Alexander and Meg are both 70 years old, retired, and enjoying their years traveling to national parks and visiting with grandchildren. When they came to us, the issues weren’t about income or wealth accumulation. They had earned and saved well, amassing assets to live comfortably for the duration of their lives and pass on a legacy to the next generation. Instead, they wanted to maximize their money by employing the best withdrawal methods for income, the most tax-efficient tactics for investing, and most important, ensuring that the assets passed as efficiently as possible with regard to estate laws. Because Alexander worked for a major corporation for more than 30 years, he had accumulated a proportionately large allocation of the company stock compared to the rest of their portfolio, but because he had owned the stock for decades, there was a large amount of unrealized capital gains, preventing him from paring down. We were able to first reallocate the rest of their assets to tax-efficient investments. That move, coupled with their now-lower tax bracket in retirement, allowed us to sell off the company stock for a healthier allocation. Because Alexander and Meg were charitably inclined, we advised them to employ qualified charitable donations from their IRAs as a way of satisfying their required minimum distributions. They realized two goals at once—charitable giving and tax efficiency. As well, once they were in the lower tax bracket we converted regular IRAs to Roth IRA, their tax outlook and estate planning improved as a result.