As the year winds down, it’s the perfect time to get proactive about your taxes. At Tavola Group, we know that waiting until tax season often leads to missed opportunities, overlooked deductions, and unnecessary stress. Preparing now can save you money, streamline your filings, and give you peace of mind. In this article, we’re walking through a comprehensive year-end tax planning checklist to help you finish the year strong.

 

Review Your Income and Expenses

The first step in any effective year-end tax plan is to review your income and expenses. Look at what you’ve earned so far and compare it to previous years. Have you exceeded projections, or were there slow months that might impact your deductions?

Tracking your expenses carefully throughout the year ensures that nothing is missed. From business-related costs to medical expenses, charitable contributions, and mortgage interest, every detail counts. Accurate records make it easier to identify deductions and credits that can reduce your taxable income.

 

Harvest Tax Losses

If you have investments in taxable accounts, year-end is a good time to consider tax-loss harvesting. This strategy involves selling investments that have declined in value to offset gains elsewhere in your portfolio.

We advise clients to approach this carefully, balancing the potential tax savings with their overall investment goals. When done correctly, tax-loss harvesting can help reduce capital gains taxes and improve your after-tax returns.

 

Consider Charitable Giving

Year-end is also a popular time to make charitable contributions. Not only does giving support causes you care about, but it can also provide deductions that reduce your taxable income. Whether through cash donations, appreciated assets, or donor-advised funds, there are multiple ways to maximize the tax benefits of giving.

We encourage planning these contributions strategically. Timing and documentation are key to ensuring you claim the maximum allowable deduction.

 

Review Itemized Deductions vs. Standard Deduction

It’s important to assess whether itemizing deductions is still beneficial for your situation. If your total itemized deductions—like mortgage interest, medical expenses, and charitable contributions—exceed the standard deduction, itemizing can save you money.

We help clients analyze their current deduction situation and identify which expenses can be accelerated into the current tax year to optimize savings.

 

Assess Estimated Tax Payments

For self-employed professionals or anyone with income not subject to withholding, reviewing estimated tax payments is essential. If you’ve underpaid throughout the year, making a final payment before year-end can help reduce penalties and interest.

We often work with clients to calculate whether an additional payment can save money in the long run, and to ensure compliance with IRS rules.

 

Plan for Major Purchases and Business Expenses

If you’re a business owner, consider timing purchases or investments strategically. Buying equipment, software, or other business assets before year-end may allow you to take advantage of Section 179 or bonus depreciation deductions.

We recommend reviewing upcoming expenses and planning purchases so that they align with both your business needs and tax strategy. Timing can make a big difference in how much you can deduct.

 

Organize Your Documentation

A well-organized set of documents is critical for year-end tax planning. Collect receipts, statements, and records for all deductible expenses, charitable contributions, and investments. If you work with a tax professional, having everything organized will make their work faster and more accurate, reducing errors and stress.

At Tavola Group, we guide clients in setting up simple yet effective systems to keep their records in order, ensuring they’re prepared for both year-end planning and eventual tax filing.

 

How to Get Ahead with Tavola Group

Year-end tax planning is your chance to take control of your finances and reduce your tax liability before the year closes. By reviewing your income and expenses, maximizing retirement contributions, harvesting tax losses, and making strategic charitable contributions, you can create meaningful savings and set yourself up for a stronger financial position in the year ahead.

It’s also important to evaluate whether itemizing deductions or taking the standard deduction is more beneficial, review your estimated tax payments, and time major purchases or business expenses strategically. Keeping organized documentation throughout this process helps ensure a smooth tax filing experience—and protects you in the event of an IRS inquiry.

At Tavola Group, we help clients turn these steps into a clear, actionable plan. Our year-end tax strategies are designed to minimize liability, maximize savings, and keep everything organized from start to finish. Whether you’re self-employed, a business owner, or an investor, taking a proactive approach now can save you both stress and money later.

Don’t wait until tax season to get organized—start now and make the most of every opportunity. We’ll help you build a tailored year-end strategy that aligns with your goals, reduces your tax burden, and sets you up for long-term success.

 

Book a Free Tax Planning Review >

See how much you could save and start the new year with confidence and clarity.

 

Download the Free Year-End Tax Planning Checklist (PDF) >

Use our simple checklist to stay organized, capture every deduction, and finish the year strong.