By Bobby Reamer, MBA, CEPA®, CFP® | Founding Partner, Keel Financial Partners
September often brings a natural opportunity to get organized. In financial planning, that can be a useful time to review key items while there is still time to consider options before year-end.
Year-end planning is not about scrambling to fix everything at the last minute. It is about taking stock of your current situation and identifying planning opportunities that may be worth discussing before certain deadlines pass. Some strategies require time, coordination, or additional analysis, so reviewing them earlier in the fall can be helpful.
Here are several areas worth reviewing before year-end.
Where Does Your Tax Position Stand?
The single most useful thing you can do in September is take stock of where your tax situation stands for the year. That means looking at your year-to-date income, understanding what bracket you are likely to land in, and identifying any moves worth making before December 31.
Estimated tax payments. If you are self-employed, have significant investment income, or receive business distributions, your third quarterly estimated payment is due September 15. Confirming that your payments are on track avoids a surprise balance due and potential underpayment penalties in April.
Capital gains and tax-loss harvesting. If you have taxable investment accounts, September and October are a good time to review your unrealized gains and losses. Tax-loss harvesting can meaningfully reduce your tax bill when done thoughtfully, but the window is best used early rather than in a December rush.
Roth conversion planning. For clients who expect to be in a lower tax bracket this year than in future years, a Roth conversion moves money from a pre-tax retirement account into a Roth, paying taxes now in exchange for tax-free growth and withdrawals later. The conversion needs to be completed by December 31. September is the right time to run those numbers.
Are Your Retirement Contributions on Track?
The 401(k) contribution limit for 2026 is $24,500 for those under 50, with an additional $8,000 catch-up contribution available for those 50 and older. Those aged 60 to 63 may contribute an additional $11,250 under the SECURE 2.0 super catch-up provision. If you are not on pace to reach your limit by year-end, now is the time to increase your contribution rate.
For business owners, the calculation is more complex. SEP-IRA, Solo 401(k), and defined benefit plan contributions each have their own rules, limits, and deadlines. If you have not yet reviewed your retirement contribution strategy for the year, that conversation should happen in the next few weeks.
Review Your Insurance Coverage
Open enrollment for many employer health insurance plans falls between October and December. Before auto-renewing last year’s coverage, it is worth taking fifteen minutes to confirm that your current plan still fits your situation.
Beyond health insurance, fall is a good time to review life, disability, and umbrella coverage as well. Has your income changed significantly? Have you added a dependent, purchased a home, or started a business? Any of these may mean your current coverage is no longer adequate.
Long-term care insurance is worth a dedicated conversation if you have not yet evaluated it. Premiums increase with age, and the window to qualify at favorable rates narrows over time.
Update Your Estate Documents and Beneficiary Designations
Estate documents have a way of falling behind life. A will drafted before a divorce, beneficiary designations that still name a former spouse, a power of attorney that names someone who has since passed away. These are things we see regularly.
Fall is a practical time to do a quick audit. Pull your will, your trust documents if applicable, and your beneficiary designations on retirement accounts, life insurance, and financial accounts. Confirm that everything still reflects your current wishes and the current people you trust.
Charitable Giving Strategy
If charitable giving is part of your financial life, the last quarter of the year is when the planning matters most.
Qualified charitable distributions allow individuals over 70½ to donate directly from an IRA to a qualified charity, satisfying required minimum distributions without the donated amount counting as taxable income. Donor-advised funds allow you to make a deductible contribution now and direct grants to charities over time. Appreciated securities donated directly to a charity avoid capital gains tax entirely.
Each of these has specific rules and timing requirements. The sooner these conversations happen, the more options are available.
Your Fall Financial Checklist
Tax planning
- Confirm Q3 estimated payment made by September 15
- Review year-to-date income and projected tax bracket
- Evaluate tax-loss harvesting opportunities in taxable accounts
- Model Roth conversion if applicable
Retirement
- Confirm 401(k) contributions on track to hit annual limit
- Review business owner retirement plan contributions and deadlines
- Reassess savings rate against current goals
Insurance
- Review health insurance options during open enrollment
- Confirm life, disability, and umbrella coverage is still adequate
- Evaluate long-term care insurance if not yet in place
Estate and legal
- Review will and trust documents for needed updates
- Confirm beneficiary designations on all accounts
- Update power of attorney and healthcare proxy if needed
Charitable giving
- Review giving strategy for the year
- Consider QCDs, donor-advised funds, or appreciated securities
- Coordinate with advisor and CPA before year-end
The Bigger Picture
Year-end planning is not about perfection. It is about reviewing whether the decisions you make between now and December 31 remain aligned with your broader financial goals, tax circumstances, and family needs.
If you would like to walk through this checklist with us and make sure nothing is falling through the cracks, we would be glad to set aside time to do that.
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Disclosures
The opinions voiced in this material are for general information only and not intended to provide specific advice or recommendations for any individual.
Financial planning is a tool intended to review your current financial situation, investment objectives and goals, and suggest potential planning ideas and concepts that may be of benefit. There is no guarantee that financial planning will help you reach your goals.
This information is not intended to be a substitute for individualized tax advice. We suggest that you discuss your specific tax situation with a qualified tax advisor.
Artificial intelligence (“AI”) tools have been used to assist with drafting, formatting, summarization, or editing this material. Any AI-assisted content has been reviewed by Winthrop Wealth prior to use. AI tools are not used to provide personalized investment advice, recommendations, or individualized financial planning analysis.
