This morning, I looked at my todo lists, my notes, and my Slack messages. Half-finished tasks. Unmade decisions. A dozen quiet things waiting for me to pick them up.
As I go down these lists, cursor pointing at each line item, saying to myself in lowercased tones: "Later", "Not yet", "Soon", "In a bit".
Okay well. Self. If not now... then when?
Sugar
When I was a little kid, there was a Disney movie I watched over and over. That VHS tape practically lived in the VCR (and then later, the VHS rewinder machine). It was The Sword in the Stone—a story about the mythical wizard Merlin mentoring a still-young, not-yet King Arthur.
One of my favourite characters wasn’t Merlin, or Arthur, or even Archimedes the owl.
It was a plucky little enchanted sugar bowl named "Sugar" (it seems). It had no lines. It just danced across the table, scooping sugar into Merlin and Arthur’s teacups with frantic silly little hops.
And at one point, Merlin says a phrase I’d never heard before:
“Say when.”
It stuck with me.
Even now—decades later—I can still picture it.
That tiny sugar pot. The clink of porcelain. The clumsy joy of getting it just right.
Time
That phrase—say when—is about knowing your limit. A gentle tap-out. A moment of decision. Not giant yeses or catastrophic nos—just tiny little whens whispered in tea rooms, in code reviews, in your own tired head.
In life and work, we’re constantly facing that question. But it’s always more complicated than it sounds.
When do we start? When do we stop? When do we ship? When do we hold? When do we speak up? When do we let go?
Not everything has a clock. But everything has a rhythm. And you don’t always hear it the first time.
Sometimes the “when” comes from you. Sometimes it comes from someone else. And sometimes… no one says anything—until it’s too late.
Tolerance
In work, “when” gets dressed up in fancier clothes.
We pretend it lives in the calendar. That it’s a milestone. A meeting. A sprint. A roadmap. But underneath all of that, there’s always a realer “when”:
When is this too much? When have we done enough? When have I had enough?
I’ve learned that every meaningful moment in my work—every peak, every shift, every turning point—has a “when” behind it.
Not just what we did. But when we decided it was time.
Observe
I think about how I handle my own versions of “when.” The invisible line between “growth” and “grind.” Between caring deeply and burning out spectacularly.
Sometimes, my fuse is short.
I’ll say it quickly—when conversations spiral, when decisions stall, when momentum breaks under the weight of circular logic.
Other times, I let things run long. (Maybe too long.)
I’ll tinker and tweak. Refactor and rethink. Convincing myself I’m almost there—still reshaping a prototype on the sidelines.
Neither is wrong.
The key is knowing which mode I’m in.
To zoom out and observe. To zoom in and listen—for that quiet part of me that says:
“Hey… say when.”
Ready...
The hardest part? Sometimes, you don’t hear it at all.
Clarity doesn’t always come like a lightning bolt. It doesn’t kick the door down. That’s why I try to leave space—for the quiet voice. The one that doesn’t shout. Doesn’t spiral. Doesn’t scramble to fix.
You don’t get unit tests that radiate green checkmark emojis for “this idea is fully formed enough to share.”
Sometimes, you just get this jittery sugar bowl in your chest saying,
“Sweet enough yet? Almost? Now?”
And you have to trust it. You have to “say when” without proof. Without certainty. Without knowing if it’s too early or too late. That’s the wild part. But sometimes, that’s all life gives us.
Vague readiness, scooped one spoonful at a time.