Hey Reader,

Welcome to the fourth issue of A Way with Words, a weekly newsletter where I share writing and editing tips to help you create clear, coherent, and compelling content. If this newsletter was forwarded to you, subscribe here to get the next edition in your inbox.

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How to overcome perfectionism as a writer

Two weeks ago, I read a Medium post I thoroughly enjoyed — "How will I start writing again?" by Tomi Adesina.

It was a vulnerable piece about her struggle to write for the past five years. But it wasn't the vulnerability that endeared me the most. I loved that she was self-aware enough to identify the reason for her protracted writer's block: perfectionism.

Nearly every writer struggles with perfectionism — even though many of them don't know it.

It manifests in several ways, but the major ones are:

a) You have an idea but keep procrastinating on the actual writing because you want fully formed and flawless sentences to populate your head first.

b) You have an idea and sit down to write. But after completing your piece — after tweaking and tinkering obsessively — you don't publish because you don't think it's good enough.

Perfectionism was why I broke up with my first love, poetry, after a long streak of posting poems on my WordPress blog.

Perfectionism was partly why I didn't publish my Substack newsletter for months, even though I wasn't bereft of inspiration. (The other part? Finding time to write, between working a full-time job and raising a toddler, is hard.)

But things are different now. Over the past few months, I've been on a journey of overcoming perfectionism in my writing — a journey I began when I realized perfectionism was preventing me from enjoying a rich, fulfilling creative life, and sharing valuable insights with people who may need them.

Below, I share three ideas that have helped to shift my perfectionist mindset.

Nobody's first draft is perfect

Ernest Hemingway famously said: “The first draft of anything is shit.” (Excuse his French.) And there are thousands of quotes from other renowned writers admitting that their first drafts usually aren't great.

If Stephen King and Chimamanda Ngozi Adichie and Junot Diaz don’t write perfect first drafts, why are you trying to?

Whenever you read a fine piece, you tend to focus on the finished product, not the process behind it. But that book, essay, or poem you admire and wish you wrote started with an ugly first draft that became beautiful after many sessions of revising and editing.

In Wordcraft, Jack Hart, a renowned writer, editor and writing coach, shares an instructive story. He had edited a feature story by Tom Hallman that won a Pulitzer Prize in 2001. Hallman later permitted Hart to post multiple markups from his rough drafts on a website available to journalists across the country.

Regarding the response, Jack Hart writes:

The magic happens after the first draft — when you revisit, rewrite, and revise until your piece is clear, coherent, and compelling (not perfect!)

So, feel free to write your half-formed ideas, your unclear arguments, and your wordy sentences in your first draft. Writing isn't a one-step process; you get many more shots to make your work better.

Your thinking doesn’t have to be completely clear before you start writing

Many perfectionists wait for perfect ideas and sentences before they write a word.

Tomi’s post illustrates this:

I also struggled to write for months in 2022 because I wanted fully formed sentences or paragraphs in my head after I got an idea. This was actually how I had always written. I would produce 60% of my first draft in my mind’s eye, so the words flowed like water when I eventually sat down to write, as if I were merely transcribing. So, I thought that was how writing always worked.

But here’s what I know now: We don’t always write to communicate already-formed thoughts and ideas. Sometimes, we write to develop and clarify unclear or half-formed thoughts and ideas.

Yes, clear writing is the product of clear thinking. But you don’t have to think EVERYTHING through before you write. Thinking happens at every stage of the writing process: you think when you get an idea or topic; you think when you create an outline; you think when you write your first draft; you think when you revise and edit.

So don’t write off your scattered thoughts. Instead, write them down and make meaning out of them.

Here’s how writing coach Don Murray puts it:

People are not interested in perfect writing

Let's be honest: we want our writing to be perfect because we crave praise for our prowess, praise that boosts our self-esteem. (Did I hear someone say, "speak for yourself"?)

But your readers don’t care about your prowess.

Think of all your favourite articles, essays, or books. Did you fall in love with them because the writer crafted perfect words in the perfect order? No, you loved them because they moved you in some way. Maybe they made you laugh or cry. Or they showed you that you weren't alone. Or they inspired you to make a difficult decision.

People don’t want to read flawless writing, whatever that is. They want to read relatable, authentic, and evocative writing, even if the writing style isn’t remarkable. If you can achieve that — if you can write honest sentences that make them see you, see themselves, and see the world more clearly — then that’s good enough.

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So, how do you apply these principles to overcome perfectionism in your writing?

1. Create a timeline for your writing projects

Now that you understand that drafting is not the only step in your writing process, be intentional about devoting time to rewrite, revise, and refine your drafts. The easiest way to do this is by creating a planner or to-do list that covers each writing stage. This helps you write your first draft without pressure or anxiety, knowing you can always improve it.
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Here’s what your planner for a personal essay may look like:

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When creating your planner, also allocate specific time slots for each writing stage. This deadline will help you move quickly rather than linger on one stage. The goal is progress, not perfection.

2. Make an outline before starting your first draft

As a perfectionist, you’re worried about hitting roadblocks when you start writing your first draft. But if you have a good idea of what you want to write before you begin, you can forge ahead with confidence.

So, before you start writing, mull over your thoughts and ideas, then organize them into an outline. If you get stuck, you can always go back to gain direction and clarity.

Your outline doesn’t have to be a list. It can be a few paragraphs summarizing your key points. It can even be a flowchart or a mind map.

Outlines don’t have to be followed rigidly. While writing, you may find that you want to rearrange the order of your ideas or even discard some, and that’s okay. What’s important is having a system that makes writing your first draft less daunting.

3. Don’t revise and edit (too much) when writing your first draft

Confession: I don’t follow this advice religiously (that’s why I added “too much” in brackets). Sometimes, I change words and rewrite sentences when drafting. But I only do this if I notice flaws right away, not by going back to read what I’ve written.

In any case, it’s solid advice and you should follow it as well as you can. Don’t judge the clarity of your ideas or the elegance of your sentences until the editing stage. And you should definitely not bother to correct spelling, grammar, and punctuation errors.

4. Get feedback

Perfectionists tend to criticize themselves more harshly than others. So, if you’ve completed your final draft, and you still don’t think it’s any good, send it to someone else — a friend, a colleague, or a professional editor. Their feedback may give you a healthier perspective on your work. Plus, any suggestions they offer will give you a better idea of the specific areas to improve.

Publishing is also an avenue for feedback. People's reception of your work will help you evaluate your writing, so that you can work hard at improving. Just remember not to take negative comments personally.

Don't rob yourself of joy

There’s indescribable joy in writing something and sharing it with the world, not unlike the joy a mother feels after birthing a child. Don’t let perfectionism make your creative life barren; don’t let perfectionism rob you of joy.

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Thank you for reading! If you enjoyed today's newsletter, please forward it to a friend or share the public link on your social networks (get the link here)

Also, I'm thinking of running a 5- or 7-day challenge to spur anyone who struggles to write or publish their drafts. If you're interested, please reply to this email.

With love and semicolons,

Oluwadunni

P.S. Need an editor or know someone who does? Reach out here.​
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