Don’t Wait for December: Your October Year-End Planning Guide
Posted October 1, 2026
Posted October 1, 2026
Somewhere around the first crisp morning of fall, the calendar starts to feel crowded. Holiday plans, school schedules, and work deadlines all compete for your attention. Your financial plan tends to slide to the bottom of the list.
Here’s our case for moving it up. The decisions you make in the next few weeks can shape your tax picture, your retirement savings, and your family’s long-term financial position for years. At Thayer Financial, we think of October as the “golden month” for year-end planning, and here’s why.
By October, most of the year’s story has been written. You have a good sense of your income, your investment gains and losses, and any big life or business changes along the way. That’s enough information to make informed decisions, and there’s still enough runway to act on them.
December is different. Everyone is trying to place trades, fund accounts, and call their CPA at the same time. Custodians get backed up, wires take longer, and you’re left making rushed decisions against a hard deadline.
Starting now lets you shift the question. Instead of asking “What can I do about my taxes?” in the last week of the year, you can ask, “What decisions can I make now that put me in a better position?”
Pull up your year-to-date 401(k) contributions and see where you stand. For 2026, the employee deferral limit is $24,500, with an additional catch-up contribution if you’re 50 or older. Those between ages 60 and 63 may qualify for an even higher catch-up amount.
One important change to know about: beginning in 2026, higher earners who want to make catch-up contributions to an employer plan may be required to make them as Roth (after-tax) contributions. If that applies to you, it’s worth understanding how it changes your tax planning.
Business owners and the self-employed often have more room than they realize. Depending on the plan you’ve set up (a Solo 401(k), SEP IRA, SIMPLE IRA, or a defined benefit or cash balance plan), you may have additional contribution opportunities worth evaluating before year-end. Some plan types must be established by a specific deadline to count for this year, so don’t assume you can wait.
Don’t forget your HSA. If you’re eligible, a Health Savings Account offers a rare combination of potentially tax-deductible contributions, tax-deferred growth, and tax-free withdrawals for qualified medical expenses. For 2026, the contribution limits are $4,400 for self-only coverage and $8,750 for family coverage, with an extra $1,000 if you’re 55 or older.
The goal isn’t to contribute the maximum just because you can. Your contributions should fit your cash-flow needs and your bigger financial picture. Tax savings are a benefit, not the whole point.
October is a good time to review your investment accounts for realized gains and positions sitting at a loss.
Tax-loss harvesting means selling an investment that has declined in value to realize a capital loss. That loss can offset capital gains and, subject to IRS limits, a portion of ordinary income. Unused losses can generally be carried forward to future years.
A few things to keep in mind:
This is also a natural time to check whether your portfolio has drifted from its target allocation. After a strong market stretch, the stock portion of your portfolio may be larger than you intended. Rebalancing, done with taxes in mind, can bring things back in line. In some cases, you may be able to use losses elsewhere in the portfolio to offset gains from trimming positions that have grown.
If you’ve had a lower-income year, perhaps because of retirement, a business slowdown, or a career change, this may be a good time to consider a Roth conversion. Converting pre-tax retirement dollars to a Roth IRA means paying tax now in exchange for potential tax-free growth and withdrawals later.
The key is knowing exactly where you stand. By October, you can often estimate your taxable income closely enough to see how much room you have in your current bracket before the next one begins. You’ll also want to consider how additional income could affect Medicare premiums (IRMAA surcharges), the taxation of Social Security benefits, and eligibility for other tax breaks.
A conversion can’t be undone, so this is a decision to model carefully with your advisor and CPA first.
If charitable giving is part of your life, year-end is the time to make sure your gifts work as hard as possible.
Donor-Advised Funds (DAFs). A DAF lets you contribute to a charitable fund, potentially receive a tax deduction in the year of the contribution, and then recommend grants to your favorite charities over time. They can be especially useful in years when you have a large charitable opportunity or highly appreciated investments. Donating appreciated securities rather than cash may allow you to avoid capital gains tax on the appreciation while supporting the causes you care about.
Bunching. If your charitable gifts alone don’t push you past the standard deduction, you can “bunch” several years of giving into one tax year. You itemize in that year and take the standard deduction in the others. A DAF makes this strategy much easier to carry out.
Qualified Charitable Distributions (QCDs). If you’re 70½ or older, you can send money directly from your IRA to a qualified charity. A QCD can count toward your required minimum distribution while generally excluding the amount from your adjusted gross income. For 2026, the annual QCD limit is $111,000 per person.
Keep in mind that the rules for charitable deductions are changing in 2026. New provisions added a floor on itemized charitable deductions and a limited deduction for those who don’t itemize. How this affects you depends on your income and whether you itemize, so it’s worth running the numbers before you give.
If you’re subject to RMDs, remember that the deadline for most accounts is December 31 each year. (The exception is your first RMD, which can be delayed until April 1 of the following year.) The penalty for missing an RMD can be significant, though it has been reduced in recent years. If you have multiple accounts, confirm that the right amounts are being taken from the right places, and that your tax withholding is on track.
If you own a business, you often have more control over when income arrives and when expenses are paid. Depending on your accounting method, entity type, and personal tax situation, you may be able to accelerate deductible expenses into this year or push some income into next year.
Equipment purchases are a common example. Under current law, business owners may be able to deduct a large share of qualifying equipment costs in the year it’s placed in service, through bonus depreciation or Section 179 expenses. But we always offer the same caution: a tax deduction does not make an unnecessary expense worthwhile. Spending a dollar to save a fraction of a dollar in taxes is still spending a dollar. The best approach is to ask whether an expense is already part of your business plan and whether the timing makes sense for your cash flow.
October is also a good time to look at the bigger picture:
Year-end is also a great time to do some estate planning housekeeping.
The federal estate tax exemption is currently $15 million per person in 2026, but state rules and future legislation can change the picture. Reviewing your plan with your advisor or estate attorney keeps it aligned with your wishes.
Here’s a simple way to approach the next few months:
The biggest advantage of year-end planning is time. Time to weigh the trade-offs. Time to coordinate with your financial advisor, CPA, and attorney. And time to make decisions on purpose, not in a panic.
Your financial plan shouldn’t run on a calendar that begins and ends with tax season. Your investments, retirement savings, charitable giving, business income, and taxes are all connected, and a proactive review brings those pieces together.
At Thayer Financial, our goal is to help you make informed decisions year-round, not just when a deadline is looming. If you haven’t reviewed your financial picture yet, October is a great time to start the conversation. And remember, the goal isn’t simply to minimize this year’s tax bill. It’s to make thoughtful decisions today that support your larger goals tomorrow.
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