Jacob Kaplan-Moss

Tag: Planning

📝 Two Scenario Threat Modeling

A trap that many people fall into when trying to threat modeling or risk planning is a fear of being incomplete that leads them to not even try. People think, “there are so many possible things that could go wrong, so many potential risks. It’s going to be such a huge effort to enumerate all possible scenarios, and I don’t have time, so I guess I can’t do threat modeling.” That is, threat modeling seems so big, so hairy, that people believe it’s too complex to tackle.

This just isn’t true! Some planning is always better than no planning. In fact, you can get a surprising amount of value out of a very simple and fast technique: imagine a couple of scenarios – just two! – and game out what you could do to mitigate them.

August 8th, 2025 • planning risk threat modeling

🔗 Prioritizing and Planning within Heroku Postgres - Craig Kerstiens (#)

My favorite planning exercise

October 31st, 2022 • management planning product

🔗 How to plan? (#)

How to plan? How hard could it be? 4k words scribbled down on a sunny October afternoon for people in tech observing the Season’s Traditional Annual Planning Process, inspired by a recent interview question (and 25 years of variously painful planning processes).

October 28th, 2022 • management planning

📝 Simple Product Management Tricks

Three simple tricks product I’ve picked up that help me be more than completely useless when I need to wear a Product hat.