Striving for imperfection

Issue #4: Embracing first drafts and continuous refinement

Is there any better way to dunk on Virgos than writing about subverting perfectionism in September? (Narrator: There is not.) I’m kidding, Virgos. My cat, who just celebrated his 18th birthday, is also a Virgo.

The refusal to accept any standard short of perfection has its benefits and major challenges is a common theme among Virgos and other humans. The benefit is it can motivate you to do top quality work. However, this can be counter-productive, inducing a lot of anxiety, fears, and insecurities.

Perfectionism is a personality trait characterized by a person’s striving for flawlessness and setting high-performance standards, accompanied by critical self-evaluations and concerns regarding others’ evaluations. This can create analysis paralysis and you may never put your idea in motion. Psychologist David Burns once said, “Reaching for the stars, perfectionists may end up clutching at air.” People often don’t launch their ideas because of what they might face as it transitions from idea to reality as a result of this fear. Sometimes you’re trying to refine something so much in your head that you later learn that someone else went and did your idea.

Sharing ideas is extremely hard. It puts you in a vulnerable space. When you keep ideas to yourself, there is no risk of critique or reaction. It’s perfect in your mind. When you create something and put it out to the world, you face critique. It’s tough to launch that app idea, only to find out it’s something nobody wanted and failed. It’s also hard to put yourself out there in a world where things are portrayed in the most idealistic. Open Instagram and within seconds you’ll often encounter perfectly staged narratives. How would you ever reach that standard?

Becoming the imperfectionist

In 2006, the world was introduced to blonde hair and blue-eyed James Bond in Daniel Craig. For those who are familiar with the Ian Fleming character, James Bond has always been portrayed as hyper-masculine, smooth, and suave. Aside from the ocean-blue eyes and blonde hair, Daniel Craig's portrayal of Bond was different. It was brutal, rugged, and inelegant.

(Spoiler alert: there's a scene where Bond orders a drink)

Bond: Vodka martini
Bartender: Shaken or stirred?
Bond: Do I look like I give a damn?

This is a rough cut of Bond. He doesn’t care about being smooth; that the job is done (In no ways am I saying Daniel Craig is imperfect). I’ve always looked at the Daniel Craig James Bond as a metaphor for being more real and unrefined in order to achieve results. Though I care about doing high-quality work, I am far from a perfectionist. My style of getting there is very rugged and often by brute force. As the saying goes, “A ship in harbor is safe, but that is not what ships are built for.” This is what Proof of Concept is about; encouraging you to get those ideas out to exist in the world so you can refine it.

The other end of the spectrum of a perfectionist is often defined as an Optimalist. This comes from the Latin word Optimus, which means both “best” and the fearless leader of the Autobots in the Transformers series.

Filling the white space

In art school, I was trained to get rid of all the white space on the canvas. In my oil painting classes, I’d apply the techniques of the artists of old like Titian to complete an underpainting, a very low fidelity pass of the entire canvas to shape up the composition. Once you mess it up, you can then refine it. This helps me cope with any sense of perfectionism that might creep in.

There is more hesitance to make a mark on a blank white piece of paper because each stroke can feel like a mistake. When it's filled, you have less to lose.

The key is you do not have to attain perfection in one iteration.

Iterate the momentum

As Dr. Julie Gurner recently said on Twitter, “What most won’t tell you? It’s not knowing what to do that it is hard…it’s actually doing it, and not allowing yourself to get in the way.”

Building momentum is the most challenging part of doing anything. One of my favorite quotes is from Pixar's 22 secrets to storytelling: "Putting it on paper lets you start fixing it. If it stays in your head, a perfect idea, you'll never share it with anyone."

Similar to my painting style, I approach writing the same way; creating mind maps of ideas and unstructured writing to help me get started. The blank canvas often the biggest blocker.

Especially now during COVID-19 where we seem to be perpetually on screens, I take my sketchbook as a way to plan my action. Whether it’s a book idea or a quick note, I scribble on paper to hash the ideas out a bit before focusing on any digital computation. I’ve also found putting thoughts on paper has put my mind at ease and makings me less anxious about any work I do. Since I spend seconds doing quick thumbnails, there is such low risk for me to re-do the work in a better way.

Sharing your drafts to the public

I’ve been so inspired by people on the web who have been sharing concepts out in the open, and I’d like to share two who come to mind. Paige Doherty is a software engineer who is working on a children’s book about venture capital and has been sharing her pen and paper pages of the book. She used Loom as a way to create an intro video to solicit feedback. I cannot wait to see where this book goes! Jordan Singer, a product designer at Square Cash with a background in computer science, has been building his ideas for many years. He created an app called Airport which lets people browse different TestFlight builds of iOS apps that people are building.

These are two of many examples of people putting work out there to get feedback and providing early access. People don’t create things out of thin air like magic. We often feel like it is so because often we don’t see the drafts and iterations. The reason someone has achieved more success is often likely they’ve failed more than you.

Non Finito can be therapeutic

The word “Non Finito” means "not finished" in Italian. I find a lot of benefits doing a "brain dump" of all my thoughts. This type of journaling has helped provide some mental relief by making it tangible and a source to start new ideas.

You don't even have to show your imperfections to the world if you're not ready for it, or if you ever are. Putting these thoughts down can help you look at things head-on and be accepting of the imperfections.

“What if I mess up and break something?”

Who cares.

Kintsugi, the art of repairing with gold is the Japanese art of repairing broken pottery by mending the areas of breakage with lacquer dusted or mixed with powdered gold, silver, or platinum. As a philosophy, it treats breakage and repair as part of the history of an object, rather than something to disguise.

It is in our imperfections and fragments where we can find a long-lasting beauty we can appreciate in an authentic and sustainable manner. Take a moment, put that idea out there. You might inspire someone to do the same. Together we can iterate more and share it with the universe.

As the artist, Salvador Dali once said, “have no fear of perfection - you’ll never reach it.”

P.S. In the spirit of idea generation on early drafts, I'd love your feedback on what you'd like for me to write about. Simply reply to this email with your idea. I appreciate any suggestions!