The Stakes

When contemplating a writing project, let just one question guide you:

What’s at stake?

Not just what’s at stake in the Story—if it’s not earth shaking, find another one to tell—but what’s at stake for you personally. If you could skip the project and forget about it the next day, it’s not one to devote years of your life to telling. Burning your creative days on something that’s not going to push you to the edge of madness is a waste of time.

You won’t get better.  You’ll sell yourself short. No matter how popular or how well praised the finished product is, you’ll know that you phoned it in.  So don’t do it.  Press yourself.

Listen to what your insides are telling you to avoid…that’s the voice of Resistance. And as Steve Pressfield points out, you need to drive headlong into that negative storm. Use it as a guide to tell you what to do next.

If you keep hearing from the chattering monkey inside your head that doing X project is a stupid idea…that no one will care…that you could make an ass out of yourself…that you need to focus on something more practical…and on and on… That’s the one you need to work on.

Today, any of us can write and publish a book. I can’t emphasize how much of a gift that is. You don’t need me to tell you that you’re worthy to get your ideas into the world. You just have to choose yourself, do the work, and to hell with what I think.

Those age old external constraints no longer exist. Barriers to enter publishing’s retail marketplace were torn down almost ten years ago. We can write our stuff, upload it to an eBook seller, print on demand company and even audio publishing companies and have our multi platform work for sale on, iTunes, Kobo, Barnes and Noble, Ingram and on and on. And no one will tell us “no.”

We can’t decry I’m a genius, but no one will give me a chance anymore.

There are a million guides out there that will walk you through the process. It’s not more difficult than making a very good cake from scratch. It’s hard, but doable.

So why don’t we?

It is the internal constraints to writing our book (little discussed but more powerful than Vladimir Putin) that make us shudder and keep us on the sidelines.

Fear. Fear of criticism. Fear of failure. But mostly, the one we can all use to trump advice givers like me…Fear of poverty. Of putting in years of blood, sweat and tears and getting nothing in return.

Let’s be practical.

A fella needs to eat, doesn’t he? And if he’s married and has kids, he has to contribute to the family bank account. Even Maslow puts those necessities before personal self-actualization on his hierarchy of needs.

This is the humdinger Resistance throw down of them all. It shuts up anyone telling you to pursue something with no immediate or guaranteed payoff.

That’s nice, but how do I make my mortgage payments while I confront my internal demons and paint my masterpiece?

But what if you were guaranteed a return?

Then you’d do it, right? No sweat. Bring on the madness.

What if a publisher called you and said they’d agree to pay you 1.5 million dollars to write your book, no matter what? They’d sign a contract stating that even if not one person bought your book, you’d still get that 1.5 million. In fact they’d hand you $375,000 just for signing the contract. You know, as some seed money to get you started.

There would just be one catch.

They would have to read your book after you delivered it and determine whether it was “editorially acceptable,” which is code for whether or not they agree that it is worth that 1.5 million dollars.

I mean you didn’t think you could turn in a bunch of rubbish and expect 1.5 million dollars in return, right? Of course not.

And if they thought what you delivered did not live up to what you promised, well, you have to give them back the $375,000 they lent you to get your started.

No hard feelings. You tried, but didn’t quite make it. It happens.

And the kicker is that even if you disagreed with them and had great arguments to support your case, there is no outside third party—no certified editorial appraiser—who would be able to come in and “objectively” evaluate your manuscript. One man’s literary gold is another’s lead.

So because they are the one’s fronting the costs to create the thing, the publisher’s subjective opinion reigns. He who writes the check makes the rules. That’s the way it works rube.

This is why so many writers don’t exhale until they’ve officially had their manuscripts “accepted.” Until they are, Damocles’ sword hangs over them.

Malcolm Gladwell was in this precarious place back in 1998. We last left him as he stared down the mess of material on his desk—the stuff that he’d have to somehow piece together into a first draft of his book The Tipping Point.

Sitting with his morning coffee, you know these realities had to have run through his mind.

A confluence of events came together in such a way that the external barriers to being published were not just removed for him; they were put in his service.  This was back in the day when the only way into a bookstore (brick and mortar or online) was through the front door of a publisher.

He got the big deal. The seven-figure contract that we read about over and over again as if it is some sort of winning ticket. It’s not. It’s the biggest mind-fucker there is.

Especially for nonfiction writers who sell their work on proposal.

Here’s why:

Big money can lead you to do one of two things:

  1. Play it safe.

Again, most nonfiction writers sell their work on proposal.   A proposal is a thirty or more page document that walks an editor/publisher through a future work. It opens with a prologue or introduction that reads “as if” it were the future book itself. And then it outlines the intentions of the writer…why this project is important, why the writer wants to write it, why he or she is the perfect one to write it etc.

 There is an art to creating an irresistible proposal. And a danger too.

If your proposal makes promises you cannot reasonably keep, you will panic when the time comes to write your first draft…if not before.

 So what many writers do is to suggest that there could be great payoffs to what they propose, but they make sure not to go “too far.” They manage expectations of the editors and publishers who read their proposals and when the time comes to write their first drafts, they use the proposal as their fail-safe security blanket.

That is, they deliver what they’ve promised in the proposal, but not more. When they deliver their draft a year or so after it has been commissioned, they do not risk a reaction like “ummm, this is interesting, but it’s nothing like the proposal that we bought…”

Those words from an editor are the precursor to “so we’re going to have to cancel this contract…here is the address to send back your check for the signing advance.”

  1. Swing for the Fences

A big deal can also have the opposite effect. Instead of the nonfiction writer playing it safe, he may find himself tempted to go for broke…to invent a wild new idiom or dive into material that he is not fully conversant.

He doesn’t look at the work as a way to hone his particular genius, to push the edge of his skill set, instead, he decides that what he can do with what he’s done in the past is not enough. If he’s a journalist, he decides that he needs to emphasize his line-by-line writing. If he’s an accomplished stylist, he decides that he should do more “on the ground” interviewing or research. He abandons his particular craft and tries to learn a new one instantly.

 In his darkest hour, he convinces himself that what he can deliver with what he has at his disposal (his craft) is not good enough. It is not worth seven figures. So he has to “reinvent” himself and find a way to be a writer worth the big bucks.

Sitting with his coffee all those years ago, Malcolm Gladwell must have weighed both of these options.

He chose a third option…He would play it safe and swing for the fences.

10 comments on “The Stakes

  1. Mary Doyle says:

    “The stakes” are everything. Thanks for emphasizing this in today’s post, and for putting us in Gladwell’s chair as he probably wrestled with this very issue. Just last night I was re-reading Seth Godin’s “What to Do When It’s Your Turn” and came upon this: “The book that will most change your life is the book you write.” Yes, the stakes are everything – as always, thanks!

  2. Tina Goodman says:

    He chose the third option! I didn’t even know there was a third option.

  3. Derick Tsai says:

    Dropping truth bombs as usual. Keep the wisdom flowing good sir.

  4. Chris Duel says:


    This was powerful, practical and exactly what I needed to hear.

    Thanks, Shawn!

  5. Shawn,
    I don’t know why I don’t just cancel all the other blogs I subscribe to, except Steven Pressfield and Seth Godin, and just read your blog. I don’t want to read another marketing blog, I want to write.
    This is so helpful.
    I am wading through your book, which I know is your blog. Writing and fighting resistance every day.
    The bigger the dragon the bigger the dream. May all your dragons be huge.

  6. Adrian Venter says:

    Thanks for the prod, Shawn.

  7. Donna Michel says:

    Perfect, absolutely perfect. Thank you!

  8. Justin Fike says:

    Thanks for returning to this series. I haven’t given much thought to non-fiction writing. For some reason it never clicked in my head as being just like fiction writing in terms of the inner way, which I’m realizing now is ridiculous. Looking forward to the next one.

  9. maggy simony says:

    Thank you for this! Led me to immediately list “playing it safe” elements of my project and what I would do if I chose to “swing for the fences” as you put it. For my project swinging for the fences would include asking for (and perhaps being rejected) pre-publication peer reviews. I did this very successfully for my first book on my topic–surprised me with its success! Why does it now scare me when I really know some of these people better now than back then?

    If it’s part of Story Grid process, could you do an article on peer reviewing? It’s something like submitting a proposal to a publisher BUT not precisely the same thing.


  10. A.R. Arias says:

    High stakes, social trends, publicity, timing, high concepts. Let’s throw in author’s voice and strong POV’s into this mix and we just might have a workable recipe to launch a successful ($$$) story. Especially if we’re obsessed by it and we have the courage to put it out there. Then we just need a bit of luck.

    I’m still all-in.

    Good stuff, Shawn. Anything other than that, we’re just pissing in the wind.

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