Navigating the 2026 Tax Landscape: Why You Need a “Human in the Loop”
According to the most recent available data, the IRS collected $5.1 trillion in taxes in 2024. Just ten years earlier, it collected $3.1 trillion.
We all grumble about paying the government this time of year. And gathering all our forms and statements while we're in the middle of a partial shutdown isn't going to make Tax Day 2026 any more pleasant. But those trillions are also signs of a healthy economy that continues to grow and generate wealth, which is good for your long-term financial planning.
Still, just because the government needs our tax dollars to provide essential services doesn't mean you should pay one dollar more than you're legally obligated to pay -- this year, next year, or over the course of your lifetime.
On today's show, we discuss some trends and best practices for both tax planning and tax prepping and why I believe that having a professional financial team in your corner is more important than ever.
22 Different Kinds of “Simple”
In 2017, the Tax Cuts and Jobs Act increased the standard deduction from $6,500 to $12,000 for single-filers and from $13,000 to $24,000 for married couples filing jointly. Inflation adjustments and the One Big Beautiful Bill Act have continued to raise the standard deduction, up to $15,750 for single filers and $31,500 for married couples filing jointly in 2025.
In part, these increases were designed to make tax filing simpler by encouraging less folks to track and report itemized deductions. And, in part, that's worked: most experts estimate that over 90% of Americans now take the standard deduction.
So, if filing your taxes is easier now, why not just sharpen a few pencils or fire up your favorite piece of tax software?
Because, in other ways, the tax code isn't actually getting any simpler.
For tax year 2025, there are 22 different variations of the 1099 form alone, including a new one, the 1099-DA, for digital asset transactions (like selling Bitcoin).
And yet, despite all those forms, the tax code still requires taxpayers to self-report a great deal about our financial lives. Cash payments received, rental estate income, and small business expenses are just a couple examples of items you won't receive a form to report.
There are also standard wealth-building strategies that you might assume the IRS is tracking when, in fact, they're not. IRA rollovers and transfers, Roth conversions and certain capital gain or loss cost basis information are up to you – and hopefully with your financial advisors’ help -- to assist you in reporting correctly so you don't pay unnecessary taxes or receive a letter from the IRS requesting additional information.
Moreover, while taking the standard deduction might be the simplest choice for most folks, it's not always the case. Folks who give a lot to charity or have high expenses related to caregiving might be better off itemizing. And recent increases to the state and local tax (SALT) deduction might change the picture for high-earners living in high-tax states.
Perhaps this disconnect between the supposed “simplicity” of tax changes and the reality is why, in a recent IRS survey, 93% of respondents reported that tax software was easy to use, but 48% of people said it is difficult to stay up-to-date on tax laws and procedures.
Beware the "Alternative."
While the process of planning and prepping your taxes is never simple, the goal should be: lowering your tax liability so that you only pay what you have to.
At Keen Wealth, that's a lifetime goal for all the folks that we work with, not just an annual goal. We're constantly monitoring our clients' financial situations to look for advantageous moves that will manage tax liability and grow wealth for the long run. There are no shortcuts in our comprehensive, checklist-driven process.
But far too many folks who do manage their finances solo are just looking for shortcuts, or "alternatives," or "secrets." Every tax season, I see more and more social media videos from financial "influencers" pitching tax loopholes that “only billionaires know about” or financial products and strategies that will lower your tax bill while also outperforming the markets.
Not only are most of these products at best risky and at worst worthless, but some of them might increase your chances of being audited!
One of the benefits of working with a fiduciary advisor, like the Keen Wealth team, is that if you see a pitch that sounds too good to be true and ask us about it, we're required by law to give you an honest assessment based on what's in your best interests. Too many folks who don't have that safety net dig themselves into financial holes that they might never be able to climb out of.
“Loop In” Keen Wealth
There are many fantastic apps and programs available today that can help folks track and manage their finances and file their taxes. And AI is only going to accelerate the usefulness of this software, not just for investors but for financial professionals as well.
But you still need the proverbial “human in the loop” who’s not flying on autopilot, who’s watching for suspicious activity that large custodians might miss, who knows you, your goals, and your dreams for retirement.
It’s not too late to book an appointment with Keen Wealth to prep for Tax Day 2026 and start making a comprehensive plan for all those tax days still to come.
About Bill
Bill Keen is a financial advisor with over 30 years of industry experience. As the founder and CEO of Keen Wealth Advisors, a registered investment advisory firm, he focuses on providing personalized retirement planning designed to help people thrive before and during their retirement years. With a passion for educating others, Bill regularly blogs about retirement planning, hosts the podcast Keen on Retirement, and has contributed to Forbes, U.S. News and World Report, Reuters, Wall Street Journal’s Market Watch, Yahoo Finance, and other publications. Based in Overland Park, Kansas, Bill and his team work with clients throughout the greater Kansas City area and across the nation. To learn more, connect with him on LinkedIn or visit www.keenwealthadvisors.com.
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