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

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Newsletter issue: #171
Read time: 1m 13s

Most people think career pivots are black and white decisions.

​Quit job → Start new career (all while praying you don't go broke).

That's like designing a product without ever talking to users. Absolutely insane.

However, it’s more like a dirt path most people don't notice, but a shortcut for those who know where to look.

I call it "Overlapping Design".

It works like this:

1. Keep your day job (that pays your bills)
2. Try a small experiment in your target field (for me, it was designing a friend's website)
3. Notice if you lose track of time doing it (I stayed up until 1AM my first week)
4. Repeat until your side gig can replace your main gig

This isn't sexy advice. It won't go viral on TikTok.

But it works.

Fun fact: I made UX playbooks for my teams at my corporate jobs. Then realized there was a market for these systems.

Today? Used by 18,000+ designers in 90+ countries.

The beauty of this approach? You're not jumping off a cliff hoping you sprout wings on the way down.

You're building a bridge while safely standing on solid ground.

Career pivots are hard. But if not now, when?​

When I wanted to get into UX (circa 2014), I had every excuse:

• ​No formal design education​
• ​Didn’t know where to start​
• No family connections
• No UX portfolio​
• Lack of time

The excuses are always there…

Crappy job.
No experience.
Family obligations.

But it's up to you to decide:

Is it an excuse to stop, or an excuse to keep going?

Below is my exact step-by-step career pivot strategy (I’ve done it at least twice, successfully). In the article, I break down how I went from $0 to six figures without going broke in the process.

🔥 HOT THIS WEEK

The goings ons

Happenings & shenanigans in the (design) world and beyond

Stripe quietly rolled out it's new logo. Love it or hate it?

Andreas Storm @avstorm stripe got a new logo old vs new 4:44 AM • Sep 23, 2025 30 Retweets 1570 Likes Read 226 replies

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Generate 3D mockups (images and videos) without Figma plugins. ContentCore let's you showcase your sick UI with a few toggles. I love their interface too!

Should I get a UX Playbook tattoo? No I shouldn't but this is ridiculous haha.

LinkedIn Lunatics @LinkedInLunat1c 5:26 PM • Sep 23, 2025 1 Retweets 19 Likes Read 2 replies

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ChatGPT adds branch conversations letting you more easily explore different directions without losing original thread. Announced earlier this month.

OpenAI is taking on LinkedIn with AI-powered Jobs Platform, saying they will “use AI to help find the perfect matches between what companies need and what workers can offer.” Is this a stunt? Or should all similar products be scared? Let's not forget, LinkedIn is also owned by Microsoft, OpenAI’s largest investor.

Last week's livestream was How To Use Behavioural Psychology In UX. We talked about UX psychology principles, behaviours & biases, and small tweaks to make huge product impact. Watch the full recording on YouTube.

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

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