Dear Leaders,

In 27 BC, Augustus Caesar created the Praetorian Guard.

They were the handpicked elite of the Roman military, entrusted with protecting the emperor and preserving order. Permanently stationed in the heart of Rome, and the only armed force permitted inside the capital.

The arrangement appeared prudent. But proximity gave the Praetorians special visibility and access: they learned how decisions were made, who feared whom, which alliances were fragile, and which doors opened at night.

Soon, they grasped their leverage: if they controlled the emperor, they controlled Rome. So they assassinated the emperor and began making and unmaking leaders. They literally auctioned the empire to the highest bidder: Didius Julianus, who, of course, lasted 66 days before they killed him too.

The institution built to protect the empire became one of the forces that eventually destabilized it.

I see versions of this often in businesses.

One person holds the client relationships no one else understands. One person knows where the bodies are buried. One person carries twenty years of undocumented judgment in their head. One person can answer the question no one else wants asked: What actually breaks if they leave?

At first, it looks like strength. A founder feels fortunate. A CEO feels relieved. The person delivers, solves problems, and spots danger early.

Then the arrangement hardens. Years pass. Processes remain informal because that person knows them. Relationships stay concentrated because clients want that person. Important decisions route through them because everyone trusts their instinct.

The business develops a peculiar fragility: the stronger that individual becomes, the more exposed the institution becomes.

A serious steward of a business has no business allowing this condition to continue. Mortality exists. Fatigue exists. Marriage exists. Illness exists. Competitors exist. A strange Tuesday morning exists when someone wakes up and decides they’ve had enough.

The prudent move is to unwind the dependency while the relationship is healthy. Spread knowledge deliberately. Move key relationships across several capable people. Document judgment. Create overlap. Let others sit in meetings they previously had no access to.

This often costs money. Pay it.

If the indispensable person needs a compelling arrangement to help transfer their arcane knowledge, structure one. A retention package, equity, or a defined transition bonus. Whatever the arrangement, make it worth their while. That is the price of de-risking your legacy.

One version of this problem is the owner, founder, or CEO as Praetorian. Every relationship runs through them. Every key decision waits for them. They are the brand, the rainmaker, and the memory. That is not a business. It’s a job with overhead. The unwinding is the same; the conversation is simply with yourself. Those are often the hardest ones.

Now, the other side:

If you are the person holding unusual leverage, understand its nature: it feels permanent; it never is. Markets shift. Technology changes with vulgar speed. A new owner appears. A recession suddenly redefines what the company values.

Leverage has a half-life. Use it while it exists, and use it intelligently.

Structure terms that reward your contribution and protect your future while helping the institution become stronger without you. Ask for the better title, the economic recognition, the longer runway, and a deal that reflects reality.

That is your sophisticated move.

The sentence that surfaces eventually is always some version of: “Worst case, I leave.” It is usually delivered like a card being placed firmly on the table. Bad move.

The moment you leave, your leverage begins to fragment. It’s highest value exists while you remain inside the structure.

Power inside a structure and power outside it are two radically different conditions. Titles and context stay behind. Institutional memory begins rearranging itself without you faster than expected. What follows is often less elegant than imagined: legal battles, invidious resentment, and a few people who suddenly remember old grievances with unusual clarity.

The careless threat to leave also reveals a shallow reading of power on your end. That possibility is already implicitly understood; making a loud and theatrical announcement devalues the threat in a way that ensures you never truly regain that full leverage.

A better sentence is this: “How do we structure this so neither of us needs to discover what worst-case looks like?”

That sentence, and that attitude, gets deals done. A well-structured settlement produced that way will give you the dignity, reward, and optionality you need.

Rome offers a useful lesson here. The Praetorians kept discovering that power near the throne can feel absolute, until the larger order eventually turned and absorbed it.

The same is true in business.

One person can become indispensable. No person stays untouchable.

The wise leader reduces that risk before circumstance does it rudely. The wise indispensable person monetizes leverage before time performs its usual act of erosion.

Every institution eventually faces this question: Is your strength truly distributed, or merely concentrated in one or two unusually capable people everyone hopes remain cheerful?

If it is the latter, the correction is overdue.

Onward,

Hamza