About Retirement Tax Matters
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All the content on Retirement Tax Matters is created with the retiree who has a net worth between $2M and $8M in mind. At this level of wealth, it can be difficult to find tax planning advice online that applies to your unique situation. Many families in this group file their annual returns and, seeing the amount paid in taxes, begin to wonder if they are doing everything they can to protect their life’s work.
The most significant mistake we see in this $2M–$8M range is treating tax planning as a reactive, once-a-year event. By the time you meet with a tax preparer to file your return in April, the December 31st deadline has already passed. Meaningful opportunities—such as strategic Roth conversions, capital gain harvesting, and proactively managing Medicare IRMAA levels—are often lost once the calendar turns to the new year.
Retirement Tax Matters exists to bring light to the best practices and tax planning ideas specifically designed for Retirees between $2M-$8M. We advocate for a tax-return driven approach to planning, highlighting why an intra-year tax projection in the fall is a non-negotiable tool for informed decision-making.
This website was born out of a clear need: while nearly 90% of wealthy investors desire tax planning, a study by CEG Insights found that only 25% of high-net-worth retirees felt their financial advisor was actually delivering on that service. Retirement Tax Matters helps close this gap by providing the education you need to align your tax reality with your legacy goals before the window of opportunity closes. You can read more about this wealth management delivery gap on the Kitces platform.
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Tax-return driven financial planning is the practice of ensuring you are aware of what is happening on your tax return from year to year and letting that drive your current year financial planning decisions.
Too often, financial advice is given without observing a client’s actual tax return, or by looking at last year’s data without asking what has changed for the current year. It is a risky game to base your future on outdated numbers!Tax-return driven financial planning begins with a deep understanding of your prior return and then moves into a process each spring where you estimate what your income will look like by year-end. This forward-looking view allows you to capitalize on market opportunities for Roth conversions, manage Medicare IRMAA levels, and prevent unexpected tax bill surprises in April. While the goal isn't always to minimize taxes this year—as it sometimes makes sense to trigger taxes now to lower a lifetime amount for you and your beneficiaries—it is about making more informed decisions.
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Too many retirees have advisors that aren’t reviewing their tax returns.
We believe it is impossible to provide good financial advice without reviewing the one document that reveals the most about your financial reality: your tax return.
If your current advisor isn't asking for this document annually—and asking you how this current year might be different than the last—it is a recipe for guessing when it comes to critical decisions like Roth conversions and IRA distribution timing.
We believe the stakes of good tax planning and tax-return awareness are much higher for retirees with a net worth between $2M and $8M, where missteps can have meaningful impact on your long-term wealth.
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In this range, your financial life becomes multi-dimensional. You face complex tax headwinds like Medicare IRMAA surcharges, the 3.8% Net Investment Income Tax, and the looming impacts of large Required Minimum Distributions that maybe you don’t need all of — yet you typically don't need the ultra-complex estate planning of the $20M+ family office.
We have stood in front of mixed audiences where it is difficult to use an example of a retiree with a $5 million IRA because that isn't a common situation in a general room. Standard financial advice often defaults to lower numbers and simpler scenarios to appeal to a larger number of retirees.
Retirement Tax Matters prioritizes advice and examples specifically for people like you in the $2M-$8M range, ensuring strategies we discuss have a higher chance of being applicable to your level of wealth.
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Providence Wealth Management, LLC is the independent, fee-based SEC-registered independent investment advisory firm where Garrett Crawford, CFP®, and Adam Reed work. Based in Knoxville, Tennessee, it serves as the professional practice behind the educational content you see on Retirement Tax Matters.
About Garrett Crawford, CFP®
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I have been a practicing financial planner since 2013, working in an independent, client-facing advisory role from day one. I earned my CERTIFIED FINANCIAL PLANNER® professional certification in 2019, a designation I believe should be table stakes for any high-net-worth retiree seeking advice. Holding this license mandates a Fiduciary standard of care for all clients, and it was during this certification journey that I first recognized the critical gap in tax planning for retirees.
I view my specific mix of experience and age as a long-term benefit for the families I serve as well as the writings on Retirement Tax Matters: I have the experience to serve my clients today, yet the runway to remain a partner throughout their retirement. Finally, I hold a B.S. in Electrical Engineering from the University of Tennessee at Knoxville. While financial planning grabbed me before I ever applied to an engineering job (a good story for another time), I credit those formative years of higher education for instilling the critical thinking and problem-solving skills I rely on every day as a planner.
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My philosophy is anchored in the belief that it’s crucial that your (1) tax return, your (2) investment plan, and your (3) long-term financial plan are better aligned.
I find that many retirees and their families in this $2M–$8M level of wealth live on less income than their portfolios actually generate. This excess creates significant financial and tax planning opportunities. When a high-net-worth retiree is proactive and forward-looking, the goal isn't always to minimize taxes in the current year. In fact, minimizing your total lifetime aggregate tax bill sometimes requires paying more tax today in efforts to lessen your overall tax in retirement and simplify for your loved ones after you.
A proactive approach allows you to lessen the heightened tax impacts of being reactive to future Required Minimum Distributions (RMDs), better evaluate the fit for systematic Roth Conversions over time, and understand the tax consequences of a surviving spouse or beneficiaries…just to name a few.
Ultimately, the goal is to understand your money better so you can deploy it more confidently—helping your kids sooner, giving more generously, and avoiding the default path of leaving your biggest tax bill for your later years.
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The other half is navigating the natural friction between our logic and our feelings. We’re rapidly approaching a day where AI will be able to answer almost any "what" or "how-to" question about our finances. However, even with access to all that information, most people are still left wondering: "Can I trust this?" and "Am I missing something?" While technology makes facts more accessible, it also creates new problems—the more information we have, the more difficult it becomes to filter out the noise.
I’ve come to believe that financial decisions shouldn’t be made in a vacuum; they are built on a foundation of trust and a deep understanding of how we respond to stress. As much as the answer is technical, it’s also relational. All the knowledge in the world struggles to compete with fear or greed when the stakes are high. It is a part of our nature that we have to work against, especially when managing a life's work.
This is why I am a proponent of tax-return driven planning as a tool to manage this friction. For example, by establishing a Roth conversion plan in the spring, we aren't just doing math; we are setting the stage for future events that might otherwise feel overwhelming. If we agree in April that a market drop is a prime opportunity for a conversion, we have reframed a stressful event into a strategic opportunity. Instead of worrying if the market drops, you have a plan for what to do when it happens. A good financial planner’s role is about helping you build a plan, but even more so helping you have the confidence to act when it matters most.
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As a practicing financial planner in Knoxville, Tennessee, our primary goal with Retirement Tax Matters podcast and website is to provide highly targeted, valuable resources for retirees between $2M-$8M. Adam and I are passionate about education and believe that a more informed person is empowered to make better financial decisions for their family.
We realize that by sharing our specific approach to planning, some may find that our philosophy deeply resonates with them and might want to see if we're a good fit to work together professionally.
If that's you, and you feel that a deeper, one-on-one conversation would be helpful, please feel free to use the link below to schedule a quick, 30-minute introductory phone call with me. There is no cost or obligation for this call.
About Adam Reed
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I have found through the years that I really have two professional passions. I love to interact with and serve people, and I love to problem solve. Our industry is full of people with a story, I enjoy hearing those stories, and playing a small part in writing the chapters to come.
This does not happen without challenges! That is where the problem solving comes in. Whether it is helping someone decide how much IRA money to convert to Roth, or what is a reasonable amount to spend on a new car, I love to walk along side people as we overcome obstacles!
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YOU! Yes, you read that right. You are the key ingredient to effective planning. Yes, there is math, projections, software, and more that goes into putting together a game plan, but ultimately a plan does not come together without you. Your hopes, your dreams, your fears, your challenges, the things that keep you up at night, and the things that get you out of bed in the morning. All of this is essential to formulating a plan that you are confident in that excites you for the future!
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There are two buckets that people can fall into. Those that are accumulating wealth and those that are preparing to, or are in distribution mode. In my years in the financial planning space I have found that those in the accumulation phase can often be paralyzed by not knowing where to start, or feeling like the end goal is too far off or intangible. I always encourage clients that progress is better than perfection. Yes, there is an ideal amount and way to save for long term goals, but starting with something often builds momentum towards accomplishing the goals you have for yourself.
For those preparing for the distribution phase, or already taking distributions I have found that a common mistake is to think that the planning is over with and the work of financial planning is behind you. Often times those in or nearing retirement have more opportunity for optimization and efficiency than their counter parts still in the accumulation phase. That is why, in large part, that we started this podcast. We want to educate and encourage those that are in retirement to do the planning to get more satisfaction and enjoyment from the fruits of their labors of saving throughout their working careers.
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I am married to my wonderful wife, Sydney, and we have three sons! We love to be outside. Golf, gardening, hiking, and attending sporting events (Specifically the Tennessee Volunteers) are some of our favorite ways to get out of the house and have a lot of fun!
I am so blessed to have an awesome family that is a joy to be around, restful, and rejuvenating. I am looking forward to serving my family, and those that I come across in financial planning for years to come!