Not long ago, I wrote a book with the title 33 Ways Not to Screw Up Your Business Emails. So imagine my embarrassment when I sent someone an email recently with the number 11,000 instead of 1,100.

Whoops!

Here’s the chapter I wish I’d included in the book: What to do when you do screw up, whether with email, writing, or life.

The answer: Practice self-compassion.

What is self-compassion exactly?

Self-compassion sounds comforting and possibly easy. That’s about half right.

To learn more about it, check out Kristin Neff’s book on the topic, Self-Compassion: The Proven Power of Being Kind to Yourself. In the book (which cites a lot of research), Neff breaks down self-compassion into three parts:

1. Being kind to ourselves rather than judging harshly
2. Recognizing that our situation is part of the human condition—we aren’t alone in our suffering
3. Being mindful or aware of our emotions rather than letting them drive us

This is powerful stuff, with clear parallels to the experience of writing.

Self-compassion and writing

Many writers have a vocal inner critic that pipes up when looking at our own work early in the process.

For example, we see a clunky sentence or lame metaphor. (We all have them!) And the critic chimes in with things like:

• You call yourself a writer?
• [Insert favorite author name] doesn’t write crap like this.
• You’re never going to be good enough to get published. You might as well give up.

Instead of assessing the sentence (useful), we judge ourselves (not helpful).

How can we approach our writing with self-compassion? Let’s revisit Neff’s definition.

Start with kindness

Want a sure way to shut down creativity? Heap constant criticism on the seedling of every idea. Fear and anxiety inhibit the Muse.

If you were mentoring another writer, would you say the things you tell yourself? Of course not. You know that harsh criticism would stop them cold rather than helping them advance.

So, why do it to yourself?

Show up like a mentor instead of a critic.

You don’t have to give up your standards. But bring them to the revision phase of the work. Even then, identify what needs fixing on the page rather than in yourself.

Recognize the universal condition

Here’s the worst-kept secret in the writing world—everyone struggles with their writing. That’s part of the writing process. Your struggle may not look like someone else’s, but we wall have them.

Drafts are ugly until we make them better. That’s why we revise.

Productive and professional writers learn to tolerate the mess and ugliness to get to the final product. But we all hear that inner voice whispering in our ears at different times.

Be aware of the inner critic and its motivations

Recognize your inner critic for what it is—simply one of many thought processes in your head, perhaps implanted from childhood.

Get some distance from the voice. It’s not you, and it’s not the universe at large.

Harshly critical thoughts often originate in fear. When you try something new or put creative work out into the world, fear may try to stop you.

Notice the fear. Then move forward anyway, for the sake of the readers.

Servant authorship can help

Here’s a fourth practice for writers—focus on the reader rather than yourself. Practice servant authorship, or writing to serve the reader.

Who do you want to serve with your writing, and what do you hope it does for them?

Keeping the reader squarely in your sights streamlines the myriad decisions involved with writing. It also gives you a way around the harsh inner critic. Because what matters isn’t what you think. It’s the value that other people will find in your work. That’s your goal.

In my experience, centering on the reader rather than on myself and my writing ability de-stresses the process. It’s not about me at all. It’s about the reader.

Give yourself permission to be messy. Show self-compassion when you’re stuck or too busy to write. And remember, it’s all part of the universal writing experience.

Related content

Watch my webinar on self-compassion for authors.

Check out the book Self-Compassion.

Where was I?

Have you ever set off to get something from the kitchen, then been distracted by some other thought? You arrive in the kitchen and suddenly think, “What was I looking for here?”

It’s frustrating.

You might retrace your steps, returning to the starting point so you can remember what you wanted.

Nobody enjoys that experience. Yet, as writers, we often inflict something similar on our readers

The “where was I?” sentence

A sentence might start by introducing the subject, then throw in extra bits of insight or qualifying information before coming to the verb. These might include:

• Clauses, sometimes bounded by commas, that expand on the content of sentence
• Parenthetical asides (like this one) that offer commentary
• Thoughts linked with semicolons or em-dashes—the signal for informal interjections—that eventually resolve at the end of the sentence.

There’s nothing wrong with these stylistic practices. They often reflect the nuanced nature of our thoughts or message. They definitely project an educated tone, if the grammar works.

But pile them together and the writing gets pretty dense. These wandering sentences require the reader to juggle different mental images in working memory. The reader needs to hold the concept from the beginning of the sentence, power through the interceding ideas, and connect them at the end.

Metaphorically, they are setting off for the kitchen at the start of the sentence. Will they remember what they were doing when they reach the end?

More common than you may realize

Here’s a fun test: When you’re reading a nonfiction book or article, make a note every time you have to double back through a sentence. Put a pencil check mark in the margin.

You may double back more than you realized, or at least stop to check yourself and remember where you started.

We don’t always notice this behavior as we read. It’s subtle. We might feel fatigue or boredom, without recognizing the culprit—juggling ideas in our head as we navigate complex sentences.

The mental multi-tasking imposes a cognitive burden. The reader tuckers out a little sooner. It’s a real problem if you’re trying to reach a reader who meets any of the following categories.

• They’re not inherently fascinated with your topic
• They’re reading because they have to, rather than because they want to
• They have other distractions. (Don’t we all?)
• They’re tired.

Does your prose tax your readers?

You probably learned to use elaborate, qualifying clauses in college or graduate school. Academic writing is rife with complex sentence structures. You may not realize you’ve got a problem.

Many of the great works we read and admire use complex sentences. Consider this doozy from the Declaration of Independence:

We, therefore, the Representatives of the United States of America, in General Congress, Assembled, appealing to the Supreme Judge of the world for the rectitude of our intentions, do, in the Name, and by Authority of the good People of these Colonies, solemnly publish and declare, That these United Colonies are, and of Right ought to be Free and Independent States; that they are Absolved from all Allegiance to the British Crown, and that all political connection between them and the State of Great Britain, is and ought to be totally dissolved; and that as Free and Independent States, they have full Power to levy War, conclude Peace, contract Alliances, establish Commerce, and to do all other Acts and Things which Independent States may of right do.

I’ve italicized the main subject and verb: We do publish and declare. See how long it takes to connect the subject with the verb!

We’ve been trained to write this way in school. Often, we must untrain ourselves.

• Grammar checkers won’t flag these sentences, assuming the grammar is correct.
• Readers won’t let you know. They might give up on the project, or force themselves through it for your sake. They may not even realize why they find it slow going, and assume it’s because of the topic, rather than your decisions.

When I’m working with a nonfiction author, I’ll mark these kinds of sentences. Authors don’t always appreciate my cries for simplification, but their readers will.

Scan your words for “Where was I” sentences

Here are a few checks you can do on your own work.

• Scan for long sentences. When you find a string of them, try breaking up a few. If nothing else, vary the rhythm for the reader. Mixing longer and shorter sentences appeals to the reader’s inner ear.
• Count how many em-dashes and parentheses you find in your writing. If they’re everywhere, then you are adding to the multi-tasking burden of your reader.
• Find a reader who is sensitive to their wandering mind and ask them to mark every time their attention flags or they have to check back in the sentence to find the subject.

Yes, this will add time to your revision process. But any time you can lessen the cognitive burden on your reader, it’s a win for both of you.

Related content

Getting Bogged Down in Revision

Two Reasons Not to Revise as You Draft

“You sure could kick high!”

That comment from my friend Freddie transported me back decades to the summer we first met at a music camp in Michigan. I’d forgotten all about my kicking ability (which I have since lost).

I showed up at that camp outclassed by everyone around me. My voice was still young. As an actress, I was better at memorizing lines than performing.

And despite years of ballet lessons and constant stretching in hopes of a perfect “turnout,” I was just meh at dancing. A ballerina? No.

When I arrived at camp that first summer and auditioned for the Gilbert and Sullivan operetta, I landed a spot in the women’s chorus for Ruddigore. There were scores of us. Our choreography was more marching band than dance. Most of the girls already knew each other, and I was just another face in a sea of choristers.

When they held auditions for featured dancers, I thought, “Why not?”

Lucky for me, they weren’t looking for finesse and grace. The show took place in a large, semi-outdoor auditorium. You know what shows up well in a huge auditorium? High kicks.

While I had been trying to learn the skills of ballet, I had unwittingly developed the ability to kick my heels over my head.

Bingo! I earned a “featured dancer” role, with a moment of glory that ended with leaping into a lead’s arms. Better yet, I formed friendships that continued the next few summers.

All that effort I put into trying to achieve a perfect turnout was misguided—and possibly damaging. I was chasing skills useful only in the world of ballet, which was not where I would land.

But being limber enough to kick my legs over my head improved my life in a meaningful way for a few golden summers.

It’s hard to know which skills and abilities you cultivate will have a meaningful impact.

Maybe your important skill isn’t the one everyone else is chasing.

What’s your undervalued writing ability?

It’s easy to read the authors we love and notice only our own deficiencies. I do that all the time.

But maybe you have the equivalent of that high kick in your writing toolbox.

What’s your overlooked ability, and how can you make the most of it?

• Are you a whiz with a witty turn of phrase? Consider adding humor to your distinct voice or try your hand at copywriting.
• Do you explain things well, with clarity and precision? That’s a rare skill—the world needs more people like you. Journalism, business writing, education, and other fields value your abilities.
• Do you write quickly? Embrace social media, blogging, or copywriting.

Beware of wishing you had had more of someone else’s abilities. Develop new skills, but don’t overlook the ones you already have.

Humor. We love reading it, but many of us shy away from writing it.

Done well, humor looks effortless. That’s usually an illusion. But, just like telling a story, getting someone to smile is a skill that we can practice and improve.

Many of the nonfiction authors I admire approach their topics with gentle humor, whether they’re writing about regrets (Daniel Pink’s The Power of Regret), climate change (Thor Hansen’s Hurricane Lizards and Plastic Squid), or deadly wildlife encounters (Mary Roach’s Fuzz).

Humor is a powerful nonfiction writing technique, even if you don’t identify as a funny person. Here are a few reasons to build your humor skills.

Memorable explanations

When you’re writing about an abstract topic, a funny story or metaphor can serve two purposes:

• Humor can help explain an aspect of the topic.

• We are more likely to remember the point if we smiled when we first read it.

Humor is all about making sense of the unexpected. The punchline of a joke surprises us—we “get” the joke when we puzzle out the sense. So, humor is itself a sense-making endeavor. We can use humor to reveal an unexpected truth about the subject.

It can be as simple as an unexpected metaphor, like the one Neil deGrasse Tyson uses to describe the strange relationship between the laws of gravity and quantum physics:

In the beginning, during the Planck era, … we suspect there must have been a kind of shotgun wedding between the two.

Neil deGrasse Tyson

Wait, a shotgun wedding? The analogy surprises us, even if we’re familiar with Tyson’s trademark style. And it’s apt: we don’t quite understand how those two forces got hitched, but that union begat the universe as we know it.

In the book Humor, Seriously, Jennifer Aaker and Naomi Bagdonas list multiple studies on the memory-enhancing capacity of humor. For example, people who watch news-based comedy shows remember more of the headlines than those who simply read the papers.

Humor belongs in business, too. In her book Hello My Name is Awesome, brand name expert Alexandra Watkins offers a SMILE and SCRATCH evaluation test to use when you come to use in deciding on a name for something. Although smile and scratch are acronyms, they work well on their own. A brand or product name should make you smile, not scratch your head in confusion.

When a name makes you smile, you are more likely to remember and share it. (Nerd Wax, Bed Head, and Scrub Daddy are among Alexandra’s all-time favorites!)

Understanding and memory—those are two powerful reasons to insert levity in your style.

But wait, there’s more! [Cue infomercial voice-over.]

Making emotional connections

Humor also connects us. It humanizes the writing by exposing the similar ways our brains work. It lowers our defenses and raises our sense of trust.

Self-deprecating humor can make you more likable and human. It narrows the perceived distance between yourself and the reader.

If you poke fun at yourself, others are less likely to take offense. Just don’t do so in a way that undermines your credibility. Focus on areas unrelated to your expertise (say, your height), or tell a story from earlier in your life, when you were less wise than you are today.

Jeff Kreisler (in an interview for Writing to Be Understood) says:

“The end of a laugh is followed by the start of a listen.”

Jeff Kreisler

How will you use humor?

Humor is a powerful writing tactic. Start small. Put a smile-inducing postscript in an email to a colleague you know well. Notice the funny things around you and note them down in a journal.

Start paying attention, and see if you can work humor into your own writing toolbox—even if your subject is serious.

Want to dive in further?

Join me at the ThinkingFunny conference on April 2-3. I’ll be doing a workshop on humor as a nonfiction writing technique.

If you enjoyed this post, pick up Writing to Be Understood: What Works and Why. There’s much more like this in the book.