By Resurgent Financial Advisors
October is a bit of a pivot point. The leaves start turning, the holidays peek around the corner, and the pace of life seems to pick up. It is also the perfect time for proactive financial planning. Many year-end strategies lose their impact if they are left to December, and several require thoughtful execution to avoid unintended consequences.
For those nearing retirement or managing significant wealth, these final months of the year can either be a quiet opportunity or a missed window. The difference is usually preparation.
Here is a practical and powerful checklist to help clients, families, and advisors finish the year financially strong.
Review Your Tax Picture Before It Gets Filed Away
Tax season feels far away in October. That is why now is an excellent time to engage with your advisor and CPA to model this year’s projected tax situation. Waiting until April means reacting to what already happened. Doing it now allows for strategy.
Look for opportunities to accelerate or delay income, realize gains or losses, and adjust withholdings. If your income was unusually high or low this year, that alone could change the calculus on which moves make sense.
A mid-fall tax projection often reveals more room for planning than people expect.
Consider Partial Roth Conversions
The fourth quarter is a strategic time to evaluate Roth conversions. Whether retired or still working, this window allows clients to move funds from tax-deferred accounts into tax-free status. This is especially useful in years where income has dipped or where large deductions were taken earlier in the year.
Unlike contributions, Roth conversions have no income limits or deadlines beyond the calendar year. Still, they need to be coordinated carefully. Converting too much can trigger unnecessary tax. Converting too little may miss a rare opportunity.
The sweet spot is different for everyone. Modeling helps find it.
Harvest Gains and Losses Strategically
Many investors think of tax-loss harvesting as a December task. By then, it is often too late to take full advantage of volatility or account for the 30-day wash sale rule.
Losses harvested in taxable accounts can offset realized gains or reduce ordinary income up to $3,000 per year. Gains can also be “harvested” intentionally in low-income years to reset cost basis without increasing tax liability.
Markets move quickly. Starting this process in October gives clients time to make decisions without pressure.
Maximize Charitable Giving with Tax Efficiency
Charitable intent is noble. Charitable strategy is powerful.
For those inclined to give, appreciated securities are often more tax-efficient than cash. Donor-Advised Funds allow individuals to make one large contribution this year, receive the deduction immediately, and distribute the funds over time.
Qualified Charitable Distributions (QCDs) from IRAs are another tool for clients over age 70½. These transfers go directly to qualified charities, satisfy Required Minimum Distributions (RMDs), and avoid adding to taxable income.
Each strategy carries different benefits. Aligning giving with tax planning turns generosity into optimization.
Use Your FSA and Evaluate HSA Contributions
Flexible Spending Accounts (FSAs) often have use-it-or-lose-it rules. Reviewing balances now can help ensure the funds do not disappear unused. Some plans offer a small rollover or grace period, but not all.
Health Savings Accounts (HSAs), on the other hand, remain one of the most tax-advantaged tools available. Contributions are tax-deductible, growth is tax-deferred, and qualified withdrawals are tax-free. Maximizing HSA contributions before year-end can be especially helpful for those looking to reduce adjusted gross income or build reserves for future healthcare costs.
October is a good month to ensure contributions align with income, benefit selections, and long-term goals.
Confirm RMDs Are On Track
Missing a Required Minimum Distribution can result in penalties of up to 25 percent of the amount not withdrawn. Even for those with automatic withdrawals set up, it is important to confirm that distributions are accurate and complete.
This is particularly important for those who turned 73 this year or inherited accounts with RMD rules. The SECURE Act changed several timelines and created some confusion, so double-checking is wise.
If charitable giving is part of the plan, QCDs may also fulfill the requirement while reducing taxable income.
Align Your Plan with Life Changes
A lot can happen in a year. People move. Businesses change. Families grow. Goals shift. The financial plan should evolve accordingly.
October is a valuable moment to revisit the big picture. Has anything changed in your life that your portfolio, insurance, or estate plan should reflect? Are your beneficiaries correct? Do your investment allocations still reflect your risk tolerance and timeline?
End-of-year reviews are not just about numbers. They are about alignment. The more aligned your financial life is, the more resilient it becomes.
Why October Matters More Than You Think
Clarity and momentum are rarely built in the final days of the year. They come from decisions made early, with enough time to adjust, align, and act intentionally. October offers that breathing room. It is a window that rewards proactive planning and thoughtful coordination.
For individuals nearing retirement, managing complex wealth, or leading others through these transitions, now is the time to get ahead of the curve. Not just to meet deadlines, but to move into the next year with greater confidence.
At Resurgent, we believe smart financial strategy should never feel rushed. It should feel planned, purposeful, and personal. Let’s make the most of this season – before the calendar makes the decisions for you.
