Answer this question first,

"New Tax Codes and Stock" Calvin, a client of yours since you opened your practice, has over the past few years become very intrigued with investing in the stock market. He has interest bearing securities and dividend paying stocks. He also owns U.S. Securities. He is considering selling $400,000 in stocks. He doesnt know if he should sell additional stock for a loss to help offset the stock sale of $400,000. Calvin called you to ask what tax consequences the interest and dividends will have along with the stock sale. What tax advice would you offer to Calvin in planning for this situation?

Then comment on this one please.

I love a client who thinks ahead. It is smart to think about selling some stock at a loss to help offset your capital gains. But I say that with caution. If you believe the stocks you are thinking about selling will produce a greater economic benefit down the road than the immediate tax benefit of selling at a loss, then do not sale. Assuming the sale of the stocks will generate long term capital gains and is subject to the 0/15/20 percent tax rate, it would be beneficial to sell stock, that will not realize a net gain. Now how much stock to sell at a loss is a different question and we would need to crunch the numbers based off how much a net gain is realized. But, for example if your net gain was $150,000, we would want to sell enough stock at a loss to bring the net gain to $78,750 (assuming you file jointly). This would save you roughly $10,690 in tax liability.

In reference to the tax consequences to your interest-bearing securities, the general rule is you will be taxed on any interest received throughout 2019. In cases where you will not receive the interest until you sell the securities or they reach their maturity date, then you will not have to pay taxes until you sell, or it reaches maturity. Regarding any dividend paying stock you own, you will be taxes on any dividends generated, even if they are reinvested, at ordinary rates. Side note, depending on the type of dividend, it could be considered a qualified dividend, in which case it would be taxed at preferential rates.