How to Make Big Decisions With Your Head, Heart, and Gut

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 wanna spend your time or where you wanna live or whatever. But I was gonna actually ask you, 'cause you and I both worked at hedge funds, and I think you coached some people who run or like have hedge funds. I'm like, 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. Mm-hmm. 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. If your intellect is like, this is a bad company, I shouldn't invest in it, unless for some reason you have this really strong gut feeling that you should, then if you talk to any investor who's been investing for a long time successfully, they will tell you there is— unless it's purely quant and algorithmic, and I'm sure more and more that'll happen with AI. Right. But human investors, there is some intuition, there is some gut feel. Like, everyone that I've heard speak about it, it's like, yes, you have to do your work, but also, 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, um, 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 heart and our gut, our feelings and our intuition. And so, I think it's useful to check in with all 3 and it's not black and white, right? It's not always totally obvious, right? Oh, yes. Right. Head says yes. Heart says yes, gut says yes, go. It's amazing when it is that, then maybe double down on that.

It's an 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—

But it sounds like the big coaching thing 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 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, 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. The example I often give— so I was a 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 are 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 they asked in Arvokan. It's 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— 'cause what's cool about that question is it takes away the idea that my choice determines my happiness. 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? It's like an impulse, it's want.

Well, one of my favorite questions I ask founders when they're starting It's a 2-part question. The first question is, if you were gonna be successful in either path you chose, which one would you pick? Kind of similar to yours.

Yeah, that's a great—

But then I've 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 wanna spend your time over the next 5 years?

Beautiful.

I should ask myself these questions.

Yeah.

But I think that actually, it really tells you like, oh, okay, so you're going to be successful in either one. Okay, then I'll do this one. And usually, when those are the same answers, you found what you want to do because you want to 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. And just to close that thread, so the failure pattern obviously is 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. It's

like sadness is the feeling of letting go or the grieving. Oh, yeah.

Sadness is the energy of letting go. 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 internalized that tomorrow.

That might be true. And businesses that might be closed and 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. Got an amazing group of founders. It was amazing. This was last year. I just did it again this year. Loved it. But, coming off the one last year, I said, oh, it would be fun to do a warm weather equivalent with wakesurfing instead of skiing and mixing in this. And so, I announced this Austin Founders Retreat in, I think it was September. Yeah. And very basically nobody signed up is the short version. And like the entrepreneur in me, you know, the intellect was like, well, 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 contacts. Like all this, like, you know, you're about to fail. Like you gotta do a bunch of— Right. You go hustle. And I just really, I attuned and I was like, I don't want to. I was like, 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 maybe common entrepreneurial or Silicon Valley kind of lore. Let's just contrast that for a second. Sun Valley retreat, I'd say had probably six or seven people sign up, but like you know half the the twelve that what I was targeting until 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 there was no part of me that was forcing myself. I genuinely wanted to do it and it worked.

Reminds me, there's a narrative in Silicon Valley that is like, follow your energy. 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. 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.