I sold some 450 June 2026 puts earlier this morning (at $18.50 and some more later at $19.45; 23% implied volatility). Still dabbling, but what's a guy to do, with prices so stubbornly high? I sold my shares at about $425, and if I can buy them back 2 years later at $450 that seems more reasonable.

You're doing better than that, really.

If your premium was around $19, that's a net entry price of strike-premium or 450-19= $431. That is pretty likely to look like a nice entry price a year from now. If things were to be sort of on-trend (ha!), you'd definitely expect a market price higher than that. Maybe $455-475 as a central expectation??

As an example, I was looking at the January $450s, which traded at $13 shortly before close. Net entry $437, which will probably be P/B in the vicinity of 1.37 P/B at the time, give or take a few points. Or a cash return of 5.1%/year rate on the capital committed. (plus, assuming no assignment, the interest you're earning on that cash, 3.83% at the moment for US cash on deposit at IB or 4.31% if you buy a T-bill). A person could do worse than a rate of 8.9-9.4%/year for sitting on cash for half a year.

Jim

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