TL; DR:

• Context shapes everything
• Stop optimizing for the perfect plan
• Know your stakeholders deeply
• Join me for the live stream (or watch the recording) on Monday, February 23rd at 7:00 PM Pacific!

---

Why Everyone Seems to Have a Different Opinion on Planning

I want to talk about planning in software engineering -- and more specifically, why people seem to have such wildly different takes on it.

Here's something I've noticed. You come across someone who's had a successful career and they describe how they do planning. Makes sense, you note it, maybe you try to apply it. Then you find someone else -- equally successful, equally confident -- doing it in a completely different way. And you're left thinking: how are both of these people right?

The answer is almost always context. When people share their perspective on planning, they almost never include the environment that shaped that perspective. And that missing context is what makes everyone sound like they're contradicting each other.

Think about someone who spent their career building satellite infrastructure or delivering government contracts. Their planning approach is going to look fundamentally different from someone who built a scrappy startup from scratch. Both of them are right -- they're just responding to completely different constraints, completely different risks. If you pulled both people into the same room and actually mapped out what they value and what they're trying to optimize for, I'd bet there's a lot more overlap than it first appears. The differences come from the environments that shaped their thinking.