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4. The intent to start taking SEPPs from traditional IRAs is exactly the kind of thing I was thinking about. I hit 55 in under 7 years, so that window aligns with potential (relatively) early retirement.

Yes, you can do the T IRA SEPP withdrawals before 59 1/2, or simply pull funds without penalty from your 401k after 55 when you quit work. If your new employer has a good plan, you might consider just rolling your current 401K into there so you don't have to deal with SEPP for a while. Or as I said, if you want to keep that option open but allow yourself all the bells and whistles of choosing your own brokerage, just keep the 401K rollover in a separate account and keep a paper trail, so that you have the option to roll it in to your current 401K later. I suspect this is contingent on what your new employer will allow. In this case you have two sets of rules to deal with...the IRS and your employer 401K.

I honestly don't know how much of a PITA SEPP is, but I am happy to be able to avoid it. But our 401K is pretty good in terms of what it lets us do.

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