[Sukotto]

One edge case to consider.

If you have stocks in a pre-tax retirement account like a traditional IRA in the US (or RRSP in Canada?), now could be a good time to sell them, move the money into a post-tax account like a ROTH IRA (or TFSA?), then buy the equivalent number of stocks there.

You will pay reduced taxes because the value of the stocks is relatively low, then pay no tax when you finally withdraw from the ROTH. (All else being equal and imho, the market is likely to recover over time)

That is, if you don't mind the risk that the market might massively rebound in the middle of the transaction.

There are a bunch of assumptions here. Do your own research and don't blindly believe a stranger on the Internet. Make sure you understand the taxes, fees, penalties, or whatever you will have to pay.

[rafiki6]

Like you rightly said, this is a gamble. You're playing against volatility we haven't seen in almost 40 years. Look at VIX. You would likely burn yourself, especially as an amateur. If you want to play this game, there is room for put options in your portfolio to counter some of the bleeding.

[aantix]

You’d have to be sitting on a cash savings equal to the value of the retirement account? Because you couldn’t use the proceeds from the retirement sale?