Jun 3, 2026 · 17 min · 7 segments
Market volatility can make even experienced investors question whether they should sell, move to cash, or wait things out. When the stock market feels shaky, fear often pushes people toward fast…
Doug GoldsteinHost
She's a retiree living in Israel, and she's built a substantial US portfolio over the course of decades.
Most of her money is in big tech stocks, companies she knows, companies she uses every day, companies she really believes in.
But lately, she's been watching the news more, reading more financial commentary, noticing how the market reacts to every rumor, every geopolitical headline, every policy announcement.
And she started thinking, what if we're heading into a real decline? What if I lose a big chunk of this right before I need it? So she came to me with a plan.
She wanted to move to a more conservative allocation, something like 35% cash, 30% in solid blue chip value stocks, and then split the rest between tech and a small amount of what she called play money.
She even joked that it felt odd doing it over Zoom, like maybe it was the kind of thing you should talk about over lunch.
And I get that, because what she was really wrestling with wasn't just a portfolio question, it was an emotional one.
She wanted to feel like she was being responsible, but she was also terrified that if she made this big move, the market would keep going up without her, and she'd be sitting in cash, kicking herself.
That tension between wanting to protect yourself and being afraid of missing out, that's one of the hardest things about investing.
And it's something almost every long-term investor goes through at some point.
So let's talk about the hidden problem here, the thing that almost never gets discussed when people talk about selling before a potential downturn.
If I think the market's going to drop, I should sell now and wait for a better time to get back in.
She's a retiree living in Israel, and she's built a substantial US portfolio over the course of decades.
Most of her money is in big tech stocks, companies she knows, companies she uses every day, companies she really believes in.
But lately, she's been watching the news more, reading more financial commentary, noticing how the market reacts to every rumor, every geopolitical headline, every policy announcement.
And she started thinking, what if we're heading into a real decline? What if I lose a big chunk of this right before I need it? So she came to me with a plan.
She wanted to move to a more conservative allocation, something like 35% cash, 30% in solid blue chip value stocks, and then split the rest between tech and a small amount of what she called play money.
She even joked that it felt odd doing it over Zoom, like maybe it was the kind of thing you should talk about over lunch.
And I get that, because what she was really wrestling with wasn't just a portfolio question, it was an emotional one.
She wanted to feel like she was being responsible, but she was also terrified that if she made this big move, the market would keep going up without her, and she'd be sitting in cash, kicking herself.
That tension between wanting to protect yourself and being afraid of missing out, that's one of the hardest things about investing.
And it's something almost every long-term investor goes through at some point.
So let's talk about the hidden problem here, the thing that almost never gets discussed when people talk about selling before a potential downturn.
If I think the market's going to drop, I should sell now and wait for a better time to get back in.
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