The Long Strange Trip Episode 25:Why Smart Retirees Struggle to Spend Their Money (And How to Enjoy Retirement) with Russ Thornton

About this episode:

Here’s my take:

If you’ve spent your entire adult life running a business or driving hard toward the next career milestone, stepping away isn't just a schedule change—it’s a total identity reset. For decades, you woke up knowing exactly who you were, what you did, and where your value came from. But what happens to your sense of self when the daily demands vanish, and you're no longer the "business guy" in the room? I teach and write about this stuff all the time, yet I still catch myself wrestling with that exact question. It’s funny how easy it is to coach others through a transition while feeling completely stuck when it’s your own life on the line.

Then there’s the money side of things, which turns out to be far more emotional than logical. You spend 30 or 40 years in pure accumulation mode, saving obsessively and treating your nest egg like a fort to be protected. So why does giving yourself permission to actually spend that money—money you worked so hard to earn—suddenly feel so terrifying? Rationally, you know the spreadsheets check out and the math says you're fine, but a lingering scarcity mindset has a way of overriding logic. We worry about running out of capital, but maybe the bigger, quieter risk is never letting ourselves actually enjoy the life we spent a lifetime building.

So where do we go from here? The mistake so many of us make is focusing entirely on what we're retiring from, rather than what we're moving to. Leaving a high-stress job creates space, but space alone isn't purpose—it’s just an empty room waiting to be filled with something meaningful, whether that’s relationships, new creative pursuits, or simply learning how to be present. I turn another year older tomorrow, and as I look at having way less life ahead than behind, I find myself caring a lot less about traditional success and a lot more about doing things that truly matter. What about you? Have you figured out what you're actually building toward next?

Transcription:

Josh: Welcome to The Long Strange Trip. I'm Josh, the host of the show. We're going to dig into six areas together, finding real work-life integration instead of that brutal 95/5 split too many business owners live with. We're going to approach retirement as an actual reinvention rather than just stopping work, and we're facing death honestly and avoiding PTSD around death. We're also building resilience when life throws us curve balls. We're sharing wisdom across generations. And finally, we're understanding the patterns that show up in all our transitions. I'm not coming at this as an expert. I'm a fellow traveler figuring this stuff out in real time, especially now as I navigate my own dual cancer diagnosis at 73. Welcome to The Long Strange Trip. I'm glad you're here.

Josh: This is Josh Patrick, and we're with Russ Thornton, and you're at The Long Strange Trip podcast. And today, Russ owns a wealth management firm. It's called Wealthcare for Women. Uh, but we're not gonna talk about the technical side of wealth management today. We're gonna talk about what many in the industry refer to as the soft side. And one of Russ's core philosophies, he says he helps clients shift focus from financial scarcity to personal priorities. So let's bring Russ on and find out what that means. Hey, Russ. How are you today?

Russ: I'm great, Josh. How are you?

Josh: I'm well, thank you. So what does it-- shifting focus from sci- financial scarcity to personal priorities

Russ: Um, you know, that means a lot of different things to a lot of different people. Um, but generally speaking, uh, in my experience, many people after working in a career or careers for thirty, forty-plus years, um, and receiving a paycheck, often a sizable paycheck, once they make that transition or begin to make the transition into retirement and the paycheck goes away, um, and m-many of my clients, uh, have been diligent savers over their career. Um, they've kind of reached the top of the metaphorical mountain, if you will. Um, and then the paycheck goes away, and they have to start using or spending all of their hard-earned and, um, and hard-saved, um, financial resources. And it's amazing to see, uh, these people, many of whom are super bright, well-educated, um, high-achieving performers or executives that were making a lot of money, all of a sudden kind of withdraw into themselves and become very, uh, miserly and seem to look at the world through a lens of scarcity, having i- literally in, in days, weeks, or just months ago been, um, much more in a, uh, abundance mindset because they had the paycheck coming in. And so there are certainly financial ramifications to that transition and those decision-making, uh, those decisions that need to be made, it's really, to me, fascinating to think about the psychological and the emotional, um, transformation that people need to go through to begin to see the potential and the possibilities beyond, you know, thinking that I have to squeeze, uh, the life out of every dollar because, um, you know, I wanna make sure the money is la- money lasts, and I wanna make sure I'll be okay.

Josh: So it sounds like one of the challenges the people you work with is what I call underspending

Russ: Yeah. I mean, that's, that's a much more succinct way to say it, but yeah, that's, that's exactly it.

Josh: Yeah, it's, in my, in my experience, my, my sister is like the poster child for this. She's got probably three or four times the amount of money she's gonna spend in her lifetime, and trying to get her to loosen up and spend a little bit more money is like pulling teeth. So what are some of the strategies that you get to do when people make the switch from earner to spender? And when they go to spender, how do you help them feel safe and realize that they really... It's, it's a stupid thing that they're concerned about.

Russ: So before I tackle that, I'll just, I'll just add a quick aside, uh, since you mentioned your sister. Um, um, a-again, I'm, I'm painting with a very broad brush here and being—

Josh: Sure.

Russ: —uh, generalized, but it's interesting to see that, um, in my experience, women are often more afflicted by this, generally speaking, than, um, than their male counterparts. Um, and my focus is on serving women, and so I encounter this all the time. But to give you an example, and, and one I think we may have talked about, um, in, in our conversations leading up to today's conversation, is that, uh, let's say, um, a, a woman can, um, comfortably afford to spend, based on my analysis, uh, $20,000 a month, um, adjusted for inflation for the rest of her life. Uh, and let's say she's only come... or only spending about eight thousand, to pick a number. Um, that's a pretty significant, uh, delta, uh, between eight and 20. Um, so how do you get her to move, uh, closer to what she can spend and, um, and hopefully avoid, uh, potential regret later in her life for missed opportunities or missed experiences? Um, and it's not an either/or. It's not spend eight or spend 20. Um, it's how, how can we i-identify maybe baby steps to get her to start testing the waters of spending a little bit more and avoiding consistent underspending? Examples are, um, literally kind of making it a project. Like, give her an assignment or give a client an assignment and say, "Hey, um, over the next three months, I want you to spend one or $2,000 more a month. So whether you spend it on yourself, your family, your friends, whether you give it to a charity or, or, or an organizations that, that's important to you, um, let's, you know, let's, let's kind of test the waters and put a project in place with a, with a goal, put some boundaries around it." Um, and then check back in with a client and say, "All right, A, did you do it? B, if you did, how do you feel? Did... You know, did it, did it give you anxiety? Were you losing sleep? Were you... Or did it feel pretty good?" Um, and then based on those, you know, experiences, feelings, emotions, reactions, we can then, um, you know, make a plan going forward to either stay at that level, test it a little higher, settle back down to where they started, and, and maybe we try again in a little.

Josh: So a more concrete example is someone that wants to fly from Atlanta, where I'm based, to, uh, Denver, let's say, to visit family. Well, sh- you know, let's say she's always flown coach. I would encourage her to, you know, upgrade to first class as an example. I think the example you had given is, um, instead of, uh, an inside cabin on a cruise, make sure you get a-an outside cabin with a, with a balcony. Um, it might cost, you know, one, $2,000 more, but it can really enrich the experience.

Josh: The, the, the other example I give with that is upgrade to a luxury cruise line.

Russ: Uh, yeah. Yeah, there you go. Exactly, yeah. So instead of being on a cruise with 3,000 of your closest friends and neighbors, uh, yeah, maybe do a, a luxury or a smaller boat where there's fewer people or, um, yeah, the... Once you really start thinking through this, the, the opportunities to test spending a little bit more are virtually endless.

Josh: Now, the, the reason I'm so, um, sort of concerned about this issue, and I, and I believe it's a huge issue by the way, is that, you know, we, we read all the time about people who don't have enough money. But the truth is, the amount of millionaires are growing at a very rapid pace in this country. You know, the middle class is shrinking, but the upper class is growing, and so is the lower class. And the issue is that if you read the press, it's we don't have a-- we don't have enough. But for the people who generally work with financial advisors, in my experience, the opposite problem exists. They have too much. And it, and it's not too much, you know, in a, in a global sense, but it's too much in a local sense 'cause they're not spending it. And in my experience, the real issue comes in when you're in your 70s. That's your golden age to actually spend more than you probably should, because when you get to your 80s, you're not likely gonna be able to.

Russ: Yeah. Yeah. I read an article by, um, um, a UK financial advisor a few weeks ago. Uh, he talks about, uh, this 12-year period from age 60 to 72 when statistically speaking, those are gonna be your, um, um, highest health, highest energy years, and you should get out and enjoy life. Um, I would agree. I think it... for a lot of people that have a little bit more wealth, take care of themselves, that can extend well into their 70s. But what I would also counter that argument too and say, for somebody that's 55 or, a-as an example, um, because of this scarcity mindset and because of the, these, this constant barrage of messages saying that people don't have enough, you need to save more, you need to have X amount of dollars by this age, people that I get introduced to and start working with, I can demonstrate to them that they can confidently and c- and comfortably retire a lot sooner than they want or, or than they thought they could. So somebody that had planned-- be planned working to 65, um, and in many respects deferring a lot of aspects of living until once they retire, I'll say, "Well, you know, why don't we retire at 58 or 60 or whatever and start going out living, l-living your life right now?" So I, I agree that you need to get out and live your life while you have the energy and the physical capability to do so, but, um, I think that can potentially start well before your 70s.

Josh: I would agree. And my question is, and I'm-- it's a question about do, do you hear this? You say, "Okay, you're 55, Mr. Client or Ms. Client, in your case, and you have... I can prove to you, and you agree that you have more than enough assets, probably four or five times more than you're gonna need for the rest of your life. So the chances if we invest your money wisely, which is what we do, the chances of you running out of money are slim and none." So when you say it's time for you to think about retirement, how often, and I don't think you're gonna hear this as much from women as you do from men, is the question is retire to what? Do you hear that often?

Russ: More often than I would like. Um, I, I, um, may- maybe this is kind of where you're going with this idea, Josh, but I, I firmly believe that people should be retiring to something as opposed to just trying to escape or retire from—

Josh: Oh, absolutely. There's no question. No, I, I agree with that 100%.

Russ: Yeah. So I, yeah, I've, I have, um, more than once I have encountered people, uh, women and men that, um, you know, so much of their identity is tied up in their work, uh, or so much of their identity has been tied up in raising their family, um, that once they, you know, retire, whether it's in their 50s, 60s or later, it's kind of like, uh, all right, well, what was all this for? And I think... I, I suspect that is a, um, that's a reason why we see so much, quote, "gray divorce," um, people getting divorced later in life because they've spent all these years raising a family and/or working, um, they retire, now they have all this time with each other that they haven't really, you know, spent as much time with over the last, let's say, 20 years, and it's kind of like, "Who is this person?" So, um, it's an interesting perfect storm of events, you know, that kind of hovers around this retirement transition that, um, a-again, it's just endlessly fascinating to me all of the emotional, um, a-and other factors that weigh into those, those decisions.

Josh: Well, do you do anything to help your clients prevent divorce when they retire and all of a sudden they and their spouse are in the same area and they don't really, um, know how to talk to each other anymore?

Russ: Yes and no. I, I wouldn't say that I, you know, I specifically have a structured conversation or process around this, but I, I do like to believe that some of the conversations I have could hopefully help bridge, uh, maybe some of those chasms that have grown over time between spouses. Um, so, um, when I talk with clients, we obviously have to address the quantitative financial technical aspects of financial planning, investing, planning, et cetera, et cetera. But I also try to spend a fair amount of time on the qualitative. Um, and so we'll do-- we'll, we'll have conversations or do exercises like, um, describe your ideal day to me, or describe an ideal week to me, or, um, you know, tell me, um, you know—

Josh: Out of, out of curiosity, Russ—

Russ: Yeah.

Josh: Many people can describe their perfect week to you?

Russ: Uh, very few. Um, it is a, um—

Josh: With thanks.

Russ: It's o-often an uncomfortable conversation, um—

Josh: Yes.

Russ: —but I like to tell clients that I'm very comfortable having uncomfortable conversations. Um, and gotten over the years at, um, embracing the silence. So, um, I'll ask a question and, and I've, I've had to fight myself over the years to r- wanna rush in and fill the, fill the, the space. But, um, I've gotten better at just asking the questions and letting them kind of fumble through it on their own. Um, but yeah, to answer your question, very few people have ever thought about how, how would I spend a random Saturday, or how would I spend a, a week now that I have this abundance of time? It's interesting to f- to contrast the, the, the abundance of time versus the, the scarcity mindset around their money once they retire as well. So it's, it's just, again, interesting.

Josh: Well, there's a, there's a whole factor with, you know, as you... And this probably is more true for men than women. Men do not do a good job, in my experience, of building outside social networks while they're working. Their social network is their work network, period. When they retire, they say, "Well, I'm no longer a senior executive. I'm no longer a business owner. Who am I?" And that question, who am I, becomes the overriding question that makes them incredibly unhappy when they retire. With women, and you can tell me this better than I can, I just have this theory, women tend to build networks much better than men do, and they do a really much better job of maintaining those networks. So when it becomes time for them to stop working, it's just a natural progression into whatever those networks are, and they don't have a hard time filling the time that they used to have at work. In fact, they may even enjoy it. Men, on the other hand, will feel incredibly lonely, and that becomes a really, really huge, huge problem. Now, it's not something I would suspect you would handle because frankly, that's therapy.

Russ: Yeah. Yeah. Um, I, I have-- I see that all the time. Um, and I, I agree with your, I agree with your theory. Um, I, I think, I think you hit it on the head. Uh, I think that is a-- has been and continues to be a challenge for many men, uh, less so for women, although it can impact women, uh, as well.

Josh: I just thought—

Russ: It's, um, it's, um... I, I think the-- think you asked the, the most important question is, who am I? Um, I jokingly kind of ask clients, like when they're approaching retirement, like, "Have you figured out who you wanna be when you grow up?" Um, and while I ask it kind of tongue in cheek, um, it's really interesting to kind of let that sit with them and let them think through it, um, and, and share their thoughts. Again, um, often an uncomfortable conversation, but an important conversation nevertheless.

Josh: These important conversations are uncomfortable.

Russ: Yeah. Yeah, they are, but they, they need to ha- they need to happen because—

Josh: —to happen. That's the, in my opinion, the good financial advisors force it.

Russ: Yeah. And you're right, I'm not a therapist, um, n- nor do I proclaim to be one. But, um, I think so much of what, um, a good financial advisor does bumps right up against—

Josh: It does. It bumps right...

Russ: —um—

Josh: —this, this close to each other.

Russ: Yeah.

Josh: And the, and the challenge comes in, I think, I used to be in your world, by the way, so I kind of understand this, is that too many advisors who are working on the, um, soft side, they get themselves into th- playing the role of a therapist, and they shouldn't be doing it.

Russ: Yeah.

Josh: I see this happen all the time. Now, it's a, for people who are on the other side that just do the technical shit, excuse my language, technical stuff, um, they could care less about this. But the folks who work, and it's a small percentage of advisors, I believe, that do this work and do it well, their challenge is when to say, "We're past my skill set. We need to bring in some other help."

Russ: Yeah. Yeah. And in my experience, um, I think you're exactly right. Uh, I would venture to say the vast majority of financial advisors are happy staying in the world of money, technical competence, investments, financial planning. Um, those that are willing to step outside those bounds and get into the, you know, the life planning, the qualitative deal- you know, dealing head-on with the emotional, psychological aspects of planning, and not just planning around money, but planning around someone's life, um, I find that many of those advisors, and, and I've been guilty of this as, as well, um, are so quick to jump in to that with both feet that, that, yeah, they can quickly find themselves in dangerous territory where they are outside of their, um, their skill set, and they could potentially do more harm than good. Um, and I, I have tried to be sensitive to that and recognize when I need to, you know, bring in another professional or suggest the client seek out another professional. But yeah, that can be, uh, that can be dicey ground, um, and it can get, it can get dangerous quickly if, if, if the advisor isn't careful.

Josh: Yeah, I find the best way to deal with these really, um, dicey areas in life, period, is through questions. Like instead of saying, "I think you should see a, a, a counselor or a therapist," I would say, um, "Out of curiosity, have you ever thought about seeing a therapist about this stuff?" So now, now we're putting ourselves into a soft question instead of a hard question.

Russ: Yeah.

Josh: At least in my experience.

Russ: Well, that's, um... I knew there was a reason I liked you, Josh. I, I too am a, a student of good questions, um, and asking questions. Um, I often have told clients like, um, "You're not coming to me for answers. You already know what you should be doing in most cases. I'm here to ask you the questions to help you surface, you know, sur-surface those answers and surface, you know, better decision-making." So, um, so I, I completely agree. Um, I'm not here to, um, I'm not here to advise the client so much as I am to guide them to reaching their own conclusions grounded in, you know, rational thought and, and, and hopefully being able to kinda get out of their own way, if you will, to a-address what needs to be, what needs to be hit head-on.

Josh: I got a question for you. Um, and this is kind of off topic, but it's my habit, so you'll have to excuse me. Is that, um, where does personal vulnerability fit into your practice? If at all.

Russ: Um, I think that, um, I think that it's super, um, important. Um, I don't know that I ever verbalize it that way, but I have heard it said that, um, every therapist and counselor, um, has to first do their own work on themselves before they can be a, a therap- a good therapist or counselor to other people. Um, I think there's a, an element of that that rings true for the work that I'm trying to do as a financial advisor. N- again, not as a therapist, but I have to be very self-aware and somewhat vulnerable, um, and be willing to, um, you know, say things like, "I don't know the answer to that, but let's, you know, let's work on finding that out together." And to be, um... The word I would be more comfortable using rather than vulnerability is just humility, um, and, and recognizing, c- and being willing to communicate the fact that, you know, I'm good at what I do, but there's a lot in the world that I have no experience with or no exp- expertise with. And whether that's bringing in other professionals or asking questions of clients to maybe encourage them to think about seeking additional help or additional resources, um, I'm very willing to do that, and I think that's an important part of the role that I play in my clients' lives.

Josh: Yeah, when I was talking about per- vulnerability, I'm talking about personal vulnerability. In other words, you being vulnerable about a particular situation when you're talking to a client. I have found that when I show personal vulnerability, it's much easier for people to, um, uh... What's the word I'm trying to think of? Uh... Well, they'll recognize that we're very similar.

Russ: So I, I don't disagree. Um, and helps frame it a little bit better in my mind. Uh, but yeah, I, I don't-- I'm not looking to go out and castigate myself and tell people about all the mistakes and, you know, um, I've made. But I, I've certainly made them, and I, I have shared that with clients, whether it's financial or personal or relational. Um, I, I try to be, um, I try to be human, um, and treat others as humans as opposed to trying to elevate everything up to like this business, transactional, formal kind of buzzword-filled jargony relationship. I kinda think that's BS. And so I do think it's important to kinda cut through that. Uh, and I agree, um, being vulnerable is one way to think about it. I, I think of it more in s- uh, in terms of storytelling.

Josh: Yeah, well that's when they t- if you're explaining your vulnerability, it's always gonna be through a story.

Russ: Yeah. So, um, so I, I appreciate you some additional clarity there, but yeah, I think that's important, and I'm sure I could do better, a better job of it, but I, uh, I, I like to think, uh, and, and act like I am a, uh, willing to be vulnerable with clients, um, especially early in new client relationships. I think, um, I think that, like you said, it makes you more relatable, um, and helps clients identify and see the person behind the financial advisor, if you will.

Josh: And I found this was especially true when I was doing some public speaking, is that, you know, my origin story I used to use was about how great I was as a business person and how I built my business from one part-time person to 90 employees when I sold it 20 years later. Well, the only thing that does, it makes me feel-- it makes the audience feel like they never can do what I did. So instead I said, "I'm gonna try something different. I'm gonna mix it up. I'm gonna talk about the warts that I had growing my business." And when I did that, the amazing thing happened was I had people in the audience, which I knew were really hard, hard asses, and they came up to me and said, "You know, because of the story you told at the beginning, the rest of what you said was believable."

Russ: Wow.

Josh: So what I learned from that is the more vulnerable I am, the more I talk about my warts, the more I talk about the mistakes I made, people can relate to that 'cause they've had similar situations in their life. Have you ever gotten fired and been, and it's been unfair? Have you ever had a boss that was unreasonable? You know, all those sorts of... How did you handle that? Um, those are all things that, that wander into our office.

Russ: Yeah, it's funny. Um, I appreciate you sharing that because I, I think m- I mean, s- as long as I can remember, there's always kind of been like the reel on the news, where you see the highlights of the game or the speech or the business transaction or whatever, and you never see all the stuff behind the scenes that went into that. Now, in the world of social media with Facebook and Instagram, and the list goes on, there's pretty much twenty-four/seven access to everyone's highlight reel. 'Cause most people aren't sharing the warts and the mistakes and the hard-learned, um, you know, lessons that they experience along the way. So I, I think it's maybe even more impactful today than it was even 10 or 20 years ago to be willing to be vulnerable and share that with people because I think that cuts through so much of the shiny, glossy surface that so many people are trying to put out into the world today through social media and, and other channels.

Josh: Yeah, if you read my Substack, you'll see that I'm very vulnerable there.

Russ: I'll have to check it out.

Josh: I talk about warts all the time.

Russ: Yeah.

Josh: So Russ, unfortunately we are out of time, and—

Russ: That kind of flew by.

Josh: Yeah, it do- it always fall, it always happens. Um, and I'm sure there are people who are watching or listening are gonna say, "Gee, Russ might be the type of advisor I want." So how would people find you?

Russ: Uh, the best way... Thank you, Josh. The best way for people to find me is through my website, wealthcareforwomen.com. Uh, I'm also on LinkedIn. Um, you can find me. Just search, uh, by my name, and that's probably the best way to, to find me. I've, I've-- I write, too. I also write on Substack, so if you just search my name in Google, I, I shouldn't be too hard to find. But if you want to kinda dive right in, probably start with my website.

Josh: That's great. And I have two things I'd like you to do. First is, if you're still watching or listening, go to wherever you're watching or listening, and please give us an honest rating and review. If you love us, give us five stars and say really nice things about us. And if you hate us, give us one star and say really mean things about us, and then I'll cry a little bit, but you won't see it, so it doesn't matter. The second thing is, if you think that you would be great on this podcast or good on this podcast or okay on this podcast and wanna give it a shot, why don't you send me an email so we can have a conversation to see if this is right for you? It's really easy. You just go to [email protected]. That's the number two, and solution is singular. So it's [email protected], and I would be glad to have a conversation with you, which is how w- Russ and I started off. So this is Josh Patrick. We're with Russ Thornton. You're at The Long Strange Trip podcast. Thanks a lot for stopping by. I hope to see you here next week.

Josh: Thanks for spending this time with me today. I really appreciate you being part of this journey. I'd be grateful if you'd leave an honest rating and review. It helps other people find these conversations, lets me know what's landing with you and what isn't. If you love the show, give us five stars. And if you hate it, give it one star and I'll just cry a little bit. Keep asking the hard questions. Keep being honest about what's difficult. And remember, we're all just trying to figure this out together. I'll talk to you next time on The Long Strange Trip. Thanks for stopping by.