The challenge of experience
Everyone always says to get more experience and it is of course good advise. The problem is that it is not that easy to do.
I know some very experienced sailors who have sailed the same boat from the same marina in the same 20 mile radius for decades. They are obviously experienced but within narrow confines.
The most striking example is a gentleman that asked me to help move his boat from RI to NYC. He explained how he had the boat for three years but just didn't want to move the boat by himself. After about five minutes on the boat I figured out he wasn't really a sailor. He drove from NYC to the boat a couple times a month and was so tired he often just slept overnight on the boat and drive home. His "experience" was probably some motoring and maybe sailing with only the jib up in 8 knots of wind for a total of 4 hours the whole time he owned the boat.
But just how much different are any of us? If you sail in FL, Maine would be a big change. LIS is vastly different from Norway.
The best I've been able to come up with it to purposely put myself in as many varied conditions as possible. Charter in other states when possible. Volunteer for deliveries whenever possible. Go out when the weather is a little more problematic than I would wish.
When conditions are normal I try maneuvers in different ways than I usually do them.
It is always a judgement call. I would prefer to not die, kill someone else, or destroy any property but to call it a challenge it has to have some element of danger.
What do you do to get more real experience or do you play it safe all the time and just have a good time?