I've adopted these as a part of my preflight / water safety process:

I visually inspect the boat's mission critical systems before I go, and also do routine maintenance on these. Also worth noting, I have “broken” or prevented a failure of every last one of these:

(* Editor's note: you have to learn what replacement schedules you want to follow for the equipment that you use. Some of the replacement frequency that Mr. Cryder practices could very well be based on the specific nature of the equipment that he uses. For example - if you use a leash that has no velcro and no metal parts or segmented connections such as a strong 1 piece dyneema kite leash and you take good care of it (don't leave it out in the sun, don't abrade it) then it is highly unlikely that you need to replace it anywhere as often as annually. But if you use a leash that is less simple and robust?….* Also - for most of us who keep our PFDs out of the sun when stored, there is no way that they will degrade to the point of needing replacement every 3 years - and PFDs can be easily inspected for their wear and reliability - 2 piece paddles on the other hand are a different question and it would not be unreasonable to replace downwind paddles after a number of years (retire them to flatwater use) or to use a 1 piece paddle for local downwinders)

• Inspect rudder yoke & pins
• Replace my rudder line bi-annually and use top shelf Q-Powerline.
• Test the leash and connection points, including the velcro, locking carabiner, and the structural connection points of the leash.
• I replace my leash annually (calendar reminder every August).
• I replace my PFD every three years. (UV degradation is nasty beyond aesthetic, it significantly weakens fabric to the point where it can be torn with little force).
• Inspect rudder line terminals & connection points to the footboard (wear points)
• Inspect footboard adjustment mechanisms
• Inspect footboard rail connection points to the boat
• Stress test the ferrule of the paddle, just to make sure it's a firm lock. The old Epic paddles are notorious for loosening up.
• Retire paddles from downwind use after three seasons. If you're using an old, shit paddle don't be surprised when it retires itself.
• I do a battery check on my VHF (there's nothing like discovering it's dead in a moment of need) (Ed. note: It is very common for VHF radios to stop charging not because there is anything wrong with the battery, but rather because the charging connections have corroded a bit - this is easily corrected with a little bit of fine grit sanding/cleaning - more commonly to the radio charge points but occasionally also the charger charging points)
• I inspect my flare system, and recovery gear (including a very nice, small pull rope setup that I keep on me at all times),

Other safety related thoughts:

• I let my fam / friends know when I'll be on / off the water and where I will be on the water. If I am doing a big solo adventure, I file a float plan with the Coasties or Rangers.
• I try to paddle when the system is supposed to weaken, not intensify.
• I don't paddle in the wind at dusk.
• I don't rush to get on the water, and I try to stay focused on my checklist - including pausing conversations.
• I practice and experiment obsessively with rescue techniques, including paddling with one half of a paddle, and with no rudder (again, both have happened to me on downwinds and both pushed me to the limit of my skill / fitness). I share ideas, concepts with pals and ask them to try stuff.
• I experiment with my clothing mix, and error on the side of hot. Yes, this means I will be slower than I could be. But “Festine Lente”… slow is smooth, and smooth is fast.
• I don't downwind if it's below 40º F, or above 50 mph.
• I set aside specific days where I do nothing but work on getting better and better in ever more challenging conditions or situations. Generally I keep it really short and do something like laps (not a full downwind) or doing slow motion figure eights. I try get just a little bit better, a little bit at a time. Sometimes I reach out to people who have a really particular skill (like surf breaks) and travel to train / learn from them.
• If I am downwinding with a group, we pair up 1:1. When the faster person stops to wait, the other paddler agrees to surf towards them. If they are more than 200' feet away they may not be visible in the waves. I've turned around to look for a paddler only to realize that they went by 500 meters away and I didn't see them. Buzzkill.
• When I paddle downwind with friends, I let them know if I am going to go hard, or chill and do technique work. There are times in a big group downwind, like Saturday, where I just want to hammer. I consider that going solo, and I let them know I am doing my own thing and won't be stopping or checking in on them.
• I obsessively verify conditions up until the last moment.
• I listen to my instincts and pick my days on the sea. There are days when my brain just says “nah. not feeling it today.” and I bail.