A/B Conversations: CFP® Your Way Out Of It – Real Advice on Building Wealth & Retirement Planning

Ep #141 - Navigating the Messy Middle of Retirement

• Benjamin Haas I Haas Financial Group

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Retirement isn’t a single event. It’s a long, evolving phase with multiple transitions. After the honeymoon ends but before the later-life simplicity sets in, there’s a “messy middle” - an emotionally complex, opportunity-rich period. Redefining goals and finding purpose may require doing some intentional planning again. Listen as Adam and Ben discuss how they help clients navigate this period of retirement with ideas, exercises, and open conversation.


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Investment advice offered through Great Valley Advisor Group, a Registered Investment Advisor. Great Valley Advisor Group and Haas Financial Group are separate entities. This is not intended to be used as tax or legal advice. Please consult a tax or legal professional for specific information and advice.

[00:00:00] Adam Werner: Hi everyone, and welcome to AB Conversations, where we will help you CFP your way out of it. A podcast where you get into the minds of a couple certified financial planners on how we think and feel about everyday financial planning questions, and what should really matter most to you. A healthier financial life starts now.

[00:00:27] Ben: Hey pal. How are we doing today? 

[00:00:31] Adam Werner: Just great. How about yourself?

[00:00:32] Ben: Yeah, good. Staring over my computer screen at a fancy blue car out there. 

[00:00:39] Adam Werner: Yeah. And the sun is shining, so, all new things here in Pennsylvania. 

[00:00:45] Ben: So, good topic today. I think in the realm of retirement, you and I sometimes have these conversations that are leading people to that phase, and we always say, that's the time to celebrate.

You made it to retirement. The truth is, retirement's not a single event. Right? The math tells us that on day one of retirement, you may buy actuarial standards, live 8,000 days in retirement. So it's like this long, evolving phase of time with multiple transitions. And I think what we're gonna talk about today is after that initial like honeymoon phase, but before things get simplified later in life where maybe you're not on the move as much health is diminishing. There's just this like messy middle. This emotional, sometimes it just feels like more financially complex, tug of war on can I spend, can I not spend, where we really just want to help people get out of that messiness and just feel like they have direction again.

So let's talk about it. 

[00:01:46] Adam Werner: Yeah. And it is such an interesting phase for people, like you said, a lot of people that we work with that are preparing for retirement, right? You just wanna get to that point and then the rest will just fall into place for a lot of people, right? I just need to get there, then I'll figure it out.

But what we have seen and have heard and what we hear anecdotally there is that initial wave of that honeymoon period, I'm retired, every day feels like a Saturday, right? I lose track of days of the week. I think that's a, that's an oddly specific for retirees, an oddly ex oddly specific experience.

I talk to my dad and he'd say, what day is it? And that happens. But then once you get beyond that phase, you said it earlier, right? Get beyond that honeymoon phase. Maybe it's a few years in, you've got your feet underneath you, but maybe you're still caught in that in between where work is behind me.

But I'm still in decent health. I'm not dealing with those later age issues with maybe forces your hand and then yeah, you're maybe just feeling like you're in that middle where I have a lot of flexibility of time. Maybe I still don't have a great structure for how I wanna spend my time.

And just that uncertainty of, but if I don't know that I have enough, financially, maybe I'm not going to do certain things. And then that just, I think, adds to just all of that messy middle where, I mean, we see it, I think economically right now with tariffs and all of that. Where in, in with the lack of clarity or certainty, often the default is, well, I'm just, I'm just gonna sit on my hands.

I'm not gonna do anything to jeopardize anything. I'm just gonna take the cautious approach and lean to doing less. And for a lot of people, that's probably not necessary. 

[00:03:33] Ben: Yeah, and we've talked about it before. We try to help people on the onset of that. There is a book that we really appreciate called What Will I Do All Day that's supposed to help people go through this process where they feel like there maybe there's some purpose drift.

Like they don't have that same structure, but I think there's also probably for many people this shift in their role. Maybe it's within the family, maybe it's now a new phase of life. It's grandparent or maybe it's the other way, working up now they're caregiving for their parents.

Maybe they're going through their own health transitions. There's just, there's a lot that can make this messy. And I do think, to your point, that does domino into this common financial uncertainty like these pit, what we'll call like pitfalls in planning where people get stuck and now we want to help them get unstuck.

[00:04:23] Adam Werner: Well, yeah, there's phases to planning, or at least there's life phases that have different strategies or different approaches or just different ways of going about it. And I think what we're talking about here, it's not, you're in between phases, right?

When you're working and you're accumulating, we've talked about this on other podcasts, we've heard from clients that would tell us that's the easy part. I can set that on autopilot. I can live within my means, I can save, and that's fine. But then again, we're not towards that end of, hopefully maybe not.

But , that end of life sequence where I've done what I wanted to do, I still have these funds. How do I want to create my legacy, right? Do I accelerate giving this away and see seeing the impact while I'm living? But for a lot of people before they get to that point, is that middle where I'm not sure it is that uncertainty.

And we've seen both sides of the spectrum where in our eyes, people that have enough to do what they would want to do but are not doing it, need a little extra encouragement. But then I feel like we've also seen the flip side where people may be leaning too hard early in retirement with, I don't know how long I have, so I'm gonna live every day like it's my last. I'm gonna take advantage while I can, but then get to the point later in life where, well, crap now I, I'm removing some of my flexibility. Maybe I think I put myself in a situation that doesn't feel so great now, and that overspending now has a trade off in the long run. It's difficult.

[00:05:55] Ben: Yeah. So what we really want to do is we want to facilitate these conversations, right? We don't want people to be stuck procrastinating when they have, what they know will be big decisions to be made at some point. Right? You gave some of them. Maybe it's downsizing. Maybe we're Moving into a different community that can support us in different ways.

We're gifting, we're traveling, whatever it is for them. Yeah. We just don't, anytime that we can be proactive in our planning instead of reactive, we're doing that because we want you to have all options. But we're recognizing here, right? That messy middle. We don't want you just sitting on cruise control, having some of these thoughts, not knowing what's financially possible, when really it is our job and how we want to help is to simply have that conversation.

We're back to the whiteboard of what is possible and what our trade-offs as opposed to some of the initial planning that usually is just, we're trying to fix things for you, right? We're trying to get things in line. We're trying to put a bandaid on this, or surgically repair this, when, now what we're talking about in this messy middle is let's reimagine what's possible.

[00:07:00] Adam Werner: Yeah. And that's, so I know we record the podcast specifically around that idea of fix, fine, flourish. 

[00:07:07] Ben: Mm-hmm. 

[00:07:07] Adam Werner: And I think this is the perfect example where we'd be in that flourish. Let's reassess. You've gotten to retirement.

Hopefully you've gone through a, a few years of it. Again, just getting your feet underneath you for what your life is going to look and feel like. Not only financially, but , how am I going to fill my time? What am I gonna do all day? So yeah, just having that conversation with hopefully, a certified financial planner to give some context and perspective on truly, yeah, what is really possible because again, these things have to align.

Someone could say, I want to gift X amount to charity and I wanna leave this money to family, and I wanna do all these things, but if the resources aren't there, then obviously, some trade offs are gonna need to be made. But just going through that thought exercise, that I feel like is a much better situation than coming from a source of excess, but having no real definition of what do I want to do with it?

What's going to be meaningful to use the savings that I built over time. I think that's a harder position for people to be into. 

[00:08:16] Ben: So let's talk about both of them and I'll maybe start with what we would do in that situation where maybe people don't have the definition and then maybe I'll just pass it back to you on like these situations that we've dealt with where we're giving permission to spend, like the idea of mental bucketing.

Yeah. But I think if somebody's really struggling with purpose, like one of the best pieces of advice that I heard, and it goes back to that book, What Will I Do All Day by Patrice Jenkins. It is really to just think about what fulfills us. Right? It is gonna be a couple different things. What gives me purpose?

What do I want to engage in? What relationships in my life like fulfill me, how do I feel accomplishment? And one of, one of the exercises is just to like, walk in the bookstore and like, what catches your eye? Are there certain hobbies that you haven't dealt with? And she tells this story of this person who was single in retirement and had always thought about traveling, but that idea of traveling and certainly traveling abroad, brought a line of anxiety on, I don't know that I'm prepared to do this.

So what was that simple next step? It was to pick up that book at the bookstore and start trying to learn the language so that she could feel comfortable and more acclimated.

Well, learning the language then became, well, I'm actually gonna take a class so that I'm like surrounded by other people immersed in this learning at the community college. Well, then it became, I'm not just gonna take this vacation over there for a week. I'm gonna go like Airbnb and I'm gonna live there.

Right? So there was just this micro action of walking to the bookstore that led to something so much greater and more fulfilling for her, had the financial means to do it. But if it's about finding what's gonna fulfill us, we have to start with just that exploratory phase. 

[00:09:49] Adam Werner: Yeah. And that's just such a behavioral finance idea, but just that idea of just breaking things down into bite size pieces. 'Cause the thought of, if I was that person thinking I want to spend a couple months in Spain, and I'm gonna go do that without building up to it, that just feels like that's a huge undertaking. It would stress me out and I probably wouldn't do it because that feels like it's too big of a leap.

But just that thought of what's the next smallest step I can take? Even if it is, I'm gonna go to the bookstore and yeah, maybe not even gonna the bookstore anymore, but I'm gonna, I'm gonna download Duolingo. Yeah. The, yeah. And start. And start to learn, start to learn the language, and then I can take that to the next step to explore further.

Just, I think just that concept of testing things, but doing it in a way that hopefully is more digestible. Right? And maybe just easier to test along the way. And maybe you, you find yourself along the way saying, I thought this was a great idea. I thought this was one I wanted, but as I got closer, maybe it's not.

And you're giving yourself that ability to adapt and you're not backing yourself into that corner, which was, well now I already paid for, a two month stay in Spain and now I can't learn the language, but I already have everything scheduled. And now if that were me. I'd feel even more anxiety and even more stress about it if I didn't go through maybe some of those micro steps in the first place.

So I I, I'm glad you said that because I think that's a great tip, or at least just something to try in many instances. 

[00:11:20] Ben: Yeah, and we're not, I mean, we're not retirement psychologists here. I'm not, I'm not suggesting that we're gonna have all those answers, but I think if we can couple that with some of the work that you and I do.

We are big proponents of mental bucketing, right? To just, create this, I'll call it pool of money that you have permission to, I'm not just gonna say spend, but play with, figure out how this is going to serve you. And I know we could probably give some examples where we've tried to coach clients into like, this is, we can call it an uncertainty bucket.

We can call it the fund money, right? This is not gonna cover your needs. Like we need to convince people that their needs are covered. Right? That's this pool of money that we've set aside. And we do this for investment purposes too. This is safe, it will take care of you. This may be what we'll call excess or this is the future fund money.

So give them that opportunity to couple these ideas together with what might serve me with permission to spend. 

[00:12:15] Adam Werner: Yeah, and I think for a lot of people, and I maybe again, it's just, just, you know, our human nature, is to go to the extremes. I'm either gonna do this thing or I'm not. Yeah. And thinking about the mental bucketing, I know we've talked about this in some other recent podcast too.

The idea of someone wanting to accelerate the payoff of a mortgage or I've had this conversation a number of times, which is, I'm retired, but we need to replace the car. Should I take from my savings, should I take from my investments, or should I take out a loan? I don't love the idea of paying interest.

So something as simple as you have, maybe it's a non-retirement investment account. This would be the scenario here. People are fearful, I think, of, of that idea of running out of money, right? It's, and rightfully so. Eating into principle of their investments doesn't feel great. But if there was a way that we just said, well, let's just turn off the dividend reinvestment, let tho those dividends accumulate in cash and whatever that is on a quarterly basis, that's what you use to put to the principle on the car loan or the mortgage or whatever that may be.

It doesn't necessarily need to be for debt. Right? That could just be the mentally accounting work. That's gonna be my gifting money to friends, family, community, whatever it may be, but just a way to build in a process, or at least you used the word permission, right? You're building in some of that permission to just spend some of these funds from your savings.

[00:13:40] Ben: Yeah. It's my treat myself money. Think of another client who just worked her whole career in this world of multiple levels of compensation, one of which was like bonus money when things were going really well or she performed really well. That was always gonna be the, that's the treat myself money then, right?

So it made a whole heck of a lot of sense, two, three years into retirement where i'm having these conversations with her like, yeah, but you're not doing the things you talk about doing in retirement. Like, why are you not? I'm afraid to spend it. Then here's what we're gonna do every quarter.

If we're having good quarters, if there is excess, I'm sending you your bonus paychecks, just like you were used to. Right? Because that was what, that was the habit, I think you and I can find ways if people tell us, right? We need to find out if you're in this messy middle, but if you're in it and part of the reason is I'm afraid to spend, then let us go through the scenario planning with you and let's figure out the mechanism, the logistics of you feeling okay spending money or exploring something new.

[00:14:39] Adam Werner: Yeah, I think that goes back to one of your, maybe it was even in the intro, right? The idea that retirement is not just circling that data on the calendar and getting to that point and, getting to the end of retirement at some point. It's all of that adaptation and the evolution along the way and the planning side of things needs to also go along with that.

Right? But I think a lot of people, when they think about financial planning, it's, just tell me what to do and I'll go do it. But the reality, what we've seen, and especially in this scenario where people may just feel, I don't wanna say lost, but just a lot of uncertainty with where things are headed.

Just going back to baseline and rerunning some of those projections. Right? Let's talk through, if you wanted to do this, based on your situation, which could be very different a few years into retirement. 

[00:15:32] Ben: Yeah. 

[00:15:32] Adam Werner: We've certainly seen that. 

[00:15:34] Ben: I wasn't willing to make what's really 

[00:15:35] Adam Werner: possible. 

[00:15:36] Ben: Yeah. I wasn't willing to make this trade off five years ago, but now my, let's use another client situation. Now, my daughter lives X hours away. I love to ski. Why don't I consider buying the ski condo so that when I go to visit her, I actually have a place to stop on the way home. Yeah. Right. Like, wouldn't win-win. Wouldn't have explored that, the onset of like building a retirement plan, but it became a situation that was worth exploring and the trade-offs that person needed to make.

They were willing to then make, right. Nothing has to be too permanent, but we have to explore those things. 

[00:16:10] Adam Werner: Yeah, and I guess that just points back to the importance of planning in general, but having those planning conversations on a more regular basis. I think maybe a lot of people do or maybe even want to have those planning conversations because yeah, even little things that people are facing in retirement or may maybe they consider it to be little, can have bigger conversations around them that can lead to some, using the word big can could potentially lead to some strategy change or some horse correction in retirement to maybe get to a point that they're feeling more content, feeling more fulfilled, and maybe feeling like their savings and wealth is actually aligned with what is important to them. 

[00:16:57] Ben: Right? 'cause that's maybe what we would want to be clear about in this situation, right?

If money is the tool to live the life you wanna live, then we as advisors have to recognize that. Just building this wealth is not the end goal. Like we need to align this wealth to what's gonna help you feel fulfilled. And I don't think there's anything wrong at any point in that relationship with coming to us and going, would you think this is possible?

Is this possible? Yeah. Like what would it take to get there? We enjoy that. I'd like to get that phone call, that email from somebody that I haven't talked to in six months that goes, Hey, I heard your podcast and I've been sitting on this idea. What do you think? That's a fun meeting. That's an exciting meeting.

Like, let's explore what's the, what's the worst thing that can happen? We explored it and it doesn't work well, you're no worse off than you were sitting on the couch thinking about it, not talking to us about it. Yes. 

[00:17:45] Adam Werner: Yep. Very well said. I agree. 

[00:17:48] Ben: So. In summary, if you're having these thoughts, if you feel like you're in the messy middle, like this is a big part of the job.

We do not want people sitting idle with these thoughts, let's schedule a meeting. Let's go through it. 

[00:17:59] Adam Werner: Yeah. Yeah. And maybe to put a bow on that, it's, I think it's different in talking to us. And I know we've said this before, most people are gonna make this decision to retire one time.

Mm. You may be looking for advice from coworkers or friends and family and hey, how did this work for you? Or what did you do? But we know that everybody's situation is different. We've been through this or I've seen it and helped people through it enough times where we have a wealth of experience and some maybe, I don't wanna call it data, but that information that people can lean on, and I know you've, this is, I have this in my head from you. It's better to learn from someone else's mistakes than your own. So lean on us. We have some experience in that world. If you are considering what's possible or want to go back to the drawing board in retirement, let's do it.

[00:18:50] Ben: Well said, sir. Appreciate you. Okay. Till next time. 

[00:18:53] Adam Werner: See ya. See ya. Bye.

 Hey everyone, Adam and I really appreciate you tuning in. Please note that the opinions we voiced in the show are for general information only, and are not intended to provide specific recommendations for any individual. To determine which strategies or investments may be most appropriate for you, consult with your attorney, your accountant, and financial advisor, or tax advisor prior to making any decisions or investing. Thanks for listening.