It is hard to believe we are approaching the halfway point of 2025. With the 2024 tax season concluded, now may be a good time to evaluate your current year tax situation to help plan for and possibly minimize any end-of-year tax surprises.
Churchill Management’s Tax Awareness Approach
By request, Churchill will have tax discussions with you and your tax preparer to help you prepare for 2025 and beyond. Often, when you meet with your tax preparer to file taxes for the prior year, it may be too late to make changes, as the prior year has already passed. At Churchill Management, we discuss tax awareness concepts, allowing you to plan around the current tax year and possibly mitigate tax surprises.lso be tax-free if used for qualified education expenses.
Taxable Investment Income Awareness
- Working with you and your tax preparer, Churchill is available for ongoing discussions regarding tax implications concerning your portfolio investment income, which may include interest, dividends, and/or capital gains.
- Churchill can also engage in discussion around tax awareness to optimize portfolio drawdowns in retirement.

Minimize Tax Surprises
- Tax calls with you and your tax preparer on your request to discuss the impact of income, capital gains & losses.
- Explore strategies to optimize your federal and state tax brackets by evaluating your estimated taxable income each year.
- Discuss how to possibly mitigate Net Investment Income (NIIT) of 3.8% and potential Medicare premium increases from IRMAA.
- Discuss whether safe-harbor tax planning may help to minimize potential underpayment penalties.
Tax Optimization Considerations
- Roth IRA conversion strategy discussions.
- Develop a plan for unwinding concentrated, low-basis stock / ETF positions.
- Aim to maximize potential tax savings through charitable gifting, which may include Donor Advised Funds (DAFs) and Qualified Charitable Distributions (QCDs).
Talk to your Churchill advisor for more details on mid-year tax considerations.
Summarized by Senior Vice President & Director of Financial Planning: Scott Perkins, MSTax, MBA, CFP®
Reach out to a Churchill advisor at (877) 937-7110 or [email protected] to discuss how to maximize your retirement accounts.
Financial Planning Services
Churchill provides financial planning services to clients that specifically engage Churchill for that service. The planning can include defining goals, designing a plan, assisting with implementing the plan, and evaluating and adjusting the plan over time, at the request of the client. The financial planning includes advice regarding securities investing and may include discussions of a client’s tax, insurance, employee benefits, estate planning, and other issues. Churchill, however, does not provide legal, insurance, employee benefit, estate planning, tax or accounting advice, and the client must rely on legal, insurance and accounting professionals for that advice and documentation. No guarantee can be made as to increasing returns to an investment portfolio as a result of financial planning.
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