there’s 2 types of terrible bosses

What's in today's newsletter?

2 types of bad managers
Alien Computer UI
Micrographics generator
Chinese cigarettes art
Career advice in the age of AI

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Years ago, my buddy texted me at 1AM.

At that hour, it’s never good news.

Friend: “Dude, I think my manager hates me.”
Chris: “What happened? Spill the tea 🍵”
Friend: “She showed up to work today.”
Chris: “...and?”
Friend: “That's it. Saw her the first time this month. She stayed for 45 minutes, then bounced.”
Chris: “Wait, what??”

Turns out, the whole design team has been dealing with this for months.

My friend’s 1:1s became therapy sessions for her (I’m still surprised she held 1:1s at all). Her qualifications for managing designers: 15 years of experience. That's it. That's the tweet.

Meanwhile, the team is convinced she’s the problem. Classic Stockholm syndrome sh*t.

Which reminded me of one of the most expensive lessons of my career:

Experience ≠ Competence.

Bad managers come in exactly two flavours:

Flavour 1: The Overwhelmed (but decent) Manager

They're drowning. Getting crushed by their own boss. Maybe dealing with personal stuff that has nothing to do with you.

They're not evil. They're just in survival mode.

Flavour 2: The (actually) Toxic Manager

The insecure one. The incompetent one. The checked-out one.

You know the type.

↓

Different flavours need different strategies.

If your manager is overwhelmed (Flavour 1):

Stop waiting for them to read your mind. Be specific.

Not: "I feel undervalued" (too vague).
But: "Include me in X meeting" (actionable)

Make their life easier. Package your updates visually. Tie everything to business outcomes. Anticipate their questions before they ask.

If your manager is toxic (Flavour 2):

Stop. Trying. To. Fix. Them.

Instead:

Find an internal sponsor (someone senior who sees your potential)
Transfer teams internally (fresh start, same company)
Build your exit strategy (update portfolio, activate network, leave professionally)

IMO, your career is a startup.

Your manager is either an investor or a roadblock.

If they're not investing in your growth, they're costing you compound interest on your potential.

Every month you stay stuck, is a month you're not levelling up somewhere else.

Wrote an article on managing up, finding sponsors, and knowing when to bounce? Read it here →

A big thanks to our friends at Mobbin for sponsoring this issue.

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So what's went down last week?

The going ons, happenings & shenanigans you might have missed ↓

Alien UI is why I watch sci-fi films.

@ChrisPirillo built this Alien Computer: Retro Sci-Fi Dashboard Terminal Emulator (it's a bloody mouthful), but it's super cool 👨‍🍳💋

Here's the use case: Make it full screen on your monitor at the office, go for a coffee break, come back and see your colleagues reaction.

Oh, don't hit refresh to find your best terminal layout.

Micrographics is making a come back. But it's not the easiest thing to design. Don't worry I gotchu.

@thezezelab made this tool to help you generate micrographics. Just smash the space bar!

Chinese ciggies and their art are phenomenal.

Turns out I'm not the only one. @0x_ultra built an Chinese Cigarette Museum with 200+ brands and 3250+ products. You can:

Discover new packs and their history
Track favorites and packs you already tried
Chat with fellow collectors
Share your collection!

YOU CAN'T MAKE THIS STUFF UP 🤣 I LOVE THE INTERNET

Even if you're a non-smoker, have fun browsing ciggies.app

Something I've been chewing on all week.

Phil Chen, an AI founder, wrote up his career advice for the next decade. He turned down Anthropic and Cursor (twice), so the man's earned a listen.

His article is aimed at engineers, but I read the whole thing thinking about designers.

The bit that stuck with me: anything you can grade, a model will eventually do better. What's left is judgment. Knowing which problem matters. Then sweating the last 10% nobody else bothers with.

We've been calling that "taste". I think that's what separates the folks that'll thrive in the next 10 years.

Do you agree with his thinking here?