To Succeed, You Must Fail

Read Time: 4 minutes

If there’s one thing that stifles creativity and stalls writers, its the fear of failure.

Failure whispers many “what-ifs” into our minds:

• What if publishers reject me?
• What if my words get ignored?
• What if I write something that gets me cancelled?
• What if I start writing a book but can’t finish it?
• What if I run out of things to say?

Pressure To Be Perfect

These questions, laden with self-doubt, cripple us creatively—if we give them credence. It’s a toxic mindset of timidity—one that creates an impossible expectation to produce nothing less than perfect prose.

Symptoms of the writer who’s afraid to fail:

• Criticism wrecks you
• You’ve given up, based on a past mistake
• You post something—then check it compulsively
• You play it safe in your writing with predictable platitudes
• You’re defensive whenever you receive honest feedback

To free you from this prison of perfectionism, today I’ll offer 2 mindset shifts and 5 diagnostic questions that will reframe how you view failure.

So you can write with more confidence, without worrying about what others think. So you can explore every idea, without dismissing it as dumb. So you can muster the courage to write about what you truly care about.

Mindset Shift #1: View failure as formative, not final.

I’m convinced that much of what we label “failure” is actually just growth. To create something meaningful, you have to wade through a lot of mediocrity.

For every great sentence, there’s a thousand throwaways.
We abandon beloved paragraphs to create better ones. As Faulkner quipped, “In writing, you must kill all your darlings.”

A few months ago, some college friends and I drove into the mountains for a weekend songwriting retreat. I’m proud of one of the songs we created, but the words didn’t just fall into our lap.

Here’s a picture of the lyrics we wrote. For every usable word or phrase, there’s 3 or 4 scribbled out.

Friends, that’s the arithmetic of creativity. You flop more than you fly.

I don’t despise these crossed-out lyrics; I celebrate them. Each scrawled out idea is not a monument to failure—it’s a sign pointing down the road that says: Keep going!

To use a sports analogy, if Michael Jordan—arguably the best basketball player in history—had a field goal percentage of 49%, that means, as writers, a lot of what we write will miss the mark. But without those temporary misses, we’d never make a shot.

Mindset Shift #2: Give yourself freedom to fail.

Confident writers normalize failure. It’s not that they enjoy it; they’ve just learned to welcome it as a teacher who—though uninvited and difficult to learn from—wields some profound and transformative lessons.

I love how Sara Blakely, the founder of Spanx, describes growing up with a dad who normalized failure in a way that changed her life:

"When my brother and I were growing up, my father would encourage us to fail. We'd sit around the dinner table and he'd ask, "What did you guys fail at this week?" If we had nothing to tell him, he'd be disappointed. The logic seems counterintuitive, but it worked beautifully.

He knew that many people become paralyzed by the fear of failure. They're constantly afraid of what others will think if they don't do a great job and, as a result, take no risks. My father wanted us to try everything and feel free to push the envelope. His attitude taught me to define failure as not trying something I want to do instead of not achieving the right outcome."

[Source: Getting There]

Some of my best ideas were born out of previous failed attempts. Were it not for those initial nosedive moments, which taught me with stinging clarity what not to do, I adjusted, and emerged a more seasoned writer who knows how to resonate with an audience.

Don’t just lament your mistakes; learn from them!

Resolve to fail well.

Failure tests what we’re made of. It also reveals who we’ll become. When we fail—whether a writing project flops, or someone points out a weakness in our prose—it’s tempting to medicate that discomfort with excuses.

But failing well (as absurd as that sounds) means being attentive to the why, not merely the what. To those who will listen, failure is an irreplaceable tutor.

Here are five questions to ask when you feel like you’re failing as a writer. My recommendation is to process these with someone you trust.

5 Questions

1. Why did this happen?
2. What can I do differently moving forward?
3. How is this experience forming me into a better writer and person?
4. How might I be tempted to repeat this mistake?
5. How can I leverage this learning to help others?

Fellow writers, do not fear failure. It does not define you, yet it has immense potential to sharpen you.

I’m rooting for you.