AI & Retirement Planning in 2026: A Financial Planner’s Perspective
Episode 35
AI & Retirement Planning in 2026: A Financial Planner’s Perspective
Published on May 13th, 2026
Episode Summary
Episode 35 of Retirement Tax Matters provides a review of the role of artificial intelligence in high-net-worth retirement planning in 2026. Garrett Crawford, CFP® and Adam Reed discuss the software paradox where the skill required to effectively use professional tools often means that if you are proficient enough to use them, you might not actually need them. The conversation transitions to a real-life scenario where Google Gemini failed to recognize real-time legislative updates like the One Big Beautiful Bill Act (OBBBA). Beyond the technical data, the episode addresses the risk of AI-driven elder abuse and the cognitive challenges of navigating financially incentivized algorithms as retirees age into their 80s and 90s. Garrett and Adam conclude that while AI may begin commoditizing parts of personal finance, the human element of fiduciary advice like addressing fears, dreams, and spending confidence will remain an important service.
Key Tax Planning Questions
Question 1: Can AI plan my retirement?
In May 2026, my perspective is that artificial intelligence can serve as a great sounding board and way to think of things you might overlook, but it falls short of being a reliable retirement planning tool. If you go back and look at the AI outputs and image generations from 2023, the amount of progress makes you wonder what the next decade will bring. However, as I have monitored the AI movement closely, and while the speed of improvement in these models is remarkable, we must separate data processing from professional judgment.
We are seeing a trend where the technical components of personal finance, such as investment expense ratios and basic portfolio allocations, are being commoditized by technology. While the cost of calculation is dropping toward zero, the value of fiduciary financial advice is increasing. If you read my FAQ, you’ll see how many advisors like me are separating out the value of financial advice and investment management. While AI can effectively synthesize vast amounts of data (usually much better and faster than me/humans) it lacks the capacity for actionable wisdom. As a financial planner, I still spend a significant time each week typing summaries for technical tax documents and software outputs into financial planning observations that account for unique human trade-offs. So many times in my tax planning, I’ll come up with multiple strategies because I know my clients might like a strategy as much as I do.
An AI chatbot might show a Roth conversion as mathematically neutral, but it cannot factor in the peace of mind that comes from protecting a surviving spouse from a future tax jump or determining the best way to pay the associated conversion taxes based on your income preferences.
Furthermore, high-net-worth retirees must remember that an AI is not a fiduciary. It does not have a legal duty of care or a duty of loyalty to your family. It carries no ethical accountability if a technical hallucination leads to an IRS penalty or a missed opportunity. For a $2M-$8M high-net-worth retiree, you will want to feel competent in all areas of financial planning and investment management to leverage artificial intelligence tools to it’s greatest potential. If you come to it with holes and gaps in your knowledge, you might end up with a tax or financial surprise that you don’t want.
Question 2: If I had access to your tax planning software, could I do what you do?
The short answer is that while you could input your data into the software, the real value lies in the professiona/competent interpretation and navigation. I use a tax planning software called Holistiplan, which has been a transformative for me since 2020. However, I have found that if a person is proficient enough to navigate professional tax software effectively, they likely already have the expertise to build their own custom tax planning guardrails and spreadsheets.
To use these tools properly, you must have a deep understanding of how the federal tax return and its various schedules interconnectedly flow. Features like Scenario Analysis and the Range Calc tool require more than just checking boxex. They require an expert understanding of the underlying assumptions. If you leave a field blank or assume a specific section is inconsequential, you face a high probability of a costly tax surprise that the software cannot prevent.
It is also important to remember that software outputs are projections and estimates, not guarantees of future tax savings. A CFP® professional is legally and ethically accountable for the advice given, whereas a software program carries no such duty of care. Even among financial advisors usage, not all financial planners are equal. While some advisors may simply run a report and email you a summary and expect you to interpret your own results (costing them 5 minutes of work!), a tax return driven financial planner uses tax planning software like to perform an estimate for income projection and help you evaluate strategic Roth conversion opportunities based on how this year is different than last year. For a retiree with a significant portfolio, the software is a powerful calculator, but it is not a substitute for discernment and financial competence.
Full Episode Transcript
Adam: Good morning, and welcome to Retirement Tax Matters. I'm Adam Reed. This is Garrett Crawford, our resident CFP® professional. How are we doing this morning, Garrett?
Garrett: Let me check my AI here and ask it how I'm doing, Adam.
Adam: Oh, no. Yeah, you have to check in with AI.
Garrett: I kind of joke about that, but how much more often are people asking us questions and we're like, "Hey, we have all this information right in our phone. Let me check." I think it will be a good lead-in.
Adam: I feel like every generation has had their thing, like looking it up in the encyclopedia or the Farmer's Almanac, then Google, or checking YouTube. It seems like this next generation coming up is typing into an AI to see what it has to say. It is definitely an interesting time. Maybe some people watched The Jetsons growing up; it almost seems like they did not even realize how far these things were going to go.
Garrett: Still waiting for the flying cars, though.
Adam: We have to be getting closer, right?
Garrett: You would think. For Elon Musk and Tesla, skip all the robots and go straight to flying cars.
Adam: It seems crazy that we would be living on Mars before we had a flying car. However, I think it is an interesting conversation because AI impacts our industry in financial planning, especially for do-it-yourselfers, in a lot of different ways. We wanted to touch on that, and as a disclaimer, we are not the experts on AI. We use it some in our work, and I think it has made our lives simpler and more efficient, but we are not AI nerds that know everything about it.
These are just some general thoughts and guidelines—things we have read that would impact us as financial planners, but also a do-it-yourselfer that is doing it on their own, or a delegator that is looking to work with an advisor now that they have AI at their fingertips. A good place to start was an article you read in the Wall Street Journal about a lady who had used AI to do her financial plan. Tell me a little bit about that and what that looked like for her.
Garrett: The backstory was that as we were prepping, my wife asked what we were talking about today. I said, "Artificial intelligence." She left the room, and as she was walking up the stairs, no less than two minutes later, she texted me—because that is the world we live in, right? She texted me a link to the Wall Street Journal this morning; they had a podcast and a full article talking about how AI can help manage a portfolio. I just laughed and thought, "This stuff is everywhere."
I want to take a few minutes this morning to keep this short so we do not risk getting into opinions we will regret in 2036. But let me start with this: I am a child of the 90s. I remember in the winter of 1994, it was the year that Windows 95 came out. I am thinking that if people out there are my dad's age, they probably remember the Gateway computer era. It was a huge jump up. I was a seven-year-old kid as that era was coming in, and I remember my dad was trying to learn how to use it. He walked down the steps and handed me a piece of paper that had a calendar printed on it. I was like, "Oh my goodness. We can print our own calendars?" My life was changed. From the age of seven, I could never get enough of technology.
My background is in engineering. I have just never been able to get enough of it. Even in the way that I used to go to google.com and do a very generic 10-word search, it has now turned into 10 sentences that I type in order to get context and nuance.
Adam: Just so everyone is aware, I have been in the office when Garrett is using AI. If the robots ever turn on us, he is going to be like their king because he is so nice to the artificial things. It is always fun to watch how different people interact with AI.
Garrett: My love of technology has caused this magnetic attraction to it. I never want to be somebody that stops learning. But as much as I am excited, I am also reserved. The question we need to spend a few minutes on is how do we see AI currently working? Is it the era of free advice? Are you and I going to be out of a job in a decade? I do not think so.
Adam: One major way AI has impacted this space is through FinTech—financial technology. 10 years ago, it was maybe 30 or 40 core softwares, and it has almost tripled now in just a few years. I have heard people asking what software we are using. What does that conversation look like for you? What would it look like for somebody to access the software that we use? Is that an option?
Garrett: I am thinking about putting that on our website because I have gotten it a lot lately: "What tax planning software do you use?" Oftentimes it is somebody that is really smart and they would like to do it themselves. The answer is Holistiplan. You can Google search it. For me, it was a career-changing software for a CERTIFIED FINANCIAL PLANNER® professional because it allowed me to start engaging in tax planning conversations with clients about IRMAA and RMDs. I think the analogy here is that if you are good enough to use the tax planning software, you might not actually need the tax planning software.
Holistiplan was built for advisors so I can interact with 100 households and provide a continuity of experience. But like building a house, I could buy every tool known to man, but that would not help me assemble the house in the right order. With AI, it can give amazing responses, but inherent in interpreting those answers, you have to have a baseline knowledge. One common issue I see is that when I use it, I see failures. I had something recently where Gemini or ChatGPT did not acknowledge that the One Big Beautiful Bill Act was passed in July of 2025. It still assumes the tax bracket is going to sunset in 2026, which is just totally wrong. As someone that interacts with the material all day, I can spot that, but if you did not know what you were doing, you could get some bad advice.
Adam: No doubt. I think another avenue is that a lot of people are in that mid to late 70s and they are just slowing down. You are just not as sharp. With cognitive decline and AI, what is the value add of an advisor versus doing it yourself at that point? How does that fall apart?
Garrett: I think we can underestimate how fast technology has changed. Retirees who are 55 or 60 now have 30 years ahead of them. The analogy I think of is grandparents whose parents used the telephone as their main communication. The amount of scams that have arisen to take advantage of seniors over the phone is crazy because it was a medium they trusted. Now scammers are using texting and AI to become even more predatory. AI is making the scams better. This stuff will not stay free forever; whether it is Google, Apple, or OpenAI, they are going to figure out how to financially incentivize these channels, and that is where it is going to get sticky. Over the course of 20 or 30 years, that is going to be a challenging medium. I think most people are going to like the human experience and Relating with people and spending less time on their device.
Adam: AI is a powerful tool. But I do think there are pros and cons. What is the value that we add? Why is the human element going to increase in value as AI becomes more prevalent?
Garrett: Adam showed me some music the other day that was not AI-generated; it was just two real people sitting in a field being recorded playing guitar. When you showed me that, it resonated that we want real. It does not matter if it is financial advice or a story; real stories resonate more. A financial planner sitting across the table from you is going to be more valuable because there is fear, dreams, and inconsistencies. Someone might say they have $6 million in an IRA and they hate IRMAA, but they don't care about the 35% RMD coming 20 years from now. We focus on the wrong things. Technology and AI are only as good as the questions you ask, and part of my job will be a little less technical and a lot more relational. I think that is a good thing.
Adam: Absolutely. It is good to have financial professionals in your corner, whether that is a CPA or a financial advisor. If you want to start somewhere—maybe you want to ask better questions to AI—our year-end tax planning checklist is a great place to start. Check out the website and go to the link. It is a great way to better inform your questions about what Tax Return Driven Financial Planning really looks like. We appreciate you guys tuning in. I'm Adam Reed. This is Garrett Crawford, CFP® professional. We're Retirement Tax Matters.