Bob also picked the best stock market to invest in. He would have done a lot worse investing in any other stock market. It's not surprising he did well, he picked the winner.

What are the chances the US is going to have the best stock market over the next 50 years? It's possible, but doesn't seem likely.

Sure, but the lesson is that the big story is what matters, way more than detailed RoR calculations. Bob made huge mistakes, but even then compounding was the stronger force and he ended up ahead.

The story makes it sounds like he's guaranteed to end up ahead. That's not true. For instance if he was investing in Germany starting before WW1 and invested at the peaks Bob would be massively underwater.

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.

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.

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.