It is pushing yourself a little, trying something you have never done before, but only after making sure that you and your boat are adequately prepared. Is there an island on the horizon you have never seen up close? Why not pay it a visit under sail? Have you never ventured beyond the harbor when there were whitecaps on the bay? Why not snug up that lifejacket, put a reef in the main, and go splash around out there for a while? Have you never gone sailing at night, never completed a passage to that cozy little harbor 30 miles to the north, or never sailed competitively? Why not give these things a try? You only live once. What are you waiting for? None of us is getting any younger! Just sailing!
Set a goal, then do what it takes to execute that goal in a seamanlike manner. Take a close look at your boat and its hull, its rig, and its keel to assess its capabilities. Take an inventory of the equipment you have onboard and gain whatever else you might need for the goal you have in mind. While you are at it, make an honest assessment of your knowledge and abilities and acquire any necessary skills you lack. Read sailing books, practice maneuvers you are not comfortable with, and daydream about what you have in mind the next time you are at home relaxing in your favorite chair. Make your goal an immediately achievable. How about going for a sail without using your auxiliary or anchoring somewhere for an afternoon picnic? You do not have to sail around the world to have an adventure. Make your goals step by step. You may be surprised where they lead.
So go out there and test yourself a little, and if things do not work out quite as planned, who cares? As long as you sail responsibly and get everyone’s homes in one piece, mistakes are the best teacher. I have learned a lot more from those challenges that ended in failure than the ones I failed to attempt. The main thing is that you are doing it, that you have chosen to take part in an activity that is infinitely complex, challenging, rewarding, and infinitely demanding an activity that gets better and better the more you do it and the more you learn. The main thing is that you are a sailor and what could be better than that?