This is how long I’ve been thinking about launching this newsletter. I had the logo. The tagline. Even a list of topic ideas. But I kept telling myself:
“Not yet. It’s not quite ready. I’m not ready.”
Which is funny, considering how often I quote Reid Hoffman in my work:
If you're not embarrassed by the first version of your product, you've launched too late.
And yes, I know what the quote actually means. It’s not a license to ship junk—it’s a reminder that feedback beats perfection, and that speed helps you learn.
But like all great quotes, it needs context.
(You see where this is going.)
But when it’s your own name on the line, your voice, your ideas——that same speed starts to feel reckless.
You second-guess. You wait. You overthink.
Especially if you’re someone who cares about doing things right.
Especially if you’re someone who thinks context matters.
That tension—between urgency and timing, action and hesitation—is exactly what this newsletter is here to explore.
I’ve worked in environments where we had no time and had to move. And I’ve been in others where launching too early could’ve wrecked everything: reputation, trust, even compliance.
One of the hardest parts of this work—any work, really—is knowing when to push and when to pause. That’s not something a framework can answer for you. But experience, reflection, and asking the right questions? That gets us closer.
When “just ship it” skips a few steps
Recently, I saw this play out in a team I worked with. A department head spun up a small side project—a feature that, to be fair, was functional and even met a real user need. It was based on a request from sales, and once the ops team caught wind of it, they handed it straight to a customer they thought would benefit.
At that point, it was “official.”
No launch. No announcement. Just a Slack message—and off it went.
The problems didn’t show up immediately. But once customers started using it, the questions started coming in.
Like: “Why does this require a separate login?”
Turns out, the feature was running on different infrastructure—not integrated with our usual systems, and definitely not part of our support or maintenance scope. Suddenly, the product team was in the dark, support had no answers, and the feature itself had just enough traction to be dangerous. The separate login alone raised potential security issues.
The original builder—understandably—couldn’t cover all the technical questions. So I had to step in, play the villain, and roll the feature back. We kept it live for two pilot customers, but the rest had to wait.
Now, we’re planning how to port the whole thing over to the proper infrastructure, which means unplanned work, shifting the roadmap, and eating time we didn’t budget for.
The problem wasn’t the speed.
It wasn’t even the feature.
It was the absence of context.
This is the start.
There’s more to come—though what it looks like?
That’ll depend on context. Naturally.
— Chris