BONUS | Why Your New Year’s Resolutions Always Fail (with Dr. Rangan Chatterjee)

Summary

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The Daily Stoic: BONUS | Why Your New Year’s Resolutions Always Fail (with Dr. Rangan Chatterjee)

Date: December 23, 2025
Host: Ryan Holiday (Daily Stoic)
Guest: Dr. Rangan Chatterjee

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Episode Overview

This bonus episode explores why New Year’s resolutions so often fail. Ryan Holiday is joined by Dr. Rangan Chatterjee—physician, author, and behavior change expert—who draws on over two decades of clinical experience and shares practical Stoic and scientific wisdom for making meaningful, lasting changes. The conversation delves into the psychological and emotional drivers of our habits, focusing on why willpower and big goals are often not enough, and what actually leads to sustainable transformation.

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Key Discussion Points & Insights

1. Why Most New Year’s Resolutions Fail

• High Failure Rate: Dr. Chatterjee points out that 80-90% of New Year’s resolutions are abandoned by February ([01:19]).
  • "Why is it that, depending on which research study you read, 80 to 90% of New Year's resolutions have fallen by the wayside by the start of February?" — Dr. Chatterjee [01:19]
• Common Mistakes:
  • People try to change too much, too quickly.
  • Lasting, overnight transformation happens usually only after major life events (divorce, loss, etc.).
  • We focus on changing the behavior rather than understanding the role that behavior plays in our lives ([01:19]–[03:32]).

2. Understanding the Root Cause of Behaviors

• All Behaviors Serve a Purpose:
  • Example: Drinking alcohol to manage stress. Merely stopping doesn't work unless you change what’s driving the behavior or find an effective substitute ([02:37]).
  • "Too often we try and change the behavior without understanding the role it plays in our life." — Dr. Chatterjee [01:58]
• Focus on 'Why' Not Just 'What':
  • Dr. Chatterjee’s latest book centers on the idea that it’s the energy behind behaviors, not the behaviors themselves, that matter.
  • “All behaviors, I believe, come from either love or fear, right at their core.” — Dr. Chatterjee [03:34]
  • Self-critical motivators (guilt, shame) are less effective than positive, compassionate ones ([03:34]).

3. The “Tomorrow” Trap and Procrastination

• Delaying Action:
  • Many people repeatedly tell themselves, “I’ll do it tomorrow,” pushing meaningful change into a perpetually distant future ([05:35]–[06:58]).
  • "That's the most insidious part of what gets in the way of so much of what we're capable of doing—we go, okay, I'm going to do it tomorrow." — Daily Stoic Host [06:10]
• Alignment with Stoicism:
  • The Stoics expose the lie in delaying action, emphasizing the necessity of starting now ([06:10]).

4. The Power of Small, Consistent Actions

• Five-Minute Rituals:
  • Dr. Chatterjee and his wife maintain a nightly “five-minute tea ritual” as a way to intentionally nurture their relationship and prevent drifting apart ([06:58]).
  • "I'm a huge fan of these small things that we do consistently. I have found time and time again with me and with thousands of my patients, these are the things that I think move the needle for most people." — Dr. Chatterjee [09:04]
• Flexibility and Impact:
  • Sometimes five-minute actions expand into meaningful, longer conversations; but the key is the daily, manageable commitment ([08:17]–[08:29]).

5. Lower the Barriers: Make Habits Easy and Automatic

• Examples in Health and Writing:
  • Writing “two crappy pages” a day lowers the bar and builds momentum ([11:32]).
    • "It seems like the opposite of how you would get good writing to set a goal to do bad writing. But what it's doing is it's dramatically lowering the stakes..." — Daily Stoic Co-host [11:37]
  • In health, choosing any exercise is better than being paralyzed by indecision ([13:06]).
  • Dr. Chatterjee keeps his workout gear in the kitchen, integrating habits with daily life for frictionless action ([15:00]).
  • "If you have to decide every morning, 'Oh, what am I going to do today?' That's procrastination, that's choice. That leads to indecision and inaction." — Dr. Chatterjee [13:46]

6. The Internal World: The Real Arena of Change

• More Information Isn’t Enough:
  • Despite the proliferation of health information, outcomes haven’t improved—because information alone doesn’t address internal drivers ([04:33], [05:07]).
  • Real change happens when we address our inner emotional landscape and motivations ([05:11]).
  • "A lot of it is internal... that's where the gold is." — Dr. Chatterjee [05:11]

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Memorable Quotes & Moments

• “Too often we try and change the behavior without understanding the role it plays in our life.” — Dr. Chatterjee [01:58]
• “All behaviors, I believe, come from either love or fear, right at their core.” — Dr. Chatterjee [03:34]
• “We know what we should do or not do." — Daily Stoic Co-host [05:07]
• "By lowering the stakes, you can create the room to create positive momentum." — Daily Stoic Co-host [11:37]
• “If you have to decide every morning, ‘What am I going to do today?’ That’s procrastination, that’s choice. That leads to indecision and inaction.” — Dr. Chatterjee [13:46]

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Suggested Action Steps / Takeaways

• Start Small and Sustainable: Choose “five minutes a day” over dramatic, unsustainable changes.
• Focus on Your 'Why': Uncover the emotional drivers and needs your current habits fulfill before trying to change them.
• Lower the Activation Energy: Make your desired actions as easy as possible to do.
• Consistency Over Intensity: Build habits through regular, manageable effort rather than rare, all-encompassing bursts.
• Compassion Over Criticism: Forgive yourself for setbacks and focus on positive motivation, not guilt or shame.
• Take Action Today: Avoid the mental trap of “tomorrow”—do something now, even if it's small.

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Noteworthy Segments & Timestamps

• [01:19] — Dr. Chatterjee explains why most resolutions fail and the problem with starting too big.
• [02:36] — Example of changing drinking habits and focusing on the purpose behind behaviors.
• [03:34] — The “love or fear” origin of habits and personal anecdote about negative self-talk.
• [05:35] — The allure of procrastination and the “I’ll do it tomorrow” lie.
• [06:58] — The five-minute tea ritual: building connection through small daily practices.
• [11:32] — The “two crappy pages” writing rule and the importance of attainable goals.
• [13:06] — Choosing any exercise versus paralysis by choice; making habits frictionless.
• [15:00] — How automating habits makes it easier to do the right thing.

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Tone and Language

The conversation is warm, practical, and motivational, blending Stoic philosophy with medical insights and real-world habit advice. Humor and humility are woven through personal stories and admissions of past struggles.

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Summary prepared for listeners seeking to apply both Stoic wisdom and behavioral science to their New Year’s resolutions in a deep and practical way.

Transcript

[Dr. Mike]

Foreign.

[Daily Stoic Host (likely Ryan Holiday)]

Welcome to the Daily Stoic podcast where.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Each day we bring you a stoic.

[Daily Stoic Host (likely Ryan Holiday)]

Inspired meditation designed to help you find strength and insight and wisdom into everyday life.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Each one of these episodes is based.

[Daily Stoic Host (likely Ryan Holiday)]

On the 2000 year old philosophy that has guided some of history's greatest men and women. Help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit Dailystoic.com.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

What do you think about New Year's resolutions? Because when I think, when people are thinking about change, they're like, I want to be a different person in 2025, or I want to be a better person. I want to be closer to the person I know I'm capable of being. How do you think about resolutions? Because the reality is a lot of people have that sensation, that feeling, that desire, and then most resolutions go nowhere and people spend another year as exactly the same person.

[Dr. Mike]

I mean, I spent a long time thinking about this because why is it that DEP. Which research study you read 80 to 90% in New Year's resolutions have fallen by the wayside by the start of February. Right. Okay. And I've got 23 years of clinical experience, so I've seen tens of thousands of patients, so I kind of feel I've got a good steer. Certainly from my own experience and what I've seen, I think there's a few things that people get wrong. Okay. I think they try and make it too big too quickly, which I have seen people do that, generally speaking, the people who can transform their lives overnight, they've generally had some really, really big life experience. A divorce, a bereavement, they've lost the house. Something big. Yeah, you can do it. But if you don't have that driving you, I think if you make it too big, you're never going to make it last in the long term. Right. So there's a couple of things to say about these resolutions. Right. So one thing I don't think people understand enough is that every single behavior in our life serves a role. Too often we try and change the behavior without understanding the role it plays in our life. So I'll give you a really practical example. If your alcohol consumption is your way of managing stress.

[Daily Stoic Host (likely Ryan Holiday)]

Yeah.

[Dr. Mike]

Right. You can white knuckle it for the first two or three weeks of January and you will stop and you'll think, yeah, I've got more energy, I'm sleeping better. Great, great, great. I have no problem with that. But if it's your way of managing stress. The only way you'll change it in the long term is by one of two things. Either the amount of stress in your life has to change so then you'll no longer need the alcohol, or you need an alternative behavior to alcohol to help you manage the stress. It sounds so obvious, Ryan, when I put it like that. But most people in my experience are caught up in their lives and they're focused too much on the behavior instead of being focused on what role does behavior play. And so I've come to the conclusion that, and this is really one of the primary thesises in Make Change that Lasts, my new book, is this idea that it's not necessarily the behavior you need to focus on, it's the energy.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

What's it doing for you? Why are you doing it?

[Dr. Mike]

And the other way I look at it for New Year's resolutions is all behaviors, I believe, come from either love or fear, right at their core. So if you feel bad about who you are, you're consumed with guilt and shame and jealousy and envy or whatever it might be. These are all things that come from the energy of fear. If your changes are coming from that kind of energy, I don't think they're going to last in the long term because you're trying to overcome, like, the behavior is in conflicts with who you consider yourself to be. This was me a few years ago, right? So I would say, right, this year I'm going to meditate and I'd do 20 minutes of meditation every morning until like, the 16th of January. Then I'll miss a day because work gets busy and I beat myself up in my head. Negative self talk. I'd be wrong. And you couldn't do it, could you, this year? You know, you're a loser. You couldn't. I used to have a really negative inner voice. I've completely changed that over the years with these kind of intentional practices. And now I find behavior change really, really simple because I've focused on the underlying energies behind that behavior change. And one of the things I try to kind of address in this book, Ryan, is I'm a doctor, right? So through the lens of health, I think we're living in a world where we've got more information than ever before. More health podcasts, more health books, more blogs, whatever it might be. But why, despite all this increase in information and knowledge, is it not translating to better health outcomes?

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

We know what we should, of us know what we should do or not do.

[Dr. Mike]

Exactly. So, you know, I really tried hard with this book. No, no, no. There's a lot of what we should be doing out there. I've written books on what we should be doing. This book addresses the why. Why are we still doing the things that we know are harming us? And I think a lot of it is internal. It comes to our internal world and people don't want to go there, but that's where the gold is.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

It's funny. So every year for Daily Stoic, we do this thing. We call it the Daily Stoic New Year, New Year Challenge. So it's like 21 days of stoic inspired challenges. It's different every year, but it's just a bunch of cool stoic practices. And the idea is one or two will stick with someone and they'll take it through the year. One will get them to think about something differently. But it's funny. We'll start talking about it in early December. The first day you announce it, bunch of people sign up. Second time you announce a bunch of people sign up, and then it sort of dips. And then the. It starts on January 1st. But like, the second biggest signup day is always like January 2nd. So, like, people want to change. Like, at some level they heard about this, they want to change. And then what we do, I think this is the most insidious part of what gets in the way of so much of what we're capable of doing is we go, okay, I'm going to do it tomorrow. They go, okay, that's. That starts on January 1st. So that's a couple weeks from now. So in a couple weeks from now, I'll get serious about thinking about signing up, and then I'll miss that. Like, which is. The stoics talk about, about how we know what we need to do, but then we say we tell ourselves this huge lie, which is like, I'll do it in the morning, I'll do it after this. I'll do it when things calm down. By just moving the timeline up a little bit, we let ourselves off the hook, and then most of us don't do it.

[Dr. Mike]

I completely agree. It's what I've seen in patients for years. It's. It's always next week or next Monday or next month, but when the kids are older. Yeah, it starts today. So another five minute practice I try and do each day is what my wife and I call the five minute tea ritual. Like many people, if you're not intentional about it, you can live in the same house, but you get so busy with work and the children and you're like passing ships. Right. So a few years ago we decided, yeah, listen, yeah, life gets busy from time to time, but we really need to intentionally focus on our relationship. So we have this practice, the five minute tea ritual, every night when the kids were younger. And we still try and do it now when they've gone to bed. Before we do anything else, we come to the kitchen, we make a pot of mint tea. So non caffeinated. And it's not the rule. The practice is that for five minutes we catch up. Right. So it's only five minutes. It's the requirement. So we're just going to ask each other about our days instead of we.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Got to get a babysitter, we're going to book a restaurant reservation. You make it too big and then you're like, we can't do it this way.

[Dr. Mike]

Yeah. And it's like before, you know, it's a few months before you did anything. And what's really interesting is, and I think this builds on this five minute action each day principle that we're talking about. It's not that some days those five minutes don't become 30 minutes or an hour.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Yes. More often than not.

[Dr. Mike]

More often than not, they do, because it's actually, oh, this is much more fun than going on Netflix or YouTube, whatever it might be. It's like, oh, this is, you know, this is why I married you. Right. We actually want to spend time together.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Wait, we like each other. Yeah.

[Dr. Mike]

Yeah. But some days, one of us will say, actually, it's just gonna be five minutes a day. Like, I've actually got a few emails to do, or whatever it might be. Whenever we felt either one of us, oh, we're too busy. And it's been a few days without that practice. It's really interesting. You can feel it in our relationship. The niggles, the small things start to bother us. There's less intimacy, there's less connection. But when we are quite disciplined about the five minute tea ritual, everything else in our relationship, and therefore our lives and our health starts to get better.

[Daily Stoic Host (likely Ryan Holiday)]

Right.

[Dr. Mike]

And so I'm a huge fan of these small things that we do consistently. I have found time and time again with me and with thousands of my patients, these are the things that I think move the needle for most people.

[Daily Stoic Host (likely Ryan Holiday)]

Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County, I drove my car about halfway down the dirt road that we live on, thought, this.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Isn'T going to work.

[Daily Stoic Host (likely Ryan Holiday)]

Stopped, parked, it walked the rest of the way home. Borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation. It was getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

We got to go deep into the.

[Daily Stoic Host (likely Ryan Holiday)]

Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn [e-mail] Trucks Adventure detours the world.

[Toyota Trucks Advertiser Voice]

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[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

I mean, there's a writing rule of two crappy pages a day.

[Daily Stoic Host (likely Ryan Holiday)]

Yeah.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

It seems like the opposite of how you would get good writing to set a goal, to do bad writing. But what it's doing is it's dramatically lowering the stakes. It's making it attainable, and it's actually hard to do crappy pages. But the idea is you got to do crappy pages, and to do great pages, they share one similarity, which is that you have to show up. And so by lowering the stakes, you can create the room to create positive momentum. And then the other thing, which I think is a rule we don't, or I guess a factor, a fact of life we don't talk about enough, which is that I think quantity is a way to get to quality. Yeah. Yeah. So it's like, let's say every day for a month, you sit down with your spouse and you have five minutes. A lot of those are Going to be five minutes of nothingness. But one of those or a handful of those are really going to be significant which you only could have had by having the larger number, right? Like, and so the more you sit down and do the thing that what you're doing is increasing your chances of having those really transcendent days. And so, but people focus on, you know what, like for writing, they're like, I'm going to rent a cabin, I'm going to go there and I'm going to have two great weeks in a row. No, you're not, you're not. First off, you're not going to do it.

[Dr. Mike]

Yeah.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

And then second, like you're going to have five of those days be crappy and, and as a result, like you're not gonna return with the things that you needed. So it's more about the day to dayness, the consistency and the quantity that gets.

[Dr. Mike]

You see this with health, right? So let's use the example of working out, which is a desire that many people have at all times, but particularly at the new year, right? It's like I wanna move my body more, I'm spending too much time at the desk. People start to get paralyzed with choice, right? Oh what, you know, I'm going to run, I'm going to do yoga, I'm going to do Pilates, I'm going to, you know, what is that I'm going to do? And I've had patients before where they've literally got angina pains in their heart. We talk about physical activity, a month later they're still coming back saying, hey doctor, I can't decide which one to do. Right? And I understand that, I have sympathy, but the point is, frankly, any of.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Them are going to help walked here.

[Dr. Mike]

And that would have, and that would have solved you. And so through the lens of my 5 minute strength workout, people say, what do you do? The same thing every day? And actually for many years I did. Because if you have to decide every morning, oh what am I going to do today? That's procrastination, that's choice. That leads to indecision and inaction. And we know this in business, in the business world, when Amazon moved to one click ordering about 10 years ago or so, estimates say their profits went up by 300 million a year. Because back then, I don't know if you can remember this but you know, there were four or five steps to take before you could purchase. You have to confirm order, put in your car details on a new screen, there's three or four Steps each time you have another option. It's a reason that you can pull out of the behavior. And so the reason we brush our teeth each night, well, one of the reasons is because the same action every day. On Tuesday evening, we don't go, you know what? I brushed yesterday. Yeah, let me do something different today. I'm gonna floss today. And then on Wednesday we don't go, I brush. And I thought, I'm just gonna rinse today. We don't do that.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

We know if you had to assemble the toothbrush, you had to package it. If you had to make the toothpaste, wouldn't do it.

[Daily Stoic Host (likely Ryan Holiday)]

Yeah, right.

[Dr. Mike]

And so that's why my dumbbell and kettlebell lives in my kitchen. My cafeteria is there. It all works together. It is so easy. I can barely not do it. Now, going back to news resolutions, there's another. I think for me, it's a big idea that I don't think we're talking about enough. Right. And I think it is a way of connecting a lot of your writings and practices with health, which. And I think sometimes people don't see the connection. Right. So I believe that a lot of the reason why we can't make changes that last is because we don't understand the internal drivers that are leading us to those practices.

[Daily Stoic Co-host or Guest (possibly Stephen Hanselman)]

Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything.

[Daily Stoic Host (likely Ryan Holiday)]

I just wanted to say thank you.

[Toyota Trucks Advertiser Voice]

The world is full of tours.

[Daily Stoic Host (likely Ryan Holiday)]

But.

[Toyota Trucks Advertiser Voice]

You don't choose a Toyota truck to follow the beaten path. You choose it to find the places.

[Dr. Mike]

Behind, between.

[Toyota Trucks Advertiser Voice]

The detours, where each adventure pulls you toward the next. And wrong turns turn out right. So why would you ever take a tour when you could take a detour? Toyota trucks.

[Toyota Trucks Customer Testimonial Voice]

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