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2024 Post-Tax Day Reflection: Planning for Next Year's Taxes Starting Today

April 2024

2024 Post-Tax Day Reflection: Planning for Next Year's Taxes Starting Today

Matt Wagner, CFP®, CTFA
Chief Practice Officer
Trust & Family Office Advisor

Ah, Tax Day. It's the day that rolls around with all the punctuality and cheeriness of a dentist's appointment—inescapable and a little daunting. Yet for the astute, it's not just a date on the calendar but a springboard for future financial finesse. When the dust settles, whether that is now or later, if you filed an extension, what's next? Welcome to the 2024 post-Tax Day reflection—where we handle last year's numbers to optimize the year ahead.

Discover the essential steps in your financial optimization checklist; evaluating your previous results, establishing ambitious tax-saving objectives, and receiving expert advice that matches your financial situation.

Evaluate Current Tax Strategy

The first step is to look in the rear-view mirror.
    • How did last year's tax strategy perform?
    • Were you as tax-efficient as you could have been, or did you face a larger bill than expected?
This can't be simply a glance, but needs a deep-dive analysis.
    • How successful were your tax loss harvesting efforts?
    • Did we capture everything that happened on the return?
    • Did you make any strategic business income decisions?
    • Were there investments that positively or negatively impacted your taxes?
Take the time to meticulously dissect those decisions, considering the nuances of the previous year, for learnings and improvements.

Instead of dwelling on missed opportunities, this reflection highlights areas for improvement and the accomplishments you made. Through comprehensive evaluation, you’re setting the stage for informed decision-making under the spotlight of past performance. Advisors adept at this discipline will collect and review tax returns for every client, providing a report with ideas to apply in the current year.

Setting Goals for the Next Year

In a world where ad hoc financial decisions can lead to missed savings opportunities, setting clear, measurable tax-saving goals is a crucial step. Every transfer of funds, new investment, and estate planning decision needs to be reviewed through a tax planning lens. Whether you're focused on securing a higher after-tax return on investments or reducing the volatility in your adjusted gross income, your objectives need to be specific and achievable.

Financial objectives for the year ahead should align with broader life goals, transfer planning in the estate, charitable giving strategies, or management of cash flow for lifestyle. Each goal should be accompanied by a tax-saving component, creating a seamless financial tapestry that showcases efficient and effective wealth management.

Maximizing Deductions and Credits

Deductions and credits are the hidden gems of tax planning, capable of significantly reducing your tax liability. Are you making the most of every opportunity?

The devil is in the details—whether it’s maximizing contributions to retirement accounts, thinking strategically about your charitable goals, or exploring opportunities under the Qualified Business Income Deduction (QBI).

Strategies for maximizing deductions and credits are not one-size-fits-all. They must be tailored to your unique financial statement and life goals. This is the time for strategic planning—to prepare and position yourself to benefit from every eligible tax-saving avenue.

Estate Planning Considerations

Estate planning is the pinnacle of legacy consideration and an essential element of any long-term tax plan. Shielding wealth from the pinch of the estate tax and ensuring a smooth transition for your heirs requires thoughtful consideration and expert advice. However, given today’s larger exemptions, optimizing the income tax benefits in an estate transfer may likely prove more beneficial for most families than being solely focused on the estate tax. This is a particularly important topic today with the looming expiration of the 2017 Tax Cuts and Jobs Act at the end of 2025. Under current laws, we are in a “use it or lose it” situation.

Your estate may fluctuate in value as assets grow and markets shift. Regular reviews and adjustments to understand what may go through probate, what is taxable in your estate, and which assets will receive a basis step up ensures your plan accurately reflects your wishes and remains tax efficient. In essence, now is the time to plan for an efficient and strategic dispersal of your wealth, understanding both income and estate taxes.

Engaging with Financial Professionals

Tax planning in the complex world of high-net-worth individuals and families is not a solo endeavor. It calls for a dream team—a corps of financial planners, accounting wizards, and legal maestros whose collective knowledge, when combined with accurate and timely data, will reign supreme. Your most valuable asset is this team, firmly grounded in the latest tax codes and financial regulations.

Too often, individuals shy away from securing professional advice, assuming their financial situation is straightforward or that digital tools are sufficient. Other times, they feel this will cost too much. For affluent families, this doesn’t cost, it pays. Personalized advice reigns supreme in the labyrinth of the tax code. The human element is irreplaceable, providing nuanced solutions and a compass to guide your financial voyage. This chance of regret from a hastily made decision declines when you engage a coach and an experienced team.


Tax planning is akin to planting a tree. The best time to start was yesterday; the second-best time is today. By looking back, setting clear goals, maximizing deductions and credits, considering your estate, and engaging with professionals, you are not just planning for next year's tax bill, but for generations of financial success.

The wealth of high-net-worth families and individuals is diverse and complex, necessitating a proactive and vigilant approach to tax planning. It’s about leveraging the past to ensure a greener, more robust financial future.

In the spirit of empowerment and exploration, we encourage you to take these reflections to heart, incorporating them into your tax planning regimen. With each proactive step, you solidify your status as the master of your financial destiny, charting a course through the waters of tax season with confidence and finesse.
Matt Wagner, CFP®, CTFA
Chief Practice Officer
Trust & Family Office Advisor
Matthew "Matt" Wagner is a dedicated advocate for our clients. He values aggregating all financial disciplines for the most effective planning. This holistic approach incorporates investment management, retirement planning, tax mitigation, risk management and estate planning.

DISCLAIMER: This newsletter is intended to provide thought-provoking commentary. The information presented herein has been obtained from and is based upon sources and vendors deemed to be reliable, but may be incomplete. Parkside Financial Bank Trust does not itself endorse or guarantee, and assumes no liability for, the accuracy or reliability of any third party data or the financial information contained herein.

Parkside Financial Bank & Trust does not provide tax, legal, or accounting advice. This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. You should consult your own tax, legal, and accounting advisors before engaging in any transaction. Investments are not insured by the FDIC or any government agency, provide no bank guarantee, are not a deposit and may lose value.

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