With summer winding down and kids returning to school with the hope of stability (sanity, for caretakers!) and routine, we find ourselves at a natural seasonal inflection point. We’re on the cusp of glorious fall weather, and the busy uptick of the holidays will be here before we know it. As we collectively catch our breaths, now is a fantastic time to Pause. Reflect. And Realign.
What have we learned? How have we grown over the last 9 months? How do we want the rest of the year to look for ourselves and our families? What if we could ___?
As we ponder our spiritual, physical, and emotional milestones and dreams, it’s only natural we consider our financial goals as well. As part of the fall seasonal reset, here’s how to approach your fall financial checkup:
Revisit your goals
Life doesn’t stand still. Maybe you welcomed a new child or grandchild this year, changed jobs, or shifted your priorities. Goals that made sense in January may feel outdated by September.
Ask yourself:
-
- Am I still saving for the right things that matter to me and my loved ones?
-
- Do my retirement contributions match my long-term vision? Accounting for bonuses, do I have bandwidth to increase my contributions through the end of the year?
-
- Has my risk tolerance for investments shifted because of life changes?
If the answer to any of these is “maybe” or “not sure,” it’s worth adjusting course now. Consider updating your cash flow spending plan to get on track with where you want to be today AND tomorrow. Meet with your financial advisor to rebalance your investment portfolio (as needed) and review your overall financial plan.
Check your tax picture
Taxes…you can’t live with them, and the IRS can’t live without them. By planning ahead now, long before the April rush, you can make adjustments without the stress. Rope in your CPA and financial advisor to review withholdings or estimated payments, potential deductions, and even potential for Roth conversions. After all, we’ll give Uncle Sam what’s due, but there’s no reason to leave him a tip!
Here are some key dates to remember:
-
- Estimated quarterly tax payments are due September 15, 2025.
-
- For those who filed an extension, you have until October 15, 2025 to file your 2024 return.
-
- Tennessee residents also qualify for disaster tax relief, and the 2024 tax filing deadline was extended to November 3, 2025. You can still make 2024 IRA contributions through the extended deadline.
Plan for year-end giving and gifting
Charitable donations and financial gifts often spike in December — but thoughtful planning in September means you can give with intention rather than in a last-minute rush.
The numbers matter, of course – donating appreciated securities, annual exclusion gifts ($19,000 per person in 2025), or qualified charitable donations (QCDs) (for those 70 ½ or older) can all carry meaningful tax benefits. Beyond the dollars, giving is about aligning your financial life with your core values.
Create space to ask:
-
- What causes mean the most to me and my loved ones this year?
-
- How can I wisely steward my resources to be a blessing to others?
-
- Would I rather support a few causes deeply, or spread support across many organizations?
Build an impactful financial plan that allows you to live generously and deliberately, walking out your purpose.
A fall survey isn’t about perfection. It’s about awareness and small adjustments that build momentum. By taking stock now, you’ll head into the holidays and the new year with less stress and more confidence and clarity. Savor the downtime while you sip your favorite fall beverage. You’re doing great, and you’re never alone! The best is yet to come.
Note for clients: Due to high demand, Benchmark requests that all gifting requests are submitted by the first week in December, so we have time to process everything before the December 31 tax deadline.
Rebalancing a portfolio may cause investors to incur tax liabilities and/or transaction costs and does not assure a profit or protect against a loss.
A Roth IRA conversion—sometimes called a backdoor Roth strategy—is a way to contribute to a Roth IRA when income exceeds standard limits. The converted amount is treated as taxable income and may affect your tax bracket. Federal, state, and local taxes may apply. If you’re required to take a minimum distribution in the year of conversion, it must be completed before converting.
To qualify for tax-free withdrawals, you must generally be age 59½ and hold the converted funds in the Roth IRA for at least five years. Each conversion has its own five-year period, and early withdrawals may be subject to a 10% penalty unless an exception applies. Income limits still apply for future direct Roth IRA contributions.
