Year-End Portfolio Checkup: 6 Tax-Smart Tips

With a few months remaining in the year, it’s a good time to review your financial plans and ensure you’re doing all you can to maximize your savings and reduce your tax bill.  Don’t wait until December to reassess your finances – you could miss out on opportunities that disappear at year-end.

Here are six things to consider doing right now:

Maximize your retirement savings: Contributions to tax-deferred retirement accounts – such as a 401(k) – reduce your taxable income and provide tax-free growth until retirement.¹ Now is a good time to re-evaluate your overall savings and determine if you can bump up what you’re putting away for retirement. You can also make lump-sum contributions from an annual bonus to give your savings a boost.  And remember, if your employer offers matching contributions – don’t leave free money on the table – it’s a good idea to take full advantage of those additional funds.

If you’re currently in a lower tax bracket and you’re likely to be in a higher tax bracket when you retire (a lot of younger people fall into this category), consider making contributions to a Roth IRA or Roth 401(k).  Though contributions to Roth accounts are made with after-tax dollars, that money can grow tax-free.  And when you retire, you won’t have to pay taxes on the withdrawals.

Those who are self-employed or business owners should consider making contributions to a tax-deferred retirement account such as a SEP-IRA, SIMPLE IRA or individual 401(k). These contributions will lower your taxable income and could help you stay under the phase-out limitations for the new 20% deduction on pass-through income.²

Consider a Health Savings Account (HSA): It’s open-enrollment season, and if your employer offers an HSA – and you qualify to contribute to one – this can be a tax-smart way of setting aside money for qualified medical expenses.³  HSAs offer a triple tax advantage: You pay no federal taxes on your contributions⁴, no federal taxes on investment earnings⁵ and no taxes on withdrawals as long as the money is used for qualified medical expenses.⁶

If you’re fortunate enough not to have too many medical expenses and have money left over in your HSA during retirement, you can use that money to pay for living expenses -the only caveat being, you’ll have to pay taxes on the withdrawals when they’re not just for medical expenses.

Give to a favorite charity: The end of the year is a time when many people think about charitable giving. As with other aspects of your finances, it’s important for charitable giving to be part of a broader financial plan.

One way to maximize the tax benefits of charitable giving is to concentrate your giving into a high-tax year. By giving a large amount one year and not the next, you could maximize your itemized deductions in that year and take the new increased standard deduction next year. Giving appreciated assets in this manner is a great way to maximize your charitable giving deduction, and a donor-advised fund (DAF) could be used to facilitate that gift.

If you’re 70½ or older, you could also consider donating directly to a charity from your retirement account, using a qualified charitable distribution (QCD).  A QCD allows you to meet the required minimum distribution and has the added benefit of not being included in your taxable income.

Gift assets to your loved ones: Each year you’re allowed to give up to $15,000 to any number of people without them having to pay a gift tax. Taking advantage of this yearly exclusion can allow you to transfer a large amount of wealth to your loved ones tax-free and without eating into your gift and estate tax exemption. Those gifts can be used for any number of financial goals, including funding a grandchild’s 529 college savings plan or helping a loved one make a down payment on a new house.

Rebalance your portfolio: The market is constantly changing, which can skew your asset allocation from its original target. Over time, assets that have gained in value will account for more of your portfolio, while those that have declined will account for less. This can leave you exposed to unintended risk if the market environment should suddenly change. That’s where rebalancing your portfolio comes in.

Rebalancing involves selling positions that have exceeded your target allocation and moving the proceeds to positions that have become under-represented. The end of the year is a good time to take a look at your portfolio allocation and make sure it’s aligned to your goals and risk tolerance. This can be especially important for people nearing or in retirement, who might be more sensitive to market volatility.

Consider tax-loss harvesting: Tax-loss harvesting is an underappreciated investing strategy that you should consider while rebalancing your portfolio. Investors have a tendency to avoid selling anything at a loss, but there can be a significant tax benefit to selling a losing position if you have capital gains to offset. Tax-loss harvesting can also serve as a motivation to sell underperforming investments or to reduce concentrated stock positions.

1. For 2019, the maximum employee 401(k) contribution is $19,000. If you’re age 50 or older, you are allowed to contribute an additional $6,000 in catch-up contributions, for a total of $25,000.
2. The 20% deduction (IRC 199A) is available to owners of pass-through entities such as sole proprietors, partnerships and S-corporations. There are numerous limitations and rules related to this deduction, so be sure to meet with a tax professional well before year end to go over your specific situation.
3. In 2019, the contribution limit is $3,500 for HSAs linked to self-only health insurance coverage and $7,000 for HSAs linked to family coverage. People age 55 or older may contribute an additional $1,000 in either scenario.
4. HSA contributions are not deductible in several states, including California, Alabama and New Jersey. Check with your tax advisor for specific tax advice.
5. State taxes may vary.
6. See IRS Publication 502 for a list of these expenses.