How Founders Can Leverage Emotional Decisions

Welcome to Heart of Entrepreneurship, where I, Jesse Pujji, talk with Dave Kashen, my long-term coach and BFF, and we explore this interesting topic of how do you build a business, how do you be an entrepreneur from heart, from love and joy versus fear and struggle. I never— well, I've started this weird thing where I don't tell Dave the topics ahead of time.

I just throw And, uh, it's fun.

And I got a good one today. Um, and it kind of keeps in keeping in line with last time we talked about sort of applying some of this stuff, you know, in a sales context, we talked about it. So I got another good one. Um, and it's something that I'm also kind of real-time dealing with, uh, around basically make decision-making. Hmm. And, you know, to set it up a little bit, like most founders, CEOs, executives, in some ways, like your whole job is just making decisions. And I think it, I noticed it with the CEOs that I work with and myself. It's like, oh man, I feel like I got to make this big decision. Do I do it this way or do I do it that way? You know, or should the company go in this direction or that direction? And those can become all kinds of interesting spirals and your brain goes in a million different directions and. And I think even more dangerous, I'll use that word, or even more maybe subtle is oftentimes, and I did this a lot early in my career, I'm like, oh, well, I'm a smart Wharton guy who worked at Goldman. I'm going to analyze this. I'm going to come up with option A and option B and run the numbers and the expected value, and then I'm going to make the right decision. And then you make it and it doesn't go the way you want. So anyway, there's this whole thing around decision-making. I think you can convince yourself you're being rational and oftentimes you're not. And so I'm curious to kind of explore your experience coaching lots of CEOs around decision-making. What are the kind of patterns you notice? How do you do that?

Before I share what's coming up for me, I thought it'd be fun to put you on the spot and say what has shifted. What have you learned from me and our work that has shifted how you make decisions?

Well, that's a lot. That could be the whole podcast. I think, um, I mean, I think maybe the number one thing is, has been, uh, to not assume— well, to learn that I'm feeling something versus assume I'm being rational all the time. I think up until we started working together, these big decisions, including probably like whether or not to marry my wife and including whether to sell the company or not, including maybe a big hire, I was always like, well, no, I'm, I'm being rational. And I thought I was being rational because I wasn't in touch with how I was feeling enough to recognize. In retrospect, it's like obvious it was all very emotional and very not rational. But I think, and then I think that gave me, um, by understanding that, it sort of gave me, you know, more both richness and perspective on, oh, what's actually happening right now. And oftentimes it was like I was feeling afraid of something or, um, or I was feeling in threat around something and getting to the bottom of that was oftentimes more more valuable than trying to make the right logical choice. So I think that's one big category. Maybe related to it is like the concept of like being right versus preference. And so this idea, I think up until, I don't know, 2018 or so, like I was like, I had to get my decisions right. They had to be correct versus what I wanted. And then conceptually, I didn't even understand what I mean. What do you mean? What do I want? Like I want to be right. And so I wasn't in touch with anything. I was like, oh, never really. I never was like, oh, what, what, what do I like? You know, what do I— what's my point of view? What do I want? It was just I have to get the answer right, which obviously I think I learned was a bit of a fool's errand. Yeah, there's probably other stuff, but those are two. I think the other— we read this book together. I read it called Decisive Ones. You remember that one? I don't know. It was a book called Decisive and like it, it had a lot of really good tidbits. One of the ones that just is jumping in my head right now was like, anytime you feel like, you know, you can't decide, you're either too, like either zoom in closer or zoom out further.

Oh, that's cool.

That's like a simple thing I do. That tactic, it's like a very simple tactic that immediately shifts either at first I go closer to the problem or I go further away from the problem and it gives me a lot more clarity.

I'll riff off what you shared and then share some other thoughts arising. And, um, I noticed I want to give a shout out to Joe Hudson because I learned a lot about decision-making from him and The Art of Accomplishment. And they actually have a course called Great— The Great Decisions Course, which I took. So some of this I'll draw from that and some from other, other sources in my own experience. Um, there was Some research that's been done, in particular what's coming to mind is there's been patients who maybe through accidents or, you know, basically had a brain injury that didn't enable them to feel their feelings, like fundamentally, like couldn't access their feelings. And what they discovered about— there's a man in particular I'm remembering, he literally couldn't make decisions. Like, like the question, you know, they'd ask him like, what would you like for lunch? And it'd be hours and hours of looping and trying to rationalize and analyze and figure out what he should have for lunch. Um, and what they discovered is that we literally, we human beings, we make decisions emotionally. Like without our emotional system, we are incapable of making choices. So it made it really apparent to me that we actually make decisions emotionally and then we rationalize them. So all the rational stuff is really just, um, a little bit of smoke and mirrors. I don't want to overstate it. There's times where we, we could do an analysis that's useful, but still at the end of the day, what leads to that moment of like, okay, I'm doing this, is, is some feeling. So, right.

I've heard, I've heard people say before that we all make emotional decisions and then we look for a rational alibi.

Oh, that's a good— Yeah, right. It's almost like, well, of course I chose that. Yeah, she was the better, blah blah blah. Or that, you know, and it's funny, Robert Rubin, the former Secretary of Treasury, spoke at my college graduation.

Hmm.

And I still remember he said, you know, one of the biggest things people get wrong is that they judge their decisions by the outcomes. Instead of judging them by the criteria they used to make them, right? So there's also a whole mess we make around like, well, I made that decision, it didn't go the way I thought it would, therefore that was a bad decision. Not necessarily. It might have been a brilliant decision, it just went a different way, right? Um, so if we go into emotion, you know, the way Joe phrases like, given that we make emotional decisions, let's learn how to make better emotional decisions.

Yep.

And, and what I have found is that most of our decisions are actually made in order to feel a certain feeling and/or avoid a certain feeling, which can be a trap, right? And, um, you know, okay, should I Should I leave my job, you know, or should I fire this employee? Oh no, when I imagine that, it feels scary. Let's just say fire this employee. I imagine other team members will quit and like, oh no, I shouldn't fire them, right? That's the rational choice. Bullshit, you know, that's not rational. It's just, I don't want to feel that fear that arises when I think about it, so I don't do it. And then I rationalize, right? Well, they're not terrible, they're doing okay. It'll take me a while to find someone. I'm very busy, we need coverage.

Right? Like disruptive.

It'll be disruptive. Other people will be upset, right? But really, we just don't want to feel that fear. So one of the most important things you can do to make better emotional decisions, which is just another way of saying better decisions, is learn to welcome and feel all of your feelings. Because if you don't need to avoid feeling any particular feeling then what that sort of unlocks is more clarity about what you really want, which is what you alluded to earlier.

And, um, it's almost like feeling— it's almost like feelings that you do don't want to feel are like a straitjacket, and if they're around you, you can't even get out of them. But if, if they're not there, then you can— you, you have more expansive, like, freedom to choose. But also, I guess, clarity. You also can see it more clearly.

Yeah, it's almost like we have a defense mechanism that won't let us access or attune to what we really want if it feels too scary or too upsetting. And so we have to learn to be okay with that upset, with that fear, with that anger, sadness, so that we can even access, or even shame, right? Sometimes people are like, ah, I'm ashamed to actually want this thing. Because I've been taught I should want this. But really, I actually just want to quit and shut down my company and go to Costa Rica and surf. Oh, but no, no, that's bad. I'd be a loser. You're supposed to endure and fight the good fight. And so, there's all these feelings that tend to get in the way of us even attuning to getting clear about what is it that I really want. From my experience—

let me interrupt real quick because I got, I got Andrew Warner's ghost in my head being like, well, hold on, Dave, hold on, hold on, hold on. Like, you coach all these CEOs. Yes. Surely they bring you business problems where they say, hey, should I sell my company to private equity for $500 million, or should I sell to a strategic for $600 million? I don't know, I'm torn. Or even like my thing right now is like, should I structure this thing I'm doing as a fund or as a holdco? And here's the different ramifications for those. And like people bring you what I will describe as like business problems.

Yeah.

Yeah. You know, and, and I'm sure that happens all the time to you. I guess, how does that— are those, are those emotional problems or are they just people aren't very strategic? They're not playing 4D chess like Peter Thiel or whatever genius out there plays 4D chess all the time.

From my experience, our authentic wants are the best guide to decision-making, um, because they, they allow us to live an authentic life, right? Like, authentic wants—

when someone brings you a problem like that, how do you— what would you say?

Yeah, so I would, um, first I would look at what like imagine option A, you, uh, I mean, we could just take yours. You do a fund structure. Like, what are the feelings that arise when you imagine that?

A real question?

Sure.

Um, I think for me there's some excitement about the, maybe the variety of different types of companies you could get involved with. You get to stay involved in a stage of building, but you're not really part of the company, like ownership, like you are in a holdco. But then like everybody tells me funds are like administratively burdensome and like you got to be fundraising all the time. And then I'm like, oh, my energy drops or I get nervous or afraid that like I don't want to put myself into something that I don't— I don't know that like feel scary.

Uh-huh. So there's excitement and fear. Mm-hmm. So could you allow yourself to feel all that excitement and all that fear?

Sure-ish.

Yes. And to the extent not, well, at least start by welcoming the resistance, and then See, um, and, and, you know, I don't want to skip over this, like, if not, you might not be ready to make a choice. Like, it might be better to just explore that. Oh, what's in the way of feeling that? I imagine it's more the fear than the excitement you're resisting, or maybe the other way around. Which, what do you— which of the emotions are you resisting?

Probably the fear. I think, I think there— again, I think there's this there's a sub-thread here of like the not knowing, which, which oftentimes— yeah. Okay. Yeah. Why don't I know the answer to this? Or why, why is this?

I'm glad you mentioned that because there's sort of two other threads that are open in my mind around this. And that's one, this— there's like figuring out, trying to figure out the right answer. So we just talk about that. And then there's the thinking you should know something you don't know. Mm-hmm. Right.

And, um, and you're thinking that surely there must be a right answer to this, like, right?

And if I was competent, like, I would know the right answer. Like, I should know. So let's just talk about that specifically because, well, two things. One, life starts to feel like a quiz in school, right? Where it's like, I gotta get the A. Like, I gotta choose the correct bubble. You know, so that does a few things. One is it makes these choices more, um, it makes life feel more binary than it tends to be. So, uh, you know, so often our mind is like, when you're making decisions, like, okay, is it A or B, right? And in reality, life is this infinite tapestry. There's probably 10 other, maybe 20 other solutions, or there's an A and B solution. Or so sometimes The reason we struggle even to like answer the question— let's go there for a second— um, what do you really want is because you perceive you can't have everything you want. So then you're in this battle of like, okay, do I want this part more? Do I want this part more? Right. And often I'll say to clients like, hold on, if you could let go of your limiting belief that there's some trade-off Like, then what do you really want? And they're like, oh yeah, well then I want to, you know, I want a, uh, holdco and I want to have $50 million. You know, it's like, right, um, suddenly it's— it becomes clear what you want. It's more just you have a limiting belief that you have to make trade-offs, and so you're— you're— you have this battle about which trade-off you want to make. So I'm a huge fan of asking clients like, how could you have it all? So that would be something to think about. And sometimes that's what causes the decision tension is the belief you can't have it all. So now you're just trying to weigh between these two different things. And when— and the truth is you want both. That's why it's a tough decision, right? Um, I was talking to a client today actually about like the Harvard Negotiation Project, where they distinguish between like position-based negotiation and interest-based negotiation. And so in some way it could be useful to be like, okay, these are positions, like holdco or fund.

That's where my head was going.

Yeah. Yeah. But like, okay, what's the underlying interest? What is it you believe that a holdco will give you? What is it that you believe a fund will give you? And then you'll get more clear about what is it you really want. And then you might find creative solutions where you can have both and maybe it's some other structure altogether. So, that's—

Yeah. Yeah. So, one of the traps is definitely getting thinking you should know the answer when you don't.

Yeah. We just named two traps. One is the binary, like either-or thinking.

Yep.

Right. And then the other is, I should know the answer. And, you know, it's literally like saying the sky should be red, right? It's like, if in this moment you don't know—

yeah.

And you say to yourself, I should know, it's just like, it's just a way you resist reality. Reality should be different. It should be this other way. Yeah.

The other thing I'm noticing, it just, just for what it's worth, just to name it, is like It just came up when you were talking. I was like, oh, there's like, why, why do I make these decisions feel bigger? And there's like various attachments I have such as like, oh, like, you know, if you're going to get money from other people, like, well then, you know, you have reputational or you have responsible, like there's all like, I'm just noticing these other attachments that are showing up. Like I was like, why, why does it feel like a heavier decision than maybe a typical, you know, another, another decision. Earlier you, you said, you mentioned, we talked about not knowing. Can you talk a little bit about, or even like a case studies, like what are some examples of client situations or things where the person's stewing on it? They were like, you kind of said, well, hey, you don't know, it's okay not to know, just be with that. And then ultimately that led to clarity, something.

Sure. First, let's, um, Let's do this in real time. Um, can you accept yourself for not knowing?

Yes, I think I can.

Yeah. What do you notice when you do?

Um, my body gets a little bit more relaxed. I'm like, I'm like, yeah, I don't, I don't know.

Yeah, it feels lighter. Um, another way I asked that question, just, just for, you know, folks listening, if you want to ask yourself, is Can I let go of the story that I should know?

Right.

You know, can you let go of thinking you should know something that you don't know? Which I'll come back to your question in a second. There's a metaphor I've often used of a— like, imagine you have like a plastic bottle of water, you know, clear plastic, and it's filled with sand. And so it's very murky, right? And you're like, I want it to be clear. And so you're shaking the bottle because you're frustrated that it's not clear. And like, of course you're making it even more murky, whereas it's obvious in that case what you need to do is just set it down and let it get still, right? And I remember reading somewhere that like, um, what creates insights is like when you connect— when your brain connects weak signals. But your brain can only hear signals above the level of noise, right? So there's just something I find powerful about like, get still get quiet, I get present. And it's not get still and be like, okay, what's the answer? What's the answer? What's the answer? I gotta figure it out, right? Right. You know, ironically, it's more like, just like, you know, this is why so many people have clarity in the shower, right? It's like when you're not thinking about it and your, your mind is more quiet, often some insight emerges or some clarity emerges. So I think there's something to just like get still Get quiet, allow clarity to emerge. Your question was—

Well, so just to recap, so we started by talking, you said all decisions are emotional and then you kind of put rationality on the back end. We talked about a couple of the traps when you think you should know the answer, you either are like saying either/or or you're mad you don't know the answer. And then we were talking a little bit about not knowing. I want to come back to something in a second, but yeah, let's talk about not knowing.

Okay, I guess we also— for the recap, we also talked about if you're making decisions to try to control what you feel, right, you're probably going to make suboptimal decisions. So learning to be with your feelings and like welcome them and not need to control them frees you up to make like more clear decisions around like, what do I really want to do? And we talked a little bit.

Yeah, actually, let's— I want to stay with that because I was sort of teased. Like, I make up Peter Thiel. I don't know Peter Thiel, but I make up he's this, like, chess player and he thinks 4 steps ahead of everyone. He's super rational, blah, blah, blah. So I'm just— he's a caricature. I don't know him actually. Right. But like, but, but there's a group of people who kind of go like, no, like, I'm a rationalist, Dave. Like, I am just going to think through all the, like, the potential future machinations of this. I'm a chess player. I'm getting ahead of the steps. How would you, how would you counter that argument with what you're saying, which is, no dude, there's no such thing as a non-emotional decision?

I think, well, what comes to my mind is one is the idea that the mind is a wonderful servant but a terrible master. So it's not that we dare— we don't use our intellect and our intelligence to make— to inform our choices. Like, right, like, I don't— I wouldn't want to, um, devalue or ignore any part of us. I just think most people way overly rely on that part. And to me, like, the recognition that we actually make emotional decisions is further sort of support for why we ought not to just rely— like, it's kind of a fool's errand, like you said, to pretend that all— it's an entirely intellectual and emotional, you know, process, right? But I don't want to deny our intelligence and the power of our intellect to, like, consider options. And so it informs. But I think what most people do is they over-rely on the intellect. And they ignore, for example, like the heart, right, their feelings, um, and the gut, the intuition, right? So, right, um, it's almost like they, they lie to themselves that it's not—

like, if you're, if you're, if you're a hedge fund trader and you're like, I've run the analysis and I'm going to go along on this stock, that involves a lot of intelligence and intellect, obviously, but at some level it has to involve your, your feelings, your belief, your your emotions, or maybe again, you don't want to be wrong. And to your point, if you're not super conscious of it, you just don't want to be wrong and you don't want to feel wrong, so you're going to make a consensus bet or—

Yeah, you can justify it either way in the end. And I think to that example, if you did all the analysis but you actually felt terrified when you considered making the investment, you probably wouldn't make it even though all of your analysis showed that it's a great bet, you know, the financial forecast, like everything made sense. But if in your body you felt terrified, you probably wouldn't do it. And then you would find some way to rationalize it.

Right.

And there's— I think there's pretty good research and studies around how people post, you know, rationalize, you know, all kinds of decisions. The other thing I just wanted to name, because you kind of mentioned, oh, it starts to feel lighter. One of the things that I learned from Joe Hudson that really resonated was we actually make choices all day long without thinking much about them, right? Like we get dressed and we have food and we have meetings and we talk to people and we say words and like everything is like at some level a decision, right? Like, am I choosing every word I'm going to say? I guess in a certain sense I am. Um, what differentiates the things that feel like, oh, this is a decision I have to make, from just all the other choices we make, is just fear. So I think that's a real— and you were, you were kind of tuning into this with your, okay, is it a holdco or is it a fund? There's some fear you have around making the wrong choice that suddenly has you stop and be like, oh wait, I need to really consider this one. And what you're really trying to do is just control life, control the future to like manage that fear.

Yeah, that resonates. Yeah, I'm trying to control some future that doesn't exist yet.

And maybe also approval, like you said, look good.

Yeah.

Avoid looking bad. Yeah. And they're very related, right? Because the reason we want to be right in our decisions is because we want to control the future, right? Right. So when I'm in threat, I'm like, I feel scared, I need to control the future, um, and now I need to be right in order to control the future because I'm right that this is the right future. Um, and what I think is most tricky about this conversation is, you know, we'll invoke Andrew or founders listening, like But isn't my job to make great decisions, is to make the right calls?

Right.

Like, isn't that my job? And to some extent, the answer is yes. Like, I think your job is to make the best decisions you can. The question is, how do you actually do that?

Yep.

And does like all the intellectual trying to figure out the right answer lead to better outcomes, better decisions, than using— letting your intellect inform you, but also tuning into your heart, tuning into your intuition, you know, tapping into, okay, what is it I— what do I really want to do here? Um, and what's wild to me is I, I have seen many times clients follow some authentic want that didn't really seem rational, maybe even counter-rational. And then only in hindsight it has become clear, like, oh my gosh, if you had done the rational thing, you know, you wouldn't have known AI was about to emerge and blah blah blah. But because you're here now, like, oh my God, you're perfectly positioned. So it's, you know, maybe that— maybe one way of saying it is let's stop pretending we can predict the future. Right, right. Like, that's in some way, that's really what we're doing when you're like, I should know the right answer. I should be able to know in advance what decision to make and be able to accurately predict the future. And, and for a long time, and to some extent still, I would just— or at least my mind would beat me up over investment decisions, right? Either way, like, if I bought—

I was gonna say, like, this makes sense for when you make like personal decisions about how you want to spend your time or where you want to live or whatever, but I was going to actually ask you because you and I both worked at hedge funds and I think you coach some people who run or like have hedge funds.

Yeah.

I'm like, how, how do you coach? The question is, how do you coach that person to actually make decisions? So, so now acknowledging that fine, emotions are a part of it, but you don't want to let go of your brain. There's like, you know, either or all these things like those people have to sit there and they actually do have to predict the future. I mean, that is their job. Like they get paid based on their ability to predict the future.

Yeah, and in some way founders do too, because if they make a great strategic choice, that might mean, you know, the company is wildly successful. And if they make a poor strategic choice, less so, right? Um, oh, I started to talk about this. There's a notion from the Conscious Leadership Group of like a whole body yes, which the way they describe it is like your head says yes and your heart says yes and your gut says yes. So I think that might be a just a nice clean way to think about it. It's not that you ignore your intellect that says no, right? If your intellect is like, this is a bad company, I shouldn't invest in it, like, unless for some reason you have this really strong gut feeling that you should, you know, then Like if you talk to any investor who's been investing for a long time successfully, they will tell you there is, I mean, unless it's like a purely like quant, you know, algorithmic, and I'm sure more and more that'll happen with AI, but human investors, there is some intuition, there is some gut feel. Like everyone that I've heard, you know, speak about it, it's like, yes, you have to do your work, but also there's some, you know, like there's some, Maybe it's just subtle pattern recognition that's just too subconscious for us to understand, but it manifests as like an intuition, a feeling. And so I think we ignore that at our peril. So the point about intellect is sometimes our intellect will say, yes, you should do this, it is the rational thing, and then we steamroll over our feeling and our gut, right? And by the way, people do this all the time when they take jobs and they, you know, choose a partner and And founders do it too, of like, well, this, this looks good. This is what my investors want me to do, right? This is what Silicon Valley says is the right thing to do. I should go bigger.

I—

even though their heart and gut is like, no, I actually want to stay small. So that's the main point around like, if we over-rely on our intellect, we can steamroll right through our, our heart and our, you know, our feelings and our intuition. And so I I think it's useful to check in with all three, and it's not black and white, right? It's not, um, it's not, it's not always totally obvious, right? Oh yes, head says yes, heart says yes, gut says yes, go. It's amazing when it is that, you know, then maybe, you know, double down on the easy decision. Yeah, yeah, that's— those are easy decisions. So there's nuance and there's attunement, and I think that's part of the—

it sounds like the big coaching thing is, is like make sure you're not only just using your head, but instead you're invoking all parts of yourself.

Yes.

When making a decision.

And there, there is metaphorically like muscles to build around attuning to your wants, attuning to your feelings, so that you can actually, um, access those sources of intelligence. It's like, you know, we have body intelligence, we have emotional intelligence, right? Gut intelligence. It's like If we just rely on our intellectual intelligence, we're, we're missing other sources of intelligence, which of course, why would you want to do?

And so that makes sense. How does that, how do you see that going wrong for, for founders? Like we talked about failure patterns last time. Like what are the failure? I can think of a few, but I'm curious what you see most commonly.

I think one of the trickiest ones is conflating feelings and wants. So, um, uh, the example I often give— so I was, I was a, um, member of the Conscious Leadership Group for a number of years. I was a team member, and I loved being a team member. I love all the humans. I love being part of it. I love going to the retreats. And, you know, And then at one point we had sort of an up or out conversation, like it's time to be all in and be a partner or time for you to go. And like, I think if not for the coaching by the founders, you know, who were part of this conversation, like I might have just stayed and like, and basically convinced myself that I was willing to you know, do everything through the Conscious Leadership Group and do all my coaching and stop other things I was doing because the amount of sadness I felt when I thought about leaving was so big and I just didn't want to feel that, right?

So the failure pattern there is like, oh, they're like not feeling willing to feel your feelings because I—

because it feels really sad when I think about leaving, that means I really want to stay. And you can see how subtle that is because you're like, well, isn't, isn't that what that means? Like, I should do what makes me happy and not do what makes me sad. But what I'm finding is like authentic wants are almost like at a different— it's like a different vector, right? It's like, if I knew— I think this is one of the questions in, in they asked in Arvakan, is something like, if you knew you'd be happy either way, then what would you do? That's more of like a, oh, like, okay, then Oh, so I— because what's cool about that question is it takes away the, like, um, the idea that my choice determines my happiness, right? This is why it dovetails really well with, like, when I'm in a state of presence, what else would I choose from than wants? Because I'm already whole and okay and happy. There's nothing wrong, nothing missing. So then it's just sort of like, okay, I guess I'll just— you know, it's like, what creative impulse arises? You know, it's like an impulse. It's one—

well, one of my favorite questions I ask founders when they're stuck. It's a two-part question. The first question is, if you were going to be successful in either path you chose, which one would you pick? Kind of similar.

Yeah, that's a great—

but then I've got, I got another version of it, which is, but now, so whatever they pick, say they pick option A. Okay, now if you're assured failure in 5 years no matter what, which one would you pick? Because that— I like that one because it actually says, how do you want to spend your time over the next 5 years?

Beautiful.

I should ask myself these questions.

Yeah.

But like, but I think that actually, it really tells you like, okay, so you're gonna be successful in either one. Okay, well then I'll do this one. And then usually when those are the same answers, you kind of have found what you wanna do because you wanna spend your time that way regardless.

Yeah. It unhooks the, like, I'm just doing it because of this thing I think it will give me.

Yeah.

And just to close that thread, like, so the failure pattern, obviously, you know, it's conflating, oh, I feel really sad about leaving. That means I shouldn't leave. So I ultimately left and I cried my eyes out. Like, I was at a funeral. I was so sad and grieving. And it was a deep learning for me of like, oh, that doesn't mean that it's the wrong choice or that at some level I don't actually want to leave.

What does it mean, though?

Oh, it means that I loved it. I loved being a part of it, and I feel sad to leave it. Like, like You know, it's like sadness is the feeling of letting go, or the, the energy of letting go. Um, grieving is the most pure way to honor something that you loved, right?

But it doesn't mean you should keep doing it.

It doesn't mean you necessarily should keep doing it.

There'd probably be a lot of marriages that would end if people internalize that tomorrow.

That might be true. And businesses that might be closed, and yeah, projects that might be shut down. I think a lot of people But the failure pattern here is sometimes like—

it's what you said earlier, which is like, you're just— because you don't want to feel a certain feeling, you basically make a choice that isn't what you truly— you're like, right?

Yeah. Let me give another example that is— could be sort of controversial, but, but it's what actually occurred, so I'll just share it. So I announced that I, you know, I, I had great success with my Sun Valley retreat, recruit, you know, got an amazing group of founders. Amazing. This was last year. I just did it again this year, you know, loved it. But coming off the one last year, I said, oh, it would be fun to do like a warm weather equivalent, you know, with like wake surfing instead of skiing and, you know, mixing in this. And so I announced this like Austin Founders Retreat in, I think it was September. And, um, very basically nobody signed up is the short version. And like the entrepreneur in me, you know, the intellect was like, well, get, get your ass in gear, right? Like reach out to Jesse, ask him to ping his people, reach out to all your, you know, VC contact. Like I have all this, like, you know, you're about to fail. Like you, you gotta do a bunch of— you go hustle. And I just really, I attuned and I was like, I don't want to. I noticed I just don't want to, right? And I allowed myself to just follow my wants and I didn't do it. And I basically said, if somehow people sign up, I'll do the event, and if not enough do, I will cancel it. And I ended up canceling it. And so, you know, there's like a common Like, I almost hesitate to share that story because it's like, oh, doesn't that mean if you follow your wants, you know, you'll fail? And like, you should push through the hard parts, right? That's the like, um, maybe common entrepreneurial or Silicon Valley kind of lore. Um, let's just contrast that for a second. Sun Valley retreat, uh, I'd say I had probably like 6 or 7 people sign up, but like, you know, half the, the 12 that what I was targeting until like a week or two prior. And I noticed I was really excited about the retreat and I wanted to get in action because I was just really excited and I wanted to have more people there to serve and to meet each other. And so I did reach out to folks and like there was no part of me that was forcing myself Like I genuinely wanted to do it and it worked and we filmed it.

And there's a narrative in Silicon Valley that is like, follow your energy. Like don't, don't try to work hard when you don't have the energy to. And it kind of reminds me a little bit of that. Is there, is there another—

that's my narrative. I don't know if that's—

well, it's like an emerging one. It's like the work like a lion versus work like a cow. Have you heard that one? I forgot who said it, but like the cow just grazes all day long. A lion rests, rests, rests. And then when it's ready to go, it goes. Um, there's like an emerging—

that really resonates with my experience. Like, I say follow your aliveness, follow your energy. Yeah, I think that is a more trustable guide to your decisions than your intellect telling you what you should be doing, right?

Your mind enslaving you. Is there another big failure pattern around people pleasing in this category? I imagine there is, right?

Oh yeah, yeah. The way I connect the dots of that is Not only do I want to control how I feel, I also want to control how other people feel, right? Especially how they feel toward me, mostly because that affects how I feel. So I want to control how you feel about me so that I don't have to feel things that I don't want to feel when you feel upset or angry. Also, there's— it's just, it's a common pattern of like a way we learn to be loved. Is to please others.

I don't want to sell my company because the return's not big enough for the investors, or my employees won't make enough money, or therefore, even though I like probably really want to sell it, like, you know, what I want is to sell it to be done, I'm gonna, I'm gonna keep hanging on, and I have like all this 100%. And it's not the obvious people pleasing, right? It's not like the, it's like sort of subtle people pleasing.

This is why I think the notion of authenticity is so important with this stuff, because All of these are flavors of, I will be inauthentic to avoid feeling something or avoid, you know, it's like, yeah, I don't want my investors to be disappointed or to think I'm a sellout or a loser or, you know, whatever. And maybe I'm afraid of what that would mean in the future. And so now I make a decision that my mind says is a good decision because it allows me to avoid these imagine future scenarios, but really it's I'm just trying to avoid some feelings I don't want to feel. Um, and yeah, people pleasing is one common pattern of that. Like, and it's part of— it's really mostly part of approval seeking is another way to say it. It's the reason I want other people to please others is because I want them to like me and think well of, of me. Um, and by the way, like, our intellect is largely informed by a lifetime of what other people have said to us. It's like our parents' voices internalized, right? That's some of the other tricky part of listening to your thoughts, you know, that say you should do this, you should do that, is you kind of end up then indexing on what other people think you should be doing instead of, again, like your authentic wants feel to me like the most clear compass for what you, you know, for your authentic truth, whereas your intellect can kind of trick you based on fear.

Yeah, I thought you were going to tie it back to control, security, and approval, which are like the 3 most common mind patterns that probably— maybe that's the answer to the, like, the most common patterns where people make decisions that they don't truly want because they end up prioritizing one of those 3 things instead.

Yeah, they, they believe that they are lacking in safety, control, freedom, or approval, and then they make decisions that they think will make them feel free or have control or safe or approved of. That's a nice simple way to describe it.

Versus slowing down, tuning into their authentic wants, and then, you know, and we could probably do a part 2 of this.

Importantly though, just in that one, In the slowing down, what's available is recognizing no lack of safety, no lack of control, right? You don't need to control anything that you don't or can't control. No lack of approval. You don't need external approval, right? Again, in presence, in a state of presence, you recognize you don't need any of that. There's none of that is lacking or missing, and therefore it wouldn't occur to you to make decisions to optimize for that, because actually, you know, there's no lack, right?

And then you can just choose whatever it is that feels right to you across the head, heart, and gut.

Yeah. And some— yeah, which is a more nuanced way of saying just kind of, what do you really— what do you really want to do, right?

Um, yeah, I love it. Well, I think, I think there's a part 2 I want to do on this next week, so I'll which I think is about kind of looking back on decisions. There's a lot of like— there's a lot of decisions are an interest. There's just such an interesting category of thing that people get charged up around. And, and I think we've sort of done the first version.

I'll plant one more seed for our— for that future discussion, which is I do sometimes ask my clients, who do you want to be? And when you're being that way, then what occurs to you to do? Yeah, and I do think that that can also be a useful frame, like, okay, I want to be courageous and, you know, passionate. Okay, well then what, you know, if you're being like— you step into that being, I'm courageous and passionate, and you feel that, then what occurs to you to do? And, and I do think different choices occur to us when we're being different ways.

Yeah, yeah. And I think part of next week is also talking about courage because I think If you can get yourself to this point of presence, you can see what you want. There's still like a courageous element to actually honoring what you want that I think is, is worth, uh, talking about.

Yeah. And there's a connection between authenticity— I really love that question of like, what, what, how is fear stopping you from being fully authentic? And that's to me a good guide to when courage really serves you.

All right, let's end there. Talk to you soon. That was fun. All right. Thanks, Dave Kashen.

Bye.