The advice is always the same: sell, diversify, spread the risk. But Merrill wealth advisor Tracy Martin says for the women who built that wealth, the hardest part isn’t the math; it’s what the stock represents.
There’s a piece of advice financial advisors give so often it’s become background noise: diversify. Don’t hold too much stock in one company. Spread the risk.
Most women who’ve built serious wealth already know this. And most of them aren’t doing it anyway.
That contradiction was the throughline of a recent conversation with Merrill wealth advisor Tracy Martin, where a room full of leaders talked through something advisors rarely get asked about directly: not whether to diversify, but why it’s so hard to actually do it. It’s a pattern Tracy has seen again and again across a decade of practice sitting with clients who’ve built serious equity in a single company’s stock, watching family members practically beg them to do something about it, and hearing some version of the same answer: I know I should sell. I just can’t quite bring myself to.
That’s the polite version. The fuller version is closer to: I built this. Selling it feels like walking away from myself.
Every advisor can explain the risk of a concentrated position. Fewer can explain why smart, accomplished people hold onto it anyway, long after the spreadsheet says they shouldn’t.
Tracy has seen this pattern play out again and again, including with a couple who spent thirty years building equity in a single employer’s stock. Her clients get tired of hearing the same pitch. “All of you advisors always just want the same thing,” one told her. “You just want me to sell my stock and diversify.” They weren’t wrong. That is usually the advice. It’s just rarely the whole conversation.
The stock isn’t only an asset. It’s a scoreboard for a career. Selling it can feel like admitting the career is over, or worse, that it never mattered as much as the money says it did. For women who’ve spent decades being told to prove their seat at the table, that attachment isn’t irrational; it’s earned. But earned attachment and sound strategy don’t always point the same direction, and pretending otherwise is how seven-figure positions sit untouched for years.
What makes this reframe useful isn’t reassurance that concentration is fine. It’s the reminder that the choice isn’t binary.
Tracy’s approach uses covered calls on a concentrated position: collect premium income against the stock without selling a share, then either live off that income or funnel it into a portfolio built specifically to harvest losses. If the stock eventually gets called away and has to be bought back, that transaction can generate a loss that can then offset gains elsewhere, or simply roll forward, since tax losses don’t expire. It’s not a workaround for the tax bill. It’s a way of using the position itself to fund the eventual exit, instead of treating the whole thing as one irreversible decision.
It’s a small shift in framing with a large effect: the stock stops being a monument you either protect or abandon, and starts being a tool you actively manage.
The most useful thing Tracy shares isn’t a tax strategy at all. It’s a description of what a real advisory relationship is supposed to feel like: “Do you get me? Do you feel what I’m saying to you? Do you see what’s going on in my life, and do you know what to do about it?”
That’s a higher bar than “manages my portfolio.” It’s the difference between an advisor who recites the standard advice and one who understands why the standard advice hasn’t worked on you yet. One of Tracy’s clients — an engineer who’d held decades of concentrated stock — wasn’t being stubborn for no reason. He was testing whether anyone would bother to ask what the stock actually meant before telling him to sell it.
There’s a phrase we use about careers: singularity is risk, optionality is power. It applies just as well to a stock certificate as it does to a career. Holding everything in one place, out of loyalty or fear or simple inertia, is its own kind of singularity, and it carries the same quiet risk as staying in one role for too long because leaving feels like losing something.
The point was never to sell the stock and feel nothing. It was to build enough optionality around it that the decision stops being all-or-nothing. That’s not a betrayal of what you built. It’s the next stage of managing it well.
Athena members can access the full recording of this salon conversation here in the Athena library. Not a member? Let’s talk.