A friend of mine — a CFO at a mid-size company — takes real pride in something. For three years running, under his leadership, the company has come in under budget.
Out of curiosity I asked him this — what’s the company doing about the ground its competitors are gaining? Is it innovating enough? What’s actually stopping it from getting out there and competing at the top of its market?
The answer, for each of them, came back to money. You need budget for marketing, for new projects, for the kind of bets that let you do something different and actually win. A tightly controlled budget is a great signal for maintenance. Competing, and winning, requires sacrifices a “well-controlled” budget was never built to make.
He’s been at this company for over a decade. Years ago, early in his tenure, he ran the numbers hard during a rough patch, recommended layoffs and serious cuts, and the company came through fine despite real industry turmoil. That one win became his template. Ever since, austerity has been his default answer — because it worked once, because a spreadsheet gave him a genuine, powerful sense of control at a moment when he badly needed one.
What he never fully clocked is that the sense of control was mostly an illusion. The market has kept moving — technology, competition, the whole shape of his industry — in ways no spreadsheet from a decade ago could have predicted. The plan that saved the company once has quietly calcified into the only plan he knows how to run, regardless of whether the actual problem in front of him has anything to do with the problem it was built to solve.
He can’t really be blamed for this. Most of us default to exactly this behavior. We crave order, and somewhere along the way we convince ourselves that planning and doing are two separate jobs — one happens in a spreadsheet, in isolation, and the other happens on the ground, executing whatever the spreadsheet decided.
You don’t need a CFO title to recognize this.
Spend months planning a road trip with three friends. A week out, one drops. Then another. Now it’s just you. Adapt, or sulk about the wasted planning, or push ahead out of sheer stubbornness because you’ve already put in the hours.
Or picture a team spending four weeks on a major client proposal. You submit it. The client shelves the whole thing indefinitely — the kind of shelving that, realistically, never quite un-shelves. You can take the skills you sharpened, document what you learned, and move forward. Or you can sit in the “I can’t believe they did this to us” zone for the next two weeks, accomplishing nothing either way.
Like the team lost in a storm who found their way home using a completely wrong map, the plan itself was never really the point. It’s whether leadership gives everyone explicit permission to set the map down the moment it stops matching the terrain. Eisenhower put it best, decades ago: plans are worthless, but planning is priceless.
Next time your own plan falls apart, the question worth asking isn’t whether the plan can be saved. It’s this: am I protecting the plan, or protecting myself from admitting it’s over?