You’ve committed to The Terrible Ten. You’re pushing through the messy first attempts. You’re Getting Shit Done. You’re building to 1,000 reps. You’re ruthlessly applying Strategic Abandonment.

You’ve committed to embracing The Terrible Ten. You’re going to push through the messy first attempts. You’ve internalized the JGSD mindset. You’re going to stop planning and start shipping.

AI can accelerate legal work, but it can also accelerate legal mistakes.

You’ve been in three meetings this week about the same initiative. There’s a Miro board with 47 sticky notes. Everyone agrees it’s important. The Slack thread has 200 messages.

You survived your first 10 attempts. The skill that felt impossibly foreign now feels merely difficult. You can execute without panicking. You know what good looks like, even if you’re not there yet.

Use AI like a junior assistant, not like a private vault.

You’re three slides into your first executive presentation. Your voice cracks. You forget your transition. The CFO is checking her phone. You can feel yourself sweating through your shirt.

Privacy in an app is not the same thing as privilege in court.

Over the past month, I’ve published a technical series on building an AI-powered Security Operations Center using open source tools. The question I keep getting from board members: “This is interesting for homelabs, but what about enterprise?” Here’s the business case.

The issue is no longer whether AI hallucinates; it is whether legal teams have controls.

A personal AI agent is not “a chatbot with a nicer UI.” It’s an assistant that can do multi-step work for you—collect information, draft outputs, and sometimes take actions across tools. Done well, it saves time and raises your AI literacy. Done carelessly, it becomes a privacy and security liability.

One fake citation can turn into a real disciplinary problem.