Meet Frank Sinatra, writing coach

Ol’ Blue Eyes is known for his voice, but the lyrics to the songs he crooned offer good insight for writers looking to turn stardust into a very good year.

I’m a longtime fan of Frank Sinatra. So are my 22-year-old triplets. One of their babysitters used to play Sinatra’s music for them and, as preschoolers, they’d walk down the street singing such songs as “Fly Me to the Moon” or “You Make Me Feel So Young.” It was adorable and often created a bit of a sensation. (Especially when my kids wore their sunglasses.)

I was thinking about Frank recently, and it occurred to me that some of his song titles offer great advice for writers. No, I’m not talking about “Wishing Will Make It So.”

Most of Frank’s songs are more on the money. Here’s a few of his titles to think about before you sit down to write:

“Accentuate the Positive”

Consider these words from songwriter Johnny Mercer:

“You’ve got to accentuate the positive

Eliminate the negative

And latch on to the affirmative

Don’t mess with Mister In-Between”

I’ve worked with many people who fear writing. The printed word holds nothing but terror for them. They worry what their boss or client is going to think. Worse, they worry about what they’re going to think of themselves. Something negative, they assume. So here’s my question: How can you write if your hands are clutched in a death-grip?

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All the evidence shows that if you’re happy and positive, you’re more likely to succeed. People who are optimistic have great social support, see stress as a challenge rather than a threat and do better at everything — including writing. Corporate trainer Sean Achor argues this point quite convincingly.

“Anything Goes”

As Cole Porter put it:

“In olden days, a glimpse of stocking

Was looked on as something shocking,

But now, God knows, anything goes.”

Smart writers know that their first job is to write a crappy first draft. It matters not one iota what goes into that draft because nobody else should see it. The benefit of the crappy first draft is that it allows you to write quickly, holding your critical faculties in abeyance. Then you edit, and you can even be harsh and demanding. When you’re writing that first draft, though, anything goes.

“In the Wee Small Hours of the Morning”

Lyricist Bob Hilliard wrote:

“In the wee small hours of the morning,

While the whole wide world is fast asleep,

You lie awake and think about your writing*

And never, ever think of counting sheep.”

*Confession: I replaced “the girl” with “your writing” in the third line.

Most writers gravitate to writing first thing in the morning or late at night. I was born a night owl but turned into a morning lark about 10 years ago. I’ve found that 6 a.m. to 7 a.m. is my most productive time, and I schedule my most important work for mornings. If you’re not a morning lark, I bet you’re a night owl. We all tend to write better when no one else can disturb us.

“I Guess I’ll Have to Change My Plan”

Howard Dietz was thinking about love when he wrote this, but writers could be forgiven for thinking he was telling their story.

“Before I knew where I was at,

I found myself upon the shelf and that was that,

I tried to reach the moon but when I got there,

All that I could get was the air.”

How many times have you written yourself into a corner? You start on a piece, thinking you have a good through-line and then, bam, you don’t know what to write next. You have some key facts or quotes to include and nowhere to put them. You’re out on a limb, grasping air. (In the song, Frank loses his girl. But if you’re a determined writer, you needn’t lose the story. You can just change your plan.)

“My Way”

The song that’s most often associated with Sinatra? It’s a cheesy Paul Anka classic. Here are a few lines to refresh your memory:

“Yes, there were times, I’m sure you knew,

When I bit off more than I could chew.

But through it all, when there was doubt,

I ate it up and spit it out.

I faced it all and I stood tall,

And did it my way.”

I give lots of general advice to writers, but I recognize that there’s no one-size-fits-all answer. We’re individuals who need to discover our own ways of getting words onto the page and making them better.

So keep your head up, keep trying and eventually you’ll find your way to achieve writing success.

A version of this article first appeared on LinkedIn.

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