Nothing Grey About Paying Taxes
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 percent 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.
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 advisor. You have a tax professional only.
Planning is where the 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 could 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 could be beneficial over the years ahead. Just as importantly, it provides confidence. 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.
Financial advisors who can interpret, integrate, and guide may be a better choice. Who understand that the tax code is not a bill to be endured, but a system to be explored and navigated. Nothing grey about, taxes are inevitable. Overpaying is optional. And the difference lies in whether you are looking backward or planning forward.
Evan R. Guido, Senior Wealth Advisor, is the Founder of Aksala Wealth Advisors LLC, a 2026 Forbes Best in State Wealth Advisor, a 2018 Forbes Top Next-Gen Advisors award recipient. Evan heads a team of financial strategists for clients who consider themselves the “Millionaire Next Door.” He can be reached at 941-500-5122 Aksala.com eguido@aksalawealth.com 6260 Lake Osprey Dr. Lakewood Ranch, FL 34240. Securities offered through Cetera Wealth Services, LLC member FINRA/SIPC. Advisory Services offered through Cetera Investment Advisers LLC, a registered investment adviser. Cetera is under separate ownership from any other named entity. The views and opinions presented in this article are those of Evan R. Guido and not of Cetera or its subsidiaries. These opinions are based on Evan’s observations and research and are not intended to predict or depict performance of any investment. These views are subject to change based on subsequent developments. Information is based on sources believed to be reliable; however, their accuracy or completeness cannot be guaranteed. These views should not be construed as a recommendation to buy or sell any securities and purely for education and entertainment. Past performance does not guarantee future results. The Top Next Gen list includes 250 rising advisors who help manage over $490 billion in client assets. Each advisor was nominated by their firm, then vetted and ranked by SHOOK Research. The rankings, developed by SHOOK Research, are based on an algorithm of qualitative criterion, mostly gained through telephone and in-person due diligence interviews, and quantitative data. Those advisors who are considered have a minimum of four years' experience and the algorithm weighs factors like revenue trends, assets under management, compliance records, industry experience and those that encompass the highest standards of best practices. The Forbes ranking of Best-In-State Wealth Advisors, developed by SHOOK Research, is based on an algorithm of qualitative data, rating thousands of wealth advisors with a minimum of seven years' experience and weighing factors like revenue trends, assets under management, compliance records, industry experience, and best practices learned through telephone and in-person interviews. Portfolio performance is not a criteria due to varying client objectives and lack of audited data. Neither Forbes nor SHOOK receive a fee in exchange for rankings. Listings in these publications and/or awards are not guarantees of future investment success. These recognitions should not be construed as endorsements of the advisor by any clients. No compensation was provided directly or indirectly by the recipient for participation or in connection with obtaining or using these third-party ratings or award.
Investors should consider the investment objectives, risks, charges and expenses associated with municipal fund securities before investing. This information is found in the issuer’s official statement and should be read carefully before investing.
Investors should also consider whether the investor’s or beneficiary’s home state offers any state tax or other benefits available only from that state’s 529 Plan. Any state-based benefit should be one of many appropriately weighted factors in making an investment decision. The investor should consult their financial or tax advisor before investment in any state’s 529 Plan. Converting from a traditional IRA to a Roth IRA is a taxable event.