The Hubris of Annual Planning

Every year since the end of 2020 I’ve scheduled an entire day for planning the upcoming year.

It’s an energizing process that ushers me into the new year while also allowing me to refine the systems of my success. When I started, it was full of excitement… and delusion. I’d often over-plan everything, and set too many goals with unrealistic deadlines and targets.

But now I’m a grizzled veteran, shaped by my past mistakes and misguided hubris. If the goal of life is to know thyself, annual planning is a mirror into your growth, and I’m learning to look into it with humility.

I’ve learned what works:

• Incremental routines with a long-term goal in mind
• Weekly totals over daily targets (steps, screen time, pages)
• Accurate, visible records (whiteboard, phone widgets)

And what doesn’t:

• Investing without existing habits (exercise)
• Rigid schedules (knowing when I’ll be tired, energized)
• Complex goals (too many and they lose their importance)

At the end of every quarter, I’ll revisit the plan to make course corrections. If I was too ambitious I’ll reset the scales and update the routine design.

For example, this year I’m tricking myself back into a full-scale exercise routine by starting simple with 30-50 daily pushups. From experience, I know that building the habit will cascade into a larger opportunity. By February I expect I’ll transition to a 30-minute workout, but I have to see how January goes first.

The Plan always shows up, unlike inspiration, excitement, and motivation.

I don’t have to make many decisions throughout the week - just follow the plan, take good notes, and enjoy the ride.