A senior executive we knew had, on paper, done everything right. Years of strong performance had been rewarded in company stock, and as he rose, more and more of his wealth quietly accumulated in that single name. He believed in the company — why wouldn’t he? Then one bad year arrived: the share price fell hard, a restructuring put his role in question, and he discovered, all at once, that his salary, his bonus and most of his savings were riding on the very same horse. Three exposures, one company.

It is the most flattering trap in corporate life. The equity that rewards your loyalty also ties your fortune to your employer — and the more senior you become, the tighter the knot.

When your pay cheque and your portfolio depend on the same company, one bad chapter can take your income and your savings together.

Why the handcuffs hold

Unvested stock is designed to keep you: walk away and you forfeit it, so you stay, and the position grows. Selling what has vested feels like two betrayals at once — a tax event, and a vote of no confidence in your own employer. So the holding compounds in a single name, and the everyday risk hides in plain sight: the company funding your lifestyle is also where most of your net worth sits.

Turn paper into independence

The discipline is unsentimental and simple to state: as equity vests, sell down on a schedule and diversify into wealth that owes nothing to your employer — a portfolio in your own name, across many companies and assets. Decide the rule in advance, say trimming a fixed share of each vesting tranche, so it runs automatically and never feels like a daily verdict on your firm. Treat ESOPs and RSUs as a bonus to be harvested, not a retirement plan to be hoarded.

Set the rule before the next vest

The cleanest way out of the handcuffs is to decide the exit in advance. Before the next tranche vests, set a simple policy — for instance, sell a fixed portion of every vesting lot and move it into a diversified portfolio, automatically, regardless of where the share price happens to sit that week. Pre-deciding turns an emotional, loaded choice into a quiet administrative one, and steadily converts concentrated paper into independence you actually own.

Believe in your company. Just don’t let it be your entire financial life. True seniority is wealth that no longer depends on the badge you carry. In twenty years, the executives who left on their own terms were the ones who quietly diversified out of their own success while it was still rising.