I'm 58, and investing in stocks since the 90s has led me to have over $4 million in my portfolio - which path should I venture down next?

One of the drawbacks of a F.I.R.E. (Financial Independence, Retire Early) high-growth portfolio strategy is the tax ramifications. Capital gains taxes, early withdrawal penalties, passive income taxes, and similar levies from Federal and Municipal governments all take a substantial bite from one's F.I.R.E. retirement funds upon withdrawal if in a retirement account, or at the end of the year as capital gains taxes if in a standard account.

Nevertheless, there is no law that requires one to pay more than the minimum legal tax, so prudent and strategic portfolio management is key to accomplishing that end. This means investors need to be intelligent about how they access their funds and manage their withdrawals to minimize their tax burden.

Taking a chance that his portfolio will continue to grow, allowing him to ride out any tax consequences, is one option. Alternatively, he can face the Federal and California Long Term Capital Gains Hit of over 30% and convert everything to index funds.

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