RSUs that kept vesting, options you never exercised, or one winner you held so long it became the portfolio. You know you should trim it. You also know what the stock did last year, and so does everyone at work.
The fear runs both directions at once, which is why you are stuck. Sell and the stock doubles, and you are the one who sold the thing everyone in the office is still holding. Hold and it halves, and you are the one who knew better and did nothing. Either way the fear is not about money. It is about being the fool in a story your colleagues will tell.
The group chat makes it worse. You see the people who held through the run and posted. You do not see the ones at the last company whose stock went the other way, because they stopped posting. The feed shows numerators only.
And underneath, the number you have not actually looked at: what you would owe if you sold, what an exercise would cost in cash and AMT, how much of your life is riding on one ticker. Known is a problem you can work. The fog is not.
Three free calculators, no email gate, that turn the paper number into something you can plan around.
Pick ISO, NSO, RSU, or ESPP, enter shares, strike, current value, and your other income; it returns the exercise cost, the AMT liability on the spread, the total cash out, and the paper value you would be holding against it.
Enter your current invested assets and what your life costs; if the position already clears Walk-Away Money or Full FI, the question is no longer whether the stock will go up, it is whether you want to keep betting your freedom on it.
Run a diversified balance and steady contributions over twenty or thirty years; it is the boring curve you are comparing the single stock against, and the one to measure your own pace by instead of a colleague’s screenshot.
Three Field Manual pages for a decision that feels like investing and is mostly about identity.
Before you hold because of what the stock did or what a colleague made, find everyone who ran the same play at other companies and ask how all of them did, then ask whose scoreboard you are on.
Write the selling rule now, in calm: what sells on a schedule as it vests, what concentration you will not exceed, what you do on a sharp drop; then the stock gets to choose the weather but not your behavior.
Open the position in full once, the tax if sold, the exercise cost, the share of your net worth in one name, not to fix anything today, so the plan starts from a known number.
Grants, vesting schedule, cost basis by lot, exercise windows, and the tax on each path. One page, in daylight, before any decision gets made.
A schedule for what sells as it vests, a concentration cap, a tranche plan for exercises you could absorb if the stock went to zero, and where the proceeds go. Set before the next earnings day, not after.
The portfolio gets designed around the concentration you already hold, your horizon, and your tax bracket, with asset location and tax-loss harvesting coordinated with the plan.
Core all-ETF portfolios run 1.00% a year on the first $250,000 and step down from there, negotiable above $1M; the combined planning and investment engagement generally starts at $500K, and a one-time equity comp analysis is available as modular planning with no minimum.
If you are looking for an opinion on whether your company’s stock will go up, I do not have one and I will not pretend to. If you want to keep the whole position and just need someone to agree with you, that is also not this.
There is no single answer, but there is a single method: decide the rule in calm rather than on an earnings day. Holding a vested share is a fresh decision to own that stock at that price, so write down what sells on a schedule and what concentration you will not exceed. The Equity Comp Optimizer runs the vesting math, and the Pre-Decision page turns the result into a written rule you follow when the stock is doing something exciting.
Exercising ISOs triggers alternative minimum tax on the spread between the fair market value and your strike price, times the shares, even though you have not sold anything. If the stock drops after exercise, you can owe AMT on gains that no longer exist. The calculator shows the exercise cost, the AMT bill, and the total cash out. The practical move it points to is exercising in tranches you could absorb if the stock went to zero, and holding two years from grant and one year from exercise for long-term capital gains treatment.
Every portfolio starts with the person, including existing concentrations like RSUs, business equity, or real estate, rather than a model portfolio you get slotted into. The rest is built low-cost and globally diversified, with asset location and tax-loss harvesting coordinated with your plan. Fee-only investment management runs 1.00% a year on the first $250,000 and steps down from there; the combined planning and investment engagement generally starts at $500K. A standalone equity comp analysis is available as a modular, flat-fee engagement with no minimum.
Run the calculators first; they are free and they do not ask for your email. If the numbers raise more questions than they answer, that is what the conversation is for.