Time to short was when DOW was flirting with 30,000.
The big money in shorting is already been made.
Let me give you an example using the oil market today ... which is completely whacky given the F'n Saudis and this coronavirus. Crude oil is cracked into two primary products, gasoline and heating oil. Given the time of year, more of one product is refined. (I think you can figure which one is refined more in summer.) Sell crude oil short, buy gasoline and heating oil long, in proportion to the crude oil that you short. If price of oil goes down, the price of heating oil and gasoline will not go down as much. You have an instant profit locked between the two. If the price of oil goes up, and there is that possibility, you know that gasoline and heating oil will go up too. Your short position on oil is covered. But guess what, gasoline/heating oil might go up more than oil and you will have a profit.
That's covering a position.
You can do that futures and options. It works with many commodities, and the same idea works with equities. You just need to know how primary products of equity companies react to one another.
These are actually conservative techniques. You can make a killing by trading naked - uncovered oil futures for example. But you can also get killed if the price goes against you. Be conservative, cover your positions, all the time.