Stock Market Volatility: How to Turn Losses Into Tax Benefits

If you’re at or near retirement age, I’m sure the last few weeks have been especially worrisome for you.

I’ve said it before and I’ll say it again: The markets will stabilize, perhaps sooner than we think. But I realize that may be cold comfort to some of you.

The good news is there’s a way to eliminate some of the sting in any losses the market volatility may have handed you. Let me explain…

The tax system allows us to make contributions to 401(k)s and individual retirement accounts (IRAs) out of pretax income. The quid pro quo is that we must withdraw that money on an annual schedule once we retire — or face big penalties for failing to do so.

Not long ago, a reader asked about these required minimum distributions (RMDs):

“I need to take my RMD. I understand I will pay taxes on these withdrawals, but I think I can keep the withdrawal invested in stocks, real estate investment trusts or use it to buy rental real estate or any other kind of asset investment. Am I right about that?”

Yes … and with the markets behaving as they have, now is the perfect opportunity to share with you how this reader (and others like him) could turn this into an advantage.

The Clock Is Ticking if You Want to Use This Strategy

As mentioned, one of your options when faced with annual required minimum distributions is to transfer stock holdings out of a tax-advantaged IRA or 401(k) and into a nontax-advantaged brokerage account.

You don’t have to sell any stocks. You just transfer them from your IRA or 401(k) to a regular brokerage account. If you’re not sure how this works, just ask whoever manages your accounts to transfer those stocks to a taxable brokerage account. It can be between accounts at the same company, such as Fidelity or Charles Schwab, for example.

Now, because you’re making a distribution from your tax-advantaged retirement account — albeit in the form of stocks instead of cash — you’ll incur federal income tax liability for the year on the value of those holdings at the ordinary income rate and not at capital gains rates. It’s always like that with retirement account withdrawals.

But here’s the trick: You can pick and choose which stocks you move out of your tax-advantaged account to minimize your tax bill.

For example, you could withdraw stocks you think are going to continue to decline in value after you transfer them to your brokerage account. This accomplishes two things:

It removes losing positions from your retirement account, leaving the winners to rack up more tax-deferred gains.
Once you’ve transferred stocks into your brokerage account, the losing stocks will start accumulating capital losses. You can offset those capital losses against your ordinary income for the year, reducing your tax bill.

That raises the question of timing.

When Should You Make the Transfer?

This strategy works best if you make the transfer as early as possible in the year so you can maximize your capital losses.

So, if you think certain stocks in your retirement account are going to do poorly this year, transfer them to your brokerage now.

Then liquidate them toward the end of the year — or whenever the stocks look like they have hit a bottom — harvesting the maximum capital loss and minimizing your tax bill.

That gives you more time to let them accumulate losses that you can offset against the tax liability you incurred when you transferred them out of your IRA or 401(k) to meet your RMD.

Voilà! A lower tax bill for next year.

Kind regards,