that you took me seriously. I’m no youngster either. As for rushing, a career change has a huge learning curve, and food writing is no exception.

  19. says

    It seems anything on that side of the brain must be conceptualized, created, and defended. People will criticize anything and everything, especially when asked. Gotta have an elephant’s skin and believe in it and defend it. Don’t have any experience with freelancing….but i have plenty of experience defending…myself, my food, my vegetarianism, my shoe selection….

    • diannejacob says

      Most of the time freelancers don’t even get criticism, just silence. I don’t know which is worse. But yet, the answer is a thick skin. And to keep going.

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>