The answer is "yes".

Your mind was designed for not getting eaten by lions, which is not the same as your goals. It shouldn't be surprising that it's possible that thinking differently (temporarily) can give you new insights. Since so many problems are due to not "thinking outside the box" (eg. aging is normal and acceptable), seeing things from new perspectives can be valuable. That is a big part of what makes talking to intelligent people interesting.

Even if you're someone that intellectually acknowledges that aging is a big problem, 50 micrograms of LSD can make you see it from the perspective of someone used to indefinite lifespans- shocked, with a "gut level" appreciation of how bad it is.

The upsides are a likely self reported "increase in wellbeing" (which I'd bet has a significant entry in your utility function), and possible new perspectives (which can be discarded if they don't make sense when sober), which are both pretty significant.

Possible downsides include the possibility of a "bad trip", the possibility of being seen as a "druggie" and the small possibility of legal trouble.

The possibility of a bad trip can be quite small if one is properly prepared, and bad trips are seldom as bad as good trips are good. Experimenting once or twice with psychedelics isn't looked down on like shooting heroin is by anyone that isn't completely ignorant on the subject, and is not a hard secret to keep.

I have not met anybody that thinks that trying psilocybin was a bad decision. While it may be hard to convince you to take psilocybin in a short comment, hopefully the sum of all comments will convince you that it's worth researching.