Play of the Week newsletter by Chris​ ​ ​​​​

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Newsletter issue: #174
Read time: 1m 59s

Ever make a decision that made you rethink your entire career?

🙋‍♂️ Raises hand

My career journey has been a rollercoaster. Epic fails and (thankfully) some wins.

I quit the best job to chase status, only to fall flat on my face.

I once spent 8 months building a product nobody wanted.

Another time, I burned through $250K of investor’s money on a dumb concept.

And let's not talk about all the "let’s start this” conversations only to have the idea fizzle out after weeks.

Each time I thought: "This is it. I'm a fraud."

Luckily I never told my Asian parents. Unsure if they’ll accept the horror from the sidelines as I kept taking risks despite the crashes.

*flying flipflop incoming 🩴 #iykyk

We all make terrible calls sometimes.

Maybe you:

• Fought stakeholders for your ego
• Hired someone who tanked team morale
• Redesigned something that crashed conversion
• Ignored user feedback because "it didn’t feel right"

The difference between good and great UX leaders isn't avoiding mistakes.

It's how quickly you recover from them.

What didn’t work:

”It was the market”
”Users just don’t get it”
”They don’t understand the value of UX!”
”If only leadership had given me more time...”
”It’s not me, it’s them…blah blah blah blah blah”

Blaming external factors is like turning up the music to drown out a smoke alarm. It might feel better in the moment, but there’s a fire and shits burning!

Instead, here’s my 5-step recovery plan:

1. Own it without the shame spiral: No BS. No excuses. "That feature didn't work, and here's why." Your team already knows anyway.
2. Dissect the failure like a UX problem: What went wrong? Which signals did you ignore? Where did your biases creep in?
3. Swap horror stories with peers: Even your unicorn engineer has "that time I completely screwed up" stories.
4. Audit your decision process: Was it rushed? Did you listen to the wrong voices? Was there enough pushback?
5. Make a bold correction, not a quiet fix: Half-measures just extend the pain. Scrap it, pivot, or reset. Just do it decisively.

After multiple fails, I decided to try once more with UX Playbook.

Today?

• 14,000,000+ content impressions in the last year
• 300,000+ weekly newsletters & blogs read
• 200,000+ visits to the website
• 93,000+ following my content
• 18,000+ designers use my UX resources
• 90+ countries and counting

What changed wasn't my strategy. It was my recovery speed.

I stopped dwelling on failures and started extracting lessons faster.

As a wise man once said: "You either get a win or an awesome story. Win-win."

What's something you want to recover from?

Want my complete framework for turning UX disasters into career wins? Get the full article with all 7 recovery steps:

🔥 HOT THIS WEEK

The goings ons

Happenings & shenanigans in the (design) world and beyond

Popeye's Tokyo Guidebook is now available in English and it's filled with guides from 2018 to 2025, for all the cool kids heading to Tokyo soon 🇯🇵 ... So what's is Popeye? Founded in 1976, initially famed for introducing American youth culture to Japanese audiences, but over the decades has evolved to document and celebrate Tokyo’s unique style, craftsmanship, and local discovery. It's a trendsetter of the city life in Japan and widely celebrated for its influential coverage of Japanese urban culture, fashion, music, food, travel, and interior design trends. Here's the story on the company behind it.

Mike shared his Contra Figma File (publicly) 🤯 It's a bloody branding masterclass! If you didn't know, Mike & Chara Smith are the creatives behind Smith & Diction. They worked on Perplexity's new logo and Gamma's new visual identity. They also spoke at Config this year sharing what happened after they shared their entire branding process via Figma Slides. Anyone here know Mike? I need some professional help!!!

Mike Smith @mikesmith187 Not every project goes the way you plan. When we were working with @contra we took a MAJOR swing on round one and missed! We listened and bounced back with the brand you see today. Want to see what starting over looks like? Here's the whole file. https://figma.com/design/Qo64brwGBmObIrPauXVxe1/Contra---Brand-Identity--public-?node-id=1494-14816&t=1wAkErs4HygtIcYK-1 4:25 PM • Oct 10, 2025 62 Retweets 1009 Likes Read 62 replies

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I've been obsessed with Pickleball 🏓 Playing (5 times last week lol), training, binging YouTube videos, even bought a paddle. It's one of those sports that's social, easy to pick-up-n-play, and spread incredibly fast. Who's your favourite Pickleball follow? Lmk

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That's it for today. Speak soon 💛 ​ ​ — Chris

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