September 21, 2026

Planning Became A Side Hustle

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Every company I've ever been part of ran planning as an annual exercise. In corporate it was formal. Everybody put together a business plan, some elaborate, some not. When I moved into executive roles, the ask grew and we built longer range outlooks on top of the annual plan. And I'll admit it, the same pattern showed up after I left corporate and started my own company. It happened at every place I've worked, including mine.

Over all those years, the long range plans held together and the 12 month plans, the ones broken into quarters with real targets attached, mostly didn't.

I've thought about why. The longer plan seemed easier to keep, maybe because there was less pressure on it, or less room to make an excuse out of the emergency of the day. It let us refocus on what we said was important, and go back and check whether the everyday decisions were moving us closer to the goal or further away. The 12 month plan lived down where the grenades landed. A key employee quits, a product goes on back order, a recall lands in your lap on a Tuesday and something else lands Wednesday. It had to compete with all of that for attention, and it lost, because it is very easy for a meeting to get louder than the goal.

The plans were good. Well thought out, with consensus from most of the room. Then people went back to doing their day job, and planning became a side hustle they didn't have time for anymore.

Fast forward to the conversations I have now with owners and CEOs. When I bring up planning, I get a bobblehead nod from almost everybody. They've been through it. They sat down with the best of intentions, they built something, an annual plan, a quarterly plan, sometimes a longer strategic outlook, and then they got caught up in doing their job day to day. When I ask them, ninety days in, whether they can tell me the primary goal on that plan and one level of detail underneath it, let alone the secondary goals, I get the deer in the headlights look. You can watch the oh shit moment happen in real time.

Nobody in those conversations abandoned their plan on purpose. There was never a decision. There was a back order and a resignation and a customer about to fire you, and the plan stopped being the thing anyone looked at.

So as year-end planning starts up, I'd spend the energy somewhere different than most people do. Keep the long range outlook, since that's the thing you steer by when a quarter goes sideways. The 12 month plan is where the work is, and that work is deciding, before January, what happens to it on the day a grenade lands: who pulls it back out, on what schedule, and whether the Monday meeting opens with the plan or with whatever was loudest over the weekend. None of that is complicated, and in my operating years it still never got decided.

So, before you book the offsite, can you say the primary goal on this year's plan, and one level underneath it, without opening the file? If you can't, book the offsite around that instead.

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