When I was in business school, I completed a senior finance project on the Walgreen Company. I poured myself into it. I produced a beautifully bound, designed, and illustrated thesis outlining how Walgreens could supercharge growth by leveraging what was, at the time, a wildly low cost of capital. The idea was straightforward and elegant: use the balance sheet and bond rating to execute a leveraged blitz of the Pacific Northwest with a flurry of new stores in strategic markets.
The financial modeling was strong. The forecasts were tight. The theory was sound. I earned an “A” and generous praise from the faculty. But a question lingered in my mind: this is academically great—but would the corporation actually do this?
So I did something that, at the time, felt bold. I asked to meet with the CFO of Walgreens. To my surprise, he agreed to review my proposal. Three weeks later, we sat down.
He started by kindly highlighting the merits of the paper and the theory that underlined it. He praised the math and all the work I’d gone through.
He paused before telling me something I remember to this day: We’d never implement any of your ideas in the real world.
Naturally, I asked why.
Again, he was kind enough to give me a genuine answer, walking me through how I had presumed the limiting factor of the company’s growth was cheap capital and a growth strategy. He then opened a thick file folder—charts, data, and long-range workforce projections—and I realized just how much I had oversimplified the problem.
He also highlighted another mistake I made. I suggested leveraging the business to accelerate growth. Looking back after decades of business leadership, I realize how short-sighted that was. Walgreens, he told me, has survived for over a century because it takes care of its people. One of the company’s commitments is never to leverage people in a bet on the future that would force them to prioritize bank covenants over 401(k)s or loyalty to long-term team members.
There was the difference. Business school trained me to think in five-year increments. Walgreens thought in fifty-year horizons.
They were comfortable sacrificing short-term speed for long-term trust, a key principle in a book he recommended I reread, Good to Great.
That conversation reshaped how I view strategy and how I evaluate “great ideas.”
Over the years, I’ve watched hundreds of millions of dollars burn by bright, capable leaders chasing ideas that looked brilliant on pitch decks and sounded logical in boardrooms, only to crash hard on the rocky shores of reality. They failed not because they lacked intelligence or ambition, but because they misunderstood—or entirely missed—the true constraints of their industry.
Every market has hidden choke points, constraints that are invisible to newcomers and often inconvenient to acknowledge. Real growth is rarely limited by what looks most obvious.
In healthcare, for example, the barriers aren’t innovation or good intentions. There are payers, HR executives, government buyers, referential pricing rules—an invisible web that quietly dictates what can and cannot scale. Trend management often matters more than health improvement. Managing the return on multibillion-dollar capital programs outweighs elegant solutions.
In energy and oil and gas, the constraint is adoption. Field operators don’t embrace tools that threaten jobs, disrupt long-standing cultures, or undermine “the way we’ve always done it.” Margin isn’t always the primary driver. Identity, familiarity, and trust are.
WeWork is another cautionary tale. It was built on the assumption of perpetually cheap debt and unprecedented market tailwinds. When reality reasserted itself and mean regression arrived, the model collapsed. It wasn’t the idea that suddenly became foolish. It was the assumptions underneath it that did.
This is the lesson I wish I had fully grasped earlier: Cool ideas are cheap. Gritty strategies are rare.
Before you fall in love with your next breakthrough, ask harder questions. What is the actual constraint to growth in this market? What barriers have already defeated well-funded, well-intentioned predecessors? Where are the rocks just beneath the surface?
If you find yourself wondering how no one has thought of this before, that’s a warning sign. Chances are, there’s a quiet graveyard of leaders who learned something expensive that you haven’t yet uncovered. Go talk to them.
I’m pro-innovation. I believe in big ideas. But I’m skeptical of shiny ones—too clean, too theoretical, too detached from human realities. The best strategies are forged in constraint, humility, and patience. They’re honest about how many variables they’re trying to solve at once.
The work of leadership is discernment: knowing which limits to accept, which to challenge, and which to build around.
I learned that lesson the hard way over a cup of coffee, a file folder of data, and a sentence that still echoes decades later: We’ll give up short-term speed for long-term trust.
If you’re building something that matters, that trade-off might be the wisest one you’ll ever make.
