The last few months of the year present some of the most valuable opportunities for year-end financial and tax planning. Whether you work with a financial advisor in Boston or manage your own finances, reviewing your financial situation before December 31 can help position you for a stronger start to the new year.

At Sherr Financial Associates (SFA), we encourage clients to view year-end as a checkpoint: a time to assess what’s working, what’s changed, and what needs attention before deadlines pass.

Below, you’ll find common year-end financial concerns we hear from clients, along with practical ways to prepare for the upcoming 2026 tax season and set yourself up for greater financial confidence in the year ahead.

Have you reviewed your financial plan recently?

One of the most overlooked parts of year-end planning is revisiting your overall financial plan. Since life doesn’t stand still, neither should your financial plan. Ask yourself these questions. If you answered yes to any of these questions, take the time to review your short-term and long-term financial goals, savings targets, and investment strategy:

• “Do my goals still reflect my current situation?”
• “Has my income, debt, or lifestyle changed?”
• “Am I still on track for retirement?”

At SFA, we often suggest clients update the following before year-end:

• Income projections and cash flow analysis
• Savings and retirement contributions
• Insurance coverage and estate documents
• Tax withholding and estimated payments
  

Updating your financial plan now helps you enter 2026 with clarity and direction.

Have you made all the deductible retirement contributions you can?

Maximizing deductible contributions to retirement accounts can reduce taxable income while helping you build future savings.

• “What are the 2025 contribution limits for 401(k)s, IRAs, or HSAs?”
• “Can I still make a catch-up contribution before year-end?”
• “Does my employer plan allow after-tax contributions or Roth options?”
  

What to do:

Before December 31, review your contributions to 401(k)s, 403(b)s, and other workplace plans. Traditional IRAs and Roth IRAs typically have a later contribution deadline (April 15), whereas employer-sponsored plans generally close at the end of the year.

If you’re age 50 or older, don’t forget about catch-up contributions, which allow you to contribute extra funds beyond the standard limit. 

If you’re self-employed, consider whether a Solo 401(k) or SEP IRA is a fit for your 2025 income.

A financial advisor in Boston (SFA) can help determine which contribution strategy best aligns with your cash flow and tax situation.

Should you harvest gains or losses before December 31?

Year-end tax strategy often centers around capital gains and losses. The goal is to understand the current state of your investments and determine whether strategic action is warranted before the end of the year.

• “Should I sell investments to offset gains?”
• “Will I trigger a higher tax bracket if I sell now?”
• “How will my investments affect my 2025 tax return?”
  

What to do:

Review your portfolio to identify potential capital gains and losses. Tax-loss harvesting, which involves selling investments at a loss to offset gains elsewhere, can help manage taxable income. Don’t forget about the IRS “wash sale rule,” which prevents claiming a loss if you repurchase the same investment within 30 days.

Talk with an experienced financial advisor in Boston (SFA) who can coordinate with your CPA to evaluate whether realizing gains or losses fits within your broader tax planning strategy.

Are you using all available tax deductions and credits?

As the year comes to a close, it’s wise to look at potential deductions and credits you might be missing. Even minor adjustments made before December 31 can have a significant impact at tax time. Proactive tax planning in Boston can help ensure your year-end decisions align with your income and investment strategy.

• “Can I deduct charitable contributions this year?”
• “What about energy-efficient home upgrades or education credits?”
• “Should I consider a donor-advised fund for charitable giving?”
  

What to do:

If you itemize deductions, review charitable giving, mortgage interest, and medical expenses. Consider bunching deductions, which combine philanthropic donations or expenses into one year to exceed the standard deduction threshold.

Be sure also to review your paycheck withholdings to avoid any surprises in April.

Have you reviewed the performance of your investment portfolio recently?

As market conditions shift, now is a good time to review whether your portfolio still aligns with your goals and risk tolerance.

• “Is my portfolio too conservative or too aggressive for my age?”
• “Do I need to rebalance after this year’s market changes?”
• “How can I improve my diversification going into 2026?”
  

What to do:

Review your portfolio’s asset allocation, performance, and diversification. You may need to rebalance your portfolio, which involves selling assets that have outperformed and reinvesting in those that have lagged to help maintain your target mix.

If you’ve experienced significant life changes or market swings this year, discuss potential adjustments with your Boston financial planner at SFA to keep your investment management strategy aligned with your objectives.

Have you updated your estate and beneficiary documents recently?

Estate planning isn’t just for retirees. Reviewing your documents annually ensures your wishes and designations still reflect your intentions.

Common concerns:

• “Are my beneficiaries up to date?”
• “Do my wills and trusts reflect recent family or financial changes?”
• “Have I reviewed powers of attorney or healthcare directives?”
  

What to do:

Confirm that all account beneficiaries are correct, especially after marriages, divorces, or births. If you’ve had a change in assets, make sure your estate plan accounts for them.

A financial planner in Boston (SFA) can work alongside your estate attorney to coordinate your investment and estate planning decisions for a more organized approach.

Are you prepared for next year’s tax deadlines?

Once January arrives, many tax opportunities close until the following year. The time to prepare is now.

• “When should I gather my tax documents?”
• “Are there moves I can make now to manage 2026 taxes?”
• “Should I adjust my estimated payments for next year?”
  

What to do:

Before year-end, make a checklist of all the tax forms you’ll need: 1099s, W-2s, and statements from investment accounts. Review estimated payments and withholdings to avoid penalties or unexpected bills. Schedule a meeting with your tax and financial advisors early in the year to discuss tax-efficient strategies for 2026.

Do you have the correct insurance coverage?

Insurance needs often change as life evolves. Reviewing your policies annually helps protect against gaps.

• “Do I have enough life or disability coverage?”
• “Should I update my property or liability insurance?”
• “Does my health coverage still fit my situation?”
  

What to do:

Review all of the various insurance policies you have, such as life, health, disability, auto, and homeowner’s. Confirm coverage amounts and update beneficiaries if needed.

If you are nearing retirement, consider evaluating long-term care insurance options and your health coverage under Medicare or employer plans.

Why Partner With Sherr Financial (SFA)?

At Sherr Financial Associates (SFA), our team of financial planners in Boston helps individuals and families coordinate all aspects of their finances, from investment management to tax planning, so that they can enter the new year with organization and confidence in their plan.

If it’s been a while since your last review, consider making year-end your starting point for a more intentional 2026. Connect with us to learn more about our year-end tax planning and investment management services.