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Chris Hutchins
There is probably something in your life right now that you're optimizing, and there is a decent chance that the optimization might be quietly destroying the thing you actually care about. Today I'm talking with Sahil Bloom, writer, investor, and someone who actually caught himself doing this and did something about it. He shares a concept called the Doorman Fallacy and why it explains so much of what we get wrong about our routines, careers, and even how we spend time with the people we love. We'll get into why he moved his entire family to a new city after just one conversation with his wife, how a lockbox fixed what willpower never could, and the six word question he uses when anxiety kicks in. We'll also talk about why he thinks now is the best time in history to be a curious person, and why he put a bunch of his own money into a skincare company he named after his son. I'm Chris Hutchins. If you enjoyed this episode, leave a comment or share it with a friend. And if you want to keep upgrading your money points in life, click follow or subscribe.
Host / Interviewer
All right, Sahil, I know most of us realize at some point that we're only going to see our parents, you know, a dozen or so times, and we kind of feel guilty and we don't really do anything. And for the second time in your adult life, you made a massive move. Talk to me about how you made that move and how quickly and how easy it was.
Sahil Bloom
My wife and I were living in the New York suburbs for the last four years. This past summer, we drove up to Boston, which is where all of our family lives, where we both grew up. My parents, her parents, my sister, our cousins, like, everyone's up there. And we drove up for her grandmother's funeral. Her grandmother had lived to 95 years old. We went to the funeral, everyone was there. And we got back in the car and we were setting into this four hour drive back home and we both just had this moment as we were driving through this small Massachusetts town. We just like looked at each other and at the exact same time had this sensation and this conversation of what? Why don't we live in Boston? This makes no sense. Why are we driving back down there? We had originally moved to New York both for her job and with the thinking that I was going to have to be in New York much more often. And the way that life works, which we don't often acknowledge, is that there's so much gravity and sort of momentum to decisions that you make. You make a decision and that's Fine. But what happens is then you sort of build up a whole lot of institutional weight and baggage around that. Over a period of years, you accumulate stuff and things and, you know, maybe friends and networks and whatever it is. And all of a sudden this decision that maybe no longer makes sense on the surface just feels very difficult to unravel. And so we had made the decision to live in New York, and the decision, objectively, from the outside looking in, no longer made sense. My wife isn't working. She's home with our son full time. I don't have to be anywhere. I can do my work from wherever I want as long as I'm near a major airport because I travel for speaking things. And yet we still had this entire life built out for hours from all of the people that we care about most. And so we very quickly, the second time, decided to rip the band aid. And within about two months of having that conversation and being in the car and having that moment, we had sold our house in New York and got into finishing building a house up in the Boston area and made the move.
Host / Interviewer
And I think that a lot of people feel like it's just such a high friction thing to move once it's done. Does it actually feel like it was easier than you thought, or was it still hard, but just worthwhile?
Sahil Bloom
I'm a huge believer in doing these big things as fast as possible. So the way that we pursued it was literally like, okay, it would be miserable if we tried to do this over the course of like, three months. And it won't be nearly as miserable if we just tell ourselves, okay, we're going to have a brutal single month. Like, October is going to suck, but October 31st is going to come around and we're going to have closed on both houses and we're going to be moved. And so you can endure a few weeks of it being miserable. And that understanding of where the end point was and how short it was going to be actually allowed us to get through it. It's sort of like, you know, if you're going to go run a race or something, like, knowing that you just have a few laps to do of the race makes it more tolerable for whatever pain you're going to endure. And so it actually created this time constraint on it that forced us to act really quickly. The big one was packing up, getting our house photographed and listed for the sale of our house in New York. And because we literally had like two or three days to do that to get it on the market for the fall market, we cranked through cleaning up the house and getting that done. Like, my wife was unbelievable. But literally, like, we got home on a Sunday night, Wednesday, the house got photographed from, like, living in a house for four years, having all sorts of stuff. It got photographed Wednesday, listed Thursday, Friday, we had already started receiving offers. And I think just forcing that time constraint, doing things quickly, whether it's moving or anything big, can really be a powerful hack for cutting through this.
Host / Interviewer
I think another thing I took away from reading the post you wrote about your move was there's a lot of ROI in these little things. And on paper, going to visit your parents and your family in Boston a few times a year kind of solved what you wanted, but in reality, it didn't.
Sahil Bloom
You know, I wrote this post that we had made that move in May of 2021 to live on the East Coast. We were going to be much closer. And I was seeing my parents probably multiple times a month at that point. Certainly once a month. We were driving and we were doing these drives. But what I realized in all of that was that all of it was surrounding these big moments. We would plan a weekend, get together, or we'd go out for a birthday or for a holiday or whatever it was. It was always some big planned, staged thing. And we had a few moments this summer where we were all just together in some tiny little thing. Like, my parents came down and we were just sitting and having dinner, drinking wine, and my son was running around. And I realized that life is really lived in the little things, in those tiny moments of nothing really happening. That is really where this texture of life gets created. And so what I realized was we had made this decision that really optimized around the big things, but we had lost the little things. We had lost sight of the importance of those little moments. And so this move, a big part of that was, okay, we're closer, it's better, but let's now build our life around these little things that we know are so meaningful. The Tuesday night date that I get to go on with my mom now, just the two of us, versus having this whole big family get together on the weekend. The texture of that, the relationship, the meaning, the depth that comes from that, getting to see my sister more often, spend time with her, get breakfast with her. Those things you can never replace.
Host / Interviewer
You wrote another post about the doorman fallacy. And it feels like the family application of there's this big thing that seems to be what you think about what you optimize for and buried, you know, within it are all these things that you might not actually be thinking about. Do you see that as an application to your family from that kind of concept?
Sahil Bloom
Yeah. Rory Sutherland, British advertising executive, very well known, had this idea where he basically creates this scenario. Imagine you are the owner of a five star hotel in New York City, and you hire a consultant to come in and advise you and give you advice on how to be more efficient, how to run your hotel more efficiently. So the consultant comes in with his pen and paper and he's looking around and he sees this doorman standing there and he's like, okay, well, he makes a note down, he delivers you this report, and the report says, hey, that doorman is costing you $40,000 a year. You could replace the doorman with an automatic door. And now you've saved $40,000 a year. Look how good I am at my job. And so you as the hotel operator, say, okay, great, you fire the doorman, you put in an automatic door. Fast forward two years and the hotel is in disarray. Because what you realize is that the doorman was actually doing a whole lot more than just opening the door. He was providing security to the front of the hotel, he was providing prestige to the hotel. He was welcoming guests, making them feel really at home, and great personalized customer service, doing all sorts of things that you didn't capture when you defined his entire role and worth around this surface level thing of opening the door. That idea of the doorman fallacy, this idea of characterizing an entire job or an entire action on the basis of the surface value that it creates is very dangerous because it misses the true value that exists often under the surface. I think that there is an obvious application of that to how we think about jobs and careers and teams that we lead in our professional lives. Like, you know, before you get rid of someone thinking you can optimize with AI or new efficiencies, make sure you understand the real thing that they're providing, not just the surface level version. Because often you rip out that headcount and then realize that they were actually doing a lot more than what you thought on the surface. But the life application of that, I think, is even more interesting, which relates to exactly what you were saying in this story that we were telling, which is just to say that there are a lot of things right now in the world that we live in where you are being told and pressured every single day to optimize these areas of your life, right? Like you log on to Twitter or Instagram or wherever you Go. And you're being bombarded by protocols and routines and things that can optimize your life, new AI tools, whatever it might be. Optimize all of your life in all of these areas. As you start to make more money, everyone tells you you need to start optimizing all of these things. But in our pursuit of optimizing these areas of your life, what you can find is that you are optimizing the life out of your life. The example that I think about often is like, everyone wants you to hire a private chef to cook your family's meals. So let's imagine that you currently spend an hour cooking dinner for your family every single night. And you're like, well, now I have the money so I can hire someone or a meal prep company to make those meals for us. Now I get the hour back, but we still get the calories from the food. And so you do that. And after about a month, you realize that both of your kids are taking their pre prepared meals and going and sitting in front of the TV or their computers, and you and your wife are going and sitting in front of your computers and sending emails. And you've now optimized something, but lost a lot of the texture and meaning that it was really about. It wasn't about the calories you were creating through the action of cooking. It was about the fact that the act of cooking brought your whole family together around the table to go and do this thing. And so I just really think about this a lot. Ever since I read this idea, it's been popping up all around me to just say it is critical with everything you look at in your own life to understand the surface level value. Yes, but also the real value that exists underneath this thing.
Host / Interviewer
So as you were saying that I was thinking back to your family, you now chose to not optimize for just the big thing of we can see them regularly, but we're going to be near them. And I'm actually curious if you've seen that work. Do you still need to schedule that thing with your mom or your sister to make sure it happens even though you're close, or does it just kind of work because you've put them together? How much can we let go of trying to orchestrate our ideal kind of circumstances versus just letting it happen?
Sahil Bloom
I still think that things need to be structured in order to create a real behavior change around them. And so your default, if you've been living far apart for a while and then you come and now you're living closer, is not Going to change from what your default behavior was before by its own. Just by virtue of the fact that you are now closer, you're still gonna default to the same behaviors that you were doing before. And so structuring in some context can really help. You're like, okay, well, one of my things is I wanna get a dinner with my dad once a month now that we live closer and now that we can do this. So let me put this on the calendar. And honestly, I need to be better about doing that for those kind of things. Like, a dinner with my parents, just the three of us would be a really nice thing. Even now saying it to you, I'm like, oh, we should just put that on the calendar for once a month that we do this and get this dinner. Because I know otherwise life happens, right? Like, it's very easy to say that you're busy or things are happening. You're not able to do it. So structuring that I do think will be really helpful. What I will say is that it at a minimum has 10 xed the random organic interactions that happen. In particular with my wife's mother, who basically is able to come over every single day and spend time with our son, help my wife get more breaks during the course of the day. That has been worth it even just on the surface, just for that. Because that natural, random interaction has meaningfully, meaningfully expanded the surface area of those. The ability to just go to random things. Cousin plays lacrosse at Bryant University and they have a game on the weekend and it's like a 30 minute drive from here. So we can just pop over to the game for 30 minutes without it needing to be this huge production that we go to one game a year. And while you're there, you see your aunt and uncle and you see your cousins and you know, your son gets to see his cousin playing in the game. Like, it's just these random things that get created through expanding your surface area of the potential that exists around them.
Chris Hutchins
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Host / Interviewer
about the kind of random things that being in close proximity to New York you might miss out on? And was that part of the calculus? Because I know one of the more defining things in the few months for me was that someone put on this like open claw event and I would never have flown to like a meetup at night, right? But like it just happened in the Bay Area and I'm here. So I drove up and I felt like I got exposed to this thing super early on. And there's a value to being close and proximity to things both professionally and personally and sometimes they might be in conflict. And I'm guessing not that Boston's not a big city, but New York City probably had a lot more things that you don't do because they're a little bit further away.
Sahil Bloom
That is the trade off of this. Like if there was a single trade off of a negative that I was giving up by making this move, it was that, right, like the surface area for interesting things happening that you are maybe going to get pulled into is much higher living in close proximity to New York or San Francisco than it is Boston. And that's not a knock on Boston. It's still young and a great city. But it doesn't happen at the same level that a New Yorker, a San Francisco does. And so you don't get invited to those things. You're not there maybe for that given moment. What I will say is for me, as I was considering that, which it was a key consideration as we were making this decision, was actually looking at my calendar from the prior year at the number of times that I really went to those things that I got invited to. And the answer was I said no almost every single time. And that's because I just am not in a stage of my life where I really want to be going out to these things. And I know that I give up something by doing that. I would say that I am lucky in the context that I can generally just seek out and have a direct one on one coffee or dinner with any of those people that I might have otherwise met at one of these events. And so now my path and what I do is that I do exactly that. Like if I do get invited to something that was in New York or if there was something interesting going on, I just seek that person out and I go to New York twice a month or once a month right now at a minimum. And I just get together with those people one on one and get to kind of do and engage in those interactions. Last thing I'll say here is that I don't like group events. I actually hate group events. I don't do group dinners as an example. And when I say I don't do like when people invite me to a group dinner with very few exceptions, I just say, hey, I don't really do group dinners. The main reason is because like I kind of have like a little bit of social anxiety in those group dinners. I don't really like like that who long table and you get, you sit down and you're stuck next to one person and if you're not having a good conversation, it's like the worst dinner of your life. And you go around the table and introduce yourselves. Like I just don't have fun at that. My maximum Is like four people to have like a cool, engaged group conversation where you're really meaningfully connecting with people. And so when I looked at my calendar, when I really thought about that trade off, the trade off was more in my mind than it was in reality. And that gave me more comfort with making that change.
Host / Interviewer
Was there anything you did other than just think through it to kind of process that? Because I think there's something to be said for, like, when you travel for work, when you're in New York now, you're not racing home to get back for bedtime, right? Like, because you're on a work trip and so you kind of like go all out. You're like, let's schedule like four coffees in a row. Let's go hang out with someone at night. Let's do something late. And then when you go home, you're not doing it. I somewhat really value that. I'm just curious if, as you went through this decision making process, if there was like a good method for kind of more deeply thinking through decisions and viewing them from other perspectives.
Sahil Bloom
You are hitting on one of the most fascinating things of this entire change. And it was one that I hypothesized. So as we were going through this, I basically wrote out, like, what are my fears about this? I kind of like took a blank sheet of paper and I wrote out, like, okay, what are my fears? Like, the concerns that I have about making this move mainly for my professional life because I knew personally it was gonna be a big win. So what are my fears? And then, like, let me deconstruct those. Like, each on the other side of the piece of paper. Like, deconstruct it. Okay, okay. What does that really look like? Why am I afraid of that? What's the worst that could happen here? And what if it's actually the opposite? What if it is actually much better than I think? Why might that come about? One of those biggest fears was like, oh, my God, I have a handful of like, close friends and professional relationships and people who are huge, incredible sparring partners and big thinkers in my life that live in New York that I'm not going to see. That was probably my number one fear, frankly. And my other side of the paper as I broke it down and tried to deconstruct it, which is really my process for managing and navigating fears, was I'm going to see those people more because I'm no longer going to be rushing in and out of the city trying to get back for bath time, or trying to get Back for dinner with my wife or see my family. I'm going to be really in it when I go to New York. And it might be that it's only once a month, but I'm really gonna be in it. That has played out to a T. I go to New York once or twice a month, and when I go, we all have dinner, we spend multiple hours doing like jam sessions at someone's office or someone's apartment. I am closer to those friends that I previously lived 30 minutes from, now that I live four hours away. Because when I go, I'm really immersed and present. I'm not pulled in multiple different directions, cognitively or emotionally. That has been the most surprising and also sort of expected thing about this change that really did come from just deconstructing it in that way.
Host / Interviewer
And it sounds like the deconstruction process for you is as simple as writing down a pro con list.
Sahil Bloom
Kind of, you know, it's like to
Host / Interviewer
take go back to something so straightforward.
Sahil Bloom
Well, I think that the cooler version of it is, you know, I do it pretty analog. I'm big on handwriting things because that's how I think and process. But I did again, I tried to do it then using an AI tool where basically I said, here's my list of fears. This is like the thing. And I took a picture of it and I was like, what I want you to do is play the devil's advocate on all of these fears. What is sort of the opposing view to all of these fears? If you were to tell me the optimistic case on all of these, like, how would you sketch that out? What might it look like? And it gave a really cool set of perspectives and different ideas on the other side of what those fears looked like. And it did spark an idea for me in general for the future of saying, like, okay, whenever I'm navigating something where I feel like my fear is holding me back, let me force it by having this AI tool play back to me the devil's advocate view on this fear and see if it just unlocks me to just think a little bit more comprehensively or at least in a more 360 degree view on what this could look like.
Host / Interviewer
Yeah, I think the fact that, that you can have access to something that can do that on a moment's notice. And I've talked previously about how you can even layer in kind of personality data into your prompts or into something so that it's not only giving you a devil's advocate approach, but doing it specifically for the Way you process information, the way you think and feel can be really valuable. On the topic of AI, I know you wrote a post recently about negativity bias around it. How much has it impacted your personal and work life and what kind of made you feel the need to write about it?
Sahil Bloom
For several years have felt that social media in general and the media more broadly creates this very negative, skewed view of reality. So there's this meme that I came across several years ago that I absolutely love of a guy in a rain jacket with an umbrella over his head, looking really sour, staring at a TV screen with a bunch of storms on it. And then you see this like bright sunshine over his head. And so it's this idea that, that is all of us. We're watching the news, we're reading and consuming things that are telling us the world is all dark and stormy. It's creating this version of reality in our minds that that is what the world looks like. So we're wearing our raincoat and having our umbrella over our head. The truth is that it's actually quite sunny and nice outside. I feel like when it comes to AI, this is going to a new extreme. Meaning the amount, even in just the last month of insane negativity about this coming apocalypse driven by AI that has gone mega viral has been crazy to see, right? Like, there was that something big is happening thing that went viral on X. Then there was the Citrini article about the global intelligence crisis that like literally cratered the market for, for a day, Jack Dorsey, the layoffs at Block. Like there's all of these narratives that are getting spun, that are getting forced into your head, that this is this massive coming apocalypse and there's all these terrible things that are coming and happening. And look, do I think there's going to be disruption from all of these new technologies? Absolutely. New technology creates disruption. This is a transformative new technology. We can't possibly comprehend some of the disruption that's going to happen, but our track record for figuring it out and, and having growth on the other side of these things and having it shape the future of the world in a positive way is quite good, actually. Perfect. And so my sort of version of reality as we talk about this is, well, look, the human and the science around all of this says that we naturally click and share things that are negative. They've studied this. Articles with negative headline words get shared and clicked multiple times more than things that have positive words. And so what happens is the negative gets shared and goes viral. And that's what you see and that's what gets pushed all around. And because the market of people that see that and see the engine around, making money around that is free, everyone floods into that, right? So like, everyone wants to create negative content because they see the clicks and shares and the money and the whole incentive economic engine that gets created. So everyone floods into that. Well, it creates this skewed perspective on reality of what the future really looks like when it comes to AI. And I personally am. I'm an optimist. I think pessimists sound smart and optimists get rich. And so I would much rather take a very optimistic lens at the future that we can create and try to engage and share in that same vein. Because I do think that if you are optimistic right now and you can take advantage of the things that exist and that are out there in front of you, it is going to be the most amazing time in history, the next decade, to be a curious high agency individual. That is the approach that I am trying to take in my own work, professional and personal. With AI, I am going to be hyper curious. Does that mean that I don't get scared by things that come up and that I look at? No, absolutely not. I get scared and I think there is a lot of concerns that I have for what the future looks like for our children in a couple of decades. But me being curious in high agency is the action that I can take right now that is going to lead to me having a slightly better future. Anxiety is like you're living in the future. That is what anxiety is. You're catastrophizing about something in the future. Whenever I feel anxiety, my default question that I ask is just six words. What can I do right now? I'm feeling anxiety. I'm catastrophizing about the future. What can I do right now? Well, it's be curious, be high agency, create movement, go and do something, take action, learn, grow. That is how you set yourself up for whatever it is that might come.
Chris Hutchins
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Host / Interviewer
I feel like the other option which yeah, I feel like I've probably shared more of anything you've written. The tweet you have that's like about complaining, if you're worried about the future, go do something or just stop. Your perspective, I think is if I'm paraphrasing is instead of complaining, either fix something or don't do it.
Chris Hutchins
Don't Complain because it doesn't achieve anything.
Sahil Bloom
It's so true that whenever I talk and write about this, it's like you're giving too much energy to the thing by complaining about it, by having anxiety over it. If you're not going to take action, if you're not going to do something about it, just let it be free from your mind.
Host / Interviewer
I share your version of it instead of mine because I always forget that second half. And I feel like when you tell someone, like, if you're not going to do anything about it, don't complain. It kind of feels like you're doing something you shouldn't do. But if you say, like, don't give it power because then it's kind of taking over your brain, it's like, oh, I'm helping you be a better version of yourself, instead of telling you that your current version of yourself is kind of annoying. But I agree with you that if you are curious and I guess have the time to be curious, with all the stuff going on right now, it feels like what we are able to do has just grown exponentially. And I'm curious what your actual AI usage, aside from the sparring partner on ideas and big decisions, are there other big uses in your life now that kind of didn't exist a few months ago?
Sahil Bloom
Yeah. My general approach to AI or outsourcing in general, like, even when I was building my team and hiring people was I only want to outsource things that I genuinely don't want to do. So, like, everyone wanted me when I was originally starting to grow my platform, like, oh, you should hire a ghostwriter, you should do these things. I'm like, but I love writing. That's the one thing that I really love doing that I'm really good at. And writing is how I think. So if I outsource that, I'm no longer going to be able to think, I'm no longer going to be able to speak. All of these things downstream are going to be negative. What I want to outsource is the things that I don't like doing or that I suck at. And there's a whole lot of things like that, by the way, like all of the ops on the back end, all of the, like, mechanics around video editing and posting things and all of that, yes, we can outsource around that. So from a team standpoint, that's what we built out now with AI. What I keep thinking about is, let me try to push the boundaries of how AI can accelerate our ability to do those things well and So I messed around with all the openclaw stuff when it came out. I don't learn personally by watching a YouTube video or reading something. I learned by trying to tinker with it and do it. And so I'm like, as much of a tech luddite as you can be. Before trying to set up openclaw, I had never opened the terminal thing on my Mac. It was embarrassing how long it took me to set this up, but I did it. And now what I've created, I would say, is just like a set of agents who enable me to kind of operate as, like, the brain function. And I can always get support with the very specific, different things that allow me to do my work better. And so if that's like, backend, basic ops, things of travel and flight bookings and stuff like that, easy if it's more detailed, like research partner alongside writing that I'm doing, to be pulling research and studies and different, different data and facts, great. The most salient and valuable one for me recently has been being, like, a true sparring partner on writing that I'm doing. I finally feel like I've gotten it to the point where it's not just overtly positive and flowery about things that I put into it from a writing standpoint, where it's like really giving me three to five pieces of thoughtful pushbacks and feedback that actually force me to think a little bit deeper about things and have improved my writing. So I would say those have been the biggest ones. And then my team on the back end, like, I'm really pushing them and encouraging them to all be using these tools to try to accelerate the way that we are able to do our work in whatever area.
Host / Interviewer
Yeah, I like the approach of using it to not give up the thing you enjoy. The thing I've gotten a lot of feedback on my side is not use it to write. It's like, use it to do research. I think the reason I love it is because when you do the research yourself, I think you can sometimes draw things out that you wouldn't necessarily see otherwise. And so if I just get a report, I'm just always questioning, like, did there report get it all right? And, like, that's my brain. And so I actually really love doing the research. And so what I like to do is not have the tools do the research, but maybe have the tools give you a new way to kind of manage and store and query and view and analyze whatever research you're doing. And so I was trying to do this stuff to augment the stuff I love.
Sahil Bloom
I think that's the right approach. Like, I think the watch out if you think of the wrong approach. I would argue that like 99% of the content that you see related to OpenClaw or any of these AI tools is like total nonsense. Because what it is is it's performative. Click generating content versus really useful things. Like, you know, you see people like, like, oh, I just changed the whole world with my 47 Mac minis that I have set up here. And you're like, okay, but what did you, what did you build?
Host / Interviewer
Right?
Sahil Bloom
Like that's the meme everyone's now commenting. Like, okay, but what did you do? Like, do you have an app? What is the thing that it's actually all doing? It's not doing anything. It's like making a fancy productivity system. And everyone is like, here are the use cases that I've done and it's like 47 versions of like daily briefing emails that it sends you. I set up all those daily briefing emails on my own just because that was the first thing that everyone had told me I should do. I just have 47 emails now in my inbox that I have to go through and I'm like, do I hire my agent to go through the emails that my agent just sent me that I created via my agent? It's absurd, literally absurd. And so what I've tried to now get to is like, okay, but what is actually genuinely allowing me to ascend the level of work that I am doing to a higher order significant level of work and that is meaningful. If I can automate this lower layer so that I can ascend, that's meaningful. If what it's doing is creating more work for me to do down here at the lower level, that is not useful. And so when we talk about like, oh well, it created this database query notion board that tracks to 17 different back end links, whatever, like, okay, but that just means that I need to spend more time in notion, which is not doing work, right? Like my work is writing or sharing things or speaking or like that is the higher order level work for me. And so I want to spend less time in my email, I want to spend less time in notion. So if I'm creating systems with this thing, that's just making it more complicated down here, that is not useful. Even saying that right now I'm thinking about like, wow, I really need to streamline some of these things because it's not actually creating that higher order page push. But I have really tried to be judicious And I think everyone should just be judicious about like, okay, how is it really enabling you to ascend in the work that you were doing versus creating more of that lower level work that we don't actually want to do?
Host / Interviewer
And one of the things that I think is an important caveat is you have a whole paradox around this, I think where a lot of people out there are giving advice and then not taking it because it's easy. And I'm guilty of this as well, right? It's very easy for me to kind of think for a friend what they should do and then just not do that same thing myself. And I think what's really tricky with AI stuff is that people are making a lot of like live stream YouTube videos and they're like just showing you what they're doing, not showing you what they've reflected on and then actually thought would be the right thing to do. It is just hard for people often to take their own advice. Is that a fair way to surmise the paradox?
Sahil Bloom
It's called Solomon's paradox, right? It's the story of King Solomon from the Bible, known as like the wisest man who ever lived, right? Like the famous story about him is that he was king and these two women come with a single baby and they both claim to be the mother. And how are you going to figure out which one is the actual rightful mother? And so King Solomon says, give me a sword and I'm going to chop the baby in half. And each one of you can take a half. And one of the women cries out, no, no, no, don't do that. She can have the baby. And King Solomon says, okay, that must be the mother, the one who cried out the story. And the reason there is a paradox associated with him is because he was extraordinarily good at giving this advice and being this wise king, judgment, discernment, et cetera, but really terrible at taking his own. He had like 300 wives, 700 concubines, growing obsession with wealth and fancy things, and his kingdom deteriorated within a decade or within a generation of him dying. And this idea of Solomon's Paradox was named for this common human cognitive flaw, that we are very good at giving advice to others that is rational and clear headed, but very bad at taking that advice ourself. And it is clear why it happens, right? Like you are so separated from other people's situations that you are able to view them clearly and logically and give them this sound advice. But in your own life you're connected emotionally to every single thing. So it is very hard to have that clear, rational perspective. And so sometimes the easiest way to solve this is to just ask yourself a very simple question when you're encountering a situation that you need to give yourself advice around, which is just to say, what would I tell my best friend to do? Like, in this situation, what advice would I give to my best friend if it wasn't me facing this situation? What would I say? Separate yourself from it. Create a little bit of that bird's eye view and you get a lot of value from it.
Host / Interviewer
Yeah, this feels like something that might also work well with kind of the AI sparring partner style. I think if I could actually generate a situation where it feels more like I'm giving my best friend advice, I think I might be able to even further remove myself than if it's an exercise, I could imagine myself being in this situation. Well, my friend doesn't really need this advice.
Sahil Bloom
That could be a good way to do it. You just say, like, here's the situation. Imagine you are my best friend, like, what advice would you be giving me? Or like, pretend you are my best friend and you have this situation. Tell me about the situation and I'm going to give you advice.
Host / Interviewer
And it sounds so crazy. And I think as voice within a lot of these tools gets easier, it's still not as commonplace to talk, But I feel like when you talk, it just kind of throws you out of the second guessing stage. I often find when I'm writing things, I second guess it way more than when I'm having a conversation. The amount of self editing I do when I'm writing. But when you're recording an episode like we are, it's like maybe once or twice in an hour, you're like, oh, let me restate that.
Sahil Bloom
I started using this tool called Lemon that is sort of like a voice agent on your computer. It does all the dictation stuff that whisper flow does, but it also is agentic, so it'll manage things on your screen and control things all over your screen. And I started using it for interacting with my agents. And it's really cool for that exact reason. It like forces me to actually talk the thing out versus trying to type it. And what I find is when I talk, it might take me a minute and I throw out a bunch of ums and ands and whatever. But in my brain, I'm actually working in a different way than if I was trying to just type it out. Like I'm able to reason it out loud. With my voice and then it sort of distills it and it's right there and I can have the interaction and engagement. So I really like that tool. It's called Lemon.
Host / Interviewer
Yeah, I've been a long time now Whisper Flow user, and I just find that, like, the more I train myself to hit that button to start talking, the better the output is because it's what I'm actually thinking versus self editing. Okay. So I'm going to take a little bit of a turn here because there's a lot of stuff going on. Right. We've got all these tools we can play with. In your case work to do, you also have a young kid running around the house. How do you kind of balance that? And now that I think you're a couple years behind me, I think that there's just so much more as these kids get older that you could do with them and that you want to do with them. And I find that it makes it really hard.
Sahil Bloom
Hard.
Host / Interviewer
And then on the counter, I also find that when there's more and more things I'm excited about, it's like harder to step away. So it's like it's both more fun to hang out with my kids and harder for me to step away. How are you balancing this with all this other stuff? Like, I constantly see you posting things about, you know, working out. Oh, my gosh.
Chris Hutchins
Where does Zyle get all the time for all these things?
Sahil Bloom
I'm very structured in my time. If there's one thing I'm really disciplined about, it is about time. Windows and time blocking, I guess you would call it. And I've been really deliberate about the way that I structure my life when I'm at home. It's why I love living in Boston actually, versus New York more than anything else, which is that I don't get pulled to random things. When I'm in Boston, I don't have like a random day where I have a meeting in the city or something like that. That just doesn't really exist. And so I can go to New York and do all that as a batch. But, like, when I'm at home, I'm really at home. And that has been important, especially now in this season of Life with my son being, you know, he's three and a half, almost four, because he's more and more aware when I'm gone. When he was younger, he didn't really understand time. There wasn't really an awareness. Now when I leave, he, like, understands that I'm leaving, that I'm Gone. He's like, where are you? What are you doing? So when I do leave and when I'm not home, I do try to explain to him much more why I'm doing these things, try to make him understand what I'm doing, why it's important, etc. But when I'm home, I really try to be judicious about the way my days look. So when you ask like where do I find time for things, it's just that it's structured. So I wake up at 4:30 from call it 5am to 7:30am is like my deep focus writing time. That is primarily my second book which I'm working on or the newsletter. I'm sitting, I'm focused. That's when I'm writing from 7:30 to maybe 10. That is like my workout time, you know, I will do my runs, that's when I'll go to the gym and get my workouts in. I say 7:30 to 10 because it's like that includes driving time and you know, stretching, like all of the different things around it. It's really like that full block. From 10 to about 12 I kind of have like a family like free window where like make breakfast, hang out, spend some time with him, whatever it might be. I'll go get a coffee at like 12 after having sort of a meal. And then from 12 to about 5 I try to be like focused on a couple of different things, whether it's related to business or investing or some of the kind of more free flowing business things that are happening. Five to seven is like another family window, cold, no phone on me now, huge like breaking my phone addiction the last month which we can talk about, which was amazing. But like 5 to 7 is like family time, dinner, bath time, hanging out, etc. And then 7 to 8 I'm like sauna reading, evening thinking time, etc. And then at 8 I'm in bed and we're starting it over again. And like my son goes to bed at 7, 7:30, my wife and I get into bed at 8, watch a show and go to bed. And that is my day. That sounds so boring to the vast majority of people, but it is like a routine that I absolutely love. And when I'm at home and I have a whole week at home with no travel, it's like the best thing in the world to me that I just get to do that over and over again.
Chris Hutchins
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Host / Interviewer
Someone listening might think, gosh, you're just so disciplined. But when you're talking about phone addiction, I saw you share that you used one of those phone lockboxes and I just want to flag that. You could say like, oh, it's so easy, I'm going to do this thing. But you're still using other things as systems to kind of make this ideal schedule work. And I think that's one of the differences is like I could sit down and write down my schedule, right, and say this is the ideal week. But then when you wake up at 4:30, you have to actually do it. And so some of that is kind of motivation and maybe we could talk about that. But some of it is like you've just found some systems that force you to do it.
Sahil Bloom
It's sort of a cliche to even say this. Like motivation is overrated. It just is. I am a highly motivated person. I can grind. I'm like willpower, all of those things. I'm probably in the top 1% on those things and that's not a flex. I'm just saying, like I'm just wired differently in that way. It still fails for me constantly if I try to rely on it. And that is coming from Someone who is in the top whatever of that domain. It still sucks. I tried to use it for the phone change. Like, hey, I'm just never gonna use my phone when I'm in the car. I'm just not gonna use it. It can be sitting there, I'm not gonna use it. Right. Or like it's gonna be on my desk, but I'm not gonna use it. It didn't work. They have teams of behavioral science PhDs who design these things to make them as addicting as possible. So if you are saying that you are going to be motivated enough to not do that thing, you're saying that you are going to be more motivated than the thousands and thousands of hours of research that has gone into making these things addicting. Like you are saying, I'm going to be more motivated than my entire body telling me that I am so tired that I can just go back to sleep for a few minutes early in the morning. It isn't going to work in the long run. And so the antidote to that is like choice architecture. Right. It's like the science around making it difficult to do the action that you don't want to do. So for me, like with Breaking the Phone addiction, the phone lockbox was a perfect example. Like, hey, I don't want to touch my phone while I'm doing deep focus writing in the morning. I don't want to be able to see my phone or touch my phone. So instead of having it sitting there and needing to be able to see it and like be like, should I grab it? Should I grab it? I'm going to put it in this lockbox. I'm going to put a two hour timer on the lockbox so that I quite literally cannot get my phone. I would have to email the company to unlock this box before the end of this two hours. Now it's not even on my mind cognitively because I know like it functionally does not exist. It's in that box. It's like this black box, like Schrodinger's cat. I don't even know if my phone is dead in there. That is so important scientifically when it comes to the phone in particular, having your phone on your desk or in your pocket makes you operate at a cognitive deficit. They've now studied this. It's very clear. Having it in a different room or in a lockbox, all of a sudden you're just operating at a higher cognitive level because it's not even pulling any of your mind or attention in that direction. So in Every area of life. When you're talking about creating these changes, when you're talking about setting up an ideal schedule, you need to think about the actual architecture of making that decision on a daily basis. For me, one of the biggest ones is I need to know what the work is that I'm doing during a window. If I have like a, oh, free focus work, whatever window on my calendar, I'm doing nothing. I'm going to sit there and like go open X, I'm going to screw around on email. I'm just going to like look around. If I put that same window and it says like clean email inbox, 30 minutes or an hour, I'm going to crank through emails for an hour. So I know that about myself. It's the same for when I get on planes. Like if I'm on a flight, if I am just like, oh, I'm going to generally do work on this flight, I will get absolutely nothing done. If I tell myself I'm gonna write two newsletters on this six hour flight, I'll write two newsletters on that flight and they'll be great. And so I have learned that about myself. Now I know I need to know exactly what I'm doing. And I'm probably gonna bring a note card with me that says those two things that I'm doing and it's gonna sit right in front of me so that I know it. That's choice architecture. So that you can override this desire to just have motivation or even discipline be the thing that you're relying on in those moments.
Host / Interviewer
Maybe we're wired differently, but I'm imagining I adopt this practice, right? You wake up, you go do your focus work, you put your phone in the lockbox that feels doable. And then as you emerge out of that, there's probably all kinds of things that you haven't checked your email for the day, you haven't done this, and then that's your kind of workout zone. And I feel like if there's a thing you use to choice architect the exercise into the day in the midst of like, there's probably dozens of competing work priorities that feel more urgent than that. Is there something you do or do you just love to work out and it's almost the opposite.
Sahil Bloom
Well, workouts for me are part of my work, just full stop. I write about and talk about health related stuff. It's important to my different platforms. I wrote a book that involves it. I have a skincare line. Like all of these things matter as it relates to my work. And so I do view it as part of the thing that I need to do every day. I would say if that is how you feel naturally to say, like, oh, I'm gonna be stressed working out during Windows when I'm getting emails, then I would recommend do the workout at the 4:30am when you wake up, because then you're gonna be like, okay, I got my workout in and I'm done. And now I can go into work mode and I can just flow in work mode and it's gonna be different buckets of work. For me personally, those early hours are my most creative time and so I need to write then. Otherwise I feel behind throughout the course of the day. But it's about finding what works for you. So I don't think my schedule is gonna be the perfect one for someone else who has a totally different wiring. If working out at 9am makes you stressed and more stressed than the benefit that you get, you shouldn't do it.
Host / Interviewer
I am of the mind that there's probably nothing that if you don't get to it by 9 or 10am, anyone's gonna be like, upset. There are things that need to happen before the end of a workday sometimes, but it doesn't have to happen by 9 or 10.
Sahil Bloom
So it also just depends on what your role is if you are running your own business. Like if I don't reply to emails for multiple days, I didn't reply to emails for multiple days. I don't know, I mean, like, I'm generally pretty bad at intentionally because I don't want people to expect that I'm going to respond in the next couple of hours. Occasionally there's emails that I need to reply to right away, but for the most part, if someone really needs something from me, they call me or text me and I can respond quickly. If you work as a lawyer or, you know, in private equity, like my old job, you probably need to respond pretty quickly. And so setting up and structuring the life that you have more touch points for those things is going to be important.
Host / Interviewer
And that might change during seasons too, right? Like there might be big projects that require something different from you. And recently I had a conversation with someone who kind of really emphasized that there are phases where missing things that are part of your routine is not the end of the world. And like, not to beat yourself up for it. If you don't work out for a couple of weeks because there's a thing that's the most exciting thing in the last couple years, don't beat yourself up if a couple months later that thing is still taking over your life. Definitely time to check in.
Sahil Bloom
Yeah. I mean, this is the paradox of routines, right? Like the routine that was meant to serve you starts to own you. And I fall victim to this a lot. And I've had to temper and sort of understand that about myself, that my bias is to, like, get really locked in on the routine that I have. And I need to once a quarter, maybe like, look at the things that I'm doing and make sure they are still serving me, that they haven't become this thing that actually hangs over my head and makes me feel this weight. Like I would be really excited working on something at night and realized that it was going to screw with my morning routine so I would stop doing the thing when, like, that didn't really make sense. The routine that had been meant to serve me and drive meaningful, productive work was now owning me. It was actually holding me back from doing that thing. And so I think auditing that, recognizing that sometimes you can be your own worst enemy in these ways is important.
Host / Interviewer
How often do you, and in what level of depth, audit what's going on in life, whether it's work or personal or with your wife, and kind of think through those things. Because I know you do a personal annual review, but I have to imagine at a more frequent interval you're checking in on things and making sure that you know the routine is serving you.
Sahil Bloom
I do a lot of like, just ongoing sort of like rolling check ins with myself. Like if things aren't feeling right or if I felt like I was out of flow for a given week, I'll ask myself just like, why did that feel like that was the case? I'm sort of in a natural cadence. I do a quarterly think week type thing where for a couple days I'll go somewhere and do like, broader reflection on the direction things are going. Sort of like a state of the union check in on stuff and then just like kind of the rolling on an ongoing basis.
Host / Interviewer
Almost everything you said was really in line with kind of what I expected you to be doing in your career for the last few years. And then you subtly hinted at skin care. And I'm just curious. I don't think I've ever asked you for the driving force that led you here. This is not a skincare beauty podcast. That's not a regular topic. But for that to be something that you wanted to dedicate time to, I feel like I need to dedicate some time to it here as well.
Sahil Bloom
I struggled with bad skin for most of my life. And it had a really negative impact on my confidence and on how I showed up in the world. Like for most of my teenage years on through my mid-20s, I was really not confident in how I showed up in the world. And, you know, even to the point where, like when I was proposing to my wife, I was less present in the moment because I was worried about her noticing blemishes on my face. And all of that changed for me when my grandmother in India did a classic grandmother thing and smeared something on my face from a jar of unknown substance, which terrified me at the time. But it turned out it was a coconut oil based thing that dramatically improved my skin over the course of a handful of weeks of then like researching and trying to understand why, I realized that the vast majority of these skincare products that we use and buy on the shelf are filled with these toxic chemicals that your body is just absorbing and rejecting in many ways. Like the whole industry has been built out around claiming natural. And then you go look at the ingredient list and it's like 40 things that you cannot possibly pronounce. And so this idea came to me in 2024 of I am hand home making all of this stuff right now that I'm using for my own skin. That transformed my skin and my confidence in a lot of ways. Why doesn't this exist for men? I'd seen a couple things that had tried to do it for women that were doing quite well. Like, men's skin care is going to be a bigger thing. Men are taking care of themselves more. It matters. And why doesn't it exist? Your skin is your largest organ on your body. It's absorbing everything you put on your body. There's all of these men that are talking about what they eat and all their workouts and all these things, and then they're putting this junk on their skin that's just getting absorbed. That can't be the best way to do this. And so I went down the rabbit hole, scaled up a team around it, invested a million dollars of my own money, spent 18 months, built out this whole thing around getting something to market and launching something in and created what I think is the single best skincare line for men in the world. It is 100% all natural. It is literally ingredients that you could actually go outside and either hunt or pick. And the whole idea was like, your grandfather should be able to understand this ingredient list. It's called Wild Roman. You can buy it now anywhere in the US it's an incredible set of products. I am the number one customer, full price paying customer. Like I think by a magnitude of 10x to date. My whole family uses it. My wife stole it and started using it. From a business business standpoint, I think there's an extraordinary opportunity in this space. Like it is growing much faster than the broader personal care market. The men's side, that is natural ingredients. Focusing on health is a huge movement that is continuing to build and grow. Ingredient quality continuing to build and grow and the premium end of this market. To say that like we're really going to take design and brand and the aesthetics and the quality ingredients extremely highly and it's not going to be a marketing line, it's going to be an actual bar that we allow to play out across the entire product that we're putting into the world. And we've done that and I'm really proud of that. When I first initially announced it, it was so funny to me because there was this broader perception that it was like influencer cash grab business and I was cracking up because I was like, man, this must be the worst freaking cash grab in the world. Like, I am in a massive hole on this and I'm going to be for a long, long time. No matter how well it goes. If I wanted to do a cash grab, I'd go launch some course or some mastermind or something like this is the worst cash grab ever. A physical product that you have to invest this much in to get to market and like, you know, massive long lead times, like, it's just, it's a terrible business. If you're going to do it for a cash grab. I think we can go build in a beautiful, amazing brand that becomes worth a whole lot. But it's only going to be because the product is extraordinary and I think people are going to share it, they're going to use it, they're going to recommend it. So I mean, look, I'm biased, but I highly recommend checking it out. It's wildroman.com and it's named after my son, that is my wild Roman, which is just something that means a lot to me. Like I wouldn't have put his name on it if I didn't really care about it.
Host / Interviewer
I would say when I saw the name of it, it was the first thing that made me think, I don't know if Sahil is going to ever be able to build a successful skincare company. I don't know anything about skincare. I don't. Nothing. But the thing that drove me to
Chris Hutchins
Say, hey, Sahil, is there any chance I could write, like, just a small
Host / Interviewer
check into what you're building was just that you named it after your son? My theory was, I think that Sahil is the kind of person that was not going to start anything, name it after his son and let it fail. That was my entire investment hypothesis. Was the name that you chose for the company. I have since used the product and enjoyed it. My wife the other day, though, was funny. She was looking at different body wash for the kids and she was just like, oh, there's so many ingredients. I was like, I thought this was organic. And she looked at what you guys built and she's like, like, oh, that's like a really clean list of ingredients.
Sahil Bloom
Exactly what we're hoping for. It's great. I mean, my son uses it. Like, we've got a number of emails now to date of, like, kids that have struggled with eczema that it cleared up. It's just the natural ingredients that are in these things and it's the highest quality bar. So I'm again, hugely biased. But I think everyone will love it.
Host / Interviewer
So it wouldn't be me if I didn't ask you if there's some kind of deal we can get anyone who wants to check it out. I probably should have asked in advance, but what do you think?
Sahil Bloom
Absolutely. Yeah, we can. You can put something in the show notes.
Host / Interviewer
All right, so take a look at the show notes for whatever kind of deal we can get Sahil. This has been great. Anything else to share or places to send people before we wrap?
Sahil Bloom
No, this is awesome. As always. Always have a blast with you.
Chris Hutchins
All right.
Host / Interviewer
Thanks for joining me.
Sahil Bloom
Thank you.
Chris Hutchins
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Host: Chris Hutchins
Guest: Sahil Bloom
Date: March 25, 2026
Theme: How to design and actually live a life you’re excited about—beyond just constantly optimizing routines, career, and productivity. Sahil Bloom shares real stories, frameworks, and hacks for escaping “the optimization trap” and reclaiming the small, meaningful moments that matter most.
This episode explores how relentless optimization—in routines, careers, and life—can backfire by robbing us of the texture and meaning in everyday moments. Sahil Bloom shares his personal journey, including a major family move, reflections on "the Doorman Fallacy", actionable strategies for designing better habits, the paradox of giving advice, practical use of AI tools, and the launch of a meaningful business. The discussion is rich with vulnerability, wisdom, and pragmatic hacks for anyone interested in living more intentionally.
Opening Insight:
Chris Hutchins introduces the idea that we often optimize parts of our lives to such a degree that we lose touch with what we actually care about. Sahil’s story is a lived example of noticing and correcting this (00:00).
Major Move for Family:
Life in the Little Moments:
Concept Definition:
The Doorman Fallacy: Defining a role (or life choice) only by its surface function, missing hidden value.
Story: A hotel replaces its doorman with an automatic door for efficiency, only to learn too late that the doorman provided security, prestige, and a welcoming atmosphere (06:45).
Application to Life:
Intentional Structure Still Needed:
Even after moving closer to family, some structure is essential to create new habits. Calendaring regular parent dinners helps ensure follow-through (11:02).
Serendipitous Joys:
But physical proximity 10x’s the random, organic interactions—making small joys more accessible and frequent (11:50).
Professional vs. Personal: The Real Tradeoff
Method for Processing Change:
Sahil uses a written fear/benefit “deconstruction” exercise, then leverages AI as a devil's advocate—helpful for challenging stuck patterns and revealing upside in big leaps (18:52–21:53).
Negativity Bias in Media:
Anxiety Hack:
“Anxiety is like you’re living in the future... Whenever I feel anxiety, my default question that I ask is just six words: What can I do right now?” – Sahil (25:55)
Don’t Outsource What You Love:
Pitfalls of Performative Productivity:
Solomon’s Paradox:
Both speakers discuss how we’re often better at giving advice than taking our own, and how imagining you’re advising a friend—or using AI to generate “external” advice—can help (36:24–38:46).
How Sahil Structures His Day:
System Over Willpower:
Routines Should Serve You:
Final note: Sahil’s episode is an invitation to “build a life you’re excited about”—one rich in meaning, relationships, and purposeful design, not just relentless optimization.