Why Your 30-Year Retirement Plan Report Feels Underwhelming
Episode 42
Why Your 30-Year Retirement Plan Report Feels Underwhelming
Published on July 8th, 2026
Episode Summary
Episode 42 of Retirement Tax Matters examines the balance between building a 30-year long-term financial plan and executing tactical annual tax planning. For high-net-worth retirees in the $2M–$8M range, a 30 year plan is essential for establishing your trajectory and understanding retirement goals. However, because the future can't be predicted, relying on a static printed binder to dictate decades of lifestyle decisions often feels underwhelming. In this episode we argue that the confidence part of retirement planning comes from pairing that long-term vision with annual tax planning that occurs every fall. By managing the tax decisions in front of you this year, such as optimizing the 24% tax bracket or navigating Medicare IRMAA cliffs before year-end, retirees can confidently make smart adjustments as their unique retirement story unfolds.
Key Tax Planning Questions
Question 1: How often should a retirement plan be updated?
The answer here is nuanced. I think a lot of people expect a retirement plan to look like a set of Weber grill instructions, with clear graphics and easy sequential steps. But life shifts and markets are unpredictable. That is exactly why we focus on tax-return-driven financial planning rather than a printed binder. Most retirees wait around for 1099 tax forms to show up in their mailboxes in the spring, but for families in the $2M–$8M range, that backward-looking approach is a costly mistake. The window to protect your wealth actually closes on December 31st, and our annual framework is designed to pivot you from reactive filing to proactive planning before the calendar turns.
Instead of constantly rewriting a multi-decade spreadsheet, we run through a rhythmic series of current-year choices. Every spring, we review your recently filed return to verify that prior-year strategies like Qualified Charitable Distributions actually showed up correctly. Then we build your rough draft Roth conversion strategy early in the year, so if a market dip happens, we already know our parameters and are ready to execute while taxes are on sale. Throughout the year, we estimate the ordinary and qualified dividends inside your taxable brokerage accounts to keep invisible income from pushing you over a Medicare IRMAA cliff or Net Investment Income Tax threshold. Finally, we spend the fall executing the final details to fill up lower ordinary income brackets before the year-end deadline closes your window.
This framework keeps your focus strictly on what you can control. If you have an unexpected household expense like a $15,000 HVAC replacement, it is just a cash flow item that rarely shifts your 30-year trajectory. You can easily handle that during a standard review. But if you decide to liquidate a rental property, exit a business, or make a permanent change to your legacy goals, those are real-world reasons to pull out the financial planning software and update the long-term plan. Logging into an online portal every month to watch account balances tick up and down sometimes just creates more stress. I think retirees will gain more by focusing on the annual tax planning projections that change the aggregate amount of taxes you pay over your lifetime. To see how these seasons connect, you can download the full breakdown on our free resources page.
Question 2: Should I delay my pension and Social Security to draw down my traditional IRA?
Traditional investment professionals love to use these terms interchangeably, making it confusing to know what you are actually paying for. But when you have a portfolio between $2 million and $8 million, understanding the distinction changes how you look at your wealth.
The way I see it, financial planning is the comprehensive look at your entire financial life. The CFP Board defines it as advising you on how to achieve both short and long-term goals by coordinating your income, insurance, and legacy wishes. Tax planning lives right inside that process. The CFP Board notes it focuses on making the most of tax-advantaged savings opportunities, maximizing breaks, and managing the timing of withdrawals to minimize tax consequences.
Both are entirely different from a standalone financial plan or annual tax preparation. A financial plan is just a snapshot in time that an advisor prints out once and leaves on a shelf. Tax preparation is simply reporting history by collecting forms each spring to calculate what already happened. Proactive tax planning requires looking forward within the current calendar year to estimate your income streams and make tactical adjustments before the hard December 31st deadline closes your window.
In the $2M-$8M asset range, retirees deal with realities like upcoming six-figure RMDs, Medicare IRMAA surcharges, and capital gains from large brokerage accounts. I would argue that it’s difficult to build out a financial plan unless you have taken the time to understand how your tax return is impacted. If your advisor has never asked to look at your recently filed tax return, you are probably not receiving tax planning and probably wonder most years if you’re going to have a big tax surprise in April.
Full Episode Transcript
Adam: Good morning, and welcome to Retirement Tax Matters. I'm Adam Reed. This is our resident CFP® professional, Garrett Crawford. How are we doing this morning, Garrett?
Garrett: Doing good. Halfway through the year. July 1st is the day that we're recording it here in the Southeast. It is like, I think I saw the other day, a 105-degree index, but, good news, the USA won their... or I guess, what match is this?
Adam: This is the knockout stage.
Garrett: The knockout stage.
Adam: The knockout stage. So they won. They did well in the group stage. The last game was a little bit disappointing, but then they won last night. So red card, that was kind of a bummer. We got Belgium up next. We'll see what happens. But it's a fun time to be a US soccer fan.
Garrett: Yeah, I feel like Adam's having to school me this year with the soccer. Did not grow up around the sport, so I'm learning on the fly.
Adam: Yeah. Well, you got offsides down, which I feel like is most people's big hurdle. If I could think of one thing that's similar in the sports world to tax planning, it's probably the offsides rule.
Garrett: Well, I just thought, are you a hockey guy? Is icing similar to offsides?
Adam: I think icing has something to do with when you spray ice on people.
Garrett: Oh, okay. Gotcha.
Adam: I think there is offsides in hockey.
Garrett: Yeah, there's some rule. I remember playing video games as a kid, and there was some rule that was kind of like that.
Adam: Maybe we'll start a parallel podcast where we go into complex sports rules. As we cover tax rules and tax planning over here, we'll cover sports rules over there. Advanced refereeing for high professional, high performance refereeing for all of our clientele out there that loves to get in the rule books. Well, anyway, I think we have a good conversation today. You had this conversation with somebody that's coming on board as a client, and I think it's just pertinent for a lot of people. We see a lot of people that come in—maybe they're a prospect that's wanting to become a client, or maybe it's a client that's done a lot of work on their own, or maybe it's people we're hearing from on here—and it's this 30-year retirement game plan. It's this big old binder, and it feels like so much, but it almost feels like nothing, and it can feel a bit underwhelming. And I've heard you talking about maybe looking back 30 years to talk about why that feels like it falls flat compared to feeling like you have all the ammo you need to take on retirement. It can almost feel like, what do I even have to take on my retirement?
Garrett: Yeah. It kind of depends on where people are coming from and what they're looking for, but I feel like these days—and especially a lot of people that are coming from podcasts and listening to the YouTube channel—by the time they show up, whether it's via Zoom appointment or in person, and they're working with a financial planner, I think the four letters in financial planner that stick out is plan.
Adam: Mm-hmm.
Garrett: People want a plan. And I think a lot of that is because there's greater peace of mind when you have a plan. Just like a lot of us, a plan is usually a step-by-step instruction booklet. I know I just built a grill a few weeks ago, and it was really nice to have step-by-step instructions on how to build that thing, because I'd never really built a grill before. So, I think it's a natural instinct for all of us to want a plan, something that we can adhere to, to do something we've never done before. I think the challenge though—and it's funny, if a lot of you all could be in financial planner circles, I feel like this has been a last decade kind of thing—is where planners in the generation before me were shifting from investment advice to financial planning.
And so what they did is they started using financial planning software and printing off these 60-page reports. For a lot of people, it was really cool. It was like, you're actually going to give me something to help me with my savings and my spendings and help me know where I'm going. So the industry went through this phase where it was a 60-page printout you'd give somebody, and people kind of liked it.
Adam: And it was almost like the more you gave someone, the more work you did, so the better you were. It almost was like a reflection of, well, it's a 180-page report, they know what they're talking about.
Garrett: Yeah. In some ways, it's our human instinct to think, hey, here's my plan. This is really good. I'll refer to this during the year. And the problem has been, in the 10 years since this has become rather popular, is that in the financial planning world, we hate giving those 60-page reports because it's almost like... and you and I both know this. We can give instructions to a client. We can have a list of maybe five, 10, or 15 things that they need to do in between appointments. 15 is probably a lot. But we're people, we're busy, we're doing other things, and a lot of times those things don't happen. Anytime you give somebody a stack of papers that big, they're going to look at it once, they're going to throw it in the back drawer when they get home, and then by the time they look at it again, their life is going to be changed.
So today's podcast topic is a public discussion of something I feel like I'm having with new clients all the time. It's this idea that I'm a financial planner, I love a financial plan, and it is very necessary, but let's not confuse a 30-year financial plan with something that it is not supposed to be—which is a one-time financial plan where you can come up with something in July of 2026 and refer to that in July of 2030, because life is going to change.
Adam: What is that quote from the old philosopher a lot of people like, Mike Tyson? Everybody has got a plan until they get hit in the mouth. And so that's life, right? Yeah, we come in here and we put together this plan and a year later we lose a spouse, or five years later the market just falls off a cliff, or a pandemic happens. That wasn't even in our vocabulary seven or eight years ago, and now it's something we're almost planning for in the back of our minds. So, help me understand the tension then. We don't want to say, don't plan, right? Oh, hey, just show up every year, look at the tax return, and we'll figure it out as we go. That feels a little bit like flying by the seat of our pants. But at the same time, to lay out a plan and say, this is what we're doing, no matter what happens, no matter what changes, we're sticking to this plan, that doesn't feel realistic. That feels almost impossible. What's the tension there, and how are you helping clients think through having a long-term vision—a long-term, 30,000-foot-view plan—but then also being able to navigate the year-to-year conversations around tax return driven financial planning?
Garrett: Yeah. I would first start by addressing the discussion point I lead off with here. I say, Mr. and Mrs. Joe and Jane Smith, I really value the importance of doing a retirement plan. We have financial planning software—it's called MoneyGuide Elite Pro—and we use that with all of our clients because I know that people want to know what trajectory they are on. Where are we going to be in 15, 20, or 30 years? And the point is, if we look back in your life 30 years ago, anybody that's listening to this and thinks back to their 30-year-younger self, I bet you wouldn't have predicted that you're exactly where you are today—probably not even close to where you are today. If you look at your portfolio, you may have thought it was going to be way bigger or way smaller. Between health, sickness, life, and jobs, you move all over the place. There are just a lot of things that we can't predict. My opinion would be that anytime we get outside of one or two years, it becomes a crystal ball of guessing. So, we really want to be at this place where we're balancing 30 years into the future, but also today.
The conversation that I have ends up being this idea we talk about all the time: tax return driven financial planning. There is a place for the 30-year projection, but oftentimes it's just hard to know what to do in the meantime. And so with these annual tax projections where we're looking at what's going to happen this year, it can push back against this idea that we don't know what the future is going to hold, because we can know what's going to happen income-wise for you this year. I kind of see it as two sides of the same coin. When it comes to goal setting, I think that's a really important thing for us with our finances. It's like dieting, which I was thinking about earlier today.
It's good to know what your goal is. Dieting is hard; we're not all nutritionists, and we don't know the calories for everything. But you want to know if you want to have a 10-pound, 20-pound, 30-pound, or 40-pound weight loss, versus just saying out of the blue, I want to be lighter. Having a plan and having something to shoot for is really good, and I think that's where the long-term financial planning software really helps. But on a day-to-day basis, that can become more challenging without the goal. When it comes to tax planning, we can take a guess at what your income projection is going to be at the end of the year. If we know what your income is going to be at the end of the year, then we have a better shot at avoiding some of these penalties.
Adam: Yeah, absolutely. And I think maybe it is a good time to touch on our year-end tax planning checklist to help people understand. A lot of you maybe got a one-time plan or have something like that, and you're do-it-yourselfers. Go check that out, because I think that would really add a lot of value to people who are saying, okay, I've got this plan in place, but now each year I want to fine-tune it and make sure I'm not missing anything and make sure I'm optimizing. Check it out; it'll be down in the description. Go to our website and trade your email address for what I would say is some really awesome content that will serve you well and give you an idea of what we do.
Maybe you go through it and you're like, hey, this is above my pay grade. I need to talk to Adam and Garrett. We're taking on clients and love working with people like you in that $2 million to $8 million space. So go check that out. You will also get emails once a week with case studies, different thoughts, and maybe a little more anecdotal content. I think some of that stuff is really fun to read because it's like, oh, that's my situation. I hadn't thought about that. It's almost like having a conversation with Garrett through email, where he is giving a lot of really good information.
So go check that out. Maybe to wrap us up for the day, could you touch on an example of how you see this—balancing the 30-year plan with looking at things annually, like maxing out the 24% bracket or something similar? Just give people a taste of what you mean when you say the 30,000-foot view is good, but let's also be flexible and able to pull some levers and press some buttons throughout the year.
Garrett: Yeah. I think about our niche, ideal prospect for this podcast: someone who has between $2 million and $8 million. One of the big things that comes up is required minimum distributions (RMDs). A lot of people are retiring early at that asset level—maybe they're thinking late 50s or early 60s. The way that RMDs are currently set up, those don't start until age 75. So there can be this very strong desire to know, hey, what is my RMD going to be 10 years from now? That can sometimes be a really hard number to predict.
We also don't know what their spending level is going to be like as they adjust to early retirement. This future idea of how RMDs are going to impact a plan is something that we address, and it's really important. But like we discuss in some of our other videos, understanding when to go from the 22% bracket to the 24% bracket, or maybe even to the 32% bracket, is a critical ingredient of long-term planning. What I find myself thinking with a lot of clients when it comes to the fall—September, October, November—is that we're sitting there thinking about RMDs five, six, or seven years down the road, but then it comes back to: okay, well, what should I do today?
For somebody who is between $2 million and $8 million, their income is going to grow. The tax planning side focuses on the idea that if they are in the 24% tax bracket, and maybe they've got $40,000 extra before their next level of the Medicare IRMAA charge kicks in, we may not know for sure if we need to go into the 32% tax bracket through Roth conversions or additional distributions because things might get out of hand down the road. But we can look at that same scenario and say, if we don't need any more income, it's September, and not a lot is going to change, we could go ahead and do a $40,000 Roth conversion. That maxes out that 24% tax bracket right up to that next Medicare IRMAA level. That is a really good decision that helps us break down this tension that we face between planning 30 years into the future versus what we know we can do prudently today. I think that's an important process for people to go through.
Adam: Yeah, and maybe to put a bow on it, I've got three young kids, so we road trip. Disney World is on our horizon. We're not quite to Disney World age yet, but I just think about how if Disney World is the end goal, that's where we go. We've got the 30,000-foot-view plan. Along the way, as parents, we've got to be flexible, otherwise we're going to die in that car on the way there. Somebody's going to have to go to the bathroom as soon as we leave a rest stop. We're going to have to peel off and do something we didn't expect. Someone's going to barf in the back seat, and we're going to have to stop and clean that up. There are a lot of different things that aren't planned for and aren't expected, but every few miles we're going to have to check in. Are the kids okay? Are we all right? Are they sleeping? Oh, thank you, Lord. Everybody's in one piece. As you go, there are just little detours and things you have to do.
We're going to get to Disney World. We're going to get to the end of that plan and accomplish the things we want to do, but along the way, we're going to have to keep an open hand and make different decisions that maybe we weren't thinking about when we left at 8:00 AM. In the same way, have the 30,000-foot view and the plan of where you want to land in retirement and what you want to do over the next couple of decades. But along the way, just keep an open hand because there might be an opportunity to do some more Roth conversions this year, or there might be an opportunity to open up a donor-advised fund, do a lot of your giving this year, and enjoy a big tax reduction. Being open to those things is really impactful and can even boost your plan. All of a sudden, you get to Disney World, you get the VIP passes, and you're like, "Oh, we crushed it. This is great." That's what our encouragement would be: feel that tension.
Garrett: Yeah, and I would say that for the 30-year plan you have printed off that's on your desk—the one somebody gave you a while back that you just don't want to look at—Adam and I would say it's okay to have that. I don't know if I've ever printed off one of those giant plans to give to a client, but it's fine to have it. However, real financial planning happens in small adjustments each year. Go ahead and have the report with you, but every year you're going to need to come to that same table and have that same conversation. You're going to need to make small adjustments and small audibles based on the surprises that life throws your way that year. That's where long-term planning really pays off—with the small adjustments each year.
Adam: Absolutely. Well, we appreciate you guys following along with us. As usual, check us out on Apple, Spotify, and YouTube. Like, subscribe, and follow all the different buttons. We appreciate you guys being here. I'm Adam Reed. This is Garrett Crawford. We're Retirement Tax Matters.