[UncleMeat]

The bob scenario is educational, but isn't relevant here. The reason why bob is still fine is that the crashes all happen during the accumulation phase. What you don't want is a crash right as you retire, causing you to rapidly liquidate a much larger portion of your savings than expected.

[ManuelKiessling]

But do you really liquidate „rapidly“ once you retire? You basically dollar-cost-average out of your portfolio when retirement begins.

That’s not to say that timing isn’t an issue — it absolutely is. It’s just not a make-or-brake issue imho.

[UncleMeat]

You liquidate rapidly if the market is way down. If you are planning on withdrawing ~4% of your stating portfolio annually to pay your expenses, the market tanking by 50% means you are now consuming 8% annually.

In the accumulation phase the value of your equities is likely to return. You never end up selling anything. But in the retirement phase you liquidate in order to pay your expenses. If you end up liquidating down too far there won't be enough future growth to cover your retirement needs.

Market crashes right after retirement are very dangerous for retirees.