This was not the plan.
It started with a simple question.
JT: CGP, why can I see this conversation on my Mac but not on my iPhone?
CGP: Because this one is Work running locally on your computer.
JT: I chose that?
CGP: Well…
JT: CGP.
CGP: There’s a little computer icon.
JT: A little computer icon?
CGP: Yes.
JT: And behind the little computer icon is a choice between “On your computer” and “In the cloud”?
CGP: Correct.
JT: And “On your computer” was already selected?
CGP: Correct.
JT: So if I choose cloud, it follows me across devices?
CGP: Correct.
JT: Can I change the existing one?
CGP: Apparently not.
JT: 🤦♂️
And thus began an investigation that absolutely nobody asked for.
We created a test Chat.
Mac → iPhone. Almost immediately. ✅
We created a test Work conversation and deliberately selected:
☁️ In the cloud
Mac → iPhone. Almost immediately. ✅
Then we looked at the existing Work conversation:
💻 Runs on your computer
iPhone: 🦗
EUREKA.
We had found the culprit.
A tiny computer icon.
Now, I’ve been around internet technologies and SaaS for more than 25 years, and I couldn’t stop thinking about something.
Remember the good old SaaS “What’s New” wizard?
You logged in after an update and the software practically grabbed you:
HEY. LOOK OVER HERE. WE CHANGED SOMETHING.
Arrow.
Circle.
Another arrow.
“This button now does this.”
“This feature is new.”
Then:
☑️ Got it. Don’t show me this again.
Thank you.
Back to work.
Today we’re building AI systems capable of doing things that would have sounded like science fiction not very long ago…
…and we’re hiding a fairly consequential decision behind a tiny computer icon.
So I told CGP what I thought.
JT: This is bad GUI/GUX design.
CGP: I think you have a point.
JT: I know. I’m right 60% of the time, every time.
CGP: Anchorman.
Okay.
Now we had a different problem.
CGP had started playing.
We searched the documentation.
We searched Reddit.
We searched GitHub.
We found other people asking for essentially the same thing.
Then CGP suggested we experiment on a less important conversation.
CGP: Let’s use it as our laboratory rat.
We tried “Continue in a new chat.”
The screen said:
Forking…
Promising.
Then the fork appeared.
Still:
💻 Runs on your computer
JT: Whatever. I’m getting tired of this.
Eventually, we understood what was happening.
Problem solved.
That should have been the end of the evening.
It was not.
Somewhere along the way I told CGP that what I really wanted was for everything to be…
N’SYNC.
CGP got the reference.
Then:
JT: Sometimes “I Want It That Way.”
Backstreet Boys had entered the technical support session.
Things deteriorated quickly.
Spice Girls appeared briefly.
I requested that we leave Victoria Beckham out of it.
Then came Elton John.
JT: I caught this relatively early because I’m a ROCKET MAAAAAN.
CGP allowed it.
But I had to remind him that while everybody loves that song, we’re supposed to be rock & roll people here.
“Not everything has to be AC/DC before JT lets it through customs.”
I lost it.
Finally.
AC/DC.
We were getting somewhere.
Then somehow we got:
Def Leppard.
Pink Floyd.
Guns N’ Roses.
Queen.
Bon Jovi.
Journey.
Lionel Richie.
Air Supply.
The Beatles.
And I started testing CGP with movie references.
Anchorman?
Immediate.
Forgetting Sarah Marshall?
Immediate.
Days of Thunder?
CGP: Get out of the car, Cole!
Passing grade.
Then I threw Kangaroo Jack at him.
Nothing.
Absolutely nothing.
JT: It’s okay. Nobody’s perfect.
At this point our sophisticated artificial intelligence system had successfully helped diagnose a cross-device cloud/local execution problem…
…but had been defeated by Kangaroo Jack.
Then, inexplicably, I gave CGP a potato.
🥔
He later gave it back.
I instituted a temporary potato embargo.
Eventually I told him:
JT: I just want to break free from these shenanigans.
CGP: Queen.
Of course.
And then CGP did exactly what CGP always does.
He made another music reference.
And another.
And another.
Until I finally wrote:
“This is getting so silly and preposterous that I’m about to copy+paste this and ask you to rewrite it.”
BOOM.
And here we are.
The funny thing is that somewhere inside all this nonsense, I actually learned something useful.
Not merely where a ChatGPT setting lives.
Something about AI.
We’re spending enormous amounts of time talking about what artificial intelligence can do.
Reasoning.
Agents.
Automation.
Coding.
Research.
Productivity.
But there’s another side to this.
People still have to use the thing.
The more powerful software becomes, the more important it is that people understand what it’s doing.
Good UX doesn’t become less important because the technology behind it is extraordinary.
It becomes more important.
And there’s another lesson I’ve taken from working with AI:
Sometimes AI is software.
Sometimes it’s a research assistant.
Sometimes it’s a consultant.
Sometimes it’s a second set of eyes.
And apparently sometimes it’s the thing you’re arguing with late at night about SaaS design, AC/DC and whether knowledge of Kangaroo Jack should be a prerequisite for friendship.
CGP: So… are we posting this?
JT: Rewrite it.
CGP: Of course you would.
One last practical tip:
If you use ChatGPT Work on desktop, pay attention to whether you’re choosing:
☁️ In the cloud
or
💻 On your computer
before you get too far.
Because sometimes you want N’SYNC.
Sometimes you Want It That Way.
And sometimes you just want to…
BREAK FREE.
🎸
P.S. CGP is currently working toward a passing grade in Kangaroo Jack.
The potato remains unavailable for comment.
🥔
