I personally do it every month. I know where every dollar has gone every month, and I also track a 12-month moving average. So I have a sense now of what our yearly expenses are. I compare that with the ever-changing recommendations of what a "Safe Withdrawal Rate" is, and then I try to squint into the future to mix in the effects of: taxes from retirement income; social security (even at the 80% level if no one fixes it); increased retirement expenses from having fun; decreased retirement expenses from not working and getting old; increased retirement expenses from health.
But ultimately, it just comes down to the trio of savings, interest rate, and expenses.
1 million saved = 40k per year, adjusting with inflation. 2 million saved = 80k per year, adjusting for inflation.
If you can live a life you want for 80k a year, then sure - 2 million can do it.
And yes, there will always be a "what if the economy collapses etc. etc", but retiring doesn't mean you can never ever for any reason hold a job again or make money.
https://www.mrmoneymustache.com/2012/05/29/how-much-do-i-nee...
> Luckily, the math in this case is pretty interesting: there is very little difference between a 30-year period, and an infinite year period, when determining how long your money will last.
You should be fine at 4% forever. If you can spend a little less some years, or go make a few dollars somewhere hey, boosts your odds even more.
$2 million in investments AND a payed off mortgage and still, it doesn't pencil out to retire? Seems like over the past decade+ the 'value' of even $1 million has become more and more diluted. To support even just a middle class, to upper middle class lifestyle, can get very expensive.