Writing

Why I stopped trusting my own roadmap

Placeholder post — replace with real copy. Kept here to verify the post template and list view render correctly.

For about two years I wrote a roadmap every quarter. Three columns, neat swimlanes, a confidence rating on each item. It felt like the responsible thing to do, and for a while I defended it hard when anyone pushed back.

Then I went back and read four of them in a row. Roughly a third of what I’d committed to shipped on time. Another third shipped much later, reshaped past recognition. The last third never happened, and — this is the part that got me — I couldn’t remember why most of them had ever seemed urgent.

The roadmap wasn’t planning. It was a way to avoid making a decision every week, by pretending I’d already made all of them in advance.

What I do now

I keep exactly one document: what I’m working on this week, and the single next thing after it. Anything further out lives as a loose list of “maybe,” explicitly unordered, explicitly not promised to anyone. When someone asks about Q3, I tell them the truth — I don’t know yet, and I’ll know more in six weeks than I do now.

It reads as less rigorous. It’s produced more finished work.