If you run a business or manage an investment portfolio, the last few months of the year usually come with a decision or two attached. Whether it's a trade you make, a contribution you top off, or a gift you time right, it can change what you owe when tax season arrives.
Selling investments at a loss to offset capital gains realized elsewhere in your portfolio continues to be one of the more effective tools available before year-end. Beyond covering those gains, it can reduce ordinary income by up to $3,000 annually, and any unused losses carry forward into future tax years. It also creates a natural opening to reposition out of underperforming assets. One thing to keep in mind, the wash sale rule blocks you from repurchasing a substantially identical security within 30 days of selling it, so timing the trade is important if you want to keep the tax benefit intact.
Current 2026 limits, along with the newly released 2027 numbers, are below.
401(k)/403(b) contribution limit: $24,500 for 2026 ($32,500 if age 50+), rising to $25,500 for 2027 ($34,000 if age 50+, $37,250 if age 60–63)
IRA contribution limit: $7,500 for both 2026 and 2027 ($8,600 if age 50+, since the $1,100 catch-up also holds steady)
HSA contribution limit: $4,400 individual / $8,750 family for 2026, rising to $4,500 individual / $9,000 family for 2027 (+$1,000 catch-up at 55+)
SEP IRA or Solo 401(k) limit for business owners: $72,000 for 2026 ($80,000 if age 50+), rising to $75,000 for 2027 ($83,500 if age 50+, $86,750 if age 60–63)
Checking these against where your contributions currently stand only takes a few minutes, and if you're behind for the year, this stretch before December 31st is the window to close that gap.
Converting traditional IRA assets to a Roth IRA can offer tax-free growth and tax-free withdrawals down the road, though the right call depends heavily on your specific situation. Comparing your current tax rate against what you expect down the line is a good starting point. Paying the conversion tax with non-retirement assets, rather than pulling from the IRA itself, tends to preserve more of the long-term benefit. A conversion can also push you into higher Medicare premium brackets or affect other income-based thresholds, so it's a decision best made with your full picture in view. Converted funds also need to sit for five years before qualifying for tax-free withdrawals.
For anyone taking RMDs, missing the December 31st deadline comes with a penalty of 25% on the amount not withdrawn. While RMD amounts are calculated based on your individual accounts, IRAs allow you to aggregate the total and withdraw it from a single account, whereas employer plans like 401(k)s must be satisfied separately for each plan. Your first-year RMD can be delayed until April 1st of the following year, though that means two distributions land in that same year. After that first year, RMDs are required annually and cannot be skipped or delayed going forward. Qualified charitable distributions can satisfy your RMD while supporting causes you already care about.
Charitable giving has always done double duty, supporting causes you care about while helping your tax picture. This year, changes under the One Big Beautiful Bill Act (OBBBA) add a few new wrinkles to understand before you give.
Qualified charitable distributions let individuals 70½ or older transfer up to $100,000 annually directly from an IRA to a qualified charity, satisfying RMD requirements while excluding that amount from taxable income.
Donor-advised funds work well for donors who want an immediate tax deduction while deciding over time which charities receive the funds. They also make sense for donating appreciated securities, since doing so avoids capital gains tax on the appreciation, and they let you bunch several years of giving into a single tax year for maximum efficiency.
Donating long-term appreciated securities directly to a charity offers a similar dual benefit, a deduction for the full fair market value of the security, and no capital gains tax on the appreciation.
The OBBBA changes the math on some of this for higher-income donors specifically. Itemizers now face a new floor on charitable deductions, only gifts above 0.5% of adjusted gross income are deductible, which works out to $500 in deductions lost for every $100,000 in AGI. Taxpayers in the top bracket also face a cap limiting the value of the deduction to $0.35 per dollar given, rather than the full benefit of their marginal rate. Both changes took effect for the 2026 tax year and carry into 2027 planning.
The law also permanently locks in the ability to deduct up to 60% of adjusted gross income for cash gifts to public charities, so donors who give heavily can plan with more certainty than they've had in years. Non-itemizers get something new as well, an above-the-line deduction of up to $2,000 for joint filers ($1,000 for individual filers) for cash donations, available whether or not you itemize at all.
The new deduction floor makes smaller annual gifts less tax-efficient than they used to be for some donors. Because of that, combining multiple years of giving into a single year through a donor-advised fund has become a more compelling strategy than it was before the OBBBA took effect.
If you own a business, there's a second layer of planning to look at before year-end, separate from the individual strategies above.
Cost segregation can accelerate depreciation on commercial property you own, reclassifying parts of a building into shorter depreciation categories so deductions land sooner rather than later. Bonus depreciation currently allows 100% write-offs on eligible assets placed in service after January 19, 2025, and it pairs well with Section 179, which lets you deduct up to $2,560,000 of eligible property placed in service this year, with the deduction beginning to phase out at $4,090,000.
The Augusta Rule is a smaller but often-overlooked option. It lets you rent your home to your own business for up to 14 days a year, deductible to the business and tax-free to you personally, provided the arrangement is properly documented and priced at a fair market rate.
Qualified plan design is another area to look at. Reviewing your current retirement plan each year can surface opportunities you might be missing, a Safe Harbor match or non-elective employer contribution can raise how much owners and highly compensated employees are able to contribute, and adding a cash balance plan alongside your existing 401(k) can increase what you're able to put away pre-tax each year. These moves depend heavily on your specific plan design, cash flow, and employee census, so this is another one to build out with your advisor and TPA together.
These strategies involve more moving parts than the individual ones above, make the most sense when evaluated in coordination with your CPA and financial advisor.
Our tax strategies checklist for business owners covers these in more depth, if you want to dig further before year-end.
The strategies above tend to work best together rather than in isolation. Looking at your income, timing, and goals as one connected picture, rather than handling each piece separately, is usually what makes the biggest difference by the time you file. Schedule a conversation with our team to discuss your situation.