The post I never wanted to write: RIP Writing Streak

My writing streak is dead. Long live the (new) writing streak.

953 days—that’s a long damn time. Sometime in May 2016, I believe, I committed to write for at least 15 minutes a day, every day. And I did—for 953 days. Until yesterday.

In the beginning, when I was ingraining it as a habit, I wrote first thing in the morning “before you check your email” as my coach Sam Bennett instructed. (No relation, except we’re both brilliant and gorgeous—so who knows?) In heath and in sickness—I even wrote the morning I had surgery. And the next day, hopped up on painkillers. Neither snow nor rain nor 11:59 at night…

I didn’t start worrying about the streak until the last six months. Travel, divorce, more travel—even dating. No matter where I was or who I was with, I did My Fifteen. Even when I spent ten hours writing for a client. Even when writing was the last thing I wanted to do. Even when I knew I’d be proving Hemingway’s observation that everyone’s first draft is shit—I wrote.

So what happened yesterday? It was an odd day to begin with—part 2 of a whirlwind trip up and down the East Coast. I got to breathe the same air as Elizabeth Gilbert for a while yesterday evening. I did take notes while she spoke—and later I tried to make that count for my 15. But it wasn’t original writing; if you’re gonna make a commitment, ya gotta stick to it.

Usually when I’ve waited too long to write, the mental reminder pops up around 10pm as I’m doing The New York Times crossword. But I was tired by then and looking forward to listening to a guided meditation when I went to bed. About halfway through the meditation, I remembered “I haven’t done my writing!” I thought about stopping the recording to do it right then, but I didn’t. I vowed that I’d do it after the recording.

“After the recording”—I’m sure you can guess—I was asleep. But I DID wake up, miraculously (the power of commitment). I grabbed my phone, opened a Notes doc, and wrote:

“I am so confused [hand hitting forehead emoji] I want up bwrite ye book as I font [hand pointing down emoji]”

Even by Hemingway’s standards I realized it was hopeless. The 953-day Writing Streak was dead—but the next one is alive and kicking.

Writing Streak—Day 1

How many rewrites until I have a final draft?

Q: How many rewrites until I have a final draft?
A: Do you want someone to publish it?

One of my writers recently admitted, “I get tired of what I’m writing after about three drafts.” Give her points for honesty. To be clear: I don’t think that means she’s giving up after three drafts. She’ll just give it a rest, until she’s got the stamina for another three drafts.

A writer I know recently sold her first article to a very prestigious publication. Took her 12 drafts. Yes, a dozen. And give her points for recognizing that each draft made the piece that much better.

Neither of those people would have passed muster in my friend Vanessa Park‘s middle school English class. This cartoon sums up the experience of one of her students—a young woman whose mother is New Yorker cartoonist Liza Donnelly.

how many drafts until the final draft?

“Uh-oh. You did 82 drafts??!” the young man says. “I only did 79!”

The point, of course, is not quantity but quality. So how do you know when to take the D-word off the top of the page and call it a finished piece?

Sometimes you run into another D-word: Deadline. I could futz and finesse all day, but if I told the client she’d have it by 5pm then by God she has it by 4:59.

But if you don’t have an external deadline, give yourself an internal one. The futzing and finessing stage can last (probably literally) forever. When you find your revisions shrinking from paragraphs to sentences to words, you’re getting as close as you’re ever going to get.

Is it perfect? No. Because it’s never going to be. As my old coach Samantha Bennett (no relation) says, “Get a C.” I can’t tell you how many times I’ve sent “C” work out into the world and found it received as an A-plus.

We writers can be unreliable judges of our own work. That’s why we need trusted colleagues to read and comment. Sometimes that’s a writing group. Other times it’s a sympathetic magazine editor who asks for Draft 9, then 10, 11, 12. Each time you get feedback, your work gets better.

How long until you have a final draft? If your editor doesn’t tell you, your deadlines will.


Of course you know how to read. But do you know how to read like a writer? Learn that essential skill in my critical reading course. Next cohort starts in late February.

15 minutes of commitment

By now, pretty much everybody in my life is used to my 15 minutes of writing a day. As I tell my writers when they start out,

If you respect your commitment, the people around you will respect it too.

15 minutesWhen I arrived at my cousin’s house the other day for a quick overnight before an early morning trip to the airport, I wanted to visit with her. But I also needed to write. So I did something I don’t usually do—I plopped down on the sofa to watch the baseball game with her (did I mention we’re related?) and I opened up my laptop. My cousin understood.

So instead of 15 minutes of focused writing, I did several innings’ worth of semi-distracted writing—the first time I’ve done that, but I don’t think it showed. Still, I’m glad I did it, because the question my cousin asked—well, the minute she asked it I knew I’d be blogging about it:

“Do you do this for yourself?”

15 minutes for me…and more

And I realized that the answer was both yes and no.

No—not in the sense she meant. She didn’t know about my blog (someone’s not reading her email; she subscribes to my Occasional Flashes of Brilliance). And I guess for a person who lives a very offline life, the idea of throwing upwards of 300 words into cyberspace every day seems a little baffling.

And yes, of course I do this for myself. My 15 minutes a day has made me a better writer. It’s helped me be braver about the topics I take on. And it’s helped me make a connection to you. I’ve enjoyed that.

My coach Samantha Bennett (no relation) suggested the 15 minutes a day format. My virtual mentor Seth Godin said that blogging every day is the best business decision he’s ever made. And who’s gonna look at Seth Godin’s career and not start blogging daily? Certainly not me.

So here we are, you and I and my 15 minutes of commitment. If you’ve ever thought about doing it, do it. Today. For yourself.


Want to communicate more courageously? Click here to get my e-book Do It Anyway: Tips for Courageous Writing

Happy anniversary, writing streak. And many more.

I’m not sure I’ve ever done anything for a full year in a row. Unless you count breathing.

Yes, breathing must surely count. But breathing is involuntary; my writing streak was—is—probably the most intentional thing I’ve ever done.

Writing streakAnd today is Day 365! So happy anniversary to me.

Not just to me, actually. Because if I hadn’t gotten the crazy idea to write every damn day, I would never have created the daily writing challenges that have helped dozens of writers to start—and continue— their own streaks.

Of all the things I’ve accomplished in the past year, I think I’m proudest of the daily writing challenges. Next 5-day challenge starts June 19th. Join us and see why I love them.

Why are writing streaks important?

The streak? It’s just a number; no big deal. What is important:

  • Empowering yourself to create
  • Creating even when you’re not “inspired”
  • Deciding to continue when giving up would be so easy

I know I wrote those words just a minute ago. But re-reading them it’s hard to believe they describe me. What I’ve done over the last year. But it’s true.

I’ve written blogs—yes, lots and lots of blogs. My one-year anniversary of daily blogging comes up in a couple of weeks, on May 11th. But I’ve also written the curriculum for my writing classes. I’ve written marketing material, emails, sales pages, my “Occasional Flash of Brilliance” (the thing other people might call a “newsletter”). When I was really pressed for time one day, I pulled into a parking lot and journaled for 15 minutes. I never had the mad dash to write before midnight, but I did have to head to my desk after a lovely dinner out once because I’d forgotten to write earlier. The point is, I did it. I cared about myself enough. I prioritized myself and my creativity. And I’m writing about it now not to celebrate myself but to model that behavior for others.

Because if I can do this thing, you can too.

Getting a C (if I’m lucky)

My coach Samantha Bennett (no relation, although we’re both smart, funny, and gorgeous—so who can really say?) says “Get a C.” Don’t aim for perfection; just get it done. That’s been my mantra this year.

I have written some great pieces during this streak. I’ve also written some absolute crap. Hopefully I haven’t published too much of the latter, but I think there’s value in being transparent about the quality of my output.

Not all of my work is brilliant. And—guess what?—not all of your work will be, either. But that doesn’t give you license to put down your pencil. You’ll write again tomorrow. And the day after. And eventually the crap-to-great ratio might even out, maybe even start to tilt in your favor. Or maybe not.

But start writing. And keep writing. It’s the only way to get better.

Meet Jon Favreau — newest guest at my imaginary dinner party

Jon Favreau, my latest imaginary dinner party guest
Jon Favreau, photo by The White House from Washington, DC – P021213PS-0265, Public Domain

Who would you invite to an imaginary dinner party? My guest list changed after reading the article I’m writing about today. Welcome Jon Favreau, former Director of Speechwriting for President Obama; I hope you’re not an imaginary vegetarian.

I’ve been a Favreau fan (a “Favan”?) for a while now. The podcast he and some cronies from the Obama Administration cooked up—Pod Save America—restores my sanity twice a week. I thought for sure I’d already blogged about their interview with President Obama, the last media interview he did as president. I will correct that oversight ASAP.

But another oversight I will correct immediately: Jon Favreau’s co-conspirators on Pod Save America are speechwriters Dan Pfeiffer, Tommy Vietor, and the (I’m sure he would describe himself as) indispensable Jon Lovett.

Jon Favreau also has a name doppelgänger, an actor
Actual Google search results for “Elaine Bennett”

I feel some affinity for Lovett, who will surely go through life being mistaken for Jon Lovitz. (Has the letter H somehow become a pariah? Um, pariah. Whatever happened to “John”?) But at least Lovitz is a real person; I’m fated to remain second in the Google search to a sitcom character.

Jon Favreau—not just a pretty face

Favreau’s invitation to my imaginary dinner has nothing to do with his boyish good looks. Or the fact that, come to think of it, he too has a name doppelgänger, a movie producer.

Nope, I’m passing the dinner rolls to Favs because we think about writing in the same way. Clearly he’s a smart dude.

This LinkedIn post by Trevor Ambrose—“Obama’s Speechwriter Shares 5 Storytelling Tips”—summarizes some of what makes Favreau’s speeches so effective. But they’re not just valuable tips for speechwriters: any writer can and should embrace these best practices.

1 – Story is key

Ambrose quotes Favreau:

“In my experience communications too often focuses on finding the right words. Of course words are important at some point in the process. But the first question you have to ask yourself is: what is the story I’m trying to sell? That is essential, and should be the starting point.”

“What is the story I’m trying to sell?” Focus on telling a story and the facts and data will slot themselves in, reinforcing the narrative. Focus on reporting facts and data and you’ll never get to the story—and the idea you’re trying to convey will never take root in the listeners’ or readers’ minds.

Too many people believe that facts are the story. Too many people end up creating boring, eminently forgettable work.

2 – Short & simple

“…a speech about everything is a speech about nothing. Narrow your story down to the essential point.”

Easier said than done, especially when you’re trying to incorporate language and feedback from many stakeholders. Even when you have only one client to please, it’s a tough sell. People seem to feel that the more they talk, the smarter they’ll sound. I’m still working on the right way to convince them otherwise. Jon Favreau and I will surely trade war stories about this over imaginary dinner.

3 – Inoculate yourself against criticism

“You should find [objections] and address them during your speech.”

I believe I let out an audible whoop when President Obama inoculated himself against critics of his efforts to halt climate change. This passage comes from his 2015 State of the Union Address. And I guess the fact that I remember it two years later negates my argument that speeches stuffed full of ideas can’t be memorable. No speech gets stuffed fuller than a State of the Union; perhaps it’s the exception that proves the rule.

Anyway, in 2015 President Obama told Congress:

“I’ve heard some folks try to dodge the evidence by saying they’re not scientists; that we don’t have enough information to act. Well, I’m not a scientist, either. But you know what — I know a lot of really good scientists at NASA, and NOAA, and at our major universities.

Unfortunately for our planet, the current Republican administration is defunding those “really good scientists.” Unfortunately for our language—and our liberties—the current president inoculates himself by spouting blatant lies. Convince enough of your base that the mainstream media lies and can anything they say or write damage you? I look forward to the imaginary discussion Favs and I will have on how (whether?) we can counter this strategy.

4 – Understand and speak to your audience

“You have to know what the world looks like when you are in [the audience’s] shoes. One of the reasons why Obama’s speeches are so successful is because they are written in the language that his audience understands, addressing the issues they are facing.”

I often run into clients who are eager to show off the bright, shiny idea their company came up with. But “Isn’t this cool?” doesn’t work as a speech premise. You have to show the audience—and note that I said show, not tell—how the cool new thing will solve their problems. And you have to do it in language they understand.There’s no point in extolling the virtues of your new creation if no one knows what it is or what it does.

Political writers have an even harder job—they have to bring abstract, often complex concepts to life in ways that resonate with audiences who have a wide range of backgrounds and experiences. Oh, and if you don’t do your job well, the polar ice caps could melt and drown Miami. But, hey—no pressure.

5 – Jon Favreau wants to connect

Of course I mean he wants his speaker to connect, and inspire. And what’s the best way to do that? See #1: Tell stories. But not just any stories:

“The best way to connect with people is through stories that are important to people’s lives.”


What’s with the dinner party, anyway?

Sometimes I ask my webinar participants to imagine their own dinner parties. I love the exercise because the first time I did it (hat-tip to Samantha Bennett, my imaginary cousin and an inspirational teacher), the reveal at the end just gobsmacked me. If you’d like to try it for yourself, I’ve uploaded a clip of it to Vimeo. Enjoy.

Perfection – the worst goal ever

“Continuous improvement is better than delayed perfection.” — Mark Twain

You can always count on Mark Twain for exactly the right sentiment. If he’d invented the greeting card industry instead of trying to automate the printing press, he might not have gone bankrupt.

I’ve written about perfection before—about how my favorite coach, Sam Bennett (no relation), reminds us to “Get a C.”

My favorite guru, Seth Godin, translates that as “Ship your work.” Don’t wait for it to be perfect, because such a state doesn’t exist.

My education primed me for this early on, because my school didn’t use letter grades. Teachers graded us on a scale of 1-100. And of course, no one ever expected to get 100 because we all—teachers and students—understood that perfection doesn’t exist. Until one of my friends produced a paper so exquisite in every way that the teacher had to give it 100—her husband, a New York Times columnist, argued her into it. It was the schoolyard equivalent of Nadia Comaneci’s perfect 10; the grade heard ’round the world. Or at least ’round the Upper East Side of New York.

But in real life, the folks judging you don’t usually get an assist from a New York Times columnist. In that world, perfection—if it exists—is fleeting and exceedingly rare. Better not to aim for the bull’s-eye of 100 when you can much more frequently hit the fatter target of the 90s. Even the 80s is perfectly respectable. But when you don’t ship your work, you have absolutely no chance of hitting the target at all.

That’s a form of perfection, too: a perfect failure. The worst goal ever.Austin Kleon reframes the idea of perfection

So don’t be perfect in your failure; be imperfect in your attempts to shine, to make a difference. Go read Austin Kleon’s invaluable book Show Your Work!—you can easily finish it in a weekend. And then do it: Show your work, warts and all.

Because nobody’s perfect. So stop trying.

Plans change. WTF?

The one thing you can be sure of about plans: Plans change.

Take this post, for instance. I planned to open with that famous quotation—you know—”The best laid plans of mice and men often go astray.”

Except that’s not the quotation. The actual quotation, written in 18th century Scottish dialect by Robert Burns, is a bit more indecipherable:

The best-laid schemes o’ mice an ‘men
Gang aft agley…

And so my plan for an opening quotation ganged agley too. (Wikipedia offers a modern translation: “Go often askew,” which barely seems better.)

So we switch from old Robbie Burns to a more modern muse:

“Everybody has a plan until they get punched in the mouth.”

That inarguable wisdom comes from boxer Mike Tyson, who should know. So should the majority of his opponents and, sadly, perhaps one of his wives.

I have never been punched in the mouth—or anywhere else, for that matter—and I’d like it to stay that way. But I have had plans change, in large ways and small.

First draft: the plan that (almost) always changes

I learned early on in my speechwriting career that changing plans went with the territory. The first time I sat in a top exec’s wood-paneled office, scribbling furiously on my legal pad as he held forth on “exactly what I want to say” in his next speaking engagement—that moment remains clearly etched in my memory.

I left the office, assembled the scribbles into a creditable speech, and returned a week later. He read it and bellowed:

“That’s not what I want to talk about.”

Now, I take meticulous notes—even with the ancient technology of paper and pencil. So I knew full well that was exactly what he’d said. But he was the one giving the speech, so he had every right to change his mind about the content.

I understood in that moment the full meaning of the phrase “first draft.” It means “Plans change.” And that’s not necessarily a bad thing. Because if  speakers can change their minds—if the first draft just exists as a catalyst for their thoughts—then it can be a catalyst for mine, too. I can offer something creative, an odd perspective, a wacky idea. And if it gets thrown out, well, plans change.

Plans change and change again

Many people’s plans changed after the election in the U.S. last week. Some may feel like we’ve been punched in the face. Others seem happier with the outcome. But I suspect people on both sides of the aisle have changed vacation plans—either scrapping them or making them.

“Plus ça change, plus c’est la même chose.”

That French saying—”the more things change, the more it’s the same thing”—has been around since the 19th century. The changes we’re experiencing right now may not seem like “the same thing,” but change happens whether we like it or not. And we need to deal with it.Plans change. We need to adapt with courage.

In my life, I’m not a huge fan of changed plans. But in my writing, I expect change; I even build it into my fee structure. How can I adopt the same equanimity outside the office?

I’m not saying we have to accept change we don’t like—especially not if that change threatens us. But I’d like to find a way to roll with the punches (again, not literally). That leaves you better able to defend yourself against fresh assaults.

I want to adapt, not necessarily accept. Just as I don’t always accept the changed plans my clients unveil. “Nope, that’s not a good idea,” I’ll tell them—and explain why. They usually listen, too, because they value my opinion.

Whatever comes, I will—as my friend Samantha Bennett (no relation, sadly) says, “use my work as a force for good in the world.” And you can too.

Not sure how? You might start with my free webinar “The Courage to Change”—Wednesday November 30th at 8pm Eastern, 5pm Pacific. Register here. And plan to join us.