The high price of guessing

From misplaced confidence to missed opportunities — and what could’ve stopped it

We’ve all worked for that one boss. 

The one who comes in hot with a bold new plan — not because it’s needed, not because anyone asked, but because they had a “feeling.” 

Maybe they saw something in a trade magazine. Maybe their cousin’s nephew mentioned it at a cookout. Either way, the plan’s already in motion before anyone else even knows about it.

You bring up concerns — politely, maybe even with examples of similar plans that failed. Doesn’t matter. They’ve already fallen in love with the decision.

And a month or two later, when the thing inevitably flops, it’s the market’s fault. Or the execution. Or the audience. Or the staff — definitely the staff. Anything but the decision itself. 

There’s always a reason it should have worked. It’s just never the one that matters most: 

Was it ever likely to work in the first place?

Blockbuster had that boss. In the early 2000s, Netflix offered to sell itself to Blockbuster for $50 million. They got laughed out of the room. Then Blockbuster doubled down on retail expansion — betting on in-store foot traffic just as the digital era was getting its legs.

By 2010, Blockbuster was bankrupt. Today, Netflix is worth more than $250 billion.

I don’t say this to pile on. Blockbuster is hardly the only company to miss a boat. But it’s a textbook case of what happens when decision-makers operate on gut instinct and misplaced certainty, rather than clear likelihoods.

The signs were there. So was the data. What wasn’t there was a model that could force the right question: What’s likely to work — not in theory, but in reality?

This is the reason What’s Likely exists. It doesn’t guess. It doesn’t hope. It doesn’t flatter the person making the call. It just runs the probabilities. 

It considers every variable that matters — from behavioral signals to execution risk — then stacks those against trends, known data, and real-world outcomes.

Most bad decisions don’t feel bad in the moment. They’re often made with confidence and backed by instinct. Confidence without clarity feels decisive in the moment — but when you’re wrong, the fallout is real. 

And, over time, it adds up — in business and everywhere else.

Jacob Brower is the founder and chief strategist of What’s Likely, a decision-support tool that forecasts the most probable path to success. He is also president of Archer's Bow Media & Marketing and ABM Strategies.