Autumn in Pasadena means the same thing every year: clients start asking whether they have missed anything before December 31 arrives. If you are within a few years of retirement, or already retired, fall is the season to move from “I should look into that” to actually doing it. A handful of decisions made between now and year-end can meaningfully shape your tax bill and your retirement income plan for years to come.

This is the same checklist I walk through with clients every October. It is general education, not personalized advice, and every item deserves a conversation about your specific situation before you act.

Confirm Your Required Minimum Distribution Number

If you are age 73 or older this year, or you inherited a retirement account, fall is when I ask clients to confirm their required minimum distribution (RMD) amount rather than waiting until the final weeks of December. Custodians can take days to process a distribution, and a late RMD carries a real penalty from the IRS.

I recently worked with someone who assumed his brokerage had calculated his RMD correctly. It had not accounted for an account he had inherited from a sibling earlier in the year, and catching the error in October rather than December gave us time to fix it without a scramble.

If this is your first RMD year: the rules allow you to delay your very first RMD until April 1 of the following year, but doing so means taking two distributions in that year, which can push you into a higher tax bracket. Fall is the right time to model both scenarios before deciding.

Evaluate a Roth Conversion While You Know the Numbers

By October, most clients have a fairly clear picture of their taxable income for the year: wages, pensions, dividends, and any capital gains are mostly known quantities. That clarity makes fall an ideal window to evaluate whether converting a portion of a traditional IRA to a Roth IRA is worth doing before December 31.

The appeal is straightforward. You pay tax on the converted amount now, at a bracket you can actually see, in exchange for tax-free growth and withdrawals later, along with no RMDs on that money during your lifetime. The trade-off is real too: converting too much can push you into a higher marginal bracket, trigger higher Medicare premiums two years down the road through IRMAA, or create a larger bill than expected. This is not a decision to make based on a headline; instead, based on your actual tax return.

Revisit Your Portfolio for Tax-Loss and Tax-Gain Harvesting

Evidence-based investing does not mean ignoring your portfolio until you rebalance. Fall is a natural checkpoint to look at taxable brokerage accounts for two opportunities:

• Tax-loss harvesting: selling a position at a loss to offset realized gains elsewhere, while being mindful of wash-sale rules
• Tax-gain harvesting: in years where taxable income is unusually low, realizing some long-term capital gains at a 0% federal rate can make sense

Neither is about predicting where the market goes next. Both are about being deliberate with the tax consequences of decisions you were likely to make anyway.

Confirm Beneficiary Designations Are Still Accurate

This is the item clients most often assume is already handled, and the one I most often find not to be. Beneficiary designations on retirement accounts and life insurance policies override what your will or trust says, which means an outdated form can undo years of estate planning in a moment.

I ask clients every fall: has there been a marriage, divorce, birth, or death in the family since you last checked? Has an account been rolled over to a new custodian, which sometimes resets the beneficiary form? A five-minute review now can prevent a significant, and sometimes irreversible, mistake later.

Revisit Your Charitable Giving Strategy

For clients who give to causes they care about, whether a local Pasadena nonprofit or their church, fall is the time to decide how this year’s giving will happen, not just how much:

• Qualified Charitable Distributions (QCDs): for those age 70½ or older, directing money from an IRA straight to a qualified charity, which can satisfy part or all of an RMD without adding to taxable income
• Donor-advised funds: bunching several years of giving into one tax year, particularly useful in a year with unusually high income

Review Withholding Before the Year Closes

If you took a larger distribution than usual this year, sold an appreciated position, or had unusually high investment income, fall is the time to check whether your withholding or estimated tax payments are on track.

Catching a shortfall in October leaves time to make a fourth-quarter estimated payment or adjust withholding on a pension or Social Security check. Catching it in April means an underpayment penalty may already be locked in.

What This Means for You

1. Confirm your RMD amount and the deadline that applies to you
2. Run the numbers on a Roth conversion against your actual 2026 tax picture
3. Scan taxable accounts for tax-loss or tax-gain harvesting opportunities
4. Pull up every beneficiary form you have and confirm it is current
5. Decide how and when this year’s charitable giving will happen
6. Check that withholding and estimated payments are on track for the full year

A Season for Clarity, Not Scramble

None of these decisions are urgent in the sense of a fire alarm, but all of them get harder and more expensive to fix the closer you get to December 31. I would rather have this conversation with a client in October, with time to think it through, than in the last week of the year, with a deadline breathing down both our necks.

If you would like to walk through your own fall checklist together, I would welcome the conversation. Schedule a discovery call, and we will go through this checklist, customized to your specific situation.