As a fiercely non competitive rider I wonder about the things we do for fun if you end up having to take two paracetamol and having to lie down for a week after each attempt. Perhaps self flagellation might be a more rewarding pastime, especially if some strava-like app could be developed to work with it.
On the other hand, I am that person too when it comes to other aspects of cycling, being in a river in Egypt (de Nile) when refusing to accept the limitations that age attempts to impose on my cycling. I suppose you just have to get your bike the most comfortable and efficient that you reasonably can, and keep riding that segment. As long as the graph of your gradual age related decline meets the graph of your achievable fitness above the point at which what you are hoping to achieve is possible, sooner or later the factors (right tailwind, feeling particularly good, etc) will line up and you'll manage it. After all, you've managed to knock off a few seconds already. Giving yourself a deadline might be a drawback but could be a motivator, too.