Seven or eight years ago, I was in a final interview with a VP of Design. It was for a company I admired and wanted to work for. After the interview, we spent the end of the day in his office talking about music (it was related to the business), experience design, and the role of taste and critique in our practice. At this point, everyone went home and it was just the two of us at the office. This design exec asked me about how do you ensure quality in the product experience of what you work on. I paused, and thought about it for a bit…

"Hate it 'til it works," I said.

“Hate it ‘til it works,” replied the design executive.

I adopted that as one of my design principles moving forward. It’s about being a short-term skeptic and long-term optimist in the work you do. This is about being hyper-critical about your own craft, not of others.

Be the biggest critic of your work and outcomes, not humans

Never apply “Hate it ‘til it works” to yourself or other humans. It’s important to be kind to humans and detach one’s self from the work. Being critical of your work with the intent to make it better creates rigor, and rigor creates design excellence. It takes an immense amount of effort to create something, even if it’s bad. Whenever I watch a show or movie I didn’t love (Ex: Book of Boba Fett) I know the people who worked on it cared deeply and put their heart and soul into it. I try avoiding being overly critical of other people’s work as people will look at mine in the same manner. I apply “Hate it ‘til it works” only to my own work to be the biggest critic of it.

Blind optimism is the enemy

Optimism is powerful and very necessary. On days when you feel things are hopeless or suffer from imposter syndrome, optimism may be your saving Grace. However, pure optimism applied in a blind manner can be dangerous and delusional. When you have blind optimism, it prevents you from addressing the root causes of the problems that need improvement.

Be the customer

If you watched cable television in the 1990s, you likely encountered commercials for Hair Club for Men—a product for men to grow their hair back. The end of the ad featured founder Sy Sperling, who proclaimed, “I’m not only the Hair Club president, but I’m also a client.” Empathizing with end customers isn’t when you manual test on a staging site, it’s using the actual product. I’m not asking you to be a balding man, only to embody who the customers you serve are experiencing. At One Medical, I was a patient. At On Deck, I was a fellow. At Webflow, I’m an end-user and working on projects of my own.

Most customers provide critical feedback not to be mean, but because they care. There is a lot at stake when someone is entrusting your product to build and maintain their projects, business, and passions. When you use your product with the same stakes as them, the product pain reveals itself. The best product designers are the ones who get frustrated with what they’re working on and are motivated to make it better.

Hate it ‘til you love it, and it is loved

The purpose isn’t to be a perceptual hater. “Hate it ‘til it works” is transformative, not an attitude. I keep a product journal on all the things I worked on. Capture details that you notice and devise what can be improved. Hate it ‘til it works, because if you put the critical rigor into the day-to-day work, you’ll create something people love.

Tweet of the week

Dagobert Renouf @dagorenouf

Twitter is the most supportive place for a startup founder 🐦

February 12th 2022

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Hype links

• If you’re looking to learn Webflow, Melissa Mendez hosts Webflow Parties. They’re very friendly for beginners

• Arix King created a really cool Chrome extension for those who love Markdown (like me!) easier to use in Webflow. Magic Paste

• A great thread on Twitter about visual gags on The Simpsons