One thing I didn’t expect from writing The Strategy Trap is how much it would force me to question my own thinking and break down assumptions I didn’t even realize I was carrying.

I’ve been using a lot of the ideas in the book for years. They weren’t new to me. And I knew they worked. I trusted them. But writing is different. You can’t skip steps. You can’t rely on tone or context or “you know what I mean.”

You have to explain things cleanly enough that someone else can actually do something with them. You know, exactly like communicating a strategy to a team that has to act on it.

In 1775, British Empire was the mightiest force on earth.

Its navy ruled the seas. Its army was professional, disciplined, and well-equipped. Across the Atlantic stood a loose collection of farmers and merchants. No standing army. Little money. Fewer weapons.

From London’s perspective, the outcome seemed inevitable.

Yet six years later, Britain surrendered at Yorktown.

In 2011, JCPenney brought in Ron Johnson, the retail star who had built Apple’s iconic stores. His mission was bold: stop playing the endless coupon game and replace it with “Fair and Square” everyday low pricing.

It was simple. It was elegant. It was revolutionary.

And it was a catastrophe.

October 1, 2013, was supposed to be a historic day.

Healthcare.gov would open its digital doors and allow millions of Americans to enroll in affordable health plans.

The policy was law. The demand was real. The deadline was immovable.

The site went live.

And it crashed almost immediately.

In 2007, Nokia controlled more than 40 percent of the global mobile phone market. Their devices were everywhere. They were profitable, admired, and dominant.

But just six years later, Nokia sold its entire phone business to Microsoft for a fraction of its former value.

What makes Nokia’s collapse so painful is this: they saw the future coming.

In early 2019, WeWork was one of the most talked-about companies in the world.

It was valued at $47 billion. Investors lined up for an IPO that was imminent. It felt unstoppable.

And then it all came crashing down.

Within months, confidence evaporated, the narrative unraveled, and the valuation collapsed with stunning speed.

It launched with nearly $2 billion in funding. It was backed by some of the most powerful names in Hollywood and Silicon Valley.

And there’s a good chance you barely remember it.

That’s the first clue.

In just six months, the company burned through its capital and shut down, becoming the fastest $2 billion failure in entertainment history.

This is the story of Quibi.

It was marketed as the ultimate luxury music experience. Supermodels on yachts. Private jets. Tickets selling for thousands—some packages over $200,000.

But when guests arrived, the reality was a nightmare. A rainstorm had soaked the site. The "luxury villas" were actually disaster relief tents, and the mattresses inside were piled up, soaking wet. The gourmet meals were cheese sandwiches in Styrofoam boxes.

In April 1846, the Donner and Reed families set out for California with one north star: arrive safely before winter.

A clear, simple goal—one that required steady progress and smart decisions along the way. But when they started falling behind schedule, they reached for a shortcut. And that’s when everything began to unravel.

In 2013, Target stormed into Canada with the confidence you’d expect from one of America’s most beloved retailers. They opened more than 100 stores in a single year.

Canadians were eager. Surveys showed 52% were excited about the launch.

But when the doors opened, the dream collapsed. Shelves were half-empty. Prices felt higher than promised. On opening day, some stores even hung signs out front that read: "We're open (mostly)."

For eighteen months, Ford built the suspense.

The Edsel would be revolutionary—the car of the future. Dealers clamored for allocation. Customers waited to see what Ford had been hiding.

Then, in September 1957, the curtain lifted.

Within three years, the Edsel was dead, leaving losses that totaled more than $2 billion in today’s dollars.

When everything feels open and comfortable, progress slows. Urgency fades away. Teams stretch work instead of tightening it.

Constraints do the opposite. They create tension. They sharpen decisions. They force us to focus on what actually matters instead of spreading effort across everything that could matter.

If you want breakthroughs, don’t give people (or yourself) more space.

The hardest part of communicating anything isn’t deciding what to say. It’s deciding what not to say.

Clear communication is a discipline. It means resisting the urge to add, even when adding feels helpful. It means stripping the message down to the parts that actually guide action and letting the rest go.

We humans aren’t good at taking in lots of completely new information. Metaphors lighten the load and speed up clarity. They pin new ideas to something people already understand so they can act on them faster.

Alignment isn’t everyone nodding in agreement. You can’t determine alignment with a yes or no question. Alignment runs too deep for that.

True alignment is when everyone making the same decision when you’re not in the room.

When alignment isn’t real, the cracks show up fast.

An emphatic statement tells. A question invites.

And that small mark of punctuation often determines whether teams react or reflect.

Statements drive activity. Questions drive accountability.

The Problem: Scoreboards don’t create clarity

A target tells you what outcome you want, but not what you must become or improve to achieve it.

Yes, teams can act on “grow revenue.” But those actions will fragment—each group doing what makes sense in their lane. One team discounts. Another raises prices. Marketing adds promos. Ops tightens costs.

Everyone’s rowing, but not in the same direction.

“Time keeps on slippin’, slippin’, slippin’ into the future…”

Some days it feels like Steve Miller was singing about my calendar.

I’ll start the morning with clarity about what really matters. Then the little things show up—emails that “just need a quick reply,” meetings that expand beyond their purpose, texts that break my focus. One after another, they eat away at my day.

Did you know the placebo effect is active in your brain every single day, not just in hospitals or clinical trials? 

Psychologists call it Expectancy Theory, and it shows that the reality we experience is driven by our expectations.

Nice is a trap. Kind is a catalyst.

At first glance, nice and kind sound like synonyms. But when coaching a team through execution, they couldn’t be further apart.