When Saving Becomes a Habit You Can’t Turn Off | Root Talks - Ready For Retirement

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 (0:00)

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

James (0:02)

Of course not.

Ari (0:04)

Do you think many people would be upset?

James (0:06)

I hope not.

Ari (0:07)

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 (1:32)

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.