I Could Tell You My AI Has Never Lied. I'm Not Going To.
Seven months, two generations, one production rebuild — and five things I learned that I did not expect to learn.
I’ve been staring at a prompt for the past twenty minutes. Not because I don’t know what to write, but because I’m trying to deliberately make it worse. More vague. Less specific. I’m trying to see how little information I can give an AI and still get something real out the other side. This goes against everything I’ve written about context engineering over the past year. In my article about building AI agents and managing their context windows, I spent thousands of words explaining why precision matters, why documentation is critical, why you need to carefully curate what information agents have access to. I described the art of spinning up fresh agents when Claude’s 200,000 token context window fills up, how to preserve project knowledge across handoffs, how to maintain a general understanding of your codebase so new agents can hit the ground running.