When Saving Becomes a Habit You Can’t Turn Off | Root Talks

Summary

---

Podcast Summary:

Podcast: Ready For Retirement
Host: James Conole, CFP® (with guest/co-host Ari)
Episode: When Saving Becomes a Habit You Can’t Turn Off | Root Talks
Release Date: November 20, 2025

---

Main Theme & Purpose

This episode tackles the unexpected challenges many diligent savers face as they approach retirement: shifting from a “saving” to a “spending” mindset. Through personal stories and client anecdotes, James and Ari explore why it's often psychologically difficult for retirees to use the wealth they've accumulated, how old habits can inadvertently diminish one’s quality of life, and practical strategies for finding more comfort and meaning in purposeful spending.

---

Key Discussion Points & Insights

1. The Trap of Endless Saving

• Ari opens (00:00): He shares a story of a retired client upset despite having $3 million because health issues now prevent her from enjoying the experiences she’d dreamed of. Key insight: accumulating more wasn’t the answer—time and life goals mattered more.
  • Quote:
    “She said, if I had $2 million, I could have done everything I wanted in retirement… I just worked the last five years and markets did well. So my 2 million became 3 million, and I was sitting the entire time, and I want to be able to hike and travel… now she's just not able to do them.” (00:18)

2. Scarcity Mindset & the Arrival Fallacy

• James reflects (01:32): Many people form their identity around saving, to the point where spending—on themselves or others—feels unnatural or even unsafe, no matter their wealth.
  • Quote:
    “There's a sense that money becomes the goal…that at some point, we're going to magically hit this point where everything feels more comfortable…and we've arrived. I think at a certain point, you start to realize this arrival fallacy. You never actually arrive anywhere.” (02:22)
• He tells the story of relatives who lived extremely frugally, “saving for a rainy day” but never actually doing what mattered to them.

3. Practical Example: The M&M’s Story

• James shares a client anecdote (03:54): Despite being given explicit permission and financial proof they could spend freely, a client couples’ long-standing thriftiness lingered. The husband couldn’t buy $5 minibar M&Ms, instead walking blocks to save a few dollars—highlighting how ingrained habits can persist.
  • Quote:
    “Why on earth, after you had literally just finished telling us we could do so much more with our money, could I not bring myself to spend an extra few bucks for bag of M&M’s?” (05:37)

4. Transitioning from Saver to Spender

• James emphasizes (06:09): Saving is critical, but there comes a moment when the challenge isn’t “saving enough,” but rather “learning to spend intentionally.” The objective isn’t to waste money, but to use it for things that truly improve quality of life.
  • Quote:
    “There’s a psychological shift that happens there… a good retirement plan is really built upon learning to exercise that new muscle of spending the money.” (06:48)

5. Financial Advising—Listening and Silence

• Ari shares an advisor lesson (07:28): He reminds listeners that the best advisors often know when “to shut up”—to let clients find their own authentic answers. In meetings, he sometimes just waits through the discomfort so clients can discover what matters most to them.
  • Quote:
    “It was almost like it would have been easier for them to go back to work instead of answer the question, ‘what would you do if I forced you to spend X number of dollars?’” (09:00)
• Anecdote: A “stuck” client eventually realizes joy might come from simple acts, like buying groceries for others—a shift toward generosity and meaning (09:15).

6. Retirement Mindset: The Dimmer Switch, Not a Light Switch

• Ari and James agree: The shift from saving to spending isn’t instant—it’s gradual, more like a dimmer switch. Most new retirees need time and encouragement (not pressure) to explore enjoyable, purposeful spending (10:27).

7. Finding Personal Meaning (James, 11:12):

• Advises listeners: If you don’t know how you want to spend money in retirement, take time away from external distractions, and privately brainstorm. The “hard part” isn’t spending, it’s clarifying what really matters to you.
  • Quote:
    “The hard part isn’t spending the money. It’s knowing what you want to spend the money on…If I was gone today… what are the things I would regret not doing? …How do we spend our money in such a way to do that?” (12:18)

8. Advisor Role: Like a Good Physical Therapist

• Ari’s metaphor (13:50): Advisors, like holistic physical therapists, want clients to “future-proof” their financial lives—but ultimately, the goal is to empower, not create dependency. True success is clients out there living their dreams, not endlessly consulting content or advisors.

---

Notable Quotes & Memorable Moments

• Ari (00:18): “If I had $2 million, I could have done everything I wanted in retirement… now she's just not able to do them.”
• James (02:22): “You never actually arrive anywhere. So it's about, how do you start developing the right habits… right now?”
• James (05:37): “Why on earth… could I not bring myself to spend an extra few bucks for bag of M&M’s?”
• Ari (09:00): “It would have been easier for them to go back to work instead of answer the question.”
• James (12:18): “The hard part isn’t spending the money. It’s knowing what you want to spend the money on.”
• Ari (13:50): “Our job is to get you out of here as quick as possible… our goal… is to make it so you’re living your best retirement.”

---

Important Timestamps

• 00:00 – 01:32: Story of the client with $3M, but regret over not using it sooner
• 01:32 – 04:13: Why accumulation can become the goal, stories of scarcity, and “arrival fallacy”
• 04:13 – 06:09: The M&M’s story – practical demonstration of psychological barriers to spending
• 06:09 – 07:28: Encouragement to develop “spending muscle” for quality of life
• 07:28 – 11:12: Role of the advisor, power of silence, practical exercises for uncovering true desires
• 11:12 – 13:50: James’s advice on self-reflection, Ari’s story on meaning and regret, life vs. retirement planning
• 13:50 – 14:55: Ari’s physical therapy metaphor & closing thoughts

---

Tone & Takeaways

The conversation combines empathy, humor, and directness, encouraging listeners to reflect deeply on the “why” behind their retirement strategies. Both hosts stress that successful retirement is about building a life worth living—using money to enable cherished experiences, relationships, and meaning, without letting habit or anxiety stand in the way.

For listeners: If you find yourself struggling to spend after a lifetime of saving, you’re not alone. Begin by reflecting on what truly gives you joy and meaning—then, slowly practice spending in ways that align with those values.

---

Transcript

[Ari]

Gave you $3 million right now. Would you be upset?

[James]

Of course not.

[Ari]

Do you think many people would be upset?

[James]

I hope not.

[Ari]

I would hope not as well. But one thing that happened is I asked a woman, hey, tell me about your retirement. She said, she's really upset. She had $3 million. I said, well, that's interesting, because there's a lot of people I know who would love to have $3 million, and I just want to learn more about that. She said, you just don't get it. I said, that's correct. Do you mind sharing? And she shared, well, I no longer have the ability to travel to the degree I want because my health isn't in a great position. I said, okay, so why don't. I'm thinking in my head, why don't you fly first class? Then you have saved well. She goes, yeah, you're missing the point. If I had $2 million, I could have done everything I wanted in retirement. And so I'm trying to connect the dots. I'm a younger advisor at this point, still going, okay, well, she has 3 million. I know. She says, 2 million is okay. What am I missing? And she said, I just worked the last five years and markets did well. So my 2 million became 3 million, and I was sitting the entire time, and I want to be able to hike and travel. And I remember her telling me about her big goals and how now she's just not able to do them. And it really struck me as, here's someone who saved and invested well, arguably too well, who now cannot do all the things she wanted to do, even though financially she's in a good position. So what we're talking about today is how do we switch that mindset focus from being a saver to a spender, and how do we think about maybe the efficient time to do so?

[James]

Yeah, there's nothing that's. I shouldn't say there's nothing sad. There's many things, but there is something. You meet these clients, you meet with these people. They've saved a tremendous amount of money over the course of our lifetime. But their lives, from the outside, looks like they have no money. And it's not necessarily a deliberate choice. It's just this scarcity mindset sometimes of these people that have saved so much, they've done so by saying no to the things they've actually wanted to do along the way. And there's varying degrees of how extreme this shows up in people's lives. I would say for most people, it's not that extreme. I remember I have some great uncles. I've only heard stories of them. I never actually met them. But the types of people that take napkins home from restaurants, because that was a napkin they could then use at home. And, like, their whole house was just these knickknacks of random things. They thought, oh, we can. If we only have to use half the napkin, we can take the other half and we can save it for a rainy day. And they end up passing with a lot of money, but their lives, they never did anything with them. I shouldn't say anything. They didn't do anything from the standpoint of what can we actually do to pursue what's important to us, to have fun, to pursue adventure, to pursue meaning and purpose and all the things that are actually worthwhile to do. And I think too often for people, there's a sense that money becomes the goal, the accumulation of money becomes the goal. And at some point, we're going to magically hit this point where everything feels more comfortable and easier and we've arrived. I think at a certain point, you start to realize this arrival fallacy. You never actually arrive anywhere. You never actually feel any different anywhere. So it's about, how do you start developing the right habits, developing the right rhythms to do the things you want to do now? How do you make sure that whatever your mindset is and your actions are like, they're. They're bringing you closer to where you want to be? And where this really hit me first. I remember I was meeting with a couple of clients who are wonderful people. They had done well, both had built and sold businesses, and they had quite a bit of money, and they had just recently retired, and we were going through some projections, and they said, yeah, we'd love to be able to do this, and we'd love to be able to do that, and we'd ideally like to be able to spend this on a monthly basis and then this for trips and all this stuff. And we said, great, great, great. Ran the projections. And what we actually saw is not only could they do all that, but they were projected to have not even a fortune left over at the end of their lifetime, simply because even after all that, after all the spending that they're projected to do, like their portfolio is going to outpace their spending.

[Client]

And so they saw that, and it was like a complete revelation. Oh, my goodness, we can actually go spend more than we were thinking we could. We could actually do more than what.

[James]

We had ever imagined.

[Client]

And the feedback was, yes, absolutely. And it was exciting. We wrapped up the meeting. And we thought, job done. They feel permission to spend, they can go ahead and do it. They happen to be vacationing in San Diego. It was like a couple weeks after, not too long after, and we got together for lunch. And we were getting together for lunch, and they said, you know, James, we just had that meeting where you closed by telling us, go do whatever you want to do. You know, these trips that you want to take, these things you want to do, full permission to do all of them. You have the portfolio and the means to do it. In fact, please go spend this because you. You're in a position where it can be fully supported. They told me that. And they said, well, the first night we were on vacation, we got back to our room. We got back to our hotel room, and we just had dinner. And the husband was like, I kind of want, like, a little bit of a sweet treat. I want something. And so I went to the hotel mini bar, and there's M and M's there. And I grabbed that bag of M&M's because that. That felt like the craving that I wanted. You know, it's perfect for that. And as I pull it up, I see on a little menu, There's M&M's. $5. And I thought to myself, that's crazy, the bag of M and M's. He thought this to himself, that's crazy. The bag of MMs cost $5. I'm gonna put this down. I'm gonna walk however many blocks it is to a 711 and get a bag of B minimums for A$50 instead. And he did that, and he came back to me and he's like, it's. Something clicked of why on earth, after you had literally just finished telling us we could do so much more with our money, could I not bring myself to spend an extra few bucks for bag of M and Ms? And you can argue, well, cool. You got to go on a walk and get the M M's. He's not a sucker. He's gonna. He's not gonna. Or you can make whatever argument you want. I'm not saying he should have or shouldn't have as much as if that would have been more convenient, if that would have been more time that he could have spent there, if that would have.

[James]

Why not? What is that mental blocker that prevents us from being able to actually use what we've worked for to do whatever we want? Whether that's convenience, whether that's travel, whether that's giving, like, whatever is actually most Important to us. It was this interesting story that really clicked for them and really clicked for me that no amount of money automatically changes your mindset and makes you a different person. And, yes, we need to work to get to that position. I wanted to make that message loud and clear. If you're don't have any savings, this the message. This message isn't for you. The message, yeah, learn how to go spent. You're probably fine there. This is the message for people that have prioritized savings, prioritized investments to the nth degree, and now have trouble getting themselves to spend. There's a psychological shift that happens there, and that's a big part of what we see and work with clients that a good retirement plan is really built upon is learning to exercise that new muscle of spending the money. Not just spending frivolously, not just spending in a wasteful way. Don't. No one wants to be that sucker that spends money to spend money. But if you can spend money, because in some ways it adds to your quality of life, it's not going to go with you when you're gone. So let's make sure we're using it for something good while we're here.

[Ari]

So powerful. And James, I very rarely disagree with you, but I remember being in a client meeting and you had shared something that made me go, maybe this guy's just not as smart as I thought he was. Now, I knew you very well at this point, but you had said, I want you to focus on your health. So I go, okay, James wants the clients to focus on their health and buy M&Ms. And I went, look, I'm not some nutritionist, but those don't add up. And then you went on to share this story and how they saved well, and they could buy the M&Ms. And at the end of that meeting, they went, okay, okay, got it. So I can buy the M&Ms. And if I don't, I'm still gonna be okay. And really, no matter what I do, I'm gonna be okay. But, wow, I have the ability to do so. And what was so powerful in this meeting? And I have a story as well to share on this that really made me go, wow, here's how we help our clients do. This is in your root ready podcast where it's designed for advisors. I know there are root clients that listen in, potential clients that listen. You share. How do you be the best advisor? And you once told me, and you said it very nicely, you said, hey, Ari, the most powerful thing an advisor can do is listen and know when to shut up. And there was a meeting I had with a client and I had shared similar feedback. You're in a good financial position. And by the way, everyone listening, James and I both recognize if you are a great spender, you're probably keyword. They're probably not in a great position to retire early because you're great at spending. Maybe you are have a great balance and you're one of the few. But we recognize you cutting the coupons and being a great saver has got you to this position where you can retire. We don't want you to be an overspender. We want you to be a successful spender. So I'm in the meeting with this client and they said, and I quote, how on earth could I look at life from the position of no matter what I do, pretty much I'll be okay. And that was the truth. If they didn't buy a private jet, you know, that would throw off their retirement plans. But outside of that, they had saved and invested so well and. And they just did not expect their business to do what it did. So I said, what would you do if I forced you to spend X number of dollars? And they just kept saying, I don't know. It was almost like it was an overwhelming question, almost like it would have been easier for them to go back to work instead of answer the question. I just asked them and I said, oh, great, then we're going to sit in silence until you come up with something. This is your time to think and it's not pressuring. I'll sit here for an hour. And I remember they finally said, you know, I don't know if this is the answer you're looking for. And I paused them. I said, I'm not looking for any answer, but I do want to make sure you're not mad at me later in life when you have plenty of money wishing you did more. They said, I remember when I was in my 20s and someone bought groceries for me and that just meant the world to me at that time. And so I would buy the person's groceries behind me. That's what I would do if I had all the money. And I said, well, how amazing. And they said, well, oh yeah, but now that's making me think maybe I would do some other charitable things. So it finally got them thinking and it took me understanding when to shut up and be silent and give someone the space to really explore this, which you talk about often in the Root Ready podcast. And so I think it's important for everyone to recognize. You don't have to have it all figured out. And if you are a good saver and now you're in a position to retire, we'll often use the Eminem analogy and we'll use the light switch. If you're retiring and now you're going, okay, I know I need to spend more. You're not. I don't need you to think about it like, wow, I'm going to flip a switch and now I'm a great spender. It's more of like a dimmer. It's going to take some time to get used to spending more. And we'll encourage someone not to send for the sake of spending, but exercises and strategies there. So I think that M and M analogy is powerful. And I remember seeing the client and thinking to myself, well, James just told them to focus on their health and eat M&M's. What the heck is this guy about to say?

[James]

The metaphorical M and M. You said two things that I'm going to reinforce. One is you, I think you said, joking that this client had a hard time thinking through, what am I going to spend? It would actually be easier for them to go back to work than it would be to spend. That's. That's not exaggeration. Like, that's true. I think for so many people, this saving and investing and working, like, it's hard at the beginning, but once you. Once you're in that habit, once you're in that routine, once you've learned that skill set, that's kind of easy. The harder thing is not spending on what you want. It's even knowing what you want in the first place. So the second thing you said, ab Sometimes we as advisors just need to shut up and let people kind of come to these realizations themselves. This is an exercise anyone can do right now is if you have no idea what you want to do in retirement, turn this podcast off right now. Grab a piece of paper and just write. Let thoughts bubble up. It's not going to come to you right away. We live in such a busy, distracted world. If you see everyone else's goals, you see these commercials. People are traveling in retirement. They're walking their dog through the woods in retirement. Retirement. They're sitting on these Adirondack chairs, like, whatever. That's not your goal. You've been messaged that so many times. But actually, what do you want? Is it buying groceries for the person behind you at Trader Joe's? Is it taking your whole family on A trip to the special place you've always wanted to go to. I mean, just sit and be quiet with your thoughts and think through and this isn't even a retirement exercise. This is a life exercise. How do you live a good retirement? Well, you live a good life. So, like, let's bypass the retirement piece. There's the financial components of retirement planning that are needed to support that. But what do you want your life to look like? The hard part isn't spending the money. It's knowing what you want to spend the money on. And so that's a creative muscle that needs to be exercised. That's a identity muscle that needs to be exercised. Of what do I actually want to do? And just think through, if I was gone today, if I were to pass away today, what are the things I would regret not doing? Something might not come up right away, but if I spend enough time just staring at that piece of paper and writing it down, I promise you it's probably gonna be something related to time with family, time with loved ones, time doing things that you didn't make the time to do. Like, what are those things? And then how can our retirement strategy become don't regret those things. Don't regret not doing those things. How do we spend our money in such a way to do that? So I think that that is something that everyone can learn from is the shut up piece, not just for advisors, but as people. What can we do to really understand where we want to go so we can start to develop the habits to get there?

[Ari]

I pay a lot of money to go to physical therapy, and this is something that I talk about frequently. I love playing soccer. I go to a physical therapy office called myodetox, and their slogan is future proof your body. And when you go, there they go, we do holistic physical therapy. We look at your whole body, and the first thing they say is, our job is to get you out of here as quick as possible. I hope all of you guys like our content. I hope you resonate with it. But if you're writing down on that piece of paper, you've got James in your head going, okay, I'm going to leave this piece of paper once I've got a few ideas. I bet watching Root Financial YouTube content is probably not at the top of the list now. I hope you enjoy our content once again. But our goal, as I see it, is to make it so you're living your best retirement. If that's scuba diving or traveling or doing whatever it is you want to do, that's awesome. I hope we give you the confidence and tools to make that the reality. But similar to my physical therapy office, they don't want me to come all the time. They want me to go to play soccer and do what I want to do. That's how we view it. So that's what we've got for this episode. Just a few stories that hopefully give you something to think about. Anything else you want to add, James?

[James]

No, I think that's it. Thanks, Ari.

[Ari]

Awesome. So, as always, guys, these podcasts drop biweekly on itunes, Spotify, Google, wherever you listen to your podcast. They're also on YouTube, so if you want to actually see us talk and interact, you can watch on Root Financial YouTube channel. On this channel, you can meet our advisors, you can see all sorts of content and you might just find one advisor, one piece of content that really resonates with you. So if that's the case, please do comment below. We make all of our topics based off what you share below. So you can go ahead and drop a comment on YouTube and we will look to address that in a future episode. That was a mouthful. You can see James's content on YouTube, my content on YouTube, and we will see.