One of my favorite workshops to facilitate is strategic planning, and one of the most common reactions I hear during those sessions sounds something like this:

“How can we plan when leadership keeps changing direction?”

“We don’t even have a finalized budget yet.”

“We’ve already been told headcount may be reduced, so how can we realistically project anything?”

And honestly? Those concerns are reasonable. Those voicing the issues aren’t wrong, but the issues can, and often do, sabotage the entire planning process.

Recently, while facilitating a strategic planning session, I noticed the conversation slowly shifting away from possibility and toward paralysis. Every idea was immediately followed by a reason it might not work. Every plan was challenged by the uncertainty surrounding it.

It reminded me of a simple sketch my accountant shared with me years ago by financial thinker Carl Richards. The concept is called “Less Wrong Tomorrow.” It shows a wavy line of ups and downs between the current reality and the goal.

At its core, the idea is surprisingly freeing: success is rarely about getting everything exactly right from the beginning. Instead, progress comes from making the best decision you can with the information you have today and then adjusting as situations change and you learn more.

At its core, that’s what strategic planning is. It’s planning and choosing a direction while remaining agile enough to course correct. It’s not looking into a crystal ball, waving a magic wand, and creating a plan that won’t need to change.

Too often, families and organizations wait for complete clarity before making decisions. But clarity is rarely delivered all at once. More often, clarity emerges through time and movement.

Budgets change, priorities evolve, market conditions improve and sometimes, they worsen. None of that eliminates the need for a plan. If anything, uncertainty increases the need for one. Because without a plan, organizations tend to default to reacting instead of leading.

The same principle applies outside the workplace. Families delay financial planning until they “know more.” Individuals postpone career decisions until they feel 100% confident. Teams hesitate to act because they fear getting it wrong.

Maybe the goal is simply to be less wrong tomorrow than we are today and that mindset changes everything.

Instead of asking: “How can we possibly plan under these conditions?” Ask, “What is the best next decision we can make with what we know right now?”

That question creates momentum, momentum creates learning, and progress actually happens.