Two questions:

• how should we measure the "success of rationalists"?
• how big success should we expect?

These are related, because the bigger the success, the easier it would be to measure it. Like, if rationalists would openly take over the world, create a Global Rationalist Government, fix poverty worldwide, make cryonics mandatory, etc., no one would be asking whether the rationalists are truly winning.

On the other hand, if I had a magical button which would guarantee that every rationalist will in five years have twice as much wealth (compared to the counterfactual world where the magic button does not work), its effects would be mostly invisible. Maybe the affected people would notice, but even they could easily attribute the effects to something else, such as their own hard work or luck. From outside: the millionaires would remain millionaires, the employees would mostly remain employees, the poor ones would remain mostly poor.

This gives us two versions of the complaint:

• if we expect big success, why don't we obviously observe it?
• if we expect small success, what makes us believe it exists, if we are not measuring it?

I believe that many people have the "small" success, but yeah, I don't have solid data to back this statement. I wish I had.

Also, we had some "big" successes. Specifically: AI safety became a mainstream topic, or the existence of effective altruism. These are easy to downplay, but I think that 10 years ago, few people would have predicted that AI safety will become a mainstream topic.

I also believe that we could do much better, and I hope that one day we will. I think that an important task will be learning to cooperate better. (Which includes learning how to avoid being exploited by malicious actors, which unfortunately also sometimes target our community. But the solution is not keeping everyone at internet distance. The solution is to develop some mechanism to "trust but verify".)

On the other hand, the stories about Beisutsukai, Anasûrimbor Kellhus, or recursively self-improving AI, primed us to expect "rationalist fast takeoff". Of which there is no evidence so far. The rationalist takeoff -- if there is such a thing -- is definitely slow. I wonder if there is a way to make it faster; I think our behavior is far from optimal, but I wonder whether it can realistically get better.

The question pops up regularly. Jacob (Jacobian on here) wrote an answer here: https://putanumonit.com/2019/12/08/rationalist-self-improvement/

One issue I see is the narrow definition of winning used here. I think that people reflective enough to embrace rationality would also be more likely to reconsider the winning criteria not to just be "become filthy rich and/or famous". Consider that maybe the prize is not worth the price. I'd be more interested into people that have become wealthy/established/successful in their fields (without becoming a rock star I mean, just plain old successful, enough to be free of worries and pursue one's one direction).

It’s solely because weird blogs on the internet make me feel less alone.

Numerous people have said this to me about the whole rationality movement. That feeling "I am not the only one". 

Talking to rationalists is not much better, since it feels less like a free exchange of ideas, and more like an exchange of "have you read post?"

With what kind of rationalists are you talking? 

So where are all the winners?

Dominic Cummings did basically out himself. Foreign Policy writes about him having had "almost total power over Britain" for some period of time. That was written back in June. Now a article from two weeks ago still describes him as one of the most powerful people in UK politics.