I wrote half a million words before making my first cent as a writer.
When I launched this website in 2018, my language was imprecise, my blog posts unwieldy. I had thought reading old books and treating my thesaurus like a bible gave me license to abuse run-on sentences and big words.
Seeing my early work now makes me cringe. Yet I’m glad I published those foundational, meandering pieces. Ask again in another five years and, if I’m doing something right, I’ll refer to my 2023 work as cringe, too.
The reason I’m here today — two books, thousands of articles, and a reporting role in a global media outlet — is because I’ve never hesitated to ship imperfect work.
The perfectionism trap
Merriam-Webster defines perfectionism as “a disposition to regard anything short of perfection as unacceptable.”
At first glance, this sounds like a helpful North star — a dictum to keep work buttoned up and standards high. Some people use the word as a humble brag. Yet countless writers have told me that being a perfectionist is what makes them unable to publish consistently. And they have a valid point. The odds you produce something lame or incomplete are high; it’s more likely than not.
But trying to write one perfect essay is nearly impossible without thousands of attempts under your belt.
Being a bad writer is the price of admission to becoming a skilled wordsmith. Even the best of the best have insecurities. Take John Steinbeck. He lamented his own lack of intellect despite writing several bestselling books. In his diary that was eventually published as Working Days: The Journals of the Grapes of Wrath, he admitted that he relied on discipline above all else to overcome his own uncertainty on his work.
My many weaknesses are beginning to show their heads…I’m not a writer. I’ve been fooling myself and other people. I’ll try to go on with work now. Just a stint every day does it.
The idea holds for anything creative or entrepreneurial. Nothing gets off the ground unless you can stomach being bad at something for a long time. Even after accolades and acclaim, you still have to battle your own judgment.
First drafts and final products
Doing great work is about iterating quickly, and being nimble and humble enough to pivot when necessary.
As long as you plan to keep showing up, and that you’re oriented in the right direction, success is inevitable. But everything collapses if you judge early work as if it were a final product.
The first draft of this essay, for example, was crap. It required several rewrites. As it stands, it’s not close to perfect, but I thought it was good enough to publish. Now I have that much more experience to write the next one.
With a long enough time horizon, it actually doesn’t matter how good your work is on a given day. Being the best at anything mostly comes down to outlasting everyone else. The projects that become moonshots are those with creators who were able to forge past being unimpressive.
You would never size up a newborn baby and say she will never amount to anything, and yet we do that with fresh ideas, essays, and projects. I don’t do it on purpose, but I routinely judge my notes and scribbles against the standards of the very best work I’ve ever produced.
In truth, all new projects start off unimpressive, and it takes a long time for your abilities to catch up to your ambition. It’s also true that your ambition balloons as your abilities improve, so it can devolve into a hamster wheel.
Ideally, you grow into a fair, just-harsh-enough critic of your own work such that you keep you from getting discouraged while also being honest about your shortcomings.
Imperfect work is ultimately the foundation to what lies ahead. It’s how you prepare for some future moment when you’re called upon to do something excellent.
Default to optimism
The fear of making something not quite right — combined with all the potential reasons for failure — means even the most enthusiastic brainstorming rarely leaves the whiteboard.
“Will this go viral?” or “Is this a million-dollar idea?” aren’t the right questions. They impose final-product expectations on early-stage ideas. Especially for younger adults, people typically don’t have the experience to accurately gauge potential in early work.
(Think of how many good ideas have been shot down because of the wrong measuring stick.)
Barring delusion, feeling inadequate becomes guaranteed when you start from this common framework.
Getting around it isn’t as simple as lowering your standards. But instead of pinpointing all the reasons something can fail, it’s helpful to do the opposite.
- What makes this project stand out?
- What are all the reasons this could succeed?
- Who would love this idea?
- What is this already better than?
Most people can’t stick with something for long enough even to get to the point of making something that embarrasses them. But when optimism becomes your default view, it’s easier to keep going and hold your head high even when you produce work that isn’t great.
Theoretical physicist Lisa Randall has said that it’s best to treat new pursuits like experiments. That way, “there’s no such thing as failing, since you learn something no matter what.”
In her words:
You treat it like an experiment in the sense that if it really rules something out, you give up and move on, but if there’s some way to vary it to make it work better, go ahead and do that.
Zero to one
Startup founders have told me that going from zero to one the hardest step to building a company. Creators tell me the same about launching a new product or media channel.
It’s harder than going from two to three, or 10 to 20. The leap requires pulling something from nothing. It’s sticking a landing that you haven’t practiced and steering a plane without wings.
I find it reassuring that early adopters and investors in Silicon Valley report finding little issue with the first versions of products, even when they are full of bugs. Generally, people are happy to provide feedback so long as the creator gave a good-faith effort. And it’s no wonder: people love to support products and systems that constantly improve.
This suggests success indeed stems from optimism combined with “good enough” work.
Maybe the most important reason to jump from zero to one, over and over, is because you suddenly get exposed to real-world calls to action. It makes you work harder. You are forced you to solve problems that may have stayed hidden if you never went to market.
When an untested idea comes into contact with reality, it will either break or prove its resilience under scrutiny. There’s an urgency that accompanies putting something in the world that just can’t be replicated in private.
For writers — even for those without readers — going from zero to one (hitting “publish”) remains critical because it’s how you get better. External feedback can upend beliefs and eviscerate ideology. Every draft impacts each successive move, and I think that’s exactly why people procrastinate publishing.
I try to operate under the assumption that whatever I create will always fall short of what it could be. But I’ve learned to find peace knowing that A) just because it isn’t perfect doesn’t mean it’s not finished, and B) imperfect ideas move the world forward.
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