Here's a strategy I use to measure my tolerance for risk. I call it the "Black Swan Defense".
Feel free to use it but be forewarned it is copyrighted by me and I will sue.

A Black Swan Event would be 50% overall drop in the stock market. Why 50%? It's just an estimate and you have to start somewhere.
I'm not anticipating the end of civilization.
I take the 3 financial investments categories (not including real estate or other stuff) which are cash, bonds, and stock.
Example:
Cash $100,000
Bonds $400,000
Stocks $500,000
Total $1,000,000
Black Swan Event = Cash + Bonds + 1/2(stock)
In the above example this would be $100k + $400k + 1/2($500k) = $750,000
So, in the event of a Black Swan Event my stock values are cut in half.
Would I still be ok if that happened? Can I continue my current lifestyle?
If I would be ok then my asset allocation is good.
If such a drop makes me queasy then I need to have more cash/bonds and less stocks.