If you’re planning to sell shares before the end of the year, you may want to consider selling some shares at a loss to offset your capital gains. You currently have a loss on the shares listed below. You can see how selling these shares will impact your tax liability.
You may want to consider moving your investments in Vanguard Health Care Fund and Apple Inc to a tax-deferred account like an IRA.
If you’re in one of the highest tax brackets, you may want to consider replacing your investment in the Total Stock Market Index Fund with Vanguard Tax-Managed Capital Appreciation Fund.
You might want to consider diversifying with a Roth IRA. Having both Roth (tax-exempt) and traditional (tax-deferred) assets when you retire can give you more flexibility when you withdraw the money.
You may want to consider speaking with a financial planner to discuss other retirement planning opportunities.