Advanced Planning: Looking Beyond This Year’s Tax Return

As a CFP® professional, one of the most valuable services we provide our clients isn’t simply picking investments or reviewing accounts—it’s helping them make smart financial decisions over time. True financial planning is about looking years, even decades, into the future—taking The Long View—and asking one simple question:

How do we help you keep more of what you’ve earned over your lifetime?

This is where advanced planning comes in.

It’s Not Just About This Year

Most people naturally focus on what’s right in front of them—their income this year, the taxes they’re paying now, and whatever feels most immediate. But some of the best planning opportunities show up during transitions, especially around retirement.

We recently worked with a couple in their first full year of retirement. Like many retirees, their situation had changed quite a bit. Their income had dropped significantly, they weren’t taking Social Security yet, and they expect both Social Security and pension income down the road. They’ve also built up substantial retirement savings in IRAs.

On paper, it would’ve been easy to say their tax situation was simple.

In reality, it was a great opportunity to plan ahead.

Looking Ahead to Future Tax Changes

While their income is low today, it likely won’t stay that way.

Over time, Social Security and pension income will increase their taxable income. Required Minimum Distributions, or RMDs, will eventually begin, and their retirement accounts will likely keep growing. Without a plan, they can push themselves into higher tax brackets later, meaning more taxes over time.

Using a Lower-Income Window Wisely

Instead of focusing just on this year, we zoomed out:

How can we use these lower-income years to improve their tax picture over the next 20-plus years?

That led to a few key strategies.

Roth IRA Conversions

We started looking at partial Roth conversions each year—moving money from a traditional IRA into a Roth, which is tax-free. Yes, that creates taxable income today, but when done thoughtfully, and with expertise from a CPA, it can be an effective way to take advantage of lower tax brackets now and reduce taxes later.

Done proactively, it can shrink future RMDs and build a pool of tax-free assets. The key, though, is figuring out how much to convert each year.

Coordinating With Their CPA

Rather than guessing on the right amount, we brought in their CPA to run projections. Together, we looked at different scenarios—what each would mean for taxes today and how their income might evolve over time.

That kind of coordination helps make sure every decision is intentional.

Donor Advised Fund Strategy

They also had highly appreciated stock in a taxable account. Rather than gifting cash to their chosen charities, we recommended contributing those shares to a Donor Advised Fund.

That allowed them to get a large charitable deduction to help offset Roth IRA conversions, avoid capital gains taxes, and still support the charities they care about over time. In other words, they were able to give the way they already wanted to—just in a more efficient way.

How the Strategies Work Together

Each of these strategies works on its own, but the real value is how they fit together. Roth conversions reduce future taxable income, the projections from their CPA help guide decisions along the way, and the Donor Advised Fund adds flexibility while helping offset taxes.

The result isn’t just better this year—it’s a more efficient plan over time.

A lot of tax planning is focused on what you owe today. We’re thinking more about how it plays out over the long run.

Why Advanced Planning Matters

For many retirees, taxes are among their largest expenses. The difference is, unlike market returns, taxes are often something you can plan around.

The years between retirement and required distributions are one of the biggest opportunities to do that, and they’re often overlooked.

Taking The Long View

Good planning isn’t about making things more complicated; it’s about being thoughtful with each decision. When you take the time to look ahead, you can reduce taxes over time, stay flexible, and keep your plan aligned with what matters most.

If you’re approaching retirement, or already there, it’s worth asking: are we simply reacting to what’s happening today, or strategically planning for what the next 20 years could look like?

That’s what we mean by taking The Long View and we’d love to help you and those you care about do the same.

July 2026

LPL Financial and Allen & Company do not offer tax advice or services.

Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual.

Traditional IRA account owners have considerations to make before performing a Roth IRA conversion. These primarily include income tax consequences on the converted amount in the year of conversion, withdrawal limitations from a Roth IRA, and income limitations for future contributions to a Roth IRA. In addition, if you are required to take a required minimum distribution (RMD) in the year you convert, you must do so before converting to a Roth IRA.