The tax code is designed for options. Incentives. Choices. It is not accidental. Lawmakers use it to encourage certain behaviors and discourage others, whether that’s investing, hiring, building, donating, or deferring. And if there is one group of professionals who should be fluent in these options, one would think it would be the tax firm you work with.
A few years ago, I sat with a couple who had just crossed into the top federal income tax bracket. They had done everything “right.” Long careers, discipline, delayed gratification. This was not inherited wealth. It was earned. When they met with a local CPA to review their return, the reaction was casual and dismissive. You did well. You’re going to owe a lot. Just pay the taxes. Roughly 40% of their income headed to the federal government. End of discussion.
The comment landed flat. It felt deflating. And I understood exactly why, because years earlier, I had heard almost the same thing myself.
I was not born with a silver spoon. I was hungry. Thirsty for knowledge. I learned through practical application, mistakes, mentors, and a relentless desire to understand how money actually works.
When we stumbled into the top income tax bracket, I expected the conversation to become more sophisticated. Instead, I got the same laissez-faire answer: just pay it.
That moment stuck with me. Not because I object to paying taxes. Most high earners don’t. What they object to is paying more than necessary simply because no one bothered to explore the alternatives. The tax code is not binary. It is not pay or don’t pay. It is a spectrum of timing, structure, and strategy.
To be clear, I am not a CPA. I do not prepare tax returns. That’s not my lane. But I do spend an enormous amount of time helping clients understand how decisions today affect taxes tomorrow and working with many tax professionals across the state.
And there is a massive difference between compliance (filing a return), glorified turbo tax and planning.
Most tax professionals are excellent at documenting what happened last year. They are historians. They record income, deductions, and credits, then file the paperwork. That work matters. But if you have never had a conversation about what happens at future dates in your life, retirement, the sale of a business, the sale of real estate, Required Minimum Distributions, Social Security elections, or legacy goals, then what you have is not a strategic adviser. You have a data-entry bean counter.
Planning is where value lives
We talked with this couple about levers they had never been shown. Not loopholes. Not gimmicks. Just tools that already exist. Paying children legitimately through a family business. Utilizing 529 plans to fund education in a tax-advantaged way. Maximizing retirement plans not just for deferral, but for future flexibility. Identifying low-tax years where potential Roth conversions make sense instead of blindly deferring everything until Required Minimum Distributions force the issue.
We discussed the difference between liquidating assets and using collateralized loans. Selling appreciated assets triggers taxes. Borrowing against them, when appropriate, can provide liquidity without immediate tax consequences. Cash flow planning matters. So does understanding how and when Social Security should be elected, and how other income sources interact with those benefits over time.
Real estate entered the conversation as well. Depreciation. Cost segregation studies. Fractional ownership. Delaware Statutory Trusts. 1031 exchanges. Each of these tools exists because the tax code intentionally encourages capital investment. Used correctly, they can materially change outcomes. Ignored, they leave money on the table.
The point is not that everyone should do all of these things. The point is that someone should be helping you see them, model them, and decide which ones fit your life. That requires forward-looking analysis, scenario planning, and an understanding that taxes are often the single largest expense a household will ever face.
Seek out a formal, written plan forward and be very happy to pay for it. Strategic tax planning is not free, and it shouldn’t be; gladly pay for it.
But that investment routinely saves thousands, sometimes hundreds of thousands, or millions over a lifetime of dollars over the years ahead. Just as importantly, it provides peace of mind. Confidence replaces frustration.
And let’s be honest about the future. The professionals whose entire value proposition is “just pay your taxes” are on borrowed time. Robots can already handle compliance faster, cheaper, and with fewer errors. AI doesn’t get tired. It doesn’t shrug. It doesn’t dismiss curiosity.
The winners going forward will be advisers who can interpret, integrate, and guide. Who understand that the tax code is not a bill to be endured, but a system to be explored and navigated. Nothing gray about; taxes are inevitable. Overpaying is optional. And the difference lies in whether you are looking backward or planning forward.
Evan R. Guido is founder of Aksala Wealth Advisors LLC, a 2018 Forbes Next-Gen Advisors List Member, and heads a team of financial strategists for clients who consider themselves the “Millionaire Next Door.” He can be reached at 941-500-5122; eguido@aksalawealth.com; 6260 Lake Osprey Drive, Lakewood Ranch, FL 34240. Read more at finance.heraldtribune.com/category/ask-guido. Securities offered through Cetera Wealth Services LLC, a member FINRA/SIPC. Advisory services offered through Cetera Investment Advisers LLC, a registered investment adviser. The views and opinions in this article are those of Evan R. Guido and not of Cetera or its subsidiaries. These opinions are not intended to predict or depict performance of any investment and are subject to change. These views should not be construed as a recommendation to buy or sell any securities and are purely for education and entertainment.
This article originally appeared on Sarasota Herald-Tribune: Are you overpaying your taxes? It’s optional | Retire on Track
Reporting by Evan Guido, Special to the Herald-Tribune / Sarasota Herald-Tribune
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