statsguy:

  So rather than a 1 in 20 chance, the odds are more like 1 in 50.

Anyway, Al your post clarified my thinking and why I am unsettled with this restarting idea. Sometimes you need to step back and think about the bigger picture.  That is what your post did for me, it said what is this probability that MC is calculating.  paraphrasing.... the probability is the chance of a portfolio not surviving a 25 to 30 year time horizon given the starting point.

For what it is worth, this is a very conservative interpretation.  But exactly the way Statsgal thinks it should work.  She insists that I do not retire until our portfolio with our withdrawal rate has a 99% survival probability in the situation where my last paycheck corresponds to another great depression starting the next day.  For me, that means three more years of work... the downside (well that is the way Statsgal sees it) is that we will have a 12 figure portfolio when we die if the next thirty years are like the previous thirty years... well maybe downside was a poor choice of words...

I do not know how much extra risk a restarter is courting but I now see why he/she has increased risk.  And also why I have been unsettled by the idea.

 

Stats 

Stats, FWIW I would have a different conclusion than working three extra years. 

What does going broke mean?...ran out of money at year 29?  You can always work a little later on, if the plan is going poorly.   Or slightly adjust spending.  Who among us, even the wealthy, are not cutting back on gasoline usage today? 

Ninety nine percent survival has a dire sound to it.  One does not die.  And if indeed this scenario occcurred, most likely society has adjusted to the lower amounts of money.  That's why a haircut can be obtained for 50 cents in some countries.

Lot's of ways to deal with a poor outcome.

R48