Metatrying - i.e. "Trying to try"

[AtheistPhil]

Is "trying to try" possible? If not, and you can't "try to try" but you can only "try" then can you ultimately do anything freely?
If "trying to try" is possible and so so is "trying to try to try" and "trying to try to try to try" and so on, can you gain control of that infinite regress?

I think it's possible. One example: if you're playing a game where you have to throw a dice and get a 6 in order to have one attempt at spinning a wheel which can make you win a prize. You are trying to try to win the prize when you're throwing the dice.
You can generalize that example and make a chain of "try" as long as you want with chance games.
Does it answer your question ?