Straight talk on making work optional and keeping it that way.
Vested RSUs are already taxed as ordinary income at vest, so holding them is the same decision as taking that after-tax cash and buying company stock with it. That is the useful way to frame it: would you buy the shares that morning? The rest of the picture is how much of your net worth already rides on your employer, trading windows, ownership guidelines, and whether a sale needs to run through a 10b5-1 plan.
Potentially, if your plan offers a self-directed brokerage account. Many large companies let an outside advisor manage your 401(k) right inside the plan, so nothing moves and you keep every benefit the plan gives you. Every company sets its plan up differently, so we'll look into yours and tell you exactly what's possible.
A common planning guideline is 10% to 20% of investable net worth, and less when that same company pays your salary. The right number depends on how much of your life already rides on that employer. Your income, your health coverage, your vest calendar, and your stock are four bets on one outcome. Diversifying is not a vote against the company. It is a decision to stop having one answer decide everything.
Typically in lower-income, lower-tax years. For a lot of people that is the stretch between the last paycheck and the year required minimum distributions begin, when taxable income is temporarily low and you control the timing. Conversions are often sized to fill a target tax bracket rather than done all at once. Two things to keep in mind: the two-year Medicare IRMAA lookback, and any Affordable Care Act premium credits you rely on before 65. Both are driven by the same income a conversion creates.
It is a written trading plan you adopt while you do not have material nonpublic information, which then sells shares on a preset schedule. It creates an affirmative defense against insider trading claims and lets sales happen during blackout periods. Insiders, Section 16 officers, and anyone whose selling keeps colliding with windows benefit most. Current SEC rules require a cooling-off period before the first trade, so the plan has to be built well ahead of when you want to sell.
Yes, and it starts at $1 million. That is one of the lowest thresholds in the country, and Oregon does not allow portability between spouses, so an exemption that goes unused at the first death is simply gone. A paid-off Portland home, a 401(k), and a life insurance death benefit can clear the line without a family ever thinking of itself as wealthy. The fix is structural, and it has to happen while both spouses are living.
It depends on your spending, not your salary. The most common shorthand is the 4% rule: a diversified portfolio has historically been able to support withdrawals of about 4% of its starting value each year, adjusted for inflation, over a 30-year retirement. So the number starts with how much after-tax spending your portfolio has to cover once pensions, Social Security, and any other income are counted. What moves it most is not the market. It is taxes, the cost of health coverage before Medicare, and the order in which you draw from your accounts.
It is the family office operating model without the family having to build the office. Investments, tax strategy, risk, and estate coordination run through one team instead of five that have never spoken. The traditional single-family office required roughly $100 million to justify the payroll. The virtual version delivers the same coordination to households with $1 million or more.
Twelve terms that show up in every employee's benefits portal and almost never get explained.
