Why Planning is Just Guessing: Embracing Flexibility Over Long-Range Forecasts

People love to plan. We make five-year strategies, detailed budgets, and project timelines with color-coded boxes. But look at any truly creative or resilient business—or even family—and you’ll find the ones who succeed are the ones who improvise. Planning feels like control, but it’s often just a guess in disguise. When big changes happen (a client drops out, a new opportunity crops up, unexpected obstacles arrive), those tightly drawn plans become a prison rather than a guide.

Instead, those who thrive treat plans as living, breathing guesses. When Sarah’s tutoring business started growing, her original plan had detailed projections for every quarter. But reality intervened—scheduling apps changed, parents’ needs shifted, and new technology meant she could tutor kids across the country, not just her local area. By checking in weekly and asking, 'What’s my next best move with what I really know now?', she stayed nimble and open to big wins she never could have predicted.

Behavioral science confirms that when we focus on just the next actionable step, rather than distant outcomes, we’re more likely to take real action and recover quickly from mistakes. Rigidity increases stress and makes teams slow to respond; improvisation and micro-adjustments let us seize opportunities as they truly emerge.

Take a breath and look at any big plan you're holding onto; mentally relabel it as your best-guess starting point instead of a fixed roadmap. At the start of this week, choose that one priority that matters most right now, focusing all your energy there. Give yourself permission to shift or let go of steps that no longer make sense as you get new information, and notice how often small pivots pay off in unexpected ways. Challenge yourself: what could you cut from your plan today that would free up more courage to actually move?