I don't think there are only 2 choices as per your poll. Even doing one activity includes a mulitude of risk factors and safety levels. But I always lean towards safety, so it's how I voted.
However to somewhat answer your question:
In my mind I play it safe. Other people however, would think I am risky.

I think there's a balance. I would say maybe that you generally want to try to stay safe but every now and then take a risk and see how it pans out. Sometimes you are keeping yourself safe against things that are all smoke and mirrors, like eternal damnation. If you never take risks, you never challenge those ideas.

Whether we think of it in this way or not, we all engage in risk management every day of our lives. We know that we could be hit by a bus crossing the street so we look both ways before stepping off the curb. I know this is a trivial example but the principle applies to all of our activities. I am personally unwilling to sacrifice liberty for safety.

The first responsibility is to ensure that you don’t subject others to risk.

I'm very willing to risk my own life while doing my best to make sure that others are safe.

Safety first hard to recover from death

Timing . I can’t answer this question . When on my 20s and even 30s , risks and risky choices were in the menu for me . No regrets . Most turned out as good choices afterall .
But now , at 49, I have 0 desire for any risks and I chose safety .