Go for it

I regret not doing something a lot more than doing it and failing.
At least there is no "What if?"

Tremors, tsunamis, hurricanes, fires, building collapses, plane crashes... everyday we see people dying, suffering - after carefully constructing their lives. I can bet the one regret they have is not doing/saying/trying something.

I think we put our lives on hold too much. True, moderation is called for. But there is great merit in "going for it". And the downside risk is highly overestimated in most cases. There is usually (for most of us) quite a strong safety net.