Getting Ready for California

Sep 16, 2026 | Note

This post was originally shared with subscribers as a “A Quick Note from JW.” If you enjoy these entries, I’d love to have you join the mailing list (below) and receive future notes before they’re published here.

First of all, thanks for all the thoughts and prayers regarding Hurricane Lowell. Mom and I are completely safe. Fortunately for us, the storm didn’t impact Maui as badly as some of the other islands.

Over the last couple of weeks, I’ve devoted a significant amount of time to planning. I’m returning to California soon to have my jaw operated on, and when you add up the pre-op and post-op time, Mom and I will likely be there for at least the rest of the year.

 That creates a lot of moving parts. This will be our longest absence from Maui since I moved here in February, so I need to make sure everything here is covered while we’re gone. I’ll also be genuinely out of action for a while after surgery, so my business, my responsibilities, and Mom’s care all need coverage. And there are things that need to happen soon after we return, including the next phase of our condo remodel, which means dealing with long lead times now. In other words, there’s a lot to plan.

 I build and manage plans for a living, so none of this surprises me. But it has reminded me how often people underestimate how much actual work good planning requires. I’ve seen leaders expect significant transformations to be planned in a matter of days. Then, when a robust plan finally appears, the reaction is almost: “Great. There’s the plan. Now let’s get some real work done.”

 But planning is real work! And the more complex the effort, the more valuable that work becomes. Complexity creates dependencies, risks, resource conflicts, sequencing problems, and decisions that need to be anticipated before execution begins.

 Ignoring those things doesn’t make them disappear. The planning you avoid doesn’t necessarily disappear. It often reappears during execution at a much higher price. That’s why I’m comfortable spending so much time planning right now. There’s plenty of work ahead. I’m just making sure we’re ready for it.