Crucial Steps for the “Pre-Go” Years Before Retirement

In this episode of Motley Fool Hidden Gems Investing, Motley Fool retirement expert Robert Brokamp discusses potential strategies with Dana Anspach, who has been a financial planner since 1995 and is the CEO and founder of Sensible Money, a fee-only planning firm in Arizona. She is also the author of three books, including her latest: Living Off Your Acorns: Your Guide to the Four Phases of Retirement. They discuss:

• How to systematically de-risk your portfolio as you get closer to retirement.
• Deciding when to retire and planning for the possibility that it may be sooner than you prefer.
• Strategies for lowering your tax bill over the course of retirement.
• The benefits of categorizing the often-complex decisions about retirement as green, yellow, and red.
• The "arrival fallacy" and steps to take to ensure your retirement is as fulfilling as possible.

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A full transcript is below.

This podcast was recorded on Aug. 22, 2026.

Robert Brokamp: What you should be doing right before and as you enter retirement, this week on the Saturday Personal Finance Edition of the Motley Fool Hidden Gems Investing podcast. I'm Robert Brokamp. Retirement is the number one financial goal for most people. We spend years squirreling away money so we eventually hope to live off it. What should we be doing as we get closer to the big day? Well, we're here to provide some suggestions is Dana Anspach, who has been a financial planner since 1995 and is the CEO and founder of Sensible Money, as the only planning firm in Arizona. She is also the author of three books, including her latest, Living Off Your Acorns: Your Guide To The Four Phases of Retirement. Dana, welcome to the show.

Dana Anspach: Great to be here. It's my first time on this podcast. I'm excited.

Robert Brokamp: Well, we're excited to have you, and you talk about four phases in your book. I think most people have probably heard of three of those phases: the go-go years, the logo years, the no-go years, terms that come from a 1998 book by Michael Stein. But in your book, you added the pre-go years, which you believe can actually be the most important. When do the pre-go years begin, and what makes this time period so crucial when it comes to retirement planning?

Dana Anspach: I think the pre-go years begin about 10 years before retirement or whenever you really get serious about, wow, I'm going to retire one day, and for some people, that doesn't happen until the year before retirement or until they get a layoff notice. It's not the way we want it to happen. I'm lucky to be in this profession that I think about these things more, and for me, my pre-go years began about two years ago at the age of 53, where I really suddenly connected emotionally to the idea that I was going to really retire one day. I'm a self-professed workaholic. I love what I do. I'm very lucky. But for me, that idea of retirement, even though I do retirement planning for a living, just I thought not for me. That's just not for me. That has shifted dramatically over the last two years because of this awakening, this idea that, wow I'm in those pre-go years. I'm starting to talk about and think about these four phases of retirement, connect more with them. Other people may connect with the idea of retirement more strongly but not have the financials in order. I talk about the importance of both. You have to have the emotional connection and the finances. I have the finances, no emotional connection. If you have the emotional connection, then that 10 years prior, that's when you really need to get your finances in order and make sure what you want to do is visible.

Robert Brokamp: I think one of the trickiest aspects of this, and perhaps one of the least appreciated aspects, is that workers in general aren't actually that good about predicting when they will retire, and you touched on that. I think some studies show that the difference is about three years, but some people retire sooner because they maybe made that emotional connection and they had enough money. Might be they didn't have a choice. They got laid off or health issues, either their own or their spouses. Do you think that everyone should plan on retiring sooner than they probably expect?

Dana Anspach: I love that idea from the financial planning perspective, so when we have someone who isn't sure about their retirement date, we like to align both the plan and the portfolio as if they do retire a few years earlier. Some people reach financial independence and decide they enjoy what they do, and they're going to keep doing it as long as that enjoyment is there, and so they may work longer, but you're going to be much better off if you've planned for an earlier retirement than if you are caught off guard and expecting those last few years of savings to get you over the hurdle of where you need to be or if you simply didn't plan ahead and you're caught off guard because, oh, my gosh I thought I was going to have five more years. I wasn't really going to think about it until the year before retirement.

Suddenly here I am having to make these readjustments very quickly. That's not a great place to be. The research also shows that when retirement is forced upon you, people have more trouble adapting, more trouble figuring out that next step of how to be happy and find purpose in retirement. There's some work there on the emotional side that has to be done when these events occur. I think of it as instead of, oh, my gosh, can't believe this happened to me, being realistic about this could easily happen to me. I could be out of work at 60 or 62 or 65 if I'd been planning to work till 70.

Robert Brokamp: Once you reach that point in your career, you could call it maybe the fourth quarter of your career, 10 years before retirement or so. Obviously, one aspect of this is the de-risking of your portfolio. Does that begin 10 years, five years beforehand, and practically speaking, how do people do that?

Dana Anspach: Ideally, the de-risking would begin 10 years out. Most people don't do it, but I like the concept of staying 100% equities until about 10 years from retirement for your retirement money. I’d rather have the potential for the returns that equities can deliver, and if I’m investing over a 30- or 40-year time horizon, to me, that makes a lot of sense. Then to begin making that shift about 10 years out. I have encountered people that stayed 100% equities until six months before retirement.

Robert Brokamp: Wow.

Dana Anspach: Until retirement. I have a paper out there called The Wind Down that talks about how you begin this shift, and it compares that strategy of waiting until the cusp of retirement to de-risk or starting farther out. Of course, it all depends on the markets. I don't want my retirement or client's retirement depending on the market outcomes. If we were to get another recession right on the cusp of retirement, I wouldn't want to take that risk with my money. Ideally, you would start, let's say you're 10 years out from retirement, you are still 100% equities. You would have a financial plan that shows you, year one of retirement in 10 years, I'm going to need, let's say, that's $50,000 of withdrawal from my portfolio. I'm going to sell 50,000 of my equity holdings, and I'm going to buy we like to use the concept of an income ladder, a CD, an agency bond, a safe investment that's going to mature at that 10-year time frame, and so I know when I get there, that $50,000 is secure. It's going to earn interest along the way, but when that principal matures, that's what I'm going to use to fund my withdrawal.

Then the next year, you're nine years away from retirement, you do that again, and then the next year, you're eight years away and you do that again. By the time you got to retirement, if the equity markets were solid along the way, you would have this 10 year income ladder, or I think of it as a runway to say, I now have $50,000 a year maturing for the next 10 years. That is what I'm going to live off of, and along the way, when equity markets are strong, I will sell some and replenish what I've used. When equity markets are not strong, I'm just going to let that part be and give it time to recover. That would be the mechanics of how you would get there. It never happens exactly like that. We have how it would work on paper, and then realistically, we could have two strong years of equity markets where you're doing a lot of de-risking and then a bear market comes along and you don't de-risk that year. Then a good market comes along, you may have another year of de-risking, and then a flat market, you don't de-risk that year. Realistically, by the time you get to retirement, if you started 10 years out, you could have anywhere from maybe a five- to a 10-year income ladder in place, depending on that de-risking path and what the markets delivered to you over that timeline.

Robert Brokamp: That's good advice for managing the portfolio, but as IRA expert slot likes to point out that we're not the sole owners of our portfolios. Uncle Sam is a part owner and in your book, you talk a good bit about taxes, and you emphasize that when it comes to tax management, it's not just how am I going to lower my taxes this year, but how am I going to lower my taxes over the course of my retirement, which is really over the course of our lives. Given that, what do you think people in the pre-go phase should be thinking about when it comes to taxes?

Dana Anspach: I think they should be thinking about something that's objective. We often see people still in the mindset that I should not withdraw from my retirement accounts until required minimum distributions begin, which is now age 73 or 75, depending on when you were born, and that's a long time to put off withdrawals. In reality, there are many we call them the opportunity years between retirement and when those required minimum distributions start, which could be a 20-year window in some cases. If you're retired at 55 and your required minimum distribution start at 75, there's a 25-year window there where tax planning opportunities are often plentiful.

By looking at when your different income sources are going to start, Social Security, maybe a pension, if you're lucky to still have that, maybe you have a rental property that you're going to sell somewhere in that timeline. You could have deferred compensation plans coming in. You could have bonuses from former employment. There's all kinds of things that can make your income path very uneven during that 20-year timeline and so that means there's planning opportunities, years where your taxable income could be quite low. We're doing either a Roth conversion or a withdrawal from retirement plan, a 401K and IRA could fill up some of those lower tax rates, and that money is then taxed at a lower rate than perhaps it would be if you waited and put those withdrawals off. It's complicated math that software now does.

I also tell people be cautious about some of the simplistic calculators. They don't take into effect some of the nuances of the tax code, for example, your Medicare Part B and D premiums are tied to your adjusted gross income. The way Social Security is taxed is dependent upon your other sources of income. Some very simplistic calculators that just look at your tax brackets aren't going to take all of that into effect but there is tax planning that can take all of that into effect, planning it all out and saying, this looks like an opportunity to strategically take withdrawals or strategically realize capital gains in a year where I might be at 0% and that can make a big difference. We've seen tax planning make as much as half a million dollars or more difference over the lifetime of someone's plan.

Robert Brokamp: Wow, that's amazing.

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Robert Brokamp: The pre-go years, eventually, the big day comes, the worker retires, and they're entering the go-go phase. First of all, why do you think they're called the go-go years and roughly speaking, in your experience as a financial planner, about how long do they last?

Dana Anspach: I think they're called the go-go years because generally we're healthy. We suddenly have free time that we didn't have before. It's often when people get excited about traveling, sometimes remodeling the home, sometimes moving to a different area of the country that they've always wanted to live in. Those are times where we have both usually the financial means and the energy and health to do these things. How long do they last? There's a great blog post by Dan Haylett. He runs the Humans versus Retirement podcast. You're familiar with him out of the U.K. and he calls it your 12 good years. Does that mean it's only 12 years for all of us? No. But looking at the stats, many people have, let's say, 60-72 or 65-80 if they're lucky.

Around age 80, for most of us, but not all of us, cognitive changes begin to impact us. We're often not even aware that these changes are happening because the part of the brain it's impacting is also impacting the self-awareness that we have around our behaviors. I have a good friend who helps place people into long-term care facilities, Denise K, and she describes it as we become basically a full-grown adult but with suddenly middle school age decision-making abilities. She sees this often happens at around age 80. There are some people that are called super cognitive agers that this doesn't seem to happen to or they remain fully capable well into their 90s. That's what we all hope for. But we need to plan that it could come earlier and for that reason, I think it's important to do the things you want to do in those go-go years.

We’ve seen people so concerned about safe withdrawal rates, which are already calculated as if the Great Depression began now at the point of retirement, and then to be even safer, they’ll use a withdrawal rate lower than that. The research shows that many of those people who were great savers end up with even more funds at the end of retirement than they had at the beginning. There's nothing wrong with that, if that's your goal, if that's where you really want to pass along wealth to the next generation. But if you are foregoing opportunities or things you wanted to do or helping the kids while you're here to see the benefit of what you're doing, or maybe that's a charity or an organization you want to contribute to, many of those things are possible if you step away from a safe withdrawal rate mindset and look at the plan holistically, and you look at it through the lens of these phases. Oh, I can spend a little more during this go-go time because spending naturally slows down during these slow-go and later years.

Robert Brokamp: That's another aspect of safe withdrawal research that is perhaps too conservative. They almost always assume that retirees need their income to go up every year, along with inflation. That's generally not what happens. We had David Blanchett on the show a few weeks ago talk about his research into that. I was going to ask you as an actual financial planner who likely works with people who have above average wealth, is that what you see in real life with your clients?

Dana Anspach: It is what we see so we try to help people spend more during those go-go years, but invariably, they will get into their mid 70s, and we have withdrawals planned and inflation increases built into the plan. We may say, hey inflation, especially the last few years, we know food costs more, and gas costs more, and electricity certainly costs more. Do we need to increase your withdrawal? We've built in an extra $1,000 a month and they'll say, no, matter of fact, we're not even spending what you're sending us now. Even despite these inflationary times, as someone enters that mid 70 time frame that is still often the answer we hear and so that tells us they're comfortable. They have the means to continue to spend at the level that we have projected, but they're not needing it. The research shows JP Morgan has some great research on the spending that even in the demographics with a 1-3 million net worth, spending often shifts toward gifting, toward more aspirational things. I think there's that shift that happens where people really realize, wow, I'm not going to run out of money. I'm OK and now they start to look for things, not to spend frivolously, but things that are meaningful, things that give them a sense of purpose, things that benefit someone they care about or an organization they care about. You will see spending shift, but even including those gifting elements, overall spending in real terms is declining. It's not keeping up with inflation dollar for dollar.

Robert Brokamp: I think the takeaway here is, and I talked about this with David Blanchett as well, is that for many people, they might be able to either retire a little sooner or maybe spend a little more in those go-go years and feel safe and enjoy the money while they can.

Dana Anspach: Yes, absolutely, and enjoy it without that constant fear of, oh, my gosh. We find as financial advisors, one of the key things we're bringing to retirees is truly that permission to spend and sometimes it's alignment between spouses. Sometimes it's simply someone who realizes there's the level of self awareness. Wow, I've worked so hard to save. I'm anchored to this net worth number and to watching my account balances, and I will not enjoy these years unless someone is telling me, yes, you can do this. Here's your monthly paycheck direct deposited into your account and it is important. We have a limited time on this earth, this amazing place, and it doesn't take money always to be happy, but there are things that can bring us comfort. I use the example of someone who for years, I tried to convince them to hire house cleaner. Either they could afford it, but in their mind, that felt perhaps extravagant, not the way they were raised. I was so happy one day when I received the email that we hired the house cleaner. It might be something simple that makes your life easier like that. It doesn't have to be big grandiose or a fancy car or eating out at the fanciest restaurants. It can be things that make a difference in our lives.

Robert Brokamp: I love that story. Anyone who reads a book about retirement planning, such as your book, might feel at times a little overwhelmed because it could be pretty complicated, a lot of things to think about. What I enjoyed about your book is that you provided this framework for categorizing decisions, red, yellow, and green. Talk a little bit about that and how that can help people figure out where the gray zone is in their retirement planning.

Dana Anspach: Red, yellow, green is a framework I love. Red would be a decision we look at, and financially, the numbers say don't do this. Green would be a decision we look at, and the numbers are like, yes, you must do this, and so many decisions fall in the yellow. I'll use a simple example of paying off your mortgage. We've had people who have mortgage rates under 3%, and we would categorize that as financially, it really doesn't make sense to pay off that mortgage. You're not going to see rates like that again. It just doesn't make sense. Now, if there's not a long time frame where the mortgage isn't that large, when we run the numbers, perhaps the couple thousand dollars of potential earnings that they could have in an account in excess of the mortgage rate aren't going to materially impact that plan. That would then turn that same decision into, well, just from interest rates, we would say red, but when I run the numbers, maybe you're $10,000 ahead if you earn 5% in your accounts and don't pay off the mortgage. That then shifts that to a yellow decision where it really becomes about your values.

Given that decision, one household may say, I just have so much peace of mind from having that mortgage paid off. I know financially I might be a little better off if I didn't pay it off at this low rate, but I'm just going to feel better, and that's an OK decision when it's in that yellow area. Another household might go, I love leverage. I love the idea of arbitrage. I love the idea that I can earn more on my investments than this mortgage rate. I get it in an inflationary environment. This low-cost debt makes sense, and they might say, absolutely, I’m not paying that off. Both households made a decision that was right for them, and that's the amazing thing about finances. It's not all math. We can run the math and quantify a decision, but ultimately, people have different values, and especially as you approach retirement, I think that sleep at night factor has to be part of the equation. That's what red, yellow, green really does is it helps quantify things and then talk about that sleep at night factor, your values, and help you weigh that out and make a decision that's right for you.

Robert Brokamp: I love it because it helps you narrow in on the tougher decisions. You have many decisions related to retirement, but if you can get the red and the green out of the way, and then I just need to focus on these in the yellow zone, it doesn’t feel quite so complicated.

Dana Anspach: Yeah, and those decisions can come down to Roth conversions often fall in the yellow decision. Delaying Social Security, not so much for most retirees. I would call that a green decision that the higher earner needs to delay unless there's some extenuating circumstances, but we've had some very high net worth households that look at those numbers, and for them, it's an immaterial decision, and they may say, I'm going to claim a full retirement age and that's where it depends on the demographics, too. The materiality of a decision for one household can be far different than that same decision for another household. For one household, a decision could be absolutely green, you need to do this, and for the next household, that same decision could fall in the yellow area.

Robert Brokamp: Let's move on to the emotional side of retirement. You talk in the book about the arrival fallacy, which is that belief that achieving a certain goal is going to bring lasting happiness and fulfillment and we've all had that. We think, if we just got a raise or we just got that new car or that new job, something, we feel good about it for a little while, but then at some point, we're like, I'm not quite as happy as I thought I would be. The research on happiness in retirement is somewhat mixed, but for many people, it is the best thing that ever happened to them. For other people, there's the honeymoon period, but then they feel a little lost. Given your experience, what have you seen in terms of happiness in retirement and preparing for that transition, that period of your life where you're completely unstructured?

Dana Anspach: What I found is that our clients are probably experiencing some of that loss. As I realized in the last few years in writing the book, they hadn't necessarily been talking to us about it. I did interviews with clients for the book, and one of my clients told me about this year-long, essentially, depression. She had left. She ran her own business. She was used to the social connections with her staff and her clients, and that sense of not feeling like she was earning every day and contributing to the household, and not having the social aspect really weighed on her, and by the time she shared it with me, she’d found a solution. She and her husband moved to an age 55-plus community. They love all of the activities. They rebuilt these friendships. It's not the original house that they had planned to retire in, but when they realized what they were doing wasn't working, they were quick to recalibrate and figure out what exactly is missing and how do we regain these types of social connections that we lost through our employment.

That was a positive story, but it made me realize how many people really do go through that sense of loss of identity. That sense of, wow what am I here for? I've heard particularly high achievers with what we might call big jobs. I always thought of myself as this. It's why I did not identify with retirement. I loved helping other people retire. We celebrate, we send them retirement baskets, but when I thought of it myself, it felt like this black hole, like oh, my gosh. It’s just amazing, really, the awareness around this and the identity and the conversations my husband and I have had, particularly him reading my book, has shifted the way he thinks about it. Suddenly, I find, while I still love what I do and I have a tremendous amount of energy for work, I now simultaneously have this energy around retiring one day that I never had before and it feels good. I'm so excited because I was terrified truly like, oh, my gosh, that is just never for me. Now we have this 15-year plan. We’ve broken it into five-year chunks, the 55 to 60, and then the 60 to 65 phase, and then the 65 to 70 phase, but of course, it’ll never go exactly like we laid it out.

But having that framework in place and the way we think about it now is a game changer that makes me think, I won't go through that depression because I've spent enough time thinking about it and even just mentally exploring possibilities and figuring out what will make me excited and what I'll find shiny when I get to that phase.

Robert Brokamp: As you alluded to in the beginning of the interview, part of it was you taking the time on a vacation, really, and having that experience. I had the same experience recently. I know you were born in Iowa. I did RAGBRAI a couple of times, the annual bike ride across Iowa. It gave me a taste of, you know what? Maybe having some time to hang out and ride my bike wouldn't be so bad, actually. I also moved up my idea of when I might retire. I'm not sure but maybe, we'll see.

Dana Anspach: I love that. That's how it started for me. I describe it as a little dimmer switch went on. I was in this dark room, and then that little dimmer switch went on two years ago, and I would say, now my dimmer switch is a fully lit room. Not a room I’m ready to step into yet, but a room that I can see more clearly, and a path I can see on how to get there, and I’m truly shocked. I'm actually shocked myself that, like, wow, one day, I'm going to be excited about retirement. This is cool.

Robert Brokamp: Well, Dana, are there any final thoughts or recommendations you have when it comes to retirement planning?

Dana Anspach: The last thing is really around planning ahead for those slow-go and no-go years. As I studied cognitive decline, as I had the experience with clients we’ve served for 25 years, in some cases, we often think we’ll plan when we get there, but because our decision-making ability changes, it’s very important during those go-go years to decide what you want your later life to look like. Just like during the pre-go years, you want to do that thought around, well, how will I transition and what will my retirement look like? Once you're five, 10 years into those go-go years, you really want to give some thought to things we don't like to think about. Which is what will the last five or 10 years of my life look like and where will I want to live and how do I want to handle that with my family and my children and begin having those discussions? Not something we all love talking about, but if we do, it can be a beautiful and peaceful transition that we have just like the transition into retirement can be.

Robert Brokamp: Well, Dana, this has been a great conversation. Thank you so much for joining us.

Dana Anspach: Thank you.

Robert Brokamp: That, my Foolish friends, is the show. Thanks so much for listening, and thanks to Bart Shannon, the engineer for this and every Saturday episode. As always, people on the program may have interest in the investments they talk about, and The Motley Fool may have formal recommendations for or agains,t so don't buy or sell investments based solely on what you hear. All personal finance content follows Motley Fool editorial standards, it is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. I'm Robert Brokamp. Fool on, everybody.

JPMorgan Chase is an advertising partner of Motley Fool Money. Robert Brokamp, CFP, EA has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends JPMorgan Chase. The Motley Fool has a disclosure policy.