Writing vacation — my week with the Willits

I met some new people on my writing vacation, the Willits. I didn’t much care for them.

I’d set myself up to have five glorious days unencumbered by client responsibilities. Time to make some serious headway on a personal project. And then I met the Willits. Annoying as all get-out.

Every time I sat down to write, one or more of them would appear:

Will it be any good?
Will it make you a laughingstock?

and the worst Willit of all:

Will it sell?

Plenty of time to answer all of those questions after the first draft. Yes, I knew enough to remind myself of that every time they popped in. Still, having to swat away “will it” questions every time you write a sentence…it’s hard to keep your focus. And the last question—I mean, any rational analysis of the publishing industry would tell you the answer to that is no. But I’m still gonna write, dammit.

I told each Willit in the strongest possible terms that none of them mattered right now. Right now, my job is just to write. They still came back. And brought their relatives.

Writing vacation surprise!

writing vacation
No Willits (2017), fine-line marker on hotel note pad

If you haven’t already met the Willits, I hope you never do. They’re a bunch of nosy bastards. But they surprised me when they showed up, because my writing life is mostly Willit-free.

When I blog every day, I open up my browser, find the appropriate web page, and most often words fall out of my fingers. Occasionally they’re good words, more often they’re merely acceptable. But I write them anyway. If people get some value out of the blog, that’s great. Will it move people?…Actually, I don’t worry a whole lot about that.

You might imagine the Willits would show up when I write for my clients:

Will it be acceptable?

But I don’t worry about that either. Because I know—and, most importantly, my clients know—that it’s a first draft. And first drafts are for experimenting, for pushing the proverbial envelope. For failing, even.

No harm, no foul; no Willits.

Of course, the writing I do for my clients isn’t personal, not to me. My blogging gets personal occasionally and, now that I think of it, I have seen a few Willits in my peripheral vision when I write pieces like this.

But I wasn’t prepared to host the Willit Family Reunion during my writing vacation this week—four generations, setting up picnic tables and volleyball nets all over my lawn. They had a blast. Me, not so much.

Next time I’ll be prepared. I’m making some lawn signs.


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

Courage and failure: “…you have to be willing to lose”

What does courage have to do with failure? Quite a lot, to judge by recent interviews with two successful women. Today’s example comes from journalist Katie Couric.

On her own podcast—which I heard when she “crossed over” to Pod Save America—Katie Couric talked about her late sister, who ran for state office in Virginia. Couric’s sister told her,

“When you run for office, you have to be willing to lose.”

Couric translated that as “You have to be true to yourself and to your core values and principles and let the chips fall where they may.”

Courage isn’t about the middle ground

We don’t often see that kind of courage in the political world.

Instead of standing up for their own beliefs, candidates instead trumpet the “least objectionable” beliefs, as determined by an endless succession of focus groups. A politician running to win would naturally attract a tribe of dedicated supporters, emotionally invested in the outcome.

But more often, politicians run to “not lose.” With no firm positions to rally around, their electoral strategy depends on maintaining a fragile coalition of people they can keep happy with vague promises. The promises have to be vague, right? Because the minute they become concrete, someone—on the right or the left—will get offended. And someone else wins the election.

But don’t we all lose when that happens? Once you run on vague promises, you’re stuck with vague solutions. If you intend to run again, you can’t ever leave the safety of ambiguity.

Katie Couric’s sister may have said it in the context of electoral politics—”When you run for office, you have to be willing to lose”—but I think this works as a mantra for any of us. Especially when we’re sticking a toe—or more—out of our comfort zone.

You can’t take a risk if you’re not willing to fail.

Tomorrow: Another podcast, another badass risk-taking woman.


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

Perfectly imperfect: What draws us in?

I have always hated being imperfect. I wouldn’t call myself a perfectionist because we’re all evolved enough to know that unless you’re a neurosurgeon, perfectionism is a character flaw. And—surprise—I don’t like thinking of myself as flawed, either.

My favorite business coach, Samantha Bennett (sadly, we’re not related), has tried to instill in me an appreciation for imperfection. “Don’t be afraid to get  a C,” Sam says. Or as PR expert Sakita Holley, the host of a delightful podcast I recently found, says in her latest episode: “Done is better than perfect.

Of course, they’re both right. I can think of only one upside to a world in which we all wait to achieve perfection before acting: A whole lot less email. Then again, we might not have any computers on which to receive it. Tech wizards have mastered the art of “ship now; debug later.” And annoying as it is when you’re the person who gets the wonky upgrade, I don’t see anyone clamoring to return to the days of carbon paper and carrier pigeon.

Imperfect is much more interesting

Cindy Crawford’s mole—a facial “imperfection”—made her millions. It made her recognizable; she stood out in the crowd of leggy beauties in our fashion magazines.

Flawless delivery, like flawless skin, is much less interesting. Think of all the boring Saturday Night Live sketches that only get funny when we watch one of the performers fight not to burst out laughing. It’s unexpected. And it’s endearing. The celebrity suddenly becomes human.

One of the reasons I find Sakita’s podcast “delightful” is that she is not afraid to be imperfect. Even though I’ve never met her, when I listen to an episode I feel like I’m gabbing with a girlfriend over tea, not listening to some blow-dried “expert.”

Now, please don’t mistake my praise of imperfection as license to be unprepared. If you stumble over a passage when delivering your speech because something distracted you momentarily—hey, it happens to the best of us. No harm, no foul.

But if you stumble because you haven’t read the thing before you stepped up to the microphone, shame on you. You’re not respecting your audience, and the time they’ve invested to listen to you.

Prepare to do your best, always—but don’t expect that “your best” will ever be perfect. It won’t be. And that’s probably a good thing.

Failing & Creating: Seth Speaks (on The Tim Ferriss Show) 1 of 3

I spend a lot of time driving these days, which means I’m constantly on the lookout for great new podcasts to listen to. The Tim Ferriss Show has quickly made it to the top of my list, and at the top of that “top of the list” is his interview with Seth Godin.

There’s so much in this marathon conversation that before I’d even finished listening, I knew I’d have to listen again. And take notes.

The interview bounced around from topic to topic and circled back several times. I organized these notes into the three categories that resonated most with me: Failing and Creating, Not Writing, and Change-Making and Writing. Have a listen for yourself, though, and you’ll probably find five other topics I could have included in these notes.

Failing and Creating

“My job is to do something that might not work.” —Seth Godin

Godin doesn’t present this statement as an elevator speech (29:10), but I can’t wait to try it out in that context. He says he’s prouder of his failures than his successes, because at least they demonstrated that he tried. His goal isn’t to get good ideas; it’s to get bad ones. Because once you get those, some good ideas will turn up in their midst. (37:00-ish)

When you’re creating something entirely new, there’s no benchmark; you can’t quantify the thing you’re doing. But these are the most important things to try: “Our soul is filled by the things that have never been done.” (59:00)

And of course it’s scary. People always feel fear, and that fear never goes away (50:00). But he offers good news from a Buddhist philosopher: “We are falling with nothing to hold onto and nothing to slow us down. The good news is, there’s no ground to land on.” (1:20:00-ish)

“Clear the decks so all that’s left is you and the muse—you and the fear, you and the change you want to make in the world.” (59:00)

Check back tomorrow for “Not Writing.”