Beyond the income plan
One company built your wealth. It should not be able to unbuild it.
What counts as a concentrated position
A concentrated position is generally any single holding worth more than roughly 10% to 20% of your investable assets. It is common for long-tenured employees who received stock grants, participated in an employee stock purchase plan, or held shares through an acquisition. The risk is that one company's bad year becomes your bad decade.
How people end up here
Almost nobody sets out to hold 40% of their net worth in one stock. It accumulates. Grants vest quarterly for a decade. An ESPP buys shares at a discount every six months and you never get around to selling them. An acquisition converts your shares into a much larger position in the acquirer.
Then the position becomes hard to unwind, because selling means a tax bill — so it grows further, and the problem gets bigger.
There is no single move, there is a sequence
Selling everything on one day is rarely the right answer, and neither is doing nothing. What usually works is a staged plan run across multiple tax years, timed around your income, your bracket, and your other planning moves.
Where it fits, that can include using long-term rather than short-term gains, offsetting with harvested losses elsewhere in the portfolio, timing sales in a low-income year between retiring and starting Social Security, and charitable strategies for the most appreciated lots.
This connects directly to your income plan
A concentrated position is not just a diversification problem — it is an income problem. If Segment 1 of your retirement plan is funded by a single stock, then your near-term income depends on one company's quarter.
We usually unwind the position and fund the near-term segments at the same time, so diversifying and building the paycheck happen in one motion rather than two.
Questions
Common questions
A common threshold is 10% to 20% of investable assets, but the honest answer depends on what else you have. If Social Security and a pension already cover your needs, you can carry more. If that stock is also your employer, you are doubling down — your paycheck and your portfolio share one risk.
Usually less than you fear, if it is staged. Spreading sales across tax years, using long-term rates, offsetting with harvested losses, and timing sales in low-income years all reduce the bill. The cost of doing nothing is rarely counted, and it is often larger.
These can have a place for a large position, and they can also create their own problems — capped upside, early assignment, and tax complications. We will tell you plainly whether one fits your situation. Often the simpler staged sale is better.
You are describing the most common version of this. Grants that vest on a schedule, plus a purchase plan buying more at a discount, means the position rebuilds itself even as you sell. That calls for a standing rule agreed in advance rather than a decision you revisit every quarter.
Also
The rest of what we do
Retirement Income Planning
Tax-Smart Investing
Across a thirty-year retirement, small tax percentages compound into real money.
Private Markets & Alternatives
Private markets can add something a public portfolio cannot.
Let us find out what your portfolio can actually pay you.
Thirty minutes to see where your income will come from. If we are not the right fit, we will tell you.