Your Fall Financial Health Checklist

Oppenheimer & Co. Inc. September 29, 2025

As summer officially ends, fall provides a window to realign your financial plan with your future goals. Now is the time to prep for the upcoming holidays, tax season, and be sure you have your agenda mapped out for 2026. Below is a checklist of 10 strategies that will help you set yourself up for financial success.

1. Review and Break Down Your Expenses

Start by tracking your recurring monthly expenses to get a clear picture of your spending habits. Identifying areas where you can make small, consistent cuts will help you redirect funds toward savings, debt reduction, and future goals.

2. Make a Debt Payoff Plan

Eliminating high-interest debt now can give you more flexibility and financial freedom later, especially in retirement. Explore options to make your debt more manageable, including:

  • Refinancing private student loans or consolidating federal ones
  • Taking out a credit card consolidation loan
  • Entering a debt management program

3. Maximize Retirement Contributions

Fall is a great time to review your retirement savings strategy. Are you contributing enough to your 401(k), traditional IRA, or Roth IRA? If you’re over 50, don’t forget about catch-up contributions. Even small increases today can significantly impact your income in retirement.

4. Rebalance Your Investment Portfolio

Your portfolio should be aligned with your risk tolerance, income needs, and long-term financial goals. Fall is a smart time to:

  • Reassess your asset allocation
  • Evaluate risk exposure in today’s market
  • Prioritize diversification and income-generating investments

A balanced, well-structured portfolio helps protect against volatility while supporting sustainable growth.

5. Get Ahead on Tax Planning

Don’t wait until December to review your taxes. Now is the time to implement tax-efficient strategies that can reduce your liabilities and boost your savings. Consider:

  • Roth IRA conversions
  • Qualified charitable distributions
  • Harvesting capital losses or gains

Consulting with a tax advisor can help you tailor these strategies to your situation.

6. Incorporate Charitable Giving

Fall is an excellent season to reflect on your philanthropic goals. Giving strategically can maximize your impact and offer potential tax advantages. Options include:

  • Donor-advised funds
  • Charitable trusts
  • Direct gifting of appreciated assets

A charitable giving plan ensures your values and legacy live on well beyond your lifetime. Learn more about charitable giving strategies here.

7. Build or Replenish Your Emergency Fund

If you haven’t already, aim to keep 3–6 months’ worth of living expenses in a liquid, accessible savings account. An emergency fund provides confidence and a buffer against unexpected events like job loss or medical bills. Read more about emergency preparedness here.

8. Update Your Estate Plan

Life changes. Major events like marriage, divorce, children, and property acquisitions can all impact your estate plan. Take time to:

  • Review your will and trusts
  • Update beneficiary designations
  • Ensure powers of attorney and healthcare proxies are current

Work with a qualified estate planning attorney and financial advisor to make sure your plan reflects your current wishes and assets. Learn more about wills and trusts here.

9. Promote Financial Literacy in Your Family

One of the best ways to create a lasting financial legacy is by educating your loved ones. Encourage open conversations about budgeting and saving, investing basics, and responsible credit use. Helping the next generation understand wealth management fosters independence and long-term success. Read about effective strategies for teaching your kids financial literacy here.

10. Stay Flexible and Informed

The economic and regulatory landscape is always evolving. Stay informed about changes in tax laws, interest rates, and market conditions. Regularly revisiting your financial plan ensures it remains relevant and aligned with your goals.


Fall is a strategic season to reassess, plan, and build financial resilience. By following this checklist, you can close out the year with confidence and position yourself for a strong start in 2026.

Speak with an Oppenheimer Financial Professional today to learn more.

DISCLOSURE

The information set forth herein has been derived from sources believed to be reliable but is not guaranteed as to accuracy and may change without notice.

Oppenheimer Transacts Business on all Principal US Exchanges and is a Member of SIPC 8397857.1