Tax Day is Over - Now the Real Strategy Begins

For most, April 15 marks the end of tax season. But for successful individuals and families, it should mark the beginning of the next — and arguably most valuable — phase of tax planning. If your financial world includes business income, private investments, real estate, or charitable giving, now is the time to step back, evaluate, and strategize.

At Buttonwood Financial Group, we believe the most impactful tax moves aren’t made at the last minute — they’re made when there’s still time to think clearly and act with intention.

Use Your Return as a Roadmap

Before you file your 2024 tax return to the archives, consider what it reveals. Your return is more than a compliance exercise — it’s a diagnostic tool. From gaps in efficiency to missed opportunities, a close review can uncover blind spots that deserve attention. Were you overly concentrated in income-producing assets? Are your charitable deductions aligned with your broader giving strategy? Did you overpay because key decisions weren’t made early enough? These are the types of questions that can lead to meaningful adjustments going forward.

Why Early Planning Matters More Than You Think

It’s tempting to wait until year-end to focus on taxes — but for high-net-worth families, that can be too late. The truth is, many of the details that shape your tax picture don’t become fully clear until Q4. K-1s from private investments often aren’t finalized until late in the year. Business owners may not know their total revenue until Q4. Executives might still be waiting on clarity around bonuses or deferred compensation.

However, by planning ahead now — in Q2 or Q3 — you give yourself the time and flexibility to act once those final numbers fall into place. It’s about setting the stage so when Q4 arrives, you're not scrambling. You’re executing.

Don’t Miss the Window for Opportunity

Some of the most effective tax strategies take time to implement and are highly dependent on market conditions and income levels. For example, gifting during market downturns can transfer significant value to future generations — but those opportunities vanish quickly once markets rebound. Waiting until December to establish a dynasty trust or make a strategic gift could mean missing the window entirely.

Roth conversions are another area where timing is everything. In lower-income years — or when the market pulls back — converting traditional retirement assets to Roth can be a smart move. It’s a way to lock in long-term tax-free growth, especially when you can “fill up” lower tax brackets and keep the tax cost manageable.

Even tax-loss harvesting, which many investors reserve for December, can be far more effective when done throughout the year. Markets move fast — what feels like a loss in April may not be there by year-end. Taking a proactive approach can open doors to better rebalancing and overall tax efficiency.

And if charitable giving is a core part of your wealth plan, it’s worth aligning that strategy well before your CPA is buried in year-end deadlines. Whether it’s funding a donor-advised fund, contributing appreciated stock, or coordinating giving across generations, thoughtful planning leads to more impact — and less stress.

The Power of Integration

Tax strategy shouldn’t be an afterthought. It should be built into every element of your financial life. At Buttonwood, our comprehensive approach brings together your tax, legal, and investment strategies to make sure every move works in concert. That means coordinating with your CPA on income planning, partnering with your attorney on entity structure or legacy design, and aligning your investment strategy with tax-conscious execution — from municipal bonds to asset location and beyond.

This is where true wealth preservation happens. Not in silos, and not in a rush.

Let’s Talk Strategy Before It’s Too Late

If your 2024 return is already filed, now is the time to pause and reflect. What worked? What didn’t? What can still be done this year to improve your long-term financial picture?

Our Team is ready to guide you through a focused session to align your strategy with what matters most to you. Together, we’ll identify opportunities, avoid surprises, and prepare for what’s ahead.

Schedule your conversation with one of our Lead Advisors today — and let’s get ahead of 2025, together.