How to Become a Bestselling Author With Ann Handley

Meet Ann Handley.

She’s a Wall Street Journal bestselling author who speaks worldwide about how businesses can escape marketing mediocrity to ignite tangible results. IBM named her one of the 7 people shaping modern marketing.

She is the Chief Content Officer of MarketingProfs, a LinkedIn Influencer, a keynote speaker, mom, dog person, and writer.

She just released the 2nd edition of her Wall Street Journal bestseller, Everybody Writes. You should buy a copy. And one for your friend.

How Did You Become a Writer?

When I was 8 years old, I launched a neighborhood newsletter called WASSUP!!! My goal was to be a roving reporter in my neighborhood and write about hyper-local news.

Like HYPER-local. Although the “news” was debatable: I wrote about someone’s new car, someone else’s driveway basketball hoop, the town’s dog leash laws. I tossed in a poem.

I delivered it on my bike. My neighbors thanked me. Look at me! I’m a writer!

I lasted four issues.

The labor of pecking out words on a typewriter, trimming my articles by hand, laying them out on construction paper, and then having my dad Xerox the whole thing at his office (he brought it back to me in a folder tucked in the pocket of his leather attaché case, which always snapped opened with an aggressive POP that caught my fingers), and still needing to deliver it….

It just got to be too much. I had math tests to study for.

I had puberty to ponder.

So I paused my publishing dreams, waiting for the Internet to happen.

How Did You Get Your First Writing Job?

In college, I went for an internship interview at a weekly financial newspaper. I didn’t want the job. I didn’t know anything about finance.

I don’t even know what I’m doing here, I thought, as I sat in the hard-backed chair in the waiting room. The receptionist – her name was Mary – offered me a Coca-Cola. (“No, thank you.”)

Then I was invited into the editor’s office. And I loved her. I wanted to be like her – so confident, assured, funny. We clicked.

Later I’d recognize that moment as the day I met my mentor. But at the time, I didn’t know that. Because I was a uniquely dumb college kid.

I made like 5 cents an hour… but! The Cokes were free! For the whole staff – whenever you wanted!

What Skills Do You Need to Be a Good Writer?

Curiosity about people. A willingness to work on your craft. The ability to show up and use your voice publicly even when it’s easier not to.

What Influences Your Writing the Most?

Writers are shaped by other writers. So I read people who rage-motivate me as well as those who inspire me.

Authors: David Sedaris, E. B. White, Ali Smith (right now).

Brands: Velocity UK, Morning Brew newsletters, anything by Ryan Reynolds. His messaging is so good it’s rage-awesome.

What Tools and Software Do You Use for Work?

Tools aren’t the most important thing about writing. But since you asked…

1. Paper notebook. I write in one daily and carry one almost everywhere.
2. Whatever pen is around. I’m not too precious about pens. People give writers pens as gifts which is cool for some… but do not give me one. I will lose them. I always do.
3. Google Docs. For writing, for organizing. Boring. But it does the job.
4. AI editing tools. Grammarly or HemingwayApp for a first editing pass. Lately, I’ve been playing with Writer.com. Lots of interesting opportunities in AI – not to write FOR us. But to help writers level up even more!
5. A human editor. Not a tool. But SO NECESSARY. In SHOUTY CAPS.
6. My dog. Walking him helps me work out things in my head that stymies me on the page. He’s @littlestAugust on Instagram. (#momager)
7. Time. I let writing sit for 24 hours whenever I can. Time magically makes writing better because it gives space for the magical little pixies to come into your head and offer ideas you can implement when you return to the page.
8. My voice. Read everything you write out loud before you publish. It’s the best step in my process because I catch many errors and awkward phrases.

What Are Your Writing Habits?

I write in the morning, when I’m freshest. And before life/work/email/social media hijacks my day.

I write long-hand at first, in a notebook.

Then switch to my laptop. I sit on the couch, my dog by my side. My desk is for non-writing work. I never write at a desk.

I hate music or any sound while I’m writing. One time I went to a coffee shop because that seemed like a fun place to write. It was hell.

What’s the Best Investment You Made in Your Career?

Building a Tiny House Studio in my backyard. I wrote about it here: Why I Built a Tiny House.

What Are the Most Influential Books in Your Life?

Reading is as critical to writing as actually writing – maybe more so.

Annual goals on apps like Goodreads have turned reading into an arms race – “Commit to reading 52 books next year!” they implore you.

Don’t fall for that trap. No shade to Goodreads – I like and use the app – but don’t treat books and reading as things to check off and optimize. Instead, slow down and read like a writer.

Consider: Why did the writer make that choice? Why does analogy work? Why does this sentence trip me up?

My favorite book of all time is Charlotte’s Web by E. B. White. It’s a study in spare storytelling masquerading as a kid’s book. It’s not a kid’s book: It’s fantastic.

What Are Your Favorite Writing Quotes?

“You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.” – Tina Fey

I think of that quote at least once a week. Because writing is never done; it’s only due. Someone else probably said that, too.

If Someone Wants to Be Where You Are Now, How Can They Get There?

You shouldn’t try to be me. You should try only to be you.

Which I know sounds like this is the last question and I don’t want to write 2-3 paragraphs. But I spent too long trying to mimic the movements of someone else. Don’t do that. It doesn’t lead anywhere you wanna be. Learn from your mentors… sure. Learn from other writers… yes. But don’t follow too closely.

God that sounds dark. It’s not. Just hack your own path.