Examining Post-Achievement with Khe Hy

[00:00:00] Introduction

This is Grief & Pizza, a podcast, exploring the highs and lows at the intersection of business and emotional wellbeing. This week, we're talking to our friend, Khe Hy, the host of the Examined Life podcast and a self-professed post achievement professional.

We unpack what that means in this episode.

Kay is a surfer who has a side job as a writer and podcaster. And I say that obviously a little bit joking because I know when I read your, bio online and you talk about, you know, Oprah for the new millennials, it brings up this interesting conversation about identity.


I think you've done some amazing content around Identity Khe and I thought it would be really fun to dig into that also because when you and I first met on the internet, we were doing a lot of Notion and productivity and supercharge your productivity and teaching online. And I feel like some things have changed since then in terms of your interests and even what you're talking about today.

So I thought that might be kind of a fun way to start the conversation of maybe who was Khe a few years ago, five, 10 years ago, and who are you today? Who is Khe? Yes. Well, thank you all. Thank you both for having me. You're some of my favorite people on the planet, so I couldn't be more honored, to be here.

[00:01:08] Exploring Identity

Man, identity. That's, uh, my friend once said, he's like, I don't want fuck you money. I want fuck you identity. And I was like, Ooh, that's good. and so, yeah, identity. I guess I would say, you know, one way that I always lead is, you know, I'm Lisa's husband and Saraya and Amelie's.

Dad, that is the identity that is tried and tested and it will be true for every single, you know, from this moment on for every breath that I have on this on this planet. So that is An easy way to answer that question, but you know that it gets more complicated in that, you know, I've had different seasons of identity, right?

And so the first season I had of identity was being a very intense. Wall Street financier, working in the hedge fund industry. That was, a big kind of 14 year period of my life up until I was 35. Then I became an accidental entrepreneur. I smashed my identity to smithereens, around my 35th.

Uh, and then wandered onto this place, this vast, expansive place called the internet where I had no fucking idea what I was doing, who I was, what needed to be done, what, how to make money, nothing. I didn't know. I still don't know anything nine years later, but I really knew nothing, uh, then. And I guess at that point, um, I anchored into a few kind of comfortable containers, so to speak, that I knew well, and they were productivity, um, you know, GTD fanboy, um, tried and tested to teach people on Wall Street how to use GTD and little known secret is.

Some leaders at some big, big financial institutions use OmniFocus and they use GTD thanks to the little lunch and learns that I did back in 2012 or something like that, 2010. Productivity is something I latched onto on the internet. Um, money, I've always liked talking about money. Um, personal finance, investing, managing your money, things like that, money and happiness.

Uh, and then kind of career. And so those were kind of the identity, uh, the identity cards that I carried on the internet. And there was always a joke for those who know me, And the joke was come for the productivity. Stay for the existential. And because really what I wanted to do was lure you in with topics that were bite sized and candy like, but really kind of talk about.

The shit that really matters, sneak the vegetables in, right? Exactly. Right. Billy, our friend, Billy calls it chocolate covered broccoli. so that was always what I, where I wanted to take things. That's really what I, what I enjoy talking about, what I enjoy writing about. And I think it all came to a head, which is the moment you were alluding to when my whole kind of online business.

You know, got smashed another thing that got smashed to smithereens in 2023 and gave me the opportunity to just kind of hit a hit a big reset and just the basic reset was like, fuck it. I'm not putting myself in any container. Hopefully for the rest of my life. I'm just going to write about shit that I want to write about and talk about things that interest me.

and we'll just see where it takes


[00:04:17] Seasons of Entrepreneurship


I know when we connected last summer, it felt like you were in the midst of wrestling with that where you were like, wait, I've built like you've built a huge community through Rad Reads. Right? Like you've talked about certain topics for a while. I'm sure you had your, your marketing buckets that you sort of felt comfortable posting content in.

And it felt like you were really wrestling with what if I've built up these expectations here and people are expecting me to write about X and I want to write about Y. So do you feel like there was like. A bit of a struggle there in that transition and how did you kind of make peace with that fuck it moment of I just want to talk about what I want to talk about and the right people will follow.

Tell me a little bit about that struggle. there's a few things to unpack there. One is that, the topics like money and productivity, they're easy. They're just kind of known. Everyone knows them. They're really expansive. Five things to do before 7am. The one thing Warren Buffett does that you don't do, like we've all seen that article. We still click it. Like I want to know the one thing Warren Buffett does that I don't do all right. And I think there's this kind of this this animal reptilian instinct to just want to consume that. It's like candy.

And so when you're on the other side of the equation, it's just so tempting and it's easier. And I think that's the thing. Um. That that for me was there's like seasons of entrepreneurship. It's it's very hard to just like come out guns a blazing is like I'm going to teach you life philosophies like no one's there like get the fuck out of here.

But if you're like I'm going to teach you how to move this widget. To this widget, they're like, okay, I knew I need some widget moving in my life. I need some, you know, I need, I need some of that. And so to some extent, I, you know, I give myself a lot of grace that like, That was the season of my life.

And that was the season of my entrepreneurship. And that was the season of my interest. Like 10 years ago, I love talking about all of the details of how to craft a perfect productivity system. Right. so that was the season and I give myself grace and that season served me very well for entrepreneurship.

I think when you caught me last summer, it was in this moment where part of it is like, I think that I operate in seven year cycles and so every seven years I do something and then I get bored. And so I think I had like my, my Wall Street kind of individual contributor that was about seven years. Then I became a manager.

That was about another seven years. Then I did kind of productivity, the more tactical side of the Internet. That was about seven years. And so now I'm 44. So seven years gets me into my fifties. And like the things that interest me, that the concerns, the concerns that I have now. Like my wife lost her father, right?

Like my parents are getting old. my kids are starting to push back on everything that I tell them to, you know, the male friendships are getting harder to maintain. Adult friendships are getting harder to maintain over the years. We have marital problems. Like these are the things that are, are, are constantly on my mind.

Not whether, uh, obsidian. Or notion is a better way to manage my grocery list. Right. And so, you know, at one point that those were top of mind. And so I think though, to answer your question, I've always been solving my own problems. Like my writing, my creativity has always been the result of me solving my own problems.

And so as my problems change, I just didn't have the confidence before to be like, no, my problems have changed. I'm moving on to this next thing. There was a sunk cost fallacy. I've got this audience. I've got this brand. I mean, so many brands like that I had, like I own notion dot courses. I was like, I was telling someone, can you imagine if my domain today was notion dot courses?

You know, that'd be a little bit of a bad, uh, situation. So. To answer to your question, I think there was a lack of confidence and I think hanging out with all, all you guys at that retreat, mastermind, you know, there was some pressure there from folks, not pressure, but some folks are saying like, you need to become the mindful money guy.

That was, that was one of the takeaways from that for me. And it was just like, we'll jump to this next container. And I think what I realized is like, look, I want to do this. Yeah. You're going to carry me out of this internet game and from for that to happen, that means I need to have the endurance for like another 20 to 30 years, and so I can't be the notion dot courses guy for 30 years.

I can't be the mindful money guy for 20 to 30, you know, more years so. I'm just going to have to be Khe.


It's like you needed to reject, reject the containers entirely. And you need to, you know, the thing is when you reject containers, it gets much harder to make money.

So we should, we should talk about that. Uh, containers help you make money. Yeah, like the being specific about, you know, who you are, what you talk about. So, so tell me about that transition then, because if money has been a big part of what you talk about, and now you're like, oh shit, how, how am I going to earn money?

What's next? What am I doing? What were some of the pivots that you, you had to make or what does it mean now to just be Khe and still make money and be good with how much you're making? Yeah, well, this is the direction of my business has not been particularly clear. Let's just say I won't be leading any masterminds for entrepreneurs.

but I think you have to start with the end in mind. And what I mean by that is you have to really, you know, most people, when they said like, oh, I'm going to be an entrepreneur, then they, they assume that the, the thing that you're trying to maximize. Is money, right? And I think that that's not true, but that's kind of the general and someone says, like, I want to be an entrepreneur.

What most people hear is like this person wants to be like wealthy. Right. And that is a consideration. And so I think with me, if I start with the end in mind that there are, you know, I have written about this. I have my what I call my success statement. And so what is success mean to me? And so success means to me is I want to Creatively express myself daily, both from what I create and also how I show up, what I wear, what I eat, you know, what music I listen to, um, Ben and I had so many great conversations about music, at the retreat. And so that that's just creative expression is really important to me. I want to control my time.

That doesn't mean that I don't want to work hard at, you know, I work, I probably average like 35 hours of work a week, but some weeks are 50 and some weeks are zero. but I want to own my time, but I want to work and I want to do, express myself creatively. I want to only be around people who inspire me who are awesome, basically.

I want to be around people who bring vibes, who bring good energy. I want to be present with the people that I'm with. You know, one of my favorite sayings is, When I'm with you, I'm with you.

Doesn't matter who you is. and then I want to surf every day. and so that's the end for me. entrepreneurship then becomes like, look, there's a certain standard of living that we want to have, and entrepreneurship becomes taking that financial standard and taking those four or five things I just listed off.

And then it's like, how do I create a container that can make all of those things possible for as many days as possible? hopefully till like forever. and that to me is entrepreneurship. So a lot of people would look at that and say, well, you're leaving a lot of money on the table. You could have ran with this productivity thing you could have made.

I mean, you know, look at some of our peers out there that are, that are, that have printed money being the writing person, the productivity person, the copywriting person, the digital marketing person. Sure. Their end is different. And I want to say part of the reason why I can be so, relaxed about it is that I entered entrepreneurship having made a decent amount of money.

And so a lot of people use entrepreneurship as their wealth creation engine. I'm very fortunate. Um, the timing of my life, the decisions that I made entrepreneurship doesn't need to be the wealth creation, mechanism for me. It's a really like the wealth maintenance, the lifestyle maintenance and like.

Little bit icing on the cake. and so I want people who are listening to. I think it's really important to share that that advice. And look, I'll be super blunt because I've shared it publicly. It's like I entered entrepreneurship with savings of around like four and a half million dollars. So it's like a lot of people become entrepreneurs to make four and a half million dollars.

So I just it's just It's just yeah um So it's just a different way to to frame it and I just I want everyone I I say that Not to brag or flex or whatever. I say that just To put all of, put everything that I'm going to say in that context, that I, you know, I'm playing a different game. Um, and that enables me to do things differently.

Yeah, it

sounds it sounds a lot like um, we're in the middle of taking uh, joe's joe hudson's great decisions course right now And the week that we're on right now is developing a set of principles that help us make the decisions That we have in our lives and two of the two of the things that it's asking you to to do is Does this principle help you make the decision does this principle?

Uh, is it does it make it more efficient when you make decisions? and It's interesting the way that you, you're describing your, what sound like principles to me and, and the way that you live your life as an, as an end result, rather than a kind of like evolution of Khe. Um, do you, do you see it like that's kind of interesting to me that you describe it as starting from the end, but it sounds like almost like you're starting from the middle and like the beginning and the end can be a little bit blurry at

some, in some respects.

I think that. It's a, it's a very astute observation and shout out to Joe. I was unable timing wise to make, make that cohort. Um, you know, I think that I am a tourist in Eastern philosophy and Buddhism. And so it's almost like the end and the present are kind of one in that in that regard. And so I think we're just we're actually saying the same thing, Ben, in the sense that I want every moment to adhere to those principles.

And when I say start with the end in mind, it was more like the destination of entrepreneurship. But to me, the destination is actually. It collapses into the journey so that they're actually part to me. They're the same thing, the journey and the destination. Uh, and so, but I could see that for others, there might be some separation, which is like, you know, aspirationally.

I, I'm not in a position where someone might listening to this might say, I'm not in a position where I can turn down clients based on whether they're assholes or nice people, but I want to get to the place. Where I can only take clients who are not assholes and so that might be where the difference is Is like how quickly you're able to pull them into your presence

[00:15:35] Post-achieving Professionals

Reducing reducing the gap between those two things and having more elasticity in your life is it sounds like a goal for you So you you talk a lot and I've been loving this phrase, but you always reference post achievement professionals now Mm hmm, and I want to ask you beyond Achieving financial success.

What are the, what are the drivers or the indicators for transitioning to a post achievement identity? What does that look like?

Well, um, the post achievement professional just to, for, for like brief context is the professional who, uh, has worshiped at the alter of achievement. Giving offerings and receiving benedictions like, uh, promotions and media features and bonuses.

And the preachievement professional is just, um, maniacal or such a devotee. Of that, uh, that way of existing, especially in their professional career. And then something happens with the post achievement professionals. They start to, they start to realize like, Hmm, maybe this isn't as good as it seems.

And you've heard the classic story where they ask a millionaire, you know, if you, how much more money would you need to be a 10 out of 10 on the happiness scale? And the millionaire says double. And then they asked someone with 3 million. How much more money would you need to be a 10 out of 10?

And they say double and they go all the way up to 10 million. Every single person, uh, says double. And there's countless studies that show this and money is a proxy, but the, the post achievement, um, so, so the transition towards post achievement often occurs with that realization. Where you're just like, wait a minute, I've been chasing, you know, I, you know, six figures, seven figures, eight figures, and so on.

And every time I get it, look, it's life is better, but that baseline feeling of deep satisfaction of contentment of inner peace of the voice in your head, quieting down of comparison, you know, drifting away, diminishing towards zero. That shit ain't happening. So what, you know, I think the post achievement professional starts to shine a light and scrutinize the playbook of achievement and say, wait a minute, have I been sold a lie?

Or is this playbook really promising what it it's meant delivering what it what it said? So that that's one is you just and that's why I left Wall Street. Right. It's, um, financial compensation to me and I think to others, but I just speak for myself displays the behavior of addiction, right? Where you get your first my first bonus.

I got a 7000 signing bonus when I was 21 years old, and I'm like, there's the most money I think. Ever seen at like one point in time and it was just like the greatest feeling ever, right? It's kind of like getting New York. Yeah, it's like growing up. I grew up in New York So I didn't have that like first car experience, uh in the suburbs But I would imagine it's akin to being a 16 year old and getting a beater of a Volkswagen or your parents old car Just the greatest feeling ever then what happens is the bonuses get bigger and bigger and bigger and you're like, yeah, this is nice But now what right and you need the bonuses to get bigger just like drinking like the first time you get drunk.

It's like takes two drinks and if you drink for 28 straight years like I did, it takes 15. Drinks to get drunk and so you need more more money, more bonuses, more alcohol just to maintain that one state and the decay of that state is is so freaking rapid, right? I'd be drunk thinking about the next time I was going to be drunk.

Right? It's like I can't even enjoy being drunk in that moment. You're just like, Oh, when is the next time I get to do this thing? So I think that that is one way that you, um, that achievement wears itself in. Um, the other is some kind of brush with mortality, you know, losing a loved one prematurely, some kind of health scare.

Um, that would be, uh, another way. Um, Another would be like people tend to think of things with different milestones, like turning and we have group coaching programs where we, which we help people with career transitions, these life transitions. It's so funny because usually the age of people joining is like 39 or 49 because they're looking down the barrel of a milestone birthday and saying, like, wait a minute, I thought I was going to be off this track, um, becoming an empty nester.

So those are all of the ways that catalyze. Uh, a shift into post achievement. And then once you get into post achievement, it is this question of identity. You, you have to be, you have to have this kind of versatile identity, shape shifting identity because the identity that you held for so long, which is achievement, right?

I am an, I am a high achiever gets, um, taken away from you. So that would be one thing. Another would be a much, much larger conversation, but kind of this question of like, what's enough money. Right, because you know that that as we know from our friend Joe, that's not actually a rational, logical question, you know, if you're scared of going broke, or if you're scared of, you know, making bad financial decisions, more money.

Usually does not make those feelings go away, right? And so it's kind of finding this peacefulness with money, which, by the way, to Murray's question earlier. All of the things that I've been writing about and talking about for the past nine years are still very relevant. It's just the way you talk about them.

It's just more in my mind. It's just it's just more mature. That's like corresponding with hopefully my. Continuing maturity.

[00:21:53] Grieving and Letting Go of Identities

we kind of hinted on it earlier about these. You said that you had these seven year periods of like, of shifting. And one thing that I took away from that retreat that we went to was that a lot of people have these long periods of identity and then they immediately transition to the next one.

And there, there,

there's a loss, a

sense of loss that isn't being grieved in, in losing that identity. And they, you know, you might, yeah. In some senses, think that you're in post achievement, but really you're still haven't really fully grieved the, you know, the loss of that previous identity. And so there, there becomes this discordance in your life if you haven't grieved it.

And one of the things I've been thinking about a lot is, is how do

we, how do we create rituals for,

for moving past these identities and even projects and things like that? Like if I've been running a software for five years and I no longer do that. Like I need to have this period of sort of like, you know, saying thank you for your service to the thing or the identity and then, and then moving past that to like this new identity.

Um, do you have anything like that in your life? Like, you know, from 2023, like the difficulty there and that sense of like losing that sense of identity there. Have you. Have you done anything in that, like ritualize that in some way to, to make it easier?

I think I'm glad that you use the word grief with an identity because I think it's a, it's a very powerful feeling that I think Achiever, Achiever types, now I'm going to speak in very general terms, but Achiever types in general dismiss the value of feelings.

And over index on the power of rationality or the intellectual mind and so like why would you feel sad? about losing an identity as a software developer or as a productivity writer and so on. It's like, what's the, what's the point of that? Just move on, you know, pick up, you know, pick yourself up by your bootstraps.

Feelings are a waste of time. You've, I've heard all these phrases on Twitter, like, you know, uh, happiness is progress. That, that's one that always befuddles me. and so I think you're right. And so for for me, and it's been really impacted by 2 things. One is meeting Joe, who has really I think that if you told me that I needed to feel I mean

my wife tells me all the, she's told me since we met that I need to feel my emotions more, but I never listened. but then Joe comes along and he says, you need to feel more. I'm like, oh, a former venture capitalist who's extremely successful, tells me I need to feel more, I should listen.

you know, and also, and

Khe, can I ask too, like, do you feel like having another male example in achievement too, talking about feelings was part of that.

Like, oh, cause I know there's a lot of sort of gendered, totally women in their feelings, you know? So I'm just curious

if, if that was Yeah, absolutely. And not, it's, it's even more than gender. It's that I could see, like Joe's career path and my career path have similar, threads So it's, relatability of which, of course gender plays a big role in relatability.

But I would go even further. I think that, you know, the way he can talk about the economy, right? It makes him very relatable to me. the way that he talks about himself, uh, as, as a father of two teenage girls is that's very relatable. There's a lesson in there and business and marketing and avatar development and so on.

but yes, I think the point that you're getting at. Uh, is, if your wife tells you something for a decade, you probably are just going to learn to tune it out. And if, uh, you know, successful older white men tells you something and you'd be like, yeah, I'm going to listen. So, so absolutely. I would say the other place to where that has shown up is, uh, and I haven't done the, the, the.

Therapy yet. But I'm very, very intrigued. Interested is internal family systems therapy. So again, funny enough, it's a modality of therapy that I spent a lot of time reading about, which is not really the way you're meant to experience IFS internal family systems. For those who aren't familiar, it's a modality of therapy like CBT, cognitive behavioral theory, therapy and A.

C. T. And others. Uh, but but I've listened to a lot of people get IFS coached, uh, like mostly podcasts and, and when I was coached by Joe, I would assume that that's a flavor of IFS and say he wouldn't call it IFS, uh, and just seeing that I'm like, Oh, there is. There's something here and meeting our friend.

Yeah, there's an end meeting. Our, our other shared friend, Johnny, Miller, who is a big proponent and advocate of the feeling side of things. so to answer your original question, Ben, the, the grieving has, the ritual has been letting myself feel these things. Uh, I stopped drinking after 28 years, right around that resort, that retreat.

Yeah. And so my capacity to feel has increased tremendously. I've always been a pretty regular meditator for about a decade now, but I've deepened that practice even more. So I think the combination, the exposure to Joe and IFS, the elimination of alcohol, Uh, listening to my wife, uh, finally, and deepening a meditation practice have have all kind of contributed to that.

Um, and I just want to add the note on grief, like I'm still grieving the loss of my Wall Street identity, right? In that, you know, that was nine years ago, but It was, you know, it was a huge achievement. It's something that I'm proud of. Um, it's something that's very in, in the social, in one of the social worlds that I operate in, that I play in or live in.

Uh, it's a very, very high status, um, kind of marker. Uh, and yeah, I, I guess. I don't want to, you know, there's a part of me that that it doesn't want to fully let that go. Um, and I think that that that's okay, right? I think that maybe in the past I was too heavily anchored to it. Um, and so it was doing me a disservice.

And now maybe I have a more healthy, healthy relationship. Um, but it just goes to show that grieving an identity, letting go of an identity it's a long, it takes a long time. It's

not a one time event,

right? You don't like push a button.

Yeah. It's like the, the cycles, the waves that maybe get smaller and smaller, but there's, there's always, it feels a bit like there's always a little bit of information to, to come back to us to reflect on, like even your relationship with status.

Right. Um, and maybe even feeling some uncomfortableness around, um, Oh, I shouldn't want that status. I'm beyond that. I'm past that, but it's still there. We have to acknowledge like, what's it, uh, there to show us. Right.


[00:28:58] Investing in Relationships

One thing I'm curious if you're open to talking about because you mentioned, um, the stuff with your wife and let's go there, uh, internal family systems, therapy, that sort of thing.

You know, you shared with me last year, maybe it was the year before around a bit of a sort of interesting therapy experience you had with your partner. I'm curious if you're willing to share a little bit about that and maybe what came up for you or even the impetus for saying, I'm going to invest in my relationship in this way and we're going to work on something together.

Yeah. Um, my wife, Lisa, she's, she's awesome. Uh, she's much wiser and much more awakened than, than I am. she, it's a, it's an interesting backdrop because we have, you know, obviously what you bring from your childhood and from your, you know, early experience shapes, shapes so many things and it shapes your relationships and how you interact with one another.

And so, yeah. I think two salient, two important facts was, um, you know, I'm, I'm Asian American and she's Caucasian. And so I grew up with a very kind of immigrant view of, of the world, kind of first generation in America, immigrant view of the world. Which is which when it comes to love and marriage, there is a sort of pragmatism to it.

It's not like arranged. My parents weren't in an arranged marriage, and they're not in a loveless marriage, but I will say that there's a there's definitely a pragmatism to it, and you could take that a step further where it's like. At least in, in culturally for, for, for me and my kind of peer group, it's like you'd rather be in a marriage that's like unsatisfying than to get divorced, right?

That's where the pragmatism takes over, over the passion or the romance or the idealism. I think she grew up in a very different, uh, household where there's a lot more, even though socioeconomically we probably ended up at the same place, but there was a lot more about like, live your full, your best life, your full potential, like possibility and so on, where, you know, probably, I don't know if abundance versus scarcity is the right, you know, duality for what I'm about to say, but I think there is this much more is like if you're not happy in your marriages get divorced and I think in Asian cultures that just divorces just so much.

Less likely. so we enter marriage with this thing where it's like, Hey, if it's not going exactly as planned, one person's like, whatever, that's just, that's the feature. And the other person's like, that's the bug, right? And so you could immediately see how that can lead to tensions because when you're married outside of the honeymoon period, you could have the two dopest people in the world.

You're still going to have issues and challenges because you're humans. Um, so I think that that was The one and then I had mentioned like I'm not a feeler and she's a deep, deep feeler. And so we're kind of like our love languages are very different. So my love language is one of action and of agency.

It's like, Oh, you're sad. Like, let me go take the kids so you can go get a massage. Right. Or let me clean the kitchen. Right. And she's like, no, I just want you to. Sit and be there for me. I'm like, what is it? I don't even know what that means. Like, can I clean the kitchen while I'm here for you? Um, so, you know, that's, that's kind of, you could see how that would lead to tension, some sort of tension.

[00:32:19] Therapy Experience

So Lisa has been very proactive in getting us, uh, marriage therapists and counselors and so on. And so the, the experience that you're referring to, uh, was, a weekend retreat with a couples, Well, just us and a couple who are the therapists and it was, you know, more traditional kind of, um, marriage counseling therapy and then, but then after the first day, they're like, Hey, you guys have done this before.

You seem to be pretty self aware and so on. Um, sometimes our clients want to you. Go a step further and, um, go on a psychedelic journey together. And we had always been, we're like super open, like down for that stuff. Me more on the party side than on the therapy side.

But, um, we, we were always down for, we just never knew. We have two young kids. You're like, our parents don't live near us. Like when would we ever have the time and the opportunity to, you know, just like burn, you know, 10 hours trippin'. Um, but. The moment was there. It found us when, when, when we needed to be found.

And yeah, it was just a really, really, really, I mean, this was 18 months ago, I think, or, or, yeah, probably, probably, or a year ago. Um, but I mean, I remember the entire experience like with, with vivid, vivid, vivid details to this day. And, um, so yeah, it's a Thursday morning or Friday morning. We've done a bunch of, Talk more traditional talk therapy 11 a.

m. They put us in this. They, they do a little ceremony. They were in an Airbnb. They give us two sleeping eye masks and what, what I guess is called a heroic dose of, um, MDMA and, uh, psilocybin. So the active, uh, ingredient in, in mushrooms. Yeah. So I think that for, for newbies, the, the MDMA kind of, Like primes you to be more happy and positive, right?

I think it kind of roughs, it sends some of the rougher edges off of the experience and then the psilocybin can drop you and how, you know, however, however you see fit. But, um, but yeah, it was so we're just laying there and they encourage you not to actually talk to one another. for a while just to process your kind of your own thoughts.

So, so it's like it's almost like the most intense vision version of the apple of oculus you've ever experienced. And you're laying in this bed, your spouse's next to you, like sweating profusely, you might throw up, uh, but just. Yeah, tons. And I mean, you, you guide me, I could tell you, you got me on where to go, but, um, a lot of, of, of really, really, really powerful.

Actually, I'll give you one. One of the powerful ones was I remember at one point, um, uh, Shaking in a good way. It was very positive for me for both of us. Um, there wasn't like a bad trip element of it, but I'm shaking and I remember just being really, really sweaty. Uh, and I'm shaking and I'm shaking and shaking and what felt like probably it probably was like 10 minutes.

But it felt like two hours and I just keep mouthing. I'm not saying it out loud, but but I keep mouthing. I just want to be a good boy. I just want to be a good boy. I just want to be a good boy. And then that's what I'm just and that like that basically distills. My psyche into, I just want to be a good boy into six words.

Um, and then this voice, which is maybe, you know, the, the conscious, I'm always like wary when, like, I could see this so clearly and people listening are like, what the fuck is this guy talking about? But whatever. Um, and this voice comes in over the top conscious, this, the, the self, I don't even know how you refer to this other voice, but not me while also being me.

And it's like, Khe, what if you don't have to be good? You just are good. And it's just like this little like re shifting and like, it's like every so much of my life, so much of so many, so many of my decisions, so much of my actions, so many of my thoughts are all in service of wanting to. It's like an idea.

I think the fact that it was a good boy and not just like I want to be a good person. It just made it so clear to me. I have chills just thinking about it that that in, you know, in this, you know, 44 year old You know, aspiring surfer body that there is, you know, this little kid that just wants people to think he's good.

Um, and that he's a good person, that he's a good boy. And it was one again, I think for, for people who haven't had an experience like this, there's just a lot of moments that you just can't unsee. Right. And I maybe I'll forget the details. They'll start to wax and wane as time goes by from that experience, but I, I will never forget that, that insight, so to speak.

And so we had a bunch of them on our own in that regards. She at least had a bunch on her on hers. And then we had some way, you know, some of them met in the middle and they, they, they proved to be more joint insights.

[00:37:39] Integration and Reflection

So in the beginning you said you were sort of meant to not, uh, share and then over time I'm guessing you begin to share more, you're talking more.

Is there some kind of integration session or time with the therapist afterward or like what did that sort of integration look like?

Yeah, there is an integration kind of that evening, but you're still pretty out of it. Uh, and they're, they're more just kind of focused, like you haven't eaten for, you know, 10 hours or so.

I was, uh, the club kid in me was just like sucking on lollipops. So I'm like, Hi, this is a familiar feeling where anyone have a glow stick. Um, but, um, then there was, uh, I think I like a two hour, a couple of hour integration the next morning. Um, where we just kind of shared, I think everything's still so raw the next morning, um, in person.

And then we went home and there were individual, maybe like. Two or three in in zoom integration sessions over over that that period, and I think for us it was I mean, we did come home and my in laws were at the house watching our kids were like, Oh, man, this is intense. Um, but, uh, we were we were able. I don't know if it was the result of the program or the way they set it up or just the, an act of, you know, the circumstances of, of the powers that be, but we were able to really, um, talk about it, um, pretty, pretty, pretty, pretty regularly.

We still reference it, uh, that experience today. So somewhat regularly.

Amazing. And I'm curious, I'm sure that sort of thing permeates not just your relationship at home, but even kind of how you're showing up at work. Right? So, um, I guess what are some of those ways of being that you're taking forward? Is it that there's less striving because you're like, I already am a good boy.

I'm a good person. I don't need to strive so hard for that acceptance. Like what's, I guess, still present for you in that experience.

Yeah. I think

you talked about the money. Yeah. Money at one point two and the enoughness of it and it's it's all kind of the enoughness of you kind of thing Yeah,

yeah So I think that the one one way that it has definitely come out is that I take criticism like very personally so even if it's I don't really post things that are that controversial on Twitter, but someone would be like, I might post something about money or some things, something about millionaires and there and someone might be like, what about all the people that can't eat, you know?

Um, and I'll like actually take it pretty personally, like Because again, I'll be like, you're attacking me as someone who doesn't care about, you know, people living in poverty, right? Or you're calling me an entitled rich fuck. Like, um, and that really hurts. And so I, I really like personal, like, you know, The common thing about feedback, which is, um, you know, you could get like 10 pieces of feedback, eight will be amazing.

And one will be average and one will be bad. And the only thing that you'll think about is the one bad one. And so I think that now I can see that a lot more clearly, um, when it's, as it's happening and I can just. I can kind of stop the chain of events where it's like, Oh, person, you know, uh, uh, Twitter anonymous account, you know, replies to one of your tweets with something calling you out and just be like, no, you're, you're, it's okay.

Okay. We, you know, we, we know where the path, we know where the road leads to and, and, and, and you're, you know, we're good. We're good. Or we, we know, we know where the path leads to. So, you know, I, Tara Brock has this. Thing of like the two wings of I forget exact two wings, where one is self awareness. So you you see what's happening in real time.

And then the other is self compassion is to not like beat yourself up for not behaving the way that you want to be behaving in that instance. So that really Is is powerful, and I'll share a funny story about that after I answer. The next thing is, you know, during the retreat, I was actually very anytime I do some I've done a few intensive coaching things that are about like my relationship to work, and I always go into them thinking that I'm going to have this epiphany that I don't want to do work anymore.

I don't want to work on this thing, and it's just I'll, like, blow it up. And, um, And so in this one, I wondered, I'm like, What's this gonna say about This was in the midst of a lot of the turmoil of the company. I was like, I wonder what it's going to say about this all. And, um, it's funny because all of these, I mean, the, I just want to be a good boy.

There was probably like six moments like that throughout the seven, eight hour period. And then every time, like my, like. My brain would be like, well, what is it saying about work? Like, what is it saying about rad reads? And, and the minute I would say, like, so it was, I was hallucinating, like, in my head these, like, it was just, like, imagine the most insane colors and just, like, visuals and so on.

And every time the thought about what should I do about work or rad reads, it would just turn into a black and white, uh, newspaper from, like, 1920. And it was just like, it would just, it would suck all the color and the vividness out of the visual. And I'd be like, this sucks. Like go back to the, and basically it was like, myself was like, don't, it's so trivial.

Like. This is this is the terrain to play in the little widgets about work and all that, like, it's just it's completely that's what I took away from it is that it's, um, it's completely insignificant.

[00:43:28] Practicing Rejection

I want to come back to Ben's question about enoughness, but it's just a funny story about rejection. I just read Noah Kagan's book.

million dollar weekend, a book on entrepreneurship, and he has one exercise in it. This goes back to the good boy, and it's blown my mind. So the exercise basically to practice rejection because one of the superpowers of being an entrepreneur is actually not being afraid to ask. And sell them similar, uh, there's similar veins.

And so he has this exercise where you go to a barista or any store and right as they're ringing you up. So it's like, Oh, that'll be, you know, 7. Uh, you just look at them dead faced and you say, can I have a 10 percent discount? Uh, and then you're not allowed to hedge and say, Oh, I read it in this book or this, and then you just they'll probably have some reaction and then, uh, and you just have to just sit with that reaction and then and then pay your bill and move on.

And so. I got, I talked to no one on my podcast and he, and I was like, I want to do it, but I'm kind of scared. This feels so awkward. All these stories. And, and, and right on the podcast, he's like, remind me to check in with Kay. Siri reminded me to check in with Khe in a week to see if he did the challenge.

I'm like, fuck, I guess I'm doing it. Um, And so I did it and at the local grocery store and it was at my heart, like my palms were sweating when I decided I was going to do it. I go up there is a guy that I'm going to see again, uh, and I'm just like, I got to do it. I got to do it. Uh, and I, and I say it and the guy just kind of like, no, and I just looked at him and then it's like, okay.

And then just paid my thing and then I walked out and just the the the wave of emotions that like leading up to it while it's happening and then after it was just it was so instructive and it does go back to that. Good boy. Because I knew I was equipped. I'm like, if he laughs at me, which I I. Thought he would.

It's not gonna challenge like who I am, you know, ethically my integrity, but it will feel like it. It's gonna feel like it like you're a shithead if you for asking. Um, and so I did it and it and and then I was like, Oh my God, that like what an intense range of emotions. And I basically gave myself the challenge.

I'm going to do it 10 more times, nine more times. And, uh, and it's all right. The second time was infinitely easier and then it already trickled into my business because now when I, I'm just more aggressive at selling, which me being more aggressive at selling is basically like, uh, moving my level of passivity towards neutral.

Which is the way a normal person would sell, not like scummy car salesperson. Um, and so, and again, and this also ties with what Joe Hudson and Johnny Miller and others talk about is just like watching that range. It's like. Hardcore physical sensations as the whole process is happening that like there's no rational like it's the the physical sensations trump the rational thoughts that you're

having all body, right?

It's all yeah.

And then it's gone. One of the, uh, the

first weeks of the decision course was around figuring out what you're, what you're afraid of, basically, and then what, what you're avoiding when you, when you resist having that emotion. And one of mine was definitely, was rejection. And. I'm in this position right now where I want to free up more of my time so that Marie and I can work on something that, you know, is really meaningful to us.

And so that meant actually like I had this pipeline of, of consulting leads that it was probably about four or five people that I'm like, yeah, I've said yes to these people that I'm going to help them with their businesses. And so my, my exercise for the week was I have to write four emails that say, Hey, I know I said I was going to work with you, but, uh, I'm gonna have to step away because I'm just I'm not feeling like I would do a great job Right now and I and I have this thing that I really want to focus on and it's not gonna I'm not gonna be able to put as much time as I want into it and like I've, I'd put those emails in draft and like sat with them for a week and they were just taunting me to send them like it was so difficult having to feel, Oh, this person's going to be upset.

I told them I would do this and da da da da. Every single email I got back was like, Thank you for your honesty. Uh, the call that the call that we had just to talk about my project was so helpful I was able to move forwards in XYZ pattern and and it was great One person was like really appreciate you telling me that you're not you don't have the capacity and that you don't you know You're not gonna show up fully for this so every single person was just showed appreciation for me telling them no and you know that like I just and it made me feel really good like oh my wow I got what I wanted and like nobody's upset with me.

Nobody rejected me Nobody thought I was flaky or anything of the sort and so I could see how doing that in those little micro Transactions would be really really helpful to practice

that Yeah. Well, kudos to you for doing that. Cause that, that is, I, I've been, you know, anyone who's listening, who fears rejection and who is, has people pleasing tendencies can relate to that.

So, um, yeah. And I think it also starts to show, I think like we have these stories in our head. Cause you're, you thought that people would be like, you're, you're a brute, you're a jerk, you're, you're so flaky and this. And I think we're so wired to the downside. Of like, what can go wrong? We never ask what can go right.

Right. And I don't think, and I think, look, things will go wrong. I think ultimately, and there's a much longer conversation is like, they're all just stories. Um, but, but let's put that, let's put that for, you know, episode, you know, version, version take two of this podcast. Um, you know, I do think, uh, you know, when I work with, um, a lot of the coaching clients I work at, like, they're so focused on about like, what can go wrong.

That they forget to ask what can go right. And so when you're only focusing

on that, I think even some of the positive emotions like sometimes I think we actually do things to avoid Positive emotions because like joy is actually threatening in a way. You're like, Oh, well, like, uh, the shoe's gonna drop.

Like, can't be too good. Like, things are too good. It's probably good. So I think sometimes we even do that. We don't even realize the ways we're avoiding the good stuff.

Oh, I'm sure. Yes, I'm sure. Yeah. Thanks for pointing that out. I definitely do that. It's like this can't be this can't last.

Yeah, I think we're all kind of guilt.

Classic over overthinkers overachievers, right? We get we get caught in that for sure.


[00:50:24] One Punch Man and Stakes

have a, I have a random question for you, Khe. Like I've been thinking about this cause as I've been watching the second season of this anime called one punch man. And, uh, I don't know if you've ever seen it before, but the main character, the main character is basically this dude who trained

for three, four years and becomes.

And basically invulnerable and like his whole, his whole deal is that he can beat anybody by just with one punch. Um, and so I've been like thinking of him as like the patron saint of like the post achievement professionals because he's so frustrated by just having no meaning in his life because nothing is challenging him anymore.

And so, but everybody around him, all the other heroes are like super envious of his, of his success. Uh. But like he's, he doesn't actually feel successful himself because all of these, you know, because he doesn't have the challenge or the enjoyment in his life. So his whole life is like just these very basic problems like when, uh, when is the grocery, when, when are the coupons going, you know, at the market or whatever.

And so he's like really obsessive, you know, obsessively seeking meaning outside of what everybody else thinks is the, uh, is the thing. Um, so I'm wondering if you have any other, other like, kind of like. Indicate like like the heroic journey or like references in in literature or something that like, you know You have these kind of like heroes who like they they've lost a kind of sense of purpose because they've achieved so much

I'd have to think of the heroes Um, but, but as you were saying, something else came up that, that was very salient was, you know, there is someone asked me, you know, I made this video about like, what, you know, what is the day in the life of Khe?

It's like, it's so chill. It's like you wake up, you meditate, you serve, you write a bed, you like make lunch for your girls. You know, it's like so chill. And, and someone asked the question, do you wish there was more struggle in your life? It was actually an interesting, yeah. Because, you know, I do, I don't have struggles in the sense of like an asshole boss or financial struggles or things like that.

I have creative struggles, but I was so I've been, I was thinking about that. I didn't know how to. I answer that whether that was a good or bad, do I miss it or not? And then I had a friend, um, and he started a Bitcoin hedge fund and he raised money and like, he got hacked by some like sovereign, like terrorist sponsored group and had to go to these like really marquee investors, like explaining that he got hacked.

And then once he recovered from the hack. He got, um, he had money with, uh, FTX. And so there was a giant hole and like there were more losses and basically it wasn't a failure, but it just, it didn't do well. And again, it had this like, who's, who's of investors. So he had to constantly go and explain himself and explain himself.

And he said, you know, he was like, Hey, for, for two, for two years. It felt like my rep, my entire reputation was like on the edge of a cliff where, you know, these people who had trusted me and all that, um, could, you know, instantly like destroy me, so to speak, all right, reputationally. And, and he said something like.

It was hell, but it also made me so much stronger and like so resilient to Any other future challenge and it kind of got me wondering it's like wow. I don't have In my daily life, like there's very little stakes, there's very little at stake, so to speak, like, and I think I tend to think that mostly that's a good thing because I don't want to be staring down precipices of things, but I do wonder.

It's like I do want to have stakes in something right? And even, you know, I've written a blog post every week for 250 weeks, there's no stakes there. Like at this point, if it sucks, like no one, like no one even reads them. So like, if it sucks, um, like it doesn't matter. Right. Same thing with like launching a podcast, it fails.

It doesn't like, there's no stakes there. So I have wondered, like, do I miss having stakes? In my life? That sounds like, like meat steaks. I think

that's really interesting, K, because what has low stakes for you feels like it might actually feel really high stakes for someone else. Like, the idea of the, of launching a podcast, like, you know, right before we hopped on, we're like, Oh, whatever.

This is a creative project. Let's see where it goes. But for other people, they're overthinking the logo. They're overthinking the metrics. They're already like 10 steps ahead and the stakes feel so high. So I partly wonder if it's like, You've had some stakes, you've had those seven year reinventions, reinventions, tossing everything to the side, you know, collapsing identities, maybe in a way you've just changed your relationship with


Yeah, I've become a vegan. Um,

I think it's, yeah, I thank you for saying I, because it doesn't, I, I'm deeply invested. So if I'm deeply invested in things, it means that I care. Which means that there must be stakes. It's just that the what's it's I think an interesting thing is like I'm not. As like you said, like people want to start this and that I'm not as scared of what goes wrong as a result of those stakes.

So I still have stakes. I'm just the downside is not scary to me, and it's definitely not debilitating.

Yeah. And, and the person asking, like, do you wish you had more struggle? It's not like there aren't struggles. Like for example, um, you know, your wife's father passing away, parents getting older. Like there are struggles that we all have that we sort of have to face no matter what.

So it's, it's not like your life is completely struggle free, but it just feels like you have a healthy relationship with like, yeah, that's the next challenge in front of me. And I'm going to face that regardless of whatever uncomfortable feelings are coming up as a result of that.

That's a good spin. I like it.

And I don't even think it's spin, like, I think it's just like, you have a healthy relationship with

it now. I agree. Maybe that's like the thing of joy. It's like, actually, like you said something nice to me and I have trouble, uh, like actually hearing it. Right. I almost have to deflect it with a joke or something.

Yeah. Well, so thank you. It does it. Thank you. Uh, it does. It is nice to be seen that way. And, uh, I appreciate you saying that.

It's like the post struggle professional. Welcome to post achievement. Yeah. Embracing, embracing whatever challenges come your way. Yeah. Amazing. I think that's a great note to wrap up on.

I mean, Khe, I have no doubt we'll be having part two, part three conversations with you because there's lots of just like fun overlap in our work and our adventures and whatnot. So I just really appreciate you as a human in our network and on the internet.

Yes. Well, thank you all. Thank you for, for, for those, everyone who listened and yeah, I'm, I'm, I, maybe this will be my plug for, for the internet and Twitter.

I mean, you two met on Twitter. And so for all the people that, that hate on Twitter, it's like, We have a friendship, a business mastermind, and a marriage, uh, that all are the result of Twitter. So Twitter, Twitter, I'm grateful for, for you both. I'm grateful that we hang out in these social, in these digital ecosystems where This is, not only is it normal, not only is it possible, it's normal.

And, um, and then we got to add the cherry on top, which is, uh, meeting once, uh, you know, at a minimum once a year in person now. So,

yeah. Yeah. Amazing. Thank you so much. Okay. Where's the, where's the best place for people to engage with your work, um, other than Twitter, I

guess. Yes. So thanks. Thanks for that.

Uh, radreads. co and sign up for our email list cause that's where you'll get, uh, get it. Okay. Thanks. Keep up to date with everything. See all the essays, um, podcasts, the examine life podcast, wherever you get your podcasts, um, most active on Twitter. And then if you just Google K H E H Y, you'll see LinkedIn, um, YouTube, we're actually doing a decent amount on, um, uh, LinkedIn, Twitter and Instagram.

Sad presences on Instagram and TikTok.

Can't be everywhere all at once, right?


Amazing. Thanks so much, Kay, for joining us today.

We appreciate it. Thank you.

Creators and Guests

Benjamin Borowski
Benjamin Borowski
Notion warlock at NotionMastery.com, Systems at WeAreOkiDoki.com, volunteer firefighter, hacker, DJ
Marie Poulin
Marie Poulin
Taming work/life chaos with Notion • Leading NotionMastery.com • Online Courses • ADHD • Permaculture
Examining Post-Achievement with Khe Hy
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