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I am about to take an early retirement (at age 55+) from my employer, but plan on continuing my career and building a second retirement in about five to seven years. My employer provided me with a savings and investment plan which consists of before-tax (401(k)) contributions, matching funds from the employer (mostly used to purchase company stock) and after-tax savings.

I am at the point in time where I wish to take control and invest all of these Foolishly by investing from a self-directed IRA (tax-deferred funds) and a regular investment account (after-tax). I plan on taking distributions from all accounts after my eventual second retirement.

I am a little confused as to the lump-sum tax ramifications on this plan mix. Some is in a well-performing indexed fund, some in company-contributed stock (as Tom and Dave say, "Free Money") and some in "post-1986 Basis" funds. How does one direct the proceeds from such a managerie keeping the best tax strategies in mind?

I'd appreciate any information . . .

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