EP 233 Fail to Plan, Plan to Fail? Your AI Annual Planning Skill!

Sound familiar? You set big goals back in January, and now it's the middle of the year and you're nowhere near where you wanted to be. Trust me, you are not alone, and it's almost never because you didn't work hard enough. It's because the plan never got broken down into something you could actually do. "If you fail to plan, you plan to fail" is a cliché for a reason, so in this episode we fix the plan itself. I walk you through a free Claude skill for annual planning that you can grab inside our free community, the AI Ops Yacht Club. It interviews you about last year (your revenue, your wins, your misses), pulls out what to start, stop, and keep, then builds your theme for the year, your goals, your metrics and targets, and the resources you'll actually need to hit them. From there it cascades everything down into quarters and even hands you a one-page plan you can share so your whole team is rowing in the same direction. Every business needs a visionary AND an integrator, and this is how Claude can play that strategic-partner role for you. By the end you'll know how to upload and run the skill, how to feed it your existing business knowledge through a Claude project, and how to pair it with the quarterly planning skill so big goals turn into daily action. We create it on paper first, then call it into existence, eating the elephant one bite at a time. This is what working strategy first, AI second actually looks like, and it's a game-changer for visionary (and ADHD!) business owners. Takeaways: An annual plan gives you the mission, vision, and path that your quarterly plan needs to even make sense Start, Stop, Keep (straight from EOS) turns last year's wins and misses into next year's direction A real plan names the goals, metrics, targets, AND the time, money, and people each one requires Cascade the year into quarters, then into daily to-dos in ClickUp, or the goals never get done Drop your annual plan into a Claude project so every future task gets checked against your goals Links referenced in this episode: Join the AI Ops Yacht Club (free) + grab the annual planning skill Companies mentioned in this episode: Claude Claude Code Cowork ClickUp EOS AI Ops Yacht Club Mentioned in this episode: Become a Member of the Ops Yacht Club I've created a free community where we are posting job opportunities for people just like you! Inside the community we also have trainings on how to structure your packages to better serve your clients, help with how to do discovery or strategy calls and give you ideas on where to find your next client. We'd love to have you a part of the community. You can join at www.opsyachtclub.com