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Nords said:
Pick the portfolio value you like the best and call that "January 1". Picking your own fiscal year start date works for Fortune 500 companies, so you could make it work for you. It'll also separate you from the "January effect" or other seasonality.

You could either pick the highest value (biggest withdrawal) or the lowest (most conservative).

I'll probably ultimately go with the end of a quarter, simply because
that is when every company I care about sends their financial statements.

However, it is sometimes really tempting to pick "the first day my portfolio
crosses the $XXX,..." mark. However, that just does not feel conservative
enough for my tastes.

I'm also not willing to say "X years, Y months, and Z days ago, my portfolio
peaked at $N, so I'll use 4% of $N as my withdrawal rate". That just feels
like cheating.

Oh well, I'll get there eventually.
 
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