So I heard folks talking about the ‘Carl Smith caddie’ approach, you know? This idea of being super focused, totally prepared, having everything mapped out. Sounded pretty good, I thought. Maybe something I could use in my own stuff, get things more organized.

I spent a bit of time trying to get into that headspace. Thinking about how they supposedly plan every little detail, stay calm under pressure. Seemed like a solid way to operate. I figured I’d give it a shot on a project I had lined up.
My Attempt at ‘Caddie’ Focus
Well, trying that out really threw me back to this one particular time a couple of years ago. It wasn’t about golf, not at all, but it was about planning, alright. I had this freelance gig, a website build. Simple enough, I thought. I spent ages mapping it all out.
- Detailed sitemap, check.
- Wireframes for every page, check.
- Content plan agreed, check.
- Timeline with milestones, double check.
I felt like I had channeled my inner Carl Smith caddie. Everything was accounted for. Ready to execute perfectly. Then I had the kickoff call with the client.
Boom. Turns out, between signing the contract and the kickoff call, they’d had a ‘major strategic rethink’. Scrapped half the features we agreed on, wanted to add a whole bunch of complicated stuff I hadn’t budgeted time or brainpower for. The whole plan just went straight into the bin. Poof.
Honestly, it was chaos for a week. All that meticulous planning? Useless. I was scrambling, trying to figure out the new scope, rejig the timeline, explain why the new features would cost more and take longer. It was messy, frustrating, and a long way from calm and collected.

We got there in the end, but it wasn’t because of the perfect plan. It was because we had to ditch the plan and just figure things out day by day, call by call. Lots of back and forth, lots of adapting on the fly. Not very ‘caddie-like’ at all, felt more like juggling knives while riding a unicycle.
So, this whole Carl Smith caddie focus thing? Yeah, sounds nice. But real life, real projects, they don’t always stick to the fairway. Sometimes you end up in the rough, and the fancy plan doesn’t help much. You just gotta find the ball and figure out how to hack it back onto grass.
Maybe the real skill isn’t just making the plan. Maybe it’s more about what you do when the plan inevitably goes sideways. That’s the part I ended up practicing, anyway. Didn’t really have a choice.