You Don't Need a New Plan

We love the safety of a plan. Plans make us feel in control. They help us imagine ideal conditions, neat timelines, and predictable outcomes. But leadership—and life—rarely obeys plans.

Leader lost in the planning

This week, as I taper for a 100-mile race, I find myself wrestling with doubt. Am I resting too much? Have I peaked too soon? Should I be doing more? On paper, the plan says I should recover. My Whoop data says I’m at 98%. Yet my mind whispers: You’re not ready.

The truth is, you don't need a new plan and I’ve done this before. I’ve completed century rides with almost no preparation, gritting through on sheer will. This time, I’ve trained. I’ve prepared. Still, the conflict arises.

And it shows up everywhere, not just on the bike. As a coach and business leader, I catch myself drawn to new ventures, new plans, new strategies. A new gym idea. A new business book. All while I’m in the execution phase of my current calling. The temptation is always to plan more—because planning feels safe. Execution feels risky.

Here’s the leadership lesson: waiting for perfect conditions is just disguised procrastination. Seneca reminds us, “We are always complaining that our days are few, and acting as though there would be no end of them.”

Leaders must embrace the wrestle. There is no right way to prepare, no flawless blueprint. There is only today’s work. The plan matters, yes—but the courage to execute matters more.

The real question isn’t “Am I ready?” It’s “Will I show up and execute anyway?”

On the bike, in business, in life—that is the race worth riding.