How to Finally Have the Talk You've Been Avoiding | Jonathan Fields

There is a conversation most of us are carrying right now. Not one we lack words for. We have plenty of those. One we keep finding reasons not to have. Not because we don't know what we'd say, but because we have become very skilled at building the case for staying quiet a little longer. Jonathan Fields has spent a lot of time in that particular waiting room. This solo episode starts with a story he describes as embarrassing in the specific way only true stories about your own behavior can be embarrassing: a decade-long friendship, a thing said in passing that he never addressed, and the slow drift that followed because he never said it. It's a story many people in midlife will recognize without needing the details changed. What you'll explore in this episode: Why intelligent, emotionally capable people are often the most skilled architects of avoidance, and what that architecture actually looks like from the insideThe difference between protecting a relationship and protecting yourself from discomfort, and how easy it is to mistake one for the otherFour distinct types of difficult conversations and why knowing which one you're actually having changes everything about how to beginWhy the perfect moment to have the conversation you've been postponing doesn't exist, and what to do insteadHow to open a hard conversation without scripting it, performing it, or trying to win itA question to carry with you, not answer immediately, that may be the most honest thing in this entire episode For anyone in midlife who has been living carefully around something true that needs to be said, this one is for you. Episode Transcript https://www.goodlifeproject.com/podcast/difficult-conversations-midlife-jonathan-fields Next week, we are sitting down with journalist Alexandra Sifferlin to talk about why millions of Americans are living with conditions that doctors simply cannot name, and what that does to a person when the system meant to help you keeps coming up empty. Be sure to follow Good Life Project wherever you get your podcasts so you do not miss any upcoming episodes. Check out our offerings & partners: Join My New Writing Project: Awake at the Wheel https://jonathanfields.substack.com/aboutVisit Our Sponsor Page For Great Resources & Discount Codes https://www.goodlifeproject.com/sponsors/ Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jonathan Fields?

  So there's a conversation that I need to have with someone I love. I have known this for a while, longer than I'd like to admit, honestly. I know the general shape of what I want to say. I know this person well enough to make some reasonable predictions about how it might go. And I have thought about it in the car at 2:00 in the morning, in the middle of other conversations that are not the one I actually need to be having. And yet, I keep not having it. There's something almost impressive about the architecture of avoidance a reasonably intelligent person can construct. The timing is never quite right. There's always something just more pressing. The relationship is in a good place right now.

• 0:44Jonathan Fields?

  And why would I introduce turbulence? I mean, I've probably built this up in my head, and the actual conversation would be fine. Maybe I'm being oversensitive. Maybe I've already processed this enough that saying it out loud isn't really necessary anymore. These are not things I believe. These are things I tell myself. And I wonder if you have one of these, a conversation that exists, fully formed somewhere in your interior life, that you have rehearsed in some form, that some honest part of you knows is overdue. Not an argument, not a confrontation, just a true thing that needs to be said

• 1:28Jonathan Fields?

  to someone who probably suspects in any way and hasn't heard it in your actual voice because you haven't said it. So today, we're going to go there. I'm going to talk about why we do this, what it actually costs us, and maybe, and hopefully most usefully, what happens when we finally don't. So excited to share this exploration with you. I'm Jonathan Fields, and this is Good Life Project.

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• 3:37Jonathan Fields?

  So I want to start with a story. It's a little embarrassing in the specific way that only true stories about your own behavior can be embarrassing. So lean in a little. I had a friend, someone I'd been close to for over a decade. We'd been through a lot together. You know, the kind of friendship that forms in your 30s, 40s, when you're both building something, you're scared in the same ways. And you find each other at exactly the right moment. Those friendships have a particular quality. They matter in a way that's hard to articulate, but it's very easy to feel. And somewhere, I don't know, maybe a decade in, something shifted. Not dramatically. There was no falling out, no event, no moment I could point to.

• 4:23Jonathan Fields?

  It was more like the friendship just very slowly began to operate on a different frequency. He was going through significant changes in his own life. His priorities were reconfiguring in ways that that just made total sense for him. And I, well, I mean, I had my own version of that. And in that drift, something happened that I never, I never quite addressed. A thing was said in passing at a moment when he probably didn't even register it as significant. But I registered it and I held on to it. Not in an angry way. I'm not someone who actually carries grudges particularly well. They're just kind of too heavy, but in a quiet way.

• 5:05Jonathan Fields?

  A way that created just enough distance that I stopped being fully myself in his presence. You know, I started managing the friendship a little, curating it and, and, and showing up as a slightly edited version of the Jonathan that didn't include the part that I had felt. And I don't know, maybe overlooked. Diminished is probably too strong a word, but kind of something in that neighborhood. For a long time, I told myself that, you know, I wasn't saying anything because there was just nothing to say. No, we were fine. The friendship was fine. Why introduce drama into something that was by any reasonable external measure, kind of working? And he had no idea anything was different.

• 5:50Jonathan Fields?

  I was being mature. I was protecting something I valued. That story was so clean and so available that I almost believed it. What I was actually doing, and this took me an embarrassingly long time to see clearly, was protecting myself, not the friendship, myself.

• 6:14Jonathan Fields?

  And from a discomfort of, you know, a potentially awkward conversation and from the chance that he might get defensive or not understand, or that I'd say it wrong and make something that was currently fine into something that was actively broken. I was running a very detailed simulation of all the ways it could go sideways and then using that simulation as evidence that staying quiet was just the wiser move. Which if you've ever tried to conduct a difficult conversation entirely inside your own head, where you control all the variables and everyone says exactly what they're supposed

• 6:54Jonathan Fields?

  to say, you know, is not actually a conversation. It's an elaborate, extremely convincing, entirely private theater production with very good special effects and a terrible third act. So eventually, you know, it got to a point where I just, I said the thing. Not because I've engineered the perfect moment, I hadn't. Not because I'd finally found the exact right words and done that either. I said it because enough time had passed that the distance between us had started to feel kind of permanent.

• 7:35Jonathan Fields?

  And I didn't want a permanent distance from someone I actually cared a lot about. And it went differently than I had rehearsed. Not worse, just kind of more human. He heard me differently than I expected. He said something I definitely hadn't written into, you know, my version of the script. And at the end of it, something shifted. Not dramatically. I mean, we didn't score some cinematic reconciliation moment. We went and got coffee, but it felt lighter in a way that I hadn't even fully noticed that I'd been heavy. And the friendship became one I was actually in again, rather than one I was just carefully maintaining from, you know, a safe distance.

• 8:20Jonathan Fields?

  And I tell you that not because my story is your story. It probably isn't. I mean, not exactly. But because I've come to believe that most people, especially in midlife, were carrying at least one version of this, often more than one. And carrying it, it doesn't make you conflict avoidant or emotionally immature or bad at relationships. It makes you human. And midlife, specifically midlife, it's the season when the weight of unsaid, it tends to make itself known in ways that are just that are increasingly difficult to ignore.

• 9:00Jonathan Fields?

  So let's talk about why and then what to do about it. Let me describe a particular category of conversation and we'll see if it lands for you. It's not a conversation you haven't thought of. You have probably many times. It's a conversation you lack words for. Someone locked you in a room and told you to write down what you'd say. You could probably fill a page without much trouble. It's not even a conversation you're convinced would necessarily go badly. You just haven't had it. It lives in this kind of permanent waiting room in your interior life, waiting for the right moment, waiting until things calm down, waiting until the relationship is in a better place,

• 9:45Jonathan Fields?

  which would actually be easier to achieve if you had the conversation. But let's not get into that particular loop right now. So I want to give this some shape because I think the more clearly you can see what we're actually talking about, the more useful this exploration becomes. These are the conversations that I mean. A truth you want someone who matters to you to know about themselves or about you. A need that has gone unnamed for so long, it's started to feel like just the way things are. Or a sense of distance from someone that you used to feel close to that you've noticed, but never really spoken aloud to them.

• 10:27Jonathan Fields?

  Or maybe it's a question about the future of a relationship, a living situation, a family structure, that both people are kind of orbiting without actually landing on. Or something you've told yourself that you forgave, but you have never actually said so, leaving the other person to live inside your unspoken verdict. Maybe it's something you're still carrying from the past that's just never been directly acknowledged by the person who gave it to you. And notice that none of these require a capital V villain. This is not about blaming someone.

• 11:10Jonathan Fields?

  If anything, it's not about winning an argument. The hardest conversations in my life, in my experience, they're almost never the ones where somebody is clearly the, quote, "bad person." They're the ones where two people who fundamentally care about each other have somehow let something important go unsaid for long enough that saying it now requires clearing its throat first. And here's the piece that I find just particularly interesting. Midlife doesn't cause these conversations, but it does something that makes them harder to avoid.

• 11:51Jonathan Fields?

  There's this body of research, Laura Carstensen at Stanford has done landmark work here on how our relationship with time changes as we age. So when we're young and time feels essentially infinite, we invest broadly in lots of relationships, lots of experiences, really keeping options open.

• 12:15Jonathan Fields?

  But as our sense of time becomes more finite, in midlife is when the shift often begins in earnest, something in us, it just kind of recalibrates. And we start caring more about depth and meaning in our close relationships. We become more honest, at least internally, about what actually matters to us. And in that shift, in that turning toward what actually matters, the things left unsaid in the relationships that matter start to press. Not because something has gone wrong, but because something actually has gone right. You're paying closer attention.

• 12:55Jonathan Fields?

  Now, where do these kinds of conversations, where do they tend to live? In my experience, they cluster around five column territories. And I want to walk you through each of them, not to tell you which one is yours, but to make it easier for you to recognize it when I describe it. So let's talk about territory one. These are conversations with your partner. The relationship closest to you. It's often where the most is left unsaid, precisely because it's the one that you feel like you can, you know, like you can least afford to get wrong. Sometimes it's the desire conversation. And I don't just mean physical or sexual desire, though that is often in there.

• 13:40Jonathan Fields?

  I mean, the broader question of how you want your life and your partnership to actually feel, you know, and which may have also changed significantly since the version of yourself who made that original arrangement was present. Sometimes it's, you know, the what are we actually doing next conversation? The shape of the chapter ahead, which assumes a shared vision that may have never been explicitly talked about or negotiated. Sometimes it's simpler and in some ways harder. You know, the things you notice about them, the things you value about them, the things you admire about them that you've just simply stopped saying out loud because you assume they just know.

• 14:25Jonathan Fields?

  And they've stopped saying about because they assume that you know. And in that mutual assumption, something quietly goes cold that doesn't have to.

• 14:36Jonathan Fields?

  There's this statistic from John and Julie Gottman's decades of research that I find genuinely sobering. They've been on the show in the past, and every time, I'm just, my jaw drops when they share this insight. Couples in troubled partnerships wait, on average, six years after problems begin before seeking any kind of help. Six years of the conversation not happening. And the problems don't get smaller in that time, they just get layered. So that's territory one. Let's talk about territory two here for these conversations. And that is with aging parents.

• 15:21Jonathan Fields?

  This one in particular has a ticking clock that most of us are acutely uncomfortably aware of and still somehow manage not to act on. You know, sometimes it's the logistical, but actually emotional conversation about what they want when they can no longer fully care for themselves, which feels like talking about death. So we don't, even though it's actually a conversation about love and dignity and what it means to take care of someone well. And, you know, sometimes it's something older and unresolved history, something from your childhood or young adulthood that was never acknowledged

• 16:04Jonathan Fields?

  or that you've told yourself and maybe even told a therapist or a friend that you've made peace with. And maybe mostly you have, except when you're in their presence for more than 48 hours, and then it's just, it's there again. And sometimes it's the simplest, most urgent one, the things you actually want to say to them while you still can, not because anything is necessarily imminent, but because you're old enough now to understand that eventually it will be. So there is a particular grief that people describe when a parent dies before a specific conversation happened. Not estrangement, not argument,

• 16:48Jonathan Fields?

  just something left unsaid that they thought they had more time for. And that's worth sitting with. So let's talk about territory three.

• 16:58Jonathan Fields?

  And we'll be right back after a word from our sponsors.

• 17:03Jonathan Fields?

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• 17:48Jonathan Fields?

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• 18:31Jonathan Fields?

  a good book. You know, the cozy feeling has just arrived, and cozy really does start at your feet. Bombas just launched new suede moccasins, cushy soles, a shearling lining, and water-resistant suede, so a little frost on the grass isn't a problem. Our whole family's sock drawers are basically shrines to Bombas, have been for years. Marina wool for chilly mornings, sports socks for when we get out and move, and compression socks for long travel days, which I'm actually about to have. Opening that drawer, they're just a right pair for whatever the day holds. But the other thing that has kept me a Bombas fan for all of these years, for every item you buy, Bombas donates and assists. Essential clothing item to someone facing housing insecurity. One purchased, one donated. Over 200 million donations and counting.

• 19:16Jonathan Fields?

  So head over to bombas.com/goodlife and use the code GOODLIFE for 20% off your first purchase. That's B O M B A S dot com slash good life. Code GOODLIFE at checkout. Good Life Project is supported by Kachava. So I used to think being salty was reserved for bad moods and pretzels. But lately I have come to realize that a little salty edge actually makes life and especially dessert way more interesting. Any pastry chef will tell you that a pinch of salt isn't there to ruin the party. It's there to make the sweet parts just really shine, which is exactly what Kachava pulled off with their new salted caramel. First sip, I actually laughed. It's that good, rich caramel, a little salty edge, and none of the sugary drawbacks.

• 20:00Jonathan Fields?

  And it's still the Kachava that I count on. Two scoops for complete nutrition with plant-based protein, fiber, greens, and so much more. No artificial flavors, colors, or sweeteners, no fillers, no nonsense. Which if you're feeling a little salty yourself is kind of the point. Embrace your salty side. Go to kachava.com and use the code GOODLIFE for 15% off your order. That's Kachava, K A C H A V A dot com, code GOODLIFE. That's the conversation with adult, kids, or siblings. These are, you know, the relationships where role expectations do enormous heavy lifting.

• 20:41Jonathan Fields?

  Where the story of who you are to each other, it was written a long time ago. Neither of you may have formally noticed that both of you have actually become really different people since then. And sometimes it's a renegotiation conversation, you know, essentially, hey, I'm not sure I'm still the person you need me to be in the way that you need me to be it. And I kind of like to talk about that. Sometimes it's a disappointment conversation carried in both directions, often for years, often beneath the performance of a perfectly functional family relationship. And sometimes. It's the reverse of all that, you know, the specific and slightly disorienting realization that an adult child or a sibling

• 21:26Jonathan Fields?

  has become someone you actually genuinely admire. And you've never said so because, I mean, when do we start saying that to each other? Which is, of course, the answer to why you should. And that brings us to territory number four. These are conversations with friends. And friendship has no formal contract, which is both its freedom and its particular vulnerability. There's the drift conversation, the one that begins simply, hey, I miss you and, you know, I'm not sure where we went and I'd really like to find out if we can come back. There's the kind of archived hurt, the thing someone said or did years ago

• 22:08Jonathan Fields?

  that you got over and you definitely have not gotten over, except it's still there when you reach for it. And then there's the authenticity conversation, the slow recognition that you've been performing a version of yourself in a friendship that really doesn't quite fit who you've actually become. And you're not sure that the friend knows who that is anymore. And you kind of miss actually being known by them.

• 22:39Jonathan Fields?

  And that brings us to the fifth territory, the conversation with, guess who? Yourself.

• 22:46Jonathan Fields?

  Then there's the one that doesn't require another person in the room, right? Which, in my experience, sometimes makes it the hardest one of all. The internal conversation you keep not finishing, the honest accounting of whether what you're building with your days is actually what you want. You know, the thing that you've been almost knowing for a while, that you've been managing to keep just slightly out of full view, again, of yourself. Because if you look at it directly, really directly, you might actually have to do something about it. The conversation that you can't quite have with someone else often begins with a conversation

• 23:29Jonathan Fields?

  you haven't yet finished having with yourself. Okay, so.

• 23:36Jonathan Fields?

  We've named the territory, the five territories now. I want to get into the psychology of why we stay out of it. Because understanding this, understanding why we don't have these conversations, why we stay on the sidelines, really understanding it turns out to be surprisingly useful. So here's the thing I find genuinely fascinating and also, I'll be honest, a little humiliating about all of this. We are systematically and reliably wrong about how these conversations will go. Not occasionally wrong, not sometimes wrong, consistently, predictably, in a very particular direction, wrong.

• 24:21Jonathan Fields?

  Nick Epley, a behavioral scientist at U of Chicago, he spent years studying what he calls under-valued conversations, you know, meaningful conversations that people are avoiding. And what his research shows over and over, it's that people consistently and significantly overestimate the awkwardness of these conversations and dramatically underestimate their value. The imagined version, you know, the one you've been running in your head is almost always more uncomfortable than the actual one. The other person is more receptive than you predicted. The relief is more immediate. The relationship more often strengthens than ruptures.

• 25:05Jonathan Fields?

  You know, it turns out that we are, in a very precise and specific sense, frightening ourselves out of something that isn't nearly as frightening as we've made it. And the question is really, why? And it's because of the avoidance. It doesn't feel like avoidance. This is the part I really, I want you to hear. It feels like wisdom. It feels like maturity. It feels like a considered decision made by a thoughtful person who has carefully weighed the costs and benefits and concluded that staying quiet is the right call. And I am raising my hand right here, saying,

• 25:45Jonathan Fields?

  I have told myself that this is the wise person making the wise decision exactly for this reason so many times. It feels like protecting the relationship, you know? I don't want to rock the boat. It feels like maturity. I've made peace with this. It feels like good timing. This isn't the right moment. It feels like consideration. They have so much on their plate right now. It feels like discernment. Is this really worth a disruption? And look, these are not lies. They contain real thoughts, real considerations. But they're also, and I say this with the full self-awareness of somebody who has used every single one of them and will again.

• 26:29Jonathan Fields?

  They're the most sophisticated rationalizations your very capable mind can produce for doing the thing that feels safer, which is nothing. Behavioral economists, they have a name for the pattern of avoiding information or conversations that might produce discomfort. The ostrich effect. Named, of course, for the popular but entirely inaccurate belief about what ostriches do with their heads. And what makes it so sticky is exactly what I just described. It doesn't register as avoidance. It registers as wisdom. And wisdom is very difficult to argue with,

• 27:11Jonathan Fields?

  especially when you're the one generating it about yourself. So what's exactly underneath it? Well, in my experience and in the research, the real reasons tend to cluster around these three fears. And I think, I think naming them clearly without judgment is more useful than trying to talk yourself out of the avoidance before you even understand what's driving it. So the first is the fear of losing control over the outcome. And when the conversation, it lives in your head, you control it completely. The other person says what you need them to say, the interaction. It goes the way you scripted it.

• 27:55Jonathan Fields?

  The moment you have the actual conversation, you give up control. And for people who are good at managing things, which describes a lot of people probably watching and listening to this right now, giving up control of something that matters is genuinely and non-trivially hard, sometimes straight up terrifying.

• 28:20Jonathan Fields?

  So the second fear is what I call identity disruption. Now, some of these conversations, if you have them, they will require you to kind of update the story that you've been telling, you know, about the situation, about the other person, about yourself. And that is not a small thing. We are narrative creatures. The stories we carry about our relationships and our histories, they're part of how we understand who we are. And revising them has real psychological weight. And our minds resist that revision, even when the revision would ultimately be healthy.

• 29:01Jonathan Fields?

  And the third, the deepest one, the one that's kind of hardest to own, is the fear that what you find out will be harder than what you currently almost know. The conversation might close the gap, or it might confirm the gap is real. And then you have to deal with it being definitively, undeniably, real, which feels harder than leaving it in the category of possibility. If you never quite look at it directly, you never quite have to reckon with it fully. So there's a kind of a fragile comfort in that, a comfort that in the end, it costs more than it saved.

• 29:44Jonathan Fields?

  Because, you know, the conversation that you're avoiding is not protecting you from a hard thing. It's guaranteeing you a slower, quieter, more private version of the same hard thing indefinitely. So where do we go from here? I want to make an argument now that I think is really important, that runs counter to how most people think about this. Choosing not to have the conversation is not the same as the conversation not happening. Let me say that again. Choosing not to have the conversation is not the same as the conversation not happening.

• 30:28Jonathan Fields?

  Silence is not neutral. Silence communicates. And the person on the other end of your science is reading it, even if they don't know they're reading it, and they're almost certainly not reading it the way that you intend it. So, you know, when, when you stay quiet in a partnership about something significant, what gets communicated, not what you mean, but what lands, can be, you know, "I've decided this is just how things are between us," or "I don't trust this relationship to hold in honesty change," even if you mean neither of those things, even if you're staying quiet

• 31:11Jonathan Fields?

  specifically because you do trust and do value the relationship, right? So, when we stay quiet with a parent about something that's between you for decades, what gets communicated can often be, "Well, everything important between us has already been said." Even when it hasn't, when you stay quiet with a friend, you know, about a growing distance, let's say, what, what gets communicated can often be, "Well, I've assessed this relationship and, you know, I've decided it doesn't merit the risk of honesty." Even when you would never in a million years choose to communicate that or feel it, the other person doesn't have access to your reasoning.

• 31:55Jonathan Fields?

  They can't read your mind. They only have access to your behavior. And your behavior right now is silence. There's also what the Gottman's research shows about what happens to unaddressed things over time in close relationships. They don't stay stable. They don't quietly resolve themselves. They calcify. They compound. Minor unaddressed irritations, they become significant resentments, not because the original thing was that large, but because the pattern of non-address, it communicates something, that this person's feelings or this dynamic between you isn't worth direct engagement.

• 32:37Jonathan Fields?

  And that message, it accumulates and eventually you stop addressing the original thing and start dealing with the entire weight of the accumulated pattern, which honestly is almost always a much heavier lift. You know, it's the conversation that is hard to have today that will be harder to have in two years, not because two years will bring clarity, because two years will just bring more and more layers.

• 33:08Jonathan Fields?

  And then there's the thing that I want to say that is less kind of research based and more, I don't know, observational. There's a weight to carrying a significant unspoken thing.

• 33:22Jonathan Fields?

  It's often not dramatic. It's often not crushing. It's more like, like a background hum, a low-grade energy cost that's kind of easy to miss because you've been paying it for so long. It's just start to feel like, you know, just the baseline cost of being you. James Pennebaker, who's actually been a guest on this show before, has spent decades studying what happens to people when they move from suppressing significant emotional content to expressing it. And what he found, what actually even surprised him, is that the physical health benefits of honest emotional expression are measurable and consistent and often huge.

• 34:04Jonathan Fields?

  Blood pressure, immune function, rates of depression, not because the problem gets solved by the expression, but because the suppression stops and there's a harm caused by that suppression. I want to be careful not to overstate this in, in a clinical direction because that's not really the point that I'm trying to make here. The point is more human than that. It's just, what would it feel like to put down something you've been carrying, even partially, even imperfectly, even without the guarantee of how the other person receives it? Because it turns out, the drawer that you've been kind of stepping around for years isn't protecting anything.

• 34:50Jonathan Fields?

  It's just heavy.

• 34:53Jonathan Fields?

  And we'll be right back after a word from our sponsors.

• 34:57Jonathan Fields?

  This message is brought to you by Apple Card. Ah, fall, that cozy season where we swap the swimwear for sweaters and sunnies for scars. But before the Halloween decorations are put away or Thanksgiving table has been set, there's already holly jolly music playing in the grocery store, reminding you that the year is coming to a close. Time to kick end of year into high gear. When you use Apple Card with Apple Pay, you earn 2% daily cash back on all purchases, including food, decorations, gifts, and more. Get a head start on your end of year purchases. Apply for your Apple Card in the Wallet app on your iPhone today and start using it right away with Apple Pay. Subject to credit approval, Apple Card is issued by Goldman Sachs Bank USA Salt Lake

• 35:42Jonathan Fields?

  City Branch. Terms and more at applecard.com. Good Life Project is sponsored by TinCan. So if you grew up in the 70s or 80s, you probably still remember your best friend's phone number and stretching the kitchen phone cord around the corner for privacy. Our executive producer, Lindsay, wanted that same freedom for her kids, eight and 10. So in January, she got them a TinCan. Now, friends call the house to chat, make plans, and check in without borrowing her phone. They even keep a handwritten phone book next to it. I kind of love that. TinCan is the new school way for kids to talk with their friends. It's a secure landline that lets them call all their favorite people, but with parental controls to keep them protected.

• 36:25Jonathan Fields?

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• 36:59Speaker 05

  With no fees or minimums on checking accounts, it's no wonder the Capital One Bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends. It's pretty much all he talks about, in a good way. What's in your wallet? Terms apply. See CapitalOne.com/Bank. Capital One, N.A., Member FDIC.

• 37:33Jonathan Fields?

  So I want to shift now because this exploration is not supposed to leave you feeling heavy. It's intended to leave you feeling like you actually have a door, a door out. So here's what I have observed. In my own life, in the stories I've gathered across thousands of conversations over the years of doing this work, about what happens when the conversation finally does happen. First, the relationships that matter most to us are almost always more resilient than we give them credit for. We protect them with silence because we believe, you know, kind of on some level, that they're fragile.

• 38:16Jonathan Fields?

  And that's a hard conversation, you know, because we think the conversation might crack something. But in doing so, when we hold back, we deprive them of the one thing that actually makes them strong: honest contact, real contact, the experience of being fully in the presence of someone rather than the carefully managed version of yourself you've been presenting. A conversation that brings something, that brings something true into the open, even if it's uncomfortable, even if it's imperfect, even if it goes slightly sideways before

• 38:55Jonathan Fields?

  it goes better, which frankly, it often does, it's almost always better for the relationship than the same thing, living unspoken, between the people who care about it. Not because it resolves everything, but because it demonstrates something, it proves something. It proves that we can be real with each other. And that proof, it's the actual material that trust is made of.

• 39:26Jonathan Fields?

  So, second thing here. You almost always learn something you didn't know when you have the conversation. And this is where the story shifts in a direction that surprises people because the learning is also almost never what you were dreading or even expecting. You know, you dreaded defensiveness, you got something more like recognition, you dreaded being dismissed and you found out they'd been carrying their own version of the thing. Or you dreaded that saying it would make the gap permanent and maybe saying it was actually what showed you the gap was crossable. The imagined conversation and the actual conversation are rarely the same conversation.

• 40:09Jonathan Fields?

  And the actual one, the real one with its mess and its unexpected turns, is very often more useful than the one you'd rehearsed. And third here, the one I want to leave you with from this part of the conversation, because I think it's kind of underrated. You become someone who said the true thing. There's a quality to that, there's an integrity to that, there's a knowing to that sense of identity that gets built around it. It's not necessarily visible to anyone else, but you carry it. The knowledge that when something important needed to be said, you said it.

• 40:53Jonathan Fields?

  That you were in the relationship rather than managing it from a safe distance, that you trusted both the relationship and yourself enough, to be honest. And that is no small thing. That actually is the thing. The relationship becomes one where you're actually in it when we do this, rather than one you're curating from that distance. Okay, so, let's get really practical here.

• 41:23Jonathan Fields?

  And I want to start with a question that may sound kind of basic to you, but that I think is worth actually spending a few honest minutes with before you do anything else. And that question is, what are you actually trying to do? I'll say it again. What are you actually trying to do? Because these conversations, they come in different flavors and knowing which one you're having, it matters. Sometimes you're trying to be known, not to resolve anything, not to extract an apology, not to change a situation, just to let someone see something

• 42:03Jonathan Fields?

  true about you that they haven't seen. Sometimes you're trying to repair something, you know, to, to address a distance that's grown and that you'd like to close. Sometimes you're trying to just release something, to say out loud what you've been carrying so it stops living just exclusively inside you. So someone else holds it with you. And sometimes, you know, you're trying to understand something, to find out what the other person actually thinks or feels about something that's kind of stayed ambiguous. These are different conversations and they require different openings and different amounts of vulnerability and different things

• 42:46Jonathan Fields?

  from the other person. So knowing which one you're actually having, being honest with yourself about that, it means you're less likely to be disappointed when the conversation doesn't accomplish something you weren't even consciously going for. So now, here's something I find genuinely useful that I want to offer as a reframe. You don't have to have the whole conversation at once. I know that the moment I say that, some of you will immediately use it as a new form of delay. Oh, I'll just add the small version of it, starting next week, maybe. I see you. I have been you and I will be you again.

• 43:31Jonathan Fields?

  So let me be specific about what I actually mean here.

• 43:36Jonathan Fields?

  There's almost always a smaller opening to these conversations. It's kind of an appetizer. Something that doesn't require laying everything on the table in one sitting that begins with the process of honest contact. That signals to the other person and often to yourself that something real is trying to come through. Now practically, that may sound like something like, hey, there's something I've been wanting to talk with you about. And I haven't quite known how to bring it up. Can I try? Or maybe it sounds like, hey, I've been aware of something between us lately that I think I've been contributing to by not saying something. And I want to try and say it.

• 44:21Jonathan Fields?

  Or maybe, and I actually find this approach disarmingly effective. Simply something like, hey, I'm going to be a little bit vulnerable here. And I want to tell you that upfront. So you know, I'm not coming at you. I just, I have something I want you to know. And these openings, they do something, they do something important before the content even arrives. What they do is they signal care. They give the other person a moment to receive rather than defend. They lower the temperature on a conversation that your nervous system has been imagining at about 900 degrees to something closer to the actual temperature in likely reach, which is usually, yeah, kind of warm.

• 45:06Jonathan Fields?

  Occasionally uncomfortable, but almost never catastrophic. So a few things to actively not try to do in these conversations, because these are the traps. First, don't try to win. Winning a conversation that matters is a periodic achievement at best. You get the point and lose something more important. These conversations are not debates. They're conversations. Two, don't try to convince. If the other person leaves the conversation with a different view than they arrived, you know, that's theirs. Your job is to say the true thing, not to engineer a specific response.

• 45:51Jonathan Fields?

  The outcome is not in your control. Say the true thing.

• 45:58Jonathan Fields?

  Then we move on to this other sort of like piece of guidance here, which is, don't try to resolve everything at once. One conversation, it rarely closes a long, open account. You're trying to open the account properly, not zero it out. And maybe, maybe the most important sort of like guidance here also is on the don'ts list. I feel weird about having don'ts lists, but it kind of works here, is don't try to be perfect. The carefully rehearsed version of, of what you want to say, delivered flawlessly, it'll

• 46:40Jonathan Fields?

  just land as a performance and, and the person across from you will experience it as one. You know, I don't know exactly how to say this, said honestly, from your actual face is a, a far more powerful opening than the version you've scripted in your head because it is real. And real is what this whole thing is about. The one last thing on timing here, because timing is the most reliable, probably delay mechanism in the avoidance toolkit. And I'd probably be doing a disservice if I didn't name it directly. There are genuinely bad moments to have these conversations. When, you know, either person is exhausted or flooded or in the middle of something

• 47:25Jonathan Fields?

  else that requires a full attention, those are real and they matter. Consider them. But the right moment, as a general principle, it doesn't exist. It will not arrive. You, you won't wake up one day and find that all the conditions have aligned and the conversation is finally risk-free. If you're waiting for that moment, you're going to be waiting a really long time. And the conversation is going to be older and heavier when and if you finally have it. You know, the right moment is the one you create imperfectly, on purpose, because you've

• 48:06Jonathan Fields?

  decided the conversation matters more than your comfort with the idea of having it.

• 48:14Jonathan Fields?

  So I want to leave you actually with one question.

• 48:21Jonathan Fields?

  And I want you to take it seriously. Which means, don't actually try to answer it right now. Let it just kind of ride with you for a day or two as you're thinking about these conversations that have been living inside of you that you haven't been having, and maybe how to have them.

• 48:42Jonathan Fields?

  Right? Just let the answer to this question find you, rather than trying to force it. And the question is, what is the conversation you keep not having? What is the conversation you keep not having?

• 49:00Jonathan Fields?

  Don't reach for the easy one here. Don't reach for the one about someone you already kind of are a little irritated with, where it wouldn't take much vulnerability to bring it up. Reach for the one you actually already know is there. The one that you've been living around carefully for a while.

• 49:22Jonathan Fields?

  The one with the person who genuinely matters to you. The one about the thing that's actually true. You don't need to have it tomorrow. You don't need to have it perfectly. I hope I've made that case to you by now. Right? Perfection is not the goal, and actually is counterproductive. You don't even need to know exactly what you want to say. But I'd invite you to stop pretending you don't know it's there. Just let yourself know it consciously, clearly. This is a conversation I'm carrying, and I'd really love to finally put it down.

• 50:07Jonathan Fields?

  So in my experience, that's enough to start. The beginning has its own momentum. You don't have to see the whole path. You don't have to map it out. You don't have to strip it out. In fact, I strongly advise you don't.

• 50:20Jonathan Fields?

  You just have to be honest about where you are on it. You know, when I finally had a conversation with my friend, the one I told you about at the top, what I remember most isn't what was said, it's the feeling afterward of being in the friendship fully again and not managing it, not curating it, just, just in it. With him knowing something real about me and me knowing something real about how he'd received it, and both of us just somehow closer for having found out. That's what's available on the other side of the conversation you keep not having. And I think that's worth it. So let's talk about some of the big ahas and actionable takeaways from this conversation.

• 51:03Jonathan Fields?

  The thing I keep sitting with is one phrase I use somewhere in the middle, the private theater production. The idea that when we rehearse a difficult conversation entirely on our own heads, where we control all the variables and everyone says what they're supposed to say, we're not actually doing the work of the conversation. We're doing the work of avoiding it while feeling like we're preparing for it. A few things I want you to walk away with here. One, the architecture of avoidance is real. And the more capable you are, the more convincing it looks. Noticing it is not a self criticism. It's just clarity.

• 51:44Jonathan Fields?

  Two, there are four different kinds of difficult conversations, being known, repairing distance, releasing something, and seeking to understand. Knowing which one you're actually trying to have, it changes everything about how you begin. And three, the smaller opening. You do not have to lay everything out all at once. You just have to signal that something real is trying to come through. The content, it can follow. If there's a conversation you have been kind of living around carefully, I'm not asking you to have it tomorrow. I'm just asking you to stop pretending that you don't know that it is there. In my experience, that's enough to start. Hey, before you leave, next-

• 52:29Jonathan Fields?

  Next week, we're sitting down with Alexandra Sifferlin to talk about why nearly everyone will experience a wrong or misdiagnosis in their lifetime and what the best diagnosticians in the world actually do differently that has nothing to do with medical genius. Be sure to follow Good Life Project wherever you get your podcasts so you don't miss that or any other episodes. Do me a personal favor, a seven second favor. Share this episode with just one person. Then use it as a reason to actually talk about what you both discovered, what landed, what it brought up, because that's how we all come alive together. This episode of Good Life Project was produced by executive producers Lindsay Fox and me, Jonathan Fields. Editing help by Troy Young. Chris Carter crafted our theme music.

• 53:14Jonathan Fields?

  And of course, if you haven't already, follow us wherever you get your podcasts so you never miss a conversation. Until next time, I'm Jonathan Fields signing off for Good Life Project.

• 53:28Speaker 05

  With no fees or minimums on checking accounts, it's no wonder the Capital One Bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends, it's pretty much all he talks about, in a good way. What's in your wallet? Terms apply. See CapitalOne.com/Bank. Capital One, N.A., Member FDIC.

• 54:02Speaker 07

  Hey, we're Nick and Jack, hosts of The Best One Yet. Behind every episode, there's research, emails, spreadsheets, and our shared Google Doc, the headline hammer. With Google Workspace with Gemini, Google's AI is built right into the premium versions of tools we already use, like Gmail, Docs, and Sheets. No new tools or extra logins, just personalized AI for the way we work. That means less time on the work around the work and more time finding the stories worth talking about. Get AI tools for work. Upgrade to Google Workspace with Gemini at goo.gle/workspacewithGemini. That's goo.gle/workspacewithGemini.

• 54:37Speaker 04

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• 55:07Speaker 02

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