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I think it's very naive to think that when you break down a system the thing that replaces it will be automatically better. Failing forward is no good strategy.
I don't think that's the case. The workers movement that lead to communism was strong because unions happened to be strong communities with strong internal loyalty.
If you want to change something focus on community building. Don't focus on what happens on the national level but focus on providing services that help people in your local community. The LW community isn't really local but it's also a community separate from the mainstream so, investing effort into making it stronger also counts as community building effort.
Don't invest your retirement money in the stock market. Invest it into a business where you know the owner personally. That can mean Angel investment.
Buying local property is also good. Buying solar panels to put on your house also decentralizes power.
If you invest your retirement money into an index fund you are actively supporting the current system. If you do protest against the rich and have your retirement money in an index fund you are not being consistent.
I put major effort in Quantified Self community building. As part of that community building I did a lot of media interview and used some of that time to say how much the status quo fails people and that people should gather data to make self determined choices instead of listening to authorities.
I do my fair share of attacking the status quo, but in the end the things that matters isn't destroying the status quo but replacing it with something better.
Having a QS community that's strong enough to be a stakeholder with certain power is a worthwhile goal. Having a LW community with is powerful to be a stakeholder with certain power is a worthwhile goal.
If you invest your money into the startup that your fellow LW community member wants to start instead of investing it into an index fund, that makes the LW community strong. Less money in the stock market in turn makes big corporations weaker.
Reallocating your investments isn't attacking the mainstream. It's focusing your resources inside your own community.
Investing your money with fellow rationalists might be an even better return on your investment than an index fund but that isn't the only point. Where you allocate your retirement money is a political question that more important as to how you vote in elections and whether corporatist party A or corporatist party B holds power.
I do in fact not have money in index funds, or any other Wall Street related investment. And I try not to support social structures I find abhorrent, occasionally as relatively significant personal cost.
However its my position that attacking the status quo is necessary, although what you suggest is also necessary. I don't think its a one or the other thing.