Operators Using AI

Not a checklist. These are milestones that mean you're actually getting somewhere. Go at your own pace.

Suggested Milestones

Build a static microsite and run it locallyDescribe a simple website (a personal page, a resource hub, a project tracker) and have Claude build it as an HTML file. Open it on your own computer. You just made a website.

Publish a microsite to the internetTake that same site (or a new one) and deploy it to Vercel or Netlify. It takes 5 minutes and now you have a live URL you can share. That's a different feeling.

Build a morning brief that pulls from your actual toolsSet up a scheduled task or Cowork session that reviews your calendar, Slack, and email, then gives you a summary of what matters today. Automate it so it's waiting for you when you start your day.

Automate one recurring task end to endPick something you do every week: a status update, a report, a data pull. Set it up so Claude handles it with minimal input from you. Measure the time you save.

Help someone else go deeper with AIShow a teammate, a friend, or someone in this group something you've figured out. Doesn't need to be a formal demo. Teaching it is how you solidify it.

The "Something New" Rule

Here's how to keep growing instead of plateauing: every 4-5 days, try something genuinely new. Not "use the same stuff in a slightly different way." Something you haven't done before.

Try a tool you haven't used yet (Cursor, Cowork, a new plugin)Create a new command or skill for a task you do regularlyTake on a more complex project than your last oneConnect a new tool via MCP or APIAsk Claude to help with something outside your usual scope

The point is to keep expanding what you think is possible. If you're comfortable, you're not learning.

Track it if you want

Keep a simple log: date, what you tried, what happened. It's useful for seeing how far you've come, and it's useful if you ever need to show your team what you've been doing with AI.

Goals to Work Toward

Suggested Milestones

The "Something New" Rule