TA #86: 🍕 Taking Risks in Marketing without Losing Your Job; 15 Writing Lessons from Famous Authors

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Artist and image credit: Reagan Lehman

Welcome to the 86th issue of Total Annarchy, a fortnightly newsletter by me, Ann Handley, with a focus on writing, marketing, life. A special Mother's Day high-five to Moms and anyone who has ever mothered anyone or anything. Thank you for being here! I appreciate you.

Boston, Sunday, May 9, 2021

Hey buddy.

Last week I saw a squirrel eating a slice of pizza.

He was high up in a tree just starting to bloom. I think it was a red maple? It was covered with red, scaly buds—like angry teen acne erupting on a hormonal spring tree.

Not that the squirrel cared. He was focused on his pizza.

He held it in his hands, tiny fingers curled on either side of the pie-shaped wedge. His technique was all wrong—it was like watching someone eat a candy bar with a fork and knife. At least he pointed the pointy end toward his face.

He took tiny bites. Maybe that's how squirrels eat everything. But it was hard not to imagine that Pizza Squirrel was savoring it.

I watched him for a few minutes. I had so many questions.

> What toppings?
> Where does he stand on pineapple pizza?
> Did he order one slice or a whole pie?

But above all...

> WHO DELIVERS TO A TREE. (Dominoes? UberEats? ToastTakeout?)

* * *

I posted a photo of my Pizza Squirrel to my Instagram Story, thinking he was one in a million. You can see the story in my Story Highlights here.)

Then I did some research. It turns out that my Pizza Squirrel is NOT one in a million. There are actually close to one million others just like him, says Google. Instagram has 1,606 photos tagged #PizzaSquirrel.

My Pizza Squirrel is apparently part of a global community of other Pizza Squirrels—from Boston to New York City to the UK and beyond.

Squirrels usually feed on buds, bulbs, and flowers. On whatever seeds and berries they can forage. And nuts, of course. Lots of nuts.

Squirrels will also ransack nests and birdhouses in search of baby birds and eggs. And they'll loot your birdfeeders and gardens.

But sometimes they will find trash on the ground and eat that, too. Also it turns out that they have paws, not hands. (That last point isn't really relevant to the story. I just thought you'd like to know.)

Google Trends data for Pizza Squirrel looks particularly robust for the past 12 months, which tells me that quarantined squirrels are ordering tree takeout far more than they're dining in.

Squirrels. They're just like us.

* * *

Pizza Squirrel nested in my brain long after I'd left him there in the tree. It was the weirdness of seeing the scene in real life, despite what the Internet tells me is common.

More and more, I started to see him as a kind of mascot of modern marketing.

(You knew I was going to bring this back to you at some point, didn't you…? LOL)

* * *

Jason Miller worked in marketing at Marketo. Then LinkedIn. Then Microsoft. Now he's head of brand at Active Campaign.

In May, Jason launched a live Late Night-style show that I can only describe as a little out of left field.

It's a monthly show that plays midday, but it follows the familiar territory of late-night talk show: A host monologue. The Paul Shaffer-style musician playing riffs between segments. Live music. Bands. Guests. And yeah... marketing insights, too.

It's fresh. It's different. It's weird. It's a risk. (One viewer told Jason: "I don't get it. I just don't have time to laugh during the day.")

As I watched the first few episodes, I kept thinking of so many creative marketers I talk to who want to try left-field weird stuff... but feel they can't. I hear their voices in my head: How did he get buy-in for that?

And more broadly: How can marketers get buy-in for anything not tried-and-true?

How can you get the green light for experimenting?

How can you feed a squirrel nuts AND pizza?

* * *

"The key is 80% safe content, 20% intelligent risk," Jason told me last week. "The safe, tried-and-true content delivers... and also buys time to be more creative."

Here's what it takes.

▶️ At least one executive or leader who isn't a scaredy cat. You need an exec in your corner.

"The difference between a great career and a merely good one can come down to one simple thing: the willingness and ability to take intelligent risks," Mike Gamson, a former LinkedIn SVP, wrote on LinkedIn during Jason's tenure there.

▶️ A mindset that embraces failure as a learning opportunity. Microsoft celebrated occasional failure by awarding the Golden Plunger Award to the biggest stinker. Award winners shared with their teams the lessons they'd learned. Leadership knew that you learn by losing as much as you do from winning.

The best thing about failing is that you'll have the answer to your question, What if?

▶️ Curiosity & a little bit of crazy. I almost didn't include this one—because of course you have these things. We all do.

None of us is pure safety marshal and mall cop—shutting down creativity and shenanigans wherever we see it. None of us is pure rapscallion and scamp, either—playfully challenging conventions.

Most of us are a bit of both. We all have a tiny rule-following mall cop inside of us, living companionably with our inner scamp.

To take intelligent risks, you have to honor both.

"I could go low and slow and just collect the dough... but I'd rather try to create the coolest marketing I can," Jason said. "I always try to one-up myself." (I love that last bit.)

▶️ Internal credibility. Credibility is rooted in C-suite confidence.

Are your marketing programs keeping the lights on? ("Lights" being leads, awareness, revenue, and so on.) Success with the tried-and-true gives you the ability and the credibility—the trust of your colleagues and higher-ups—to try new things.

▶️ 80% nuts; 20% pizza.

The 80% is the stuff you need to keep your business running.

The 20% is the stuff that—if it works—people will talk about. They'll Instagram it. (And maybe that will inspire others to draw that Instagram—like artist Reagan Lehman did in the header image after she saw my Story.)

* * *

Here's why Pizza Squirrel is our mascot: He doesn't have to choose. He can have both.

You don't have to choose, either.

You don't have to define your marketing, or yourself, as tried-and-true all-nuts—no pizza.

You can do both. And most important: you can be both.

* * *

Here are a few things worth sharing this week.

Everybody Writes Writing Tip of the Week

Use YOU + YOUR like you just picked up a year's supply at a BOGO sale. Right in your subject line. Directly in your copy. "You" signals intimacy, belonging, relevance.

You will connect with your reader better. Because you want to connect with one other person—not an "audience."

Not a "segment." Not a "list." One person. At one time.

QUICKIES

This is Jason's show, BTW. I just realized I didn't link to it above. Doh.

How I learned to let go and be less controlling. My chat with my longtime right-hand-Jess on her fantastic new podcast.

15 writing lessons from famous authors. "Habit is persistence in practice."

CONTENT TOOLS

A content tool I discovered this week

Lose the Very. "Very" is not the strongest of modifiers. This fun tool can help you rely on it less.

DEPARTMENT OF SHENANIGANS

Could this meeting have been an email? (Where has this been all my life?!)

LOVE LETTERS

💌 To Paul Ince and the gang at MarketEd.Love for naming me one of 30 inspiring marketers for 2021.

💌 To Trevor at Email On Acid for naming me as one of his fave thought leaders.

💌 To Grace Donelson at Tagger Media for including me on this list of B2B influencers.

💌 To the awesome Jon-Mikel Bailey for the shout in his piece on understanding modern digital marketing strategy.

💌 To the Pittsburgh Business Times for the shout in this profile.

* * *

Thanks for reading this far. Thanks for your kindness and generosity.

Stay safe. Stay sane. Wear a mask. We're *so close*.

I'll be back on May 23.

P.S. If you like this newsletter and want to support it, you can:

1) buy a book.
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Ann Handley is the author of Everybody Writes and other books.
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TA #86: 🍕 Taking Risks in Marketing without Losing Your Job; 15 Writing Lessons from Famous Authors

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TA #85: 🔑 Should you ungate your content in 2021? And: A copywriting tip for the lazy.

TA #84: ⚓ The World's First B2B Sea Shanty; One Simple Way to Revive an Apathetic Audience

TA #83: 📬 When You Should Write Your Book; How to Ask Better Questions; WTOTF

TA #82: ✍️ Creator Coins; the One Word That Makes Your Customers Snap into Action; Make Your Writing Come Alive

TA #81: ✍️ The Creative Process; Writing Advice from Warren; Reader Challenge Results!

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