I find that the thing I’m most likely to have trouble sleeping over isn’t that I didn’t make money—it’s that chunk of paper unrealized loss. Even though I know it doesn’t really count until I’ve sold, my brain still automatically plays out “what if it drops a little more—then what should I do?” Paper gains feel light and floaty. In my head, I default to thinking, “The market gave me this, and it could just as easily take it back,” so I don’t dare to get too happy. To put it simply, losses pull your attention back from the narrative to reality: liquidity, exit routes, and the worst-case scenario.

Recently, I’ve been re-pledging and doing the same “shared security” setup that’s been criticized as “nested dolls.” I can understand why people say that. Stacking yields on top of each other sounds pretty good, but by layering it one step at a time, you also stack the risks. And if something really goes wrong, you don’t even have time to figure out whose fault it is. Now I’m setting rules for myself: only take the positions that I can sleep soundly with—everything else I’ll treat as tuition fees… for now, that’s it.