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

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Newsletter issue: #183
Read time: 1m 35s

Let me confess something embarrassing…

I used to think journaling was for teenage girls and people who wear crystals.

Then my brain exploded when I was trying to manage an entire design department.

Suddenly I had:

• 20+ designers reporting to me
• A product roadmap that made zero sense
• Countless stakeholders with "quick requests"
• Meetings with 30 people but only 2 would speak
• 6M+ monthly active users depending on our product

My solution? Alcohol.

Just kidding (But not really).

My actual solution was journaling with prompts.

Not AI prompts.
Not the “Dear Diary, today I felt sad” kind.

I'm talking about brain dumps triggered by weird questions that would make your therapist raise an eyebrow.

You see, my UX brain is like that junk drawer in your kitchen, stuffed with random ideas, half-baked solutions, and that one thing you know you'll need someday but can't remember why you kept it.

Most journaling advice is like being told to "organize your junk drawer" with no further instructions.

But what if instead someone said:

“Find the weirdest thing in your junk drawer and tell its life story?”

Suddenly, you're engaged. You're digging. You're thinking laterally.

That's what good prompts do.

Try these:

1. "If your current project was a movie genre, what would it be and why?"
2. "What design crime have you committed that you don't regret?"
3. "If your coffee could talk, what insult would it toss at you this morning?"

The magic isn't in writing profound shit every day.

(even though I try)

It's about giving your brain 5 minutes to breathe without Slack notifications, client feedback, or that one PM who thinks UX means “U Xcecute my ideas” 🥲

When I started using prompts daily:

• My team stopped avoiding me (less cranky)
• My productivity got better (more focused)
• My meetings got shorter (I was clearer)

And ironically, by writing about pickle brands and fictional villain origin stories, I stumbled into more solutions than any brainstorming session.

Your brain just needed permission to play again.

Here's 50 more UX journal prompts to turn creative chaos into your secret career weapon. And it's a bit of fun.