My advice to you is to do the inadvisable. Figure out the riskiest thing you do often. It might be eating McDonald’s and it might be driving in traffic and it might be taking on your cell phone and it might be doing all three at once. Find out just how risky this is. It should be something you don’t particularly relish and if it can be pleasurable, you take it for granted.
Now you have a baseline for the amount of risk you are willing to carry for an activity that doesn’t even make you happy. The next time you consider whether to do something that might be fun, weigh the personal risk associated with that activity against the baseline. You might surprise yourself by discovering that you have been turning down acceptable risks for great rewards.
Example: tonight I rode my motorcycle through a terrible storm while lightning struck and rain poured all around me. I looked at the storm and I looked at a hotel and then I chose the storm and I put on my rain gear and rode into it. Is that any more dangerous than riding in Austin traffic or driving in the same traffic with a hamburger in one hand and a cell phone in the other? Unlike Austin traffic, the cars around me drove with extreme caution and at speeds under the limit. And the exhilaration of storm riding surpassed every other risky activity in recent memory.
That doesn’t mean I’d make the same decision again and I certainly wouldn’t go that way in a group riding situation. It’s only my personal justification for what you would probably regard as a stupid move.