At what point do I start taking money out of my VTI holdings and parking it in cash - there is no way the market keeps going up.

First, don't park it in actual cash or you'll lose value to inflation which is currently running high. At a minimum put it in treasuries.

Second, trying to time the market is almost always a suboptimal strategy. The question is when will you likely need the money? If you won't need it for 10 years or more, keep it in index funds. Otherwise, treasuries.

Historically even if you invest into index at the worst possible time (prior to a crash) and keep holding you still outperform inflation long term. Timing the market is impossible. Just keep an emergency fund in a money market or savings account and hold the rest.

Others have given practical replies, so here's a philosophical one: Sometimes it's just not practical to make much money from being right.

I want to acknowledge and empathize how much it sucks, while also putting it out there so that nobody suffers blaming themselves for something that might not be achievable.

Disclosure: I've been waiting-and-seeing too long myself, and I should probaby stop trying to time/strategize.

Just need a larger emergency fund to mitigate the risk, especially if you work in tech and you feel the crash would heavily impact your labor earnings (including possibly extended unemployment)

There is no law that prices must revert to a mean.

The market can keep going up in dollar terms while losing real value if we enter a phase of high inflation.

Park it in BRK?

> there is no way the market keeps going up.

There is no way the US’s leaders let the prices of publicly traded securities go down or even stagnate relative to the US dollar. These publicly traded securities make up a significant portion of the US leaders’ and most active voters’ assets, plus almost all state and local US governments depend on the securities’ price growth to meet their deferred compensation obligations.

The alternative to risk in US securities isn’t the USD, it’s a stake in other stable countries with resources.

Market goes up when the dollar crashes you're fine

already did mate, after Trumps first pump and dump with Iran

what's your risk tolerance?

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It’s such an obvious Ponzi scheme the companies should get delisted.