I have a sole proprietor client who is age 60 and wants to start a 401(k) Plan with the initial contribution being designated as a Roth contribution. His thinking is that he wants to make an investment that he feels will increase in value substantially within the next year or two. He would than like to terminate the plan and receive this money tax free. Assuming he closes down his sole proprietorship and is at least age 60, would this meet the "separation from service" exemption for Roth distributions so that he wouldn't have to wait 5 years before he could take the money without taxes and/or penalties.?
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I think that I found out my answer. There is really no way around the 5 year waiting period short of maybe taking substantially equal periodic payments. So if my client wants to do this, he needs to be prepared to take out periodic payments for a while.