If you have several substantial bequests to charities in your will, this Kiplinger's article asks if it would be better to see the charity use the money during your lifetime—when you could get some personal gratification from it. Add to that a big income tax deduction!
The article "Are You Losing Big Tax Savings on Your Charitable Bequests?" says that you shouldn't be too concerned that this approach might leave you short on funds for living expenses now.
Transfer the money that you're planning to leave to charity at death to a charitable remainder trust now. With a charitable remainder trust, you'll retain an income from the trust and whatever principal that's left when you pass away would go to the charities designated in the trust. The income would be a fixed percentage of the initial contribution to the trust (a "charitable remainder annuity trust" or "CRAT") or a fixed percentage of the value of the trust as of the last day of the prior year (a "charitable remainder unitrust" or "CRUT").
The nice thing about using a CRAT is that you'll know the amount of the income each year. Contrast that with a CRUT, where you would have the opportunity for the income to grow if the assets of the trust experience growth in excess of the payment.
In addition, if the return on the assets isn't great enough, you could deplete the assets of the trust with a CRAT because your income isn't dependent on the amount of assets in the trust. You'd have that same issue if you didn't put the assets in the trust but continued to take the same income—an income amount not supported by the investment return.
A CRUT sets your income as a percentage of the value of the account each year. If the account decreases, your income the following year would be adjusted accordingly by the normal operation of the trust. As a result, the income wouldn't deplete the trust, but it might get pretty small at some point with continual investment underperformance.
Ok, now lets' talk about that income tax deduction for creating the trust. This deduction can be spread over six years if your income isn't high enough to use the deduction in one year. Cha-ching, that's extra money to enjoy today! What's more, you can also be the trustee of the trust, so you are still able to control how the money is invested.
Reference: Kiplinger's (June 2016) "Are You Losing Big Tax Savings on Your Charitable Bequests?"