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Vanguard’s Advisor’s Alpha research found that good advice can add roughly 3 percentage points of value a year, on average — some years more, some years less. Most of that doesn’t come from picking better investments. It comes from things like not panicking during a downturn, choosing the right accounts, and drawing money out in the right order. It’s an industry estimate, not a guarantee.
Without one, transition deadlines pass silently: a Medicare enrollment window closes, a pension survivorship election locks by default, the withdrawal order gets set by whichever account was easiest to tap. With one, someone whose job is watching your deadlines catches these while they’re still movable — and keeps your CPA, attorney, and accounts working from the same plan.
What the relationship actually looks like, decision by decision →
A concentrated position is usually the reason someone did well. It is also the reason a single company’s bad year can undo a decade, and the two facts are uncomfortable to hold at once.
Options expire. Vested options have a last day, and leaving a job usually shortens it to a window measured in weeks. Expired options are worth nothing regardless of the share price, and this is the most common avoidable loss in equity compensation.
Different grants are taxed at different moments. Some are taxed when they vest, some when you exercise, some when you sell. The date that triggers the tax is often not the date the money appears, which is how people end up owing on stock they never sold.
When you can sell may not be up to you. Trading windows, blackout periods and holding requirements limit insiders and employees. Pre-arranged selling plans exist precisely because they have to be set up while you are permitted to trade — which is rarely the moment you decide you want to.
Selling all at once is rarely the only option. Reducing a position gradually, borrowing against it, or giving some of it away each change the timing and the tax differently. None of them are exotic, and which one fits depends on whether the constraint is tax, liquidity, or a restriction you cannot negotiate.
The question is not whether to diversify. It is which constraints are real, which deadlines are fixed, and what can still be done inside them.