High earners still in the accumulation years, with compensation that is more complicated than a salary. Equity awards, concentrated positions in an employer, what to do once the obvious accounts are full, and planning around a business you own.
For a high earner the 401(k) fills early in the year and the interesting question is what comes next. The HSA, which is the most tax-advantaged account available to most people and is frequently misused as a spending account. Backdoor and mega backdoor Roth contributions, where the plan permits them. Deferred compensation, which carries credit risk people rarely price. Then taxable, which is not a consolation prize once it's built properly.
The order matters more than any individual account.
RSUs, incentive stock options, non-qualified options, and ESPP shares are four different instruments with four different tax treatments, and being paid in one doesn't teach you how the others work.
Two things cost high earners the most here. The withholding gap: statutory withholding on a large RSU vest is frequently well below your actual marginal rate, which produces a surprise the following April. And the alternative minimum tax exposure created by exercising incentive stock options and holding them, which is the single most expensive mistake we see in this area.
The decisions and the timing are here.
If you're compensated in stock, concentration isn't a choice you made once. It accumulates on a vesting schedule, and your career and your net worth end up depending on the same company at the same time. That's a genuine risk regardless of how good the company is.
People don't unwind it because of the embedded gain, and the tax cost is usually smaller than it feels once examined. Staged selling, charitable routes, and hedging all exist.
When a large expense arrives, selling appreciated assets to fund it can be the most expensive available option. Borrowing against a portfolio is sometimes better and sometimes considerably worse, and the risk in securities-based lending is genuinely misunderstood: the problem isn't the rate, it's what happens to the collateral requirement in a decline.
When borrowing beats selling, and when it doesn't.
Business owners and executives tend to have the most complexity and the least time, which means the decisions with quiet deadlines are the ones that slip. Deferral elections, exercise windows, and conversion years don't announce themselves.
If you'd like someone to look at the whole picture rather than one account, we're happy to start there.
