Early in my career, a mentor kept a worn copy of the I Ching on his desk, wedged between quarterly reports. I assumed it was decoration. It took me another decade of deals, cycles, and a few costly mistakes to understand it was closer to a working manual.
Shí — the concept of the right moment
The I Ching organizes much of its wisdom around shí, roughly translated as "timing" or "the moment." Not chance, and not passivity — a disciplined attention to when conditions favor action and when they favor patience. Western business culture tends to treat hesitation as weakness. The I Ching treats it as a skill, distinct from and sometimes more valuable than speed.
Two deals, two very different lessons in patience
I once pushed a cross-border acquisition forward against the advice of a partner who felt the target's home market was entering a difficult cycle. We closed on schedule and spent the next two years managing a currency headwind we could have avoided with an eighteen-month delay. Years later, I sat on a nearly identical opportunity for almost two years, waiting for a regulatory environment to stabilize. That deal, when it finally closed, performed better than any acquisition I had led before it. Same conviction in the underlying business. Completely different outcomes, driven almost entirely by timing.
Reading conditions instead of forcing outcomes
The hexagrams of the I Ching are, at their core, a framework for reading the total situation — the internal state of the actors involved, the external conditions, and the relationship between the two — rather than fixating on a single desired outcome. In practice, this looks like asking not "how do I make this deal happen" but "what is actually true about this situation right now, and what does it call for."
The market does not reward conviction. It rewards conviction applied at the right moment. Confusing the two is one of the most expensive mistakes a leader can make.
What this looks like in a modern advisory practice
I do not consult hexagrams before client meetings. But the underlying discipline — separating "is this a good idea" from "is this the right moment for this idea" — has become one of the more useful filters I apply to every cross-border recommendation I make. Clients rarely regret a well-reasoned delay. They almost always regret a good idea executed at the wrong time.
Forty years in global banking and cross-border advisory taught me plenty about structures, contracts, and negotiation tactics. But it was an ancient text, older than any market I have ever operated in, that taught me the most durable lesson: strategy without timing is just activity.
