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What You'll Learn In Today's Episode
  • Analogies for explaining multiple tax concepts to clients
  • Why you need to be thinking about (and planning for) 2026 with your clients right now
  • How to setup rules around tax planning before decisions have to be made.


In this episode Steven is joined by Derek Mazzarella, CFP and the two share ideas on how to best articulate complex tax planning in a way that resonates with clients. Derek shares how he is already incorporating tax law changes that won’t happen until 2026 into his planning with clients and why he is such a big fan of having analogies for everything he does (bonus: he shares several of his favorites). Steven and Derek also touch on the tax implications around equity compensation and the inevitability that spending and income will not be linear in retirement.

Ideas Worth Sharing:

“I think we want to make sure that we're taking action, we're doing it smart, we're doing it in a measured way, and if we do that over time, it's typically going to win out.” Derek Mazzarella Click To Tweet “What elevates the experience for clients and elevates the confidence level is when you can simplify otherwise complex issues for them in a way that they're going to remember.” Steven Jarvis Click To Tweet “I often tell my clients, we want you to operate like a casino, no gambling, but what casinos do well is they tilt the odds in their favor a little bit, but then they multiply that over and over and over again.” Derek Mazzarella Click To Tweet

About Retirement Tax Services:

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Read The Transcript Below:

Steven (00:06):

Hello everyone, and welcome to the next episode of the Retirement Tax Services podcast, Financial Professionals Edition. I’m your host, Steven Jarvis, CPA, and with me today on the show I have Derek Mazzarella, who is a CFP at Gateway Financial Partners, and someone who is excited to get on today and talk to me about taxes. So Derek, welcome to the show.

Derek (01:08):

Oh, thanks for having me, Steven. Appreciate it.

Steven (01:09):

Yeah, I’m really looking forward to our conversation today. There were a couple of things that came out as we were getting ready. It’s like, oh, those are some really good points that I think get missed a lot. But just for context for everybody listening, give me just a little bit about your background and what it is you do and who you serve so that we have context for the things you do in practice every day.

Derek (01:27):

Sure. Well, I’ve been a financial planner since 2009. Basically got in right after the market crash, which was excellent timing for me, right?

Steven (01:34):


Derek (01:36):

But basically, my main set of clients is typically, usually executives. They tend to have stock options, but it is generally people that are about to retire. So usually when I find ’em is their kids just graduated college now their next milestone is retirement. And they think, okay, now I can actually think about myself for the first time in probably 20 plus years, and usually working with those people and retirees and just trying to figure out how to make that next step in retirement.

Steven (01:59):

Derek, one of the things that came up as we were getting ready for this is tax law changes that we know are coming in 2026. And this is something I talk about all the time. I’m constantly reinforcing to clients that, Hey, we already know taxes are set to go up and if Congress does nothing, which is what they’re best at, taxes will increase. But I don’t always hear advisors proactively including this in their plan. So I’d love to hear how you’re framing this to clients and the types of things that come into the picture for you when you think about what’s going to happen in 2026.

Derek (02:28):

Sure. So I think people are underestimating the tax impact of these changes, and I think people will think, oh, maybe Congress, depending on whose president will reduce taxes again or keep them lower. But when you look at the deficit, when you look at how much they’re spending, reasonable people would probably assume that, Hey, we need to get more revenue, not just cut spending. So if that’s the case, I mean, we’re always working on an assumption, and I think you and I always know that tax law can always change regardless of what it’s, so that’s the one rub of tax planning in general, but really looking at, okay, we really have three tax years left to take advantage of the lower rates. The big thing is they’re going to increase the rates a little bit, not like we’re going from 5% to 30%, but they’re going to go up in certain brackets. So we have to pay attention to that. And the bigger thing is everyone’s been so into the standard deduction lately, right? I mean, so it’s a point where we’re almost honestly no one, but not that many people itemize anywhere. I feel like I haven’t had many conversations with clients the past few years about, Hey, what do we itemize here? Let’s maybe give a little bit more to charity there. So that’s not really happening as much. So basically what I’m saying is, okay, what can we do right now that can help maybe smooth out our tax base moving forward?


Especially with the market being down. One of the main conversations I’m having with clients, is it a good time to do Roth convergence, right? So should we push some more income in now comparatively to waiting next year? So I mean obviously a lot of that depends on where they are financially, where their tax rates are. But that’s number one that I’ve been having. And I think another thing that we kind of talked about before was is this even a good time to realize gains? I think we always talk about tax loss harvesting, but we rarely talk about tax gain harvesting. So those are definitely some other conversations I’m having with clients and frankly is, okay, well let’s project this out and what does that actually look like in the future? Maybe we pay a little bit more taxes now, but especially if you’re younger and you have 30-plus years of growth, what are we looking at here? So that’s one area I’m really kind of making sure we’re paying attention to.

Steven (04:15):

Yeah, there are several things in there that I think are really important to highlight. I like that all of your language in there was conditional. So this isn’t, Hey, I’m mandating for all of my clients. They have to convert X amount, that this is absolutely what we’re going to do, but it’s something we want to consider for all of our clients. We want to go through the steps. We want to go through the analysis to say, would this make sense? Because I love that you brought up capital gain harvesting. It doesn’t get nearly enough attention. And I think part of that is that there are definitely, especially for high earning clients, it’s going to be more the exception that we can recognize capital gains that in the 0% bucket, but these opportunities get missed if someone’s not paying attention, especially if you’ve got clients who are going to be retiring in the next couple of years. We can get strategic about the timing of income and when we’re going to do Roth conversions versus capital gains harvesting. And geez, I don’t know that there’s many things that will light up a client’s eyes helping them realize that they can recognize income at 0%. That is everyone’s favorite tax rate for some reason.

Derek (05:14):

Yeah, well, it’ll be mine too. Well, the other thing is too, we’ve talked about tax loss harvesting often, but the one thing we don’t talk about when we talk about that is you’re resetting the basis again.

Derek (05:23):

So there’s definitely a piece of that that we need to be aware of when we’re doing either gains harvesting or loss harvesting. And with the market being as volatile is this year and last year, are there opportunities for them to both offset each other? So those are the things we just want to make sure we’re paying attention to and looking at when it comes to the tax planning piece for clients and making sure, okay, does this make sense for you to do right now or do we do pieces over the next couple of years? How does this look for us?

Steven (05:46):

Derek, I don’t remember if you were referring to taxes or not, but as I was going through your LinkedIn profile, cause I’m a huge fan of LinkedIn, you had a recent post that was talking about Goldilocks and the three little bears. This idea that it can be really tempting to wait and try to find that sweet spot where it’s just right, that can really be a detriment to taking action and that this isn’t whether we talk about capital gains harvesting or Roth conversions or anticipating 2026, this isn’t about trying to find that perfect amount or that mathematically optimal outcome. This is about making sure we’re going in the right direction and that we take action, that we don’t let perfection stand in the way of action.

Derek (06:22):

Exactly. And I think one of the things I’ve learned over my career, and probably some of the mistakes I’ve made if I’m being honest, is kind of overrating certain aspects of things like, oh, do we have to wait until this is perfect or I don’t know exactly what’s going to happen, so maybe we shouldn’t do it. Or we would never tell our clients, Hey, don’t take that $50,000 bonus, you’re paid taxes. That’s ridiculous. So I think we want to make sure that to your point, we’re taking action, we’re doing it smart, we’re doing it in a measured way, and if we do that over time, it’s typically going to win out. We’re not going to hit the cover the ball every single time, but if we’re hitting singles, doubles and triples all the time consistently, I think that’ll add up over time.

Steven (06:56):

Yeah, consistent action over time. That’s really what it comes down to. Those are the people that I see that get the furthest ahead when it comes to sanding the rough edges off of their retirement tax bill, especially on a topic like taxes sometimes, well, not sometimes, quite often, social media and even more traditional media does a real disservice by highlighting the extreme examples. And so people think, Hey, if it’s not a grand slam, why even attempt it? But it’s like, oh, okay, no, you’ve got between your working years and your retired years, hopefully, you’ve got 60 plus years where you’re paying taxes. I know that sounds bonkers for me to say that I hope you pay taxes for 60 years, but that’s just the reality of it. You’re going to pay taxes for a very long time. And so if we’re only thinking about, Hey, how do I set up some wonky trust in the Cayman Islands that is going to save all of my taxes and probably send me to jail? Let’s instead look at what little things we can do over time, even if it’s small Roth conversions, even if it’s just a little bit of capital gains harvesting. If we do these things consistently over time, we can make a big impact on our ability to reduce the amount of taxes we legally have to pay.

Derek (08:02):

Yeah. I often tell my clients, we want you to operate like a casino, no gambling, but what casinos do well is they tilt the odds in their favor a little bit, but then they multiply that over and over and over again. So if we’re doing even just small little things like that over time, it’s going to create good results for us. So we just want to make sure we’re consistent with those approaches and what can we find that our little things here or there that can add up over time. I mean even like a silly one is I talk about asset location, the dumb analogy I use, I’m big on analogies with my clients, but I talk about do you put your milk in the pantry. If you went to a friend’s house and they had that, you’re like, this person’s weird, right? But what are the assets that we should be putting in Ross versus investment accounts using ETFs versus mutual funds? Are we using bond funds versus growth funds? What are we putting in the types of accounts and paying attention to small stuff like that? That may not seem like much, but that does add up over time. You want to put the milk in the fridge.

Steven (08:57):

I’m laughing because I’m going to bet that you haven’t spent time in Eastern Europe and we won’t go down this rabbit hole, but depending on how the milk gets processed, there are actually places where you will find people’s milk in the pantry until they open it. But your point is still very relevant and that’s why I love having these conversations, and for some people in my audience, it’s really easy to think, well, geez, Steven talks about Roth every third episode, and that’s probably true, but that’s how impactful of a strategy it can be, and it’s so great for me. I love learning how other people are approaching this, how you’re explaining it to clients, how you’re getting people on board with this idea, because I’ve never sat down and tried to explain the ins and outs and the intricacies of how Roth actually works. In fact, a lot of clients still think that Roth is an acronym and not a person’s name. Those details aren’t really relevant. We need them to understand enough of the logic behind it to be on board with what we’re trying to accomplish and definitely to understand that this is a little bit of a guessing game. Any planning for the future is, but here’s why we’re doing it, why we feel confident about it.

Derek (09:57):

Yeah, I think that’s important. I think the biggest misconception I run across Steven is always people think that a Roth is an investment, and I have to always tell ’em like, no, it’s not the investments, the tax shelter. I always say, look, think of the IRA Roth IRA, an investment account. Those are all garages and the car is the investment, so make sure we’re putting the right cars in the right investment. You can move any car in that garage. Just the tax piece of it is what is really important to understand with each of those types of accounts.

Steven (10:23):

Well, the other thing I want to highlight is we’re having this conversation, Derek, for people listening, is really pay attention to how seamlessly Derek switches to these analogies. He’s not stumbling over any of these. They flow naturally into conversation. This is why it’s so important to practice and use the same things over and over again. I would imagine that you can’t even count the number of times you share these analogies with clients. It’s what elevates the experience for clients and elevates the confidence level is when you can simplify otherwise complex issues for them in a way that they’re going to remember. Because if you really hammer home the technical nuance details of why we’re doing a Roth conversion as opposed to hey, saying, Hey, let’s move the car within the garage, the clients are going to remember, oh, that’s right Derek, we need to put the car in a different spot in the garage. People are going to remember that.

Derek (11:05):

Definitely. One thing I’m trying to really work on is how to make these complex things simple. Because easy in our industry to hide behind jargon and acronyms especially, and most people don’t understand that at all, and it’s just helpful to how do you reframe this where, okay, how can I relate to this to someone and what’s a part of someone’s life that I can bring someone into? So I think it’s always important to really break this stuff down and explain it in a very simple way as much as you can.

Steven (11:26):

Yeah, absolutely. On that topic, one of the other things that came up as we were getting ready for this was talking about spikes in spending, especially during retirement, because it can be really easy when we plan for the future to just lay things out in a nice little spreadsheet where everything happens evenly over time and we figure out exactly the dollar amount we need every month. Why would anything ever be different? But as we talk about some of these tax buying strategies, one of the things it does is create flexibility for us for those unexpected things that might come up in life. So talk about how you incorporate this into your planning and your conversations with clients as far as helping them anticipate that there could come a time when they see a spike in their income needs.

Derek (12:03):

Yeah. Well, I think most people underestimate how long retirement typically is for people. So most retirees are actually going to retire for 20 to 25 years, maybe sometimes 30. I mean, if you’re like my great-grandmama, she’ll do 105. So you get a lot of time to do it, and most people think about what happened during Covid when everyone’s sitting in their house all day every day looking at their kitchen and be like, oh, I think I should change that, or these strips are kind of annoying. So the retirees are in their house all day. Inevitably in the first couple of years, I’d have retirees say, I’d really like to redo my kitchen. I’d really like to redo the bathroom, whatever. So if you think about it from a planning standpoint, what we’re always taught, or especially what retirees at this age level have been taught is put everything in a pre-tax bucket, put everything in the 401K, you’re going to have a lower tax rate in retirement.

Derek (12:45):

Everyone has been taught that. Most people assume that’s still the case, but let’s say flash forward a couple of years in retirement, your only income source is a traditional 401K or traditional IRA. Now kitchen’s going to redo is what, $50,000 let’s say. So now you have to take out 50,000. Well, now you have to also pay taxes on that. So maybe you’re taking out 70, 75,000, so now you’re in another bracket, potentially. Now maybe your Medicare bracket has gone up. So there’s a lot of ripple effects that contend to happen with these spikes that we may not necessarily be planning for. If all we’re doing is assuming, hey, if we get a four and a half percent return being conservative with our investments and we’re going to spend $6,000 a month, you’re going to have a hundred percent success rate. Even the really good financial planning tools still bring in assumptions that are annual averages.

Derek (13:29):

They’re not using like, oh, this year we’re going to get 20%. Next year we’re going to get down 10%. They’re not calculating that when we do our projections. So I always try and in the software, at least at a minimum, add in a few spike spends because over 25 years, you’re probably going to want a new car, probably going to need one. Who knows, maybe we’ll have Uber driving us everywhere in 25 years. But that’s a different scenario. So that’s kind of how I typically go through with clients and having different types of accounts lets you pull different levers, say, okay, well maybe I’ll take 10 grand out of the kitchen from the IRA, but I’m taking the other 40 from the Roth, for example. So you want to make sure you have different levers to pull in retirement.

Steven (14:01):

Yeah, I like that. That’s one of the things I reinforce constantly as we talk about Roth converting to Roth does have the potential for actual tax savings. That’s why it’s such a great planning tool, but it’s not the only benefit we should be highlighting to clients. In fact, I constantly want to reinforce the flexibility that comes along with it. I mean really for a couple of reasons, not the least of which is that if you tie, especially if you try to get really specific, if you’re trying to be Goldilocks and find the just right amount, and you tell a client that, you know what? $47,312 is the right amount to convert to Roth and it’s going to save us $7,012 in taxes. Now the client has latched onto, okay, they’re anchored to, these are my numbers, and they’re going to come back and ask you at some point, well wait, should we have done 48,000? Did I really save that much in taxes? Should I have saved more? We want the tax savings, but we want this flexibility. We want it to be part of this bigger picture.

Derek (14:51):

Our financial tools now are so much better than they were when I first started, especially I remember having to do the Roth conversion math. I was going back and forth and it took me three hours for one client to figure out, okay, how much do we actually go up to the tax bracket and how does it impact it? Now it’s like with the push of a button to your point, to give you actually to the dollar how much you should do, which is a little scary, how do they exactly assume all of this stuff when you think about it? So I think we need to also be a little careful when they’re doing things like that. But I think Steven, to your point, it is really about how do we create the most amount of options, the most amount of flexibility for our clients when it comes to tax planning, right? We want ’em to be able to say, okay, we’re going to pull money from this bracket, or if X, Y, Z happens, this is what we have available and this is where we’re taking from because I think you want to have more confidence in where the money’s coming from and how is it going to impact us down the line versus saying to the dollar, we’re saving X amount on taxes.

Steven (15:39):

Yeah, absolutely. Derek, I know one of the other things that you come across with a lot of your clients working with executives, stock-based compensation. Obviously, there’s different forms of stock-based compensation, and there’s going to be some tax elements of all of them because of the dollar amounts that can be associated with equity comp. This is an area that can be very, very painful for clients. And so for advisors who have clients with equity-based compensation, I mean for me, there’s at least some minimum level of involvement they need to have to at least make clients aware of, here’s what might be coming, but there’s planning that we can do from there to help even more. So I’d just love to hear how you approach this with your clients and how you incorporate it into your planning.

Derek (16:18):

Great question. Obviously, there are several different types of stock compensation for clients available, so I think you really have to be a little bit knowledgeable on all of ’em. They’re running across the ISOs versus the RSUs and all those items. So I think more often than not, we’re seeing restricted stock units of the RSUs. I think the couple things I always bring up, can we take advantage of down markets? So when we’re looking at last year, for example, even right now when the market’s dipping a little bit, do you have 83B election conversations with them and what does that look like? And for those that don’t know, the 83B election is where you pay the income taxes on the grant date. That could be good if you have a high growth stock and if you know you’re staying at the company while, so you want to make sure you’re having that conversation with a client, well, do you think you’re going to be here in a couple of years the way that works out?

Derek (17:01):

And then you want to have the two-year, one-year role conversation. Okay, so two years from the grant date, when you get the vesting date, are we going to sell it before the year after that or not? Those are the conversations really want to make sure you’re having with clients. I mean, I tend to try and set up rules for clients when it comes to stock compensation. I think what happens inevitably is most people get a little paralyzed by it or they get just so into the company, well, I’m working really hard, I’m really smart. I know we’re doing really well, so if I do well, the company’s going to do well and I’m going to be rich because of it. If we can get in that trap with the stock options where we’re just keeping and holding and holding and holding it, all of a sudden now becomes 10 or 12% of our portfolio or maybe even more in one stock. And I saw a stat the other day. It was from 2017 to 2020, a third of companies lost money, publicly traded companies less money. The stock actually didn’t do well, right? So I think the odds that you have a great company all the time may not always be there. So how do you diversify that? How do you sell that out and how do you create a system around that? So really talking with clients about what they feel comfortable with, but just making sure we’re doing the tax planning around that too.

Steven (18:04):

I really like what you said there about setting up rules ahead of time. I’ve seen advisors do this in other areas and have a lot of success with that. I love that you do it around stock-based comp as well, because it takes the decision out of that emotional moment when they see the numbers. Because this can go in a couple of different ways, and sometimes it’s that they get excited, they have an equity comp that vest, and they’re like, well, fantastic. I’m buying that new car. I’m remodeling my house, whatever it might be. The other assumption that I see get made way too often if people don’t have somebody in their life to help them understand this is that, oh, just like my paycheck has taxes withheld, the equity must be covered by what the company is doing, and I’m not going to have to worry about this later. And the number of people I work with who get hit with these huge tax bills the first time they come and work with me because they haven’t understood before what they need to do different when there’s a vesting or some other tax trigger event, and it takes what should have been an exciting event when they have this vesting and turns it into some incredibly painful experience when 6, 7, 8, 9 months later, they have to now write a check back to the IRS.

Derek (19:07):

Well, especially they just bought a boat with it. You want to really be careful about, all right, what do you spend? What do we have to liquid? We need to keep some for taxes. You’re going to have to pay taxes on this, remember that. So generally, my role, in case you guys are curious, it’s typically keep about 10 to 20% in the company stock if they want to. And then we divest the rest, and then we basically say, okay, some for taxes. Hey, let’s have some fun with it. Let’s have some for fun. We’re not just about trying to maximize money all the time, let’s actually enjoy life. And then the rest we’ll just diversify with something else. We just really kind of create rules that the clients are comfortable with and we set reminders up. So I mean, generally they’re in the spring and fall typically I’ve seen with these stock compensations. So you just want to know, okay, hey, it’s March, your vesting data’s up. What are we doing with the stock?

Steven (19:48):

Out of curiosity, how big of a range do you have across your clients of what those rules look like? Is this pretty consistent that you come to them and say, Hey, this is what I typically see working well, so we’ve got it dialed in? Or do your clients give a lot of input or pushback to say, wait, no, I want it to be 30%, not 10%. Help me with what the reality of that is.

Derek (20:07):

Yeah, actually, that’s a good question, Steven. Now that I think about it, I don’t think a lot of people really push back on it. I haven’t even say, oh, really? I really keep 50% of my company stock. I think most people generally like, okay, yeah, that makes sense. I mean, think about it. The risk is all tied to your company because your compensation is tied there. Then you have the stock. So most people I think, get that you and I have multiple clients, but they only have one client and that’s their company. So there’s some risk inherent risk there with that. So most people are pretty good about keeping the range. I mean, some people want to go a little bit higher, but if we have to adjust it, we adjust it. I’m never hard and fast, this is the way I do it. Or you’re going to get fired as a client.

Steven (20:41):

Yeah, it’s not 10% or bust.

Derek (20:43):

No, no.

Steven (20:44):

I appreciate you sharing that because it can be easy to worry that every client’s going to want this super unique and different approach that you’ve never done before. But this is the value of working with similar clients across your book of business is that a lot of these things like talking about stock-based comp, how much of the company stock we hold, these are things that the client isn’t going to think about unless you bring it up to them. And so it doesn’t have to be this great debate or huge argument. You are giving them information and helping them make a better decision.

Derek (21:13):

Yeah, exactly. And I think for some clients, a lot of the stock is almost, I don’t want to say an afterthought, but it’s not their primary. They kind of plan their world based on what they’re getting from their W2 salary or bonuses and things like that. And they’re not always necessarily saying, okay, well, I’m going to every year pull out $40,000 of my company stock to do X, Y, Z or buy my groceries with, they’re generally not. They’re kind of saying, this is my vacation funder, maybe this is my X, Y, Z.

Derek (21:38):

And a lot of ’em, honestly, they just forget about it and they’re like, oh, yeah, where do I have that? And they have to dig and look up where those stock, I mean, just reality, because usually people that are getting stock options, Steven, they’re busy. They’re typically higher up in the company, their director level or above, and they just don’t have the time. And I think that’s where as advisors, we can provide some value for ’em. Say, Hey, let’s take a step back. Let’s figure out where everything is and let’s create a plan with how we’re going to deal with your regular compensation, but also the equity comp that we’re dealing with. So that’s kind of what I’ve seen more often than not. I don’t know, maybe your viewers are listeners are going to come back and say like, I’m an idiot, but you never know.

Steven (22:14):

If they do, I’ll invite ’em to stop listening to the show. Derek, It’s such a great point because again, taxes is an easy topic for this, but there’s lots within financial planning where it can be easy to get sucked into. I want to do the most complicated intricate planning. And there are some clients where that might make a lot of sense, where you got to really dive deep on the technicalities of what you’re going to do together. But for most people, even people who are at high earning levels or high savings levels have lots of investments, it’s consistently doing those small things. It’s these things that they’re never going to take the time to do on their own. And they’re probably plenty intelligent to figure it out if they dedicated the time, but they’re not going to dedicate the time. That’s why they come to a financial advisor. That’s why they come to a tax advisor. They want someone to help them do those things. And there can be massive value from the simple things if we give clients a way to consistently execute.

Derek (23:09):

Yeah, I think it’s more about how do we make things easier for our clients. What’s the thing that we can do to take off their plate?

Derek (23:15):

And a lot of it too is knowledge and research. So the amount of time that we spent understanding tax code or understanding X, Y, Z topic, it takes a while. I mean, I typically try and do a few hours a week of just research and reading articles and understanding markets or whatever topic there is. I don’t think most clients know about things like 83B elections, for example. I don’t think they hear about that even from their other coworkers. I think a lot of ’em will turn immediately to their coworker like, well, what are you doing with your stock options? Well, I don’t know what are doing. You may have one person in the company that knows everything that everyone turns to, and they may not be right either, so who knows? So I think a lot of it is about let’s create ideas. But going back to your point, I think most people, I’d say 80%, 75% of the planning is going to be the same.

Derek (24:01):

Most people want to retire. Most people have kids, they want to help them with their education. Most people want to pay a hundred percent of people, I would say, want to pay less taxes. So that’s probably the one thing I could say for sure. But I think for the most part, the planning is very similar for most people. It’s just all the stuff on the edges is like, what are we doing that’s different based on their circumstances? And I think that’s where the different values can provide with actually looking at a unique way for clients.

Steven (24:24):

Derek, I really appreciate you coming on and sharing your perspective on all this, and especially the analogies you use and the way that you communicate this to clients. Unless I completely misunderstood, I believe you’ve written a book. Tell me a little bit about that before we wrap up.

Derek (24:37):

So the book is called, and I’ve got a copy here. It’s basically called “Just Retire Already”. Basically, the book is nerding for retirees or Pre-retirees thinking about, okay, what are the main retirement risks out there? So I talk about things like sequence returns and market risk and longevity and long-term care, all that stuff. And then I talk about all the tools we have to solve it. And I don’t say, this is what you have to do. It’s like, Hey, this is the tool. This is when you can use it and how. But I think one of the things that maybe makes the book a little different, and I’m sure you’ve noticed listening to this podcast so far, is that I use a lot of analogies. So every chapter basically has an analogy to explain the concept. So if you find yourself struggling, okay, this is how wish I explain this concept to a client.

Derek (25:17):

I think for a financial advisor, this could be a good book for you to say, okay, this is an interesting way I can explain it. So basically, it’s meant to be fun. There’s a lot of jokes in there, some of ’em are good, some of ’em are not great. I’ll let you be the judge of that one. But yeah, it’s just meant to be a simple, easy read, less than 200 pages, so I don’t have a lot of fluff in there. A lot of self-help books do where you just talk ramble on and on about me. There’s one quick chapter about me, and then everything else is about how to retire well. And there are some questions you could ask yourself as a retiree or pre-retiree to make sure you’re on track. And then one of the things we talked about was at the end of the book, there are action items. So I have a whole checklist. Don’t just read the book, do something with it. 

Steven (25:49):

Love it.

Derek (25:50):

So I want to make sure people actually do that. So you can get just retire already on Amazon, Barnes and Noble, Walmart. It’s available wherever you buy books. And you can go to

Steven (26:00):

Congratulations. Writing a book is no small feat. That’s really exciting that you’ve done that. So very nicely done.

Derek (26:05):

Yeah. Well, I know you’ve written a book. So I’ve read yours, so I know it’s a labor of love, but actually, what I learned through this whole process, it takes a lot longer to get it published than it does the right actually write it.

Steven (26:14):

It is quite the process. But congratulations on the book ј And Derek, you mentioned it, we’re all about taking action so that information has value. So as you think about the conversation we’ve been having today, other than going out and buying your book, what are action items you’d recommend to listeners?

Derek (26:28):

Well, if you’re a financial advisor and you listen to this, I would maybe just look at your process and think about, okay, if I’m planning out for retirees, how am I planning to spike years? I think that’s one thing that we don’t do enough. So I would definitely check into that. And then really create around if you have clients with restricted stock or employee stock options, one of the things I like to do is just set reminders on my CRM, so okay when I know when clients’ stock options are coming up. So that’s an easy, simple thing to do, and just making sure you’re creating a system around that stuff. So I think those are probably my top two actually. The third one I would say is let’s make sure we dive back into the 2026 planning. I think we both have conversations on this all the time. There’s a small window where we can do some pretty significant tax help for clients. And I think having conversations with them now about that and projecting out where they are is important.

Steven (27:18):

Yeah, absolutely. The other thing that stood out to me from what you talked about today, Derek, is I love this idea of setting up rules ahead of time. Whether we’re talking about stock-based compensation or other areas of tax planning, Roth conversions, it really doesn’t matter. Things that you know are going to come up, set the stage ahead of time, have these rules that you’ve established with clients so that when the opportunity presents itself, you’re not having to re-pitch this idea, say, oh, that’s right. We talked about this and here’s what we talked about doing, and let’s go ahead and execute, and then it’s okay, full steam ahead. So I love that as well. And then if you’re not already subscribed, go to and get subscribed to our weekly tax email. You will get an email every week from me. It’s nerdy tax stuff, but if you’re listening to the podcast, you’re going to enjoy the newsletter as well. Again, Derek, thank you for your time today. Really appreciate you coming on the podcast.

Derek (28:04):

Oh, thank you for having me, Steven. Appreciate it.

Steven (28:06):

And to everyone listening, until next time, good luck out there. And remember to tip your servers, not the IRS.


The information on this site is for education only and should not be considered tax advice. Retirement Tax Services is not affiliated with Shilanski & Associates, Jarvis Financial Services or any other financial services firms.

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