Why September Matters for Year-End Tax Moves (and What I’m Watching)

Can you believe we’re already staring down the last quarter of 2026? September has a quiet way of sneaking up on people. Summer ends. People get back into the swing of their normal lives. And Halloween décor and pumpkins start popping up everywhere.

For long-term investors, September is important because we enter a period where tax moves need to be decided before year-end.

Why September Matters More Than It Looks

Between now and December 31, several planning decisions have hard deadlines. For example: Roth conversions, required minimum distributions for those who take them, and estimated taxes for those required to pay them.

All of these are easier to size carefully in September and October than in the last week of December.

What’s Working Lately and Asset Allocation Updates

Over the last few months, value-oriented parts of the market have generally been rewarded more than growth. As a result, we’ve been slowly shifting toward a more value-oriented posture. This means more dividend-oriented stocks and slightly higher cash allocations for many of our investors.

Why does this happen?

In an ever-changing market, style leadership rotates. Sometimes growth leads for long stretches. Sometimes value does. Neither pattern is a permanent law of nature, and nobody, myself included, knows how long the current preference will last. What we can do is pay attention to where leadership is showing up, manage risk thoughtfully, and keep an open mind.

In plain English: I’m responding to what the market has been rewarding recently, not declaring that value will “win” forever. If the leadership changes, our process is built to notice that too.

Stay flexible. Stay disciplined. Stay patient.

The Roth Conversion Window Is Open

If there is one educational theme worth sharing this month, it’s this: September and October are often the clearest months of the year to evaluate a Roth conversion for 2026.

Why now?

Because most of the year’s income is already visible. That makes it easier to estimate where you sit in the tax brackets, and whether converting some pre-tax retirement dollars to a Roth this year fits your plan. Conversions completed by December 31 count for the 2026 tax year. There is no April extension the way there is for IRA contributions.

A few notes:

• A Roth conversion means paying tax on pre-tax dollars now so future qualified withdrawals may be tax-free.

• How much to convert (if any) depends on your whole picture: income, deductions, Medicare considerations, and long-term goals. It’s not a one-size-fits-all rule.

• For people on Medicare, income today can affect premiums later because of IRMAA’s (Income-Related Monthly Adjusted Amount) lookback. A conversion that looks “cheap” in the tax bracket table can still have second-order costs.

• Some retirees also need to weigh newer deduction rules that phase out as income rises. The sticker tax rate doesn’t always tell the full story.

None of this is a recommendation to convert a specific amount or to convert at all. It’s a reminder that the calendar creates a planning window, and windows close. The thoughtful move is usually to model first, then decide, rather than rush in December.

If you’ve been wondering whether a conversion belongs in your plan this year, this is a good month to talk it through.

A Small Office Upgrade

On the practice side, I’ve started using software that takes notes for me during meetings. If we are on a Zoom meeting, you’ll notice it as an additional participant.

When I’m not dividing my focus between listening and typing, I can stay more present with your concerns and questions. And when follow-up items are captured more completely, fewer details slip through the cracks afterward. I believe this is a good investment for us in continuing our efforts to serve you at the highest level.

In Closing

Markets will keep rotating. Tax rules will keep changing. And life will keep interrupting the plans you had for it.

My job isn’t to pretend I can forecast every twist and turn. My job is to stay process-oriented: notice what’s changing, consider year-end decisions while there’s still time, and keep the client conversation clear and straightforward.

Thank you, as always, for your trust.

If you know someone in your circle who feels unsure about year-end tax moves, their investments in this unpredictable market, or simply wants a calmer second opinion on their plan, I would be grateful for an introduction. Referrals from clients remain the most meaningful way this practice grows.

We appreciate you!

All my best,

Garrett

Disclosure:

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

*This information is not intended to be a substitute