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#885: How to Simplify Your Life — Tips from Oliver Burkeman, Chip Conley, Elizabeth Gilbert, and More

from The Tim Ferriss Show ·

46m 33s

#885: How to Simplify Your Life — Tips from Oliver Burkeman, Chip Conley, Elizabeth Gilbert, and More

This episode explores how to simplify life through personal, practical insights from key figures. Chip Conley shares how life-altering experiences—like a near-death incident and cancer diagnosis—led him to embrace mindful decoupling, where he let go of identity and roles to foster personal growth. He introduces the "month I died" experiment, where he disconnects from technology and society to deliver social eulogies, reinforcing the importance of present-moment focus and emotional honesty. David Allen emphasizes the value of externalizing mental clutter through physical lists to reveal unmet personal agreements and reduce internal stress. Elizabeth Gilbert advocates for a simple, boundary-setting "thank you and no" response to protect relationships and self-respect, especially in close connections. Oliver Berkman challenges common simplification techniques, arguing that true simplicity lies in an attitude of acceptance and detachment rather than rigid systems. The endowment effect is illustrated through personal stories, showing how ownership distorts value and makes letting go difficult. Collectively, these perspectives highlight that simplification is not about reduction but about deepening self-awareness, creating space for authenticity, and aligning actions with core values—especially in midlife and in the face of uncertainty.

Transcription

8887 Words, 46072 Characters

English
Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show. This time around, we have a different format from my usual long-form interviews. This is bite-sized tips from people I love who've been on the podcast. And here's the theme. Many of us feel like we're drowning in complexity. I think day on day, the world just seems insane, whether that is with respect to inboxes or decisions or otherwise. Perhaps you're even slipping in and out of overwhelm. I've been there. So I wanted to hit pause myself, figured some of you might want to do the same thing, and ask a question. What are a few decisions, say one to three, that could dramatically simplify my life in 2026? To explore that, I invited listener favorites to chime in with their personal stories and what they have done themselves. Past episodes of this Simplify series feature lessons from Derek Sivers, Seth Godin, Martha Beck, Maria Popova, Morgan Housel, Cal Newport, and many others. So be sure to check those out. But in the meantime, please enjoy this wide-ranging but intensely practical episode on how to simplify your life. First up, Chip Conley. Hi, I'm Chip Conley, the founder and executive chair of MEA, and also formerly the modern elder of Airbnb and the founder and CEO of Joie de Vivre, the second largest boutique hotel company in the US. Tim asked me to talk about simplifying life. My God, I don't know why he would ask me because I tend to complicate my life. But I'm going to do it. I'm going to do it. I'm going to do it. I'm going to do it. I can say that I've had two experiences in my life where my health forced me to simplify my life. And then I learned some new tools and practices. Let me give a little storytelling. When I was in my late 40s, I had this boutique hotel company, Joie de Vivre, which means joy of life, that I'd started in San Francisco. Ultimately, we had 52 hotels around California. We were the second largest boutique hotelier in the US. But in my late 40s, my life was really complicated. We were going through the dot-com bust, and I had a lot of money, and I had 11, and then we were going through the Great Recession, and I didn't want to be doing this anymore. And I ended up having an NDE, a near-death experience. And the NDE happened because I had an allergic reaction to an antibiotic. I was giving a speech on stage in St. Louis, and I went flatline and ended up in the hospital for three days because they were trying to figure out what went wrong. You know, why did I go flatline nine times over 90 minutes? And bottom line was, that experience woke me up. The hotelier needed a wake-up call. And the wake-up call was this. I had started that company because I wanted creativity and freedom. But with 3,500 employees and going through our second once-in-a-lifetime downturn in the same decade, I realized that the identity that I was attached to, being the founder and CEO and the VIP status I had, was less important to me than my health. And while it wasn't, I didn't have a heart attack, it was an allergic reaction to an antibiotic, it might as well have been a heart attack. Because I was living my life, very complicated life. And so I decided to do something that I call mindful decoupling. Mindful decoupling. This is not conscious uncoupling. This is not a Gwyneth Paltrow thing. Mindful decoupling means I said, I don't know what I'm supposed to do next, but I know I'm not supposed to do this anymore. I don't know what my next identity is going to be, but I know that the identity that I have been so reliant upon, the VIP status, now, I may be a PIP, a previously important person. I know that that is what I need to move toward. I need to move toward this fertile ground, this chrysalis space. Between Caterpillar and Butterfly, there is a chrysalis. In the chrysalis, the transformation happens. And what I learned by selling my company at the bottom of the Great Recession, by actually changing a lot of my habits, and even changing friendships, and ending a romantic relationship that wasn't working anymore. But I wasn't willing to leave it because I felt like it was my life preserver I was holding onto at a difficult time. I made space in my life. And what I wanted to say is, if you are a talented person, create space in your life, especially in midlife. I have become sort of an expert on midlife. And midlife is where we actually have to let go of who we've been in order to allow something else to emerge. But in the meantime, in between, the decoupling that has to happen is you have to be willing to let go of who you've been in order to allow something else to emerge. Let go of the identity and the roles in order for something new to emerge. I spent two years from age 50 to 52 in what I would call, or Mary Catherine Bateson, Margaret Mead's daughter, would call the midlife atrium. So what we know about an atrium is it's a very simple space. An atrium has light and air and all kinds of beauty that allows you to see what's going to actually emerge from that space. Between age 50 and 50, it's a very simple space. It's a very simple space. It's a very I spent a lot of time in a hammock in my backyard. I did a lot of reading. I got really curious. Curiosity is not something you do when you're really busy. So I got curious about hot springs. So I went around the world exploring hot springs and learning about the geothermal properties of hot springs. I got interested in emotions because when I was struggling through my emotions in my late forties, I didn't feel like I was emotionally fluent. And ultimately, I wrote a book called Emotional Equations, which became a New York Times bestseller. But the thing that was the most interesting was that I was able to read a book called Most Fun. I decided I wanted to go around the world and become the world's leading expert on festivals. I was the first board member of Burning Man. Who knew Burning Man had a board? But the six founders of Burning Man came to me and said, Chip, we're going to take our for-profit and turn it into a nonprofit. We want you to be part of the board. So I spent two years going around the world. I went to 36 festivals in 16 countries just in one year. I brought Tim, Tim Ferriss, to my 50th birthday party at Burning Man. And I, I learned an awful lot about the cultural curiosity that happens in festivals around the world. And then at age 52, in the midst of all that, I got asked by the three founders of Airbnb, a company nobody had heard of, but was also based in San Francisco like I was, to join them. And so I created the space. I simplified my life. I went out and had fun. I got curious. And out of that fertile ground, that good soil, came this Airbnb opportunity, which was quite beautiful. I loved it. And I spent seven and a half years there helping the founders of Airbnb turn that little tech startup into the world's most valuable hospitality company. So that's one experience about simplifying life. And from that simplified life, something beautiful grew. The more recent experience that I'm going to talk about, I talked with Tim about it in 2019 when I was on his show. Tim surprised me. He showed up in Austin and we were going to have lunch before we did the show. And I was talking about the fact that I had found out I had cancer, prostate cancer. At that point, it was stage one. And we talked a lot about it on the show. Over the course of the last seven years, since that time, seven and a half years, my cancer has moved from stage one to stage two to stage three. And I have learned that I've done what I've always done. I've made my life more complicated, but it's not so much just being complicated. It's like I have such a sense of calling in what I'm doing that I take on a lot a lot. And when I have the sense, I'm now at stage three with my cancer, I have this thing called holy urgency. I call it holy urgency, the sense like I have a calling and I'm supposed to pursue it because I don't know how much time I have left. But it actually makes me a little bit manic. And the thing I'm learning right now is how do I turn manic into magic? It's just changing one letter to go from manic to magic. So the kinds of things I'm doing to simplify my life, to try to be more magical in my approach to my calling are number one is I do a Sunday sabbatical as much as I can. I try to take Sundays off and I try to do that. And I try to actually not look at, I go offline for the day. And I do that partly because it's great for my nervous system. It's great for my creativity. It gives me time to meditate for an extended time. It gives me time to take long walks. I'm also doing something this coming February that I'm really excited about. I call it the month I died. And I think one of the things that's really interesting about our lives is we do a very poor job of telling people how much we love them while they're living. At the funeral, we do the eulogies, but we don't do that while we're living. And so I call this a social eulogy. So in February, I'm going to take the whole month off. Sabbatical, but I'm going to do it in a sort of a radical kind of way. I'm going to actually do the following. I'm going to wake up one day, the first day of February and say, who am I? My real name, you know, and my passport, Steve, and chip off the old block. I'm Steve Junior. I am going to be Steve for the month. I have nothing on my calendar. I'm not going to use my phone. I'm going to have a burner phone. I am going to simplify my life by not checking email for the whole month. I am going to just almost disappear. But what I'm going to do before I actually take this month off where no one will know where I am, except for a couple of friends in case there's an emergency. And I have no idea where I'm going to be, by the way, I'm going to wake up and just say, like, where do I want to be? But what I'm going to do is I'm going to do these social eulogies. I'm going to simplify my social life down to having three sociologies. one in san francisco i have a lot of friends one in santa fe where mea the modern elder academy has a campus and i have a lot of friends and the last one in baja where mea also has another campus where i have groups of friends and with small groups of friends we're going to actually come together have a dinner and we're going to give the eulogy for each other that we would give if we were to die tomorrow because when you have stage three cancer and i don't know how much longer i'm going to live i want to hear that while i'm still living because one of the things that's beautiful about the experience i had when i was 47 years old and i had my flatline experience is what i experienced was i saw birds during my time in that liminal space between life and death i was in this 40 foot tall ceilinged living room and i had the capacity and ability to fly and there were all these small birds in there and i could talk bird talk and they could talk to me and so they were saying to me slow down you can't see beauty and awe unless you slow down so my life today in terms of simplifying my life is learning how to fuse or alchemize slowing down with holy urgency slowing down because often when i slow down i have my best ideas i have my best conversations i feel a sense of spaciousness i do love my sundays i love my silent retreats that i do often with mea at one of our mea campuses but i also have that holy urgency that sense of purpose that sense that what i'm supposed to do in my life i'm doing and i feel very passionately about it so my biggest lesson in life right now is how do you alchemize two things that sound opposites slow down holy urgency and most importantly i think what's true of many people as they get closer to death and laura karstensen at stanford has proven this at the stanford center of medicine and i think that's what's true of many people at stanford the less perceived time you have left in your life the more you focus on what's important you don't focus on the future or the past you focus on the present moment and in focusing on the present moment you often are happier so how could you go out and focus on the present moment how could you go out and get curious and create the space for something to emerge i hope this was helpful simplifying is something that is really bounded in wisdom mea is the world's first midlife wisdom school dedicated to helping people in midlife get wiser and the difference between knowledge and wisdom is knowledge is something you accumulate you add wisdom is something you distill you simplify it's like the difference between a plus sign and a division sign and the square root of something so simplification is what wisdom is all about thanks so much tim for letting me share this and wishing you all the best next up i write very long-winded books and i've done them over a pretty long period of time so every once in a while i get quoted and i feel lost so if that happens let me know i have everything in front of me but could you talk about the endowment effect and how you turn around questions people might ask themselves about certain things whether that is something they own or an opportunity that gets presented to them so i think this is really important let's use a metaphor to get to the endowment effect our closet is a pretty good metaphor for the endowment effect and i think it's a good metaphor for the problem and what to do about it so for a lot of people listening even as you say they don't feel incredibly successful financially incredibly successful in all the things in their life right they probably still have more things in their closet that they actually can use usefully it's a bit cluttered maybe it's a lot more than a bit cluttered i talked to somebody not so long ago and they said oh greg my closet is it you've identified the pain point they said i have my closet organized by decade they had organized it but they said you don't have a closet you have a museum man you know they have the 70s and the 80s like she's not using any of these things she just has them and that's an organized version of the problem which is that we just have so much stuff and that is true in the physical stuff it's literally true in the closet but in the closet of our lives it is equally true now just staying with this metaphor for a moment almost everybody has had a moment where they said i've had enough i'm going to organize my closet and they begin the process and they take an item off the shelf off the floor and they say it's time to just get rid of this item and in the moment of picking it up and reflecting on it as if to give it away something mysterious almost magical seems to happen to many of us which is in that moment we're looking at we think well you know yeah but i'm not sure i want to get rid of it right i might i could use it sometime in the future as you know and so and so gave it to me and i and there's something somehow in the act of giving it away it's harder to give it away than it was before we picked it up to give it away so what's going on and as it turns out there's a heuristic a brain here is the predisposition that we have to all physical objects in our life and also in fact all the opportunities that we have in our life too and and it is this it's that we value things more because we have them that's a good thing in certain situations i mean that's why you owning a home is generally a good thing because people look after the home better it explains the phenomenon of why nobody in the history of the whole world has washed their own rental car you know it's a positive phenomenon until and unless we overvalue something that we really ought not to have in the closet at all it ought to go it is actually not useful to us it's not valuable to us but we are overvaluing it and therefore keeping it so it's overvaluing because we own it or it's endowed to us so in our lives that is an incredibly real problem i'll give you an illustration it's not in the book but it's something that happened to me that really hits a chord and it happened when i was staring at myself in the mirror dressed from head to toe in a stormtrooper outfit we're all a good epiphany start right and i'm looking at myself and i realize two things i realize that i have been thinking of this moment in some small degree for 30 years this is true i realize i'm standing there staring i'm in the halloween store yeah this is not a cheap suit that i'm trying on and i remember that this is goes back to like when i'm 10 years old and you know maybe return of the jedi come out or one of the star wars movies and my older brother one of my older brothers had said to me in passing but with quite a lot of enthusiasm wouldn't it be great to own a stormtrooper outfit just like from the movies like really like the real thing and somehow that got lodged in me well that's an idea that's something you should pursue yeah that's what would be so cool but all the brother thinks so so it must be so and somehow in the back of my mind there it lives unquestioned for 30 years and finally i'm in the store you know thinking about whether to buy this and in that moment i actually have a sort of a did have a eureka moment which is there is no part of me that wants this it's stayed with me but i don't and my four-year-old self does not need this one is it this is ridiculous what i why are you in this suit right now and so i i was able to sort of separate myself from the moment that's exactly what i'm advocating here i'm saying that for a lot of us we have a lot of became a shortcut phrase my wife will say it sometimes to me now is that a stormtrooper that you're pursuing is that stormtrooper opportunity that you used to think this was the thing but you're pursuing it because you just sort of have it you caught onto it you feel a sense of this endowment effect this sense of it's my opportunity it's my thing it's my goal it's not serving me anymore i think a lot of people have a lot of stormtroopers in their life and so it's not about the closet it's not about the stormtrooper but it's about the stuff that we need to get past and let go so that we can pursue the right things now not just the things that we are pursuing because at one time we wanted to pursue them or one time they came into our life and it seems like there are a number of ways to identify these whether they're stormtroopers or items opportunities that we are endowing with greater value because we have them because we're we either own them or being presented with them right so you could take say that sweater from aunt mildred or whatever it is and rather than asking how much do i value this item you turn it around and ask if i did not own this item how much would i pay to obtain it right that turnaround seems really important to me or in the case of opportunities and i'm quoting directly from you here but you know how will i feel if i miss out on this opportunity instead of that if i did not have this opportunity how much would i be willing to sacrifice in order to obtain it that strikes me as a very powerful reframe and is certainly also i think it was andy grove at intel who also used this field and there are many other business examples but if we were not already in this line of business how much would we pay to pursue it or would we pursue it in the first place as a way of pruning activities and conserving resources so they can be applied to the most important things and the idea is to trick your brain into putting it in the position where you don't own the thing where you don't have the opportunity so you you have to reflect on it afresh You have to say, okay, starting now, do I want this now? thing now how hard would i go after this now if i didn't own it if i didn't have it and it helps us to evaluate things more without this inflation of the fact that we own it which is of course the endowment effect next up david allen what are the first questions you ask or exercises you do when you sit down with high functioning but nonetheless overwhelmed people to work with them what are some of the first things that you do with them well aside from establishing rapport right which is you know hi and why did you bring me in here what is your presenting issue as best you can describe it and you know and here's a little bit about who i am kind of what we're going to do but ideally and over the years i discovered the less i tell people about what we're going to do the better surprise so if i just walked in cold the tabula rasa here is first thing i would do tim with you would be let's make sure you have an entry a physical entry we have some place to throw stuff until we can make decisions about what it means what you're going to do about it but we need to collect a bunch of stuff first so that's what we're going to do first is get some sort of a material version of collection or capturing stuff that has people's attention so we just get a big stack of printer paper a favorite pen or pencil sit them down say okay what's on your mind what has your attention oh i need cat food oh i need a life oh i need to do vice president marketing oh our next vacation is coming up oh god my cell phone just crapped out the printer broke uh daddy yet and we literally start writing they write each one of those items that has their attention on a separate piece of paper and they toss that into their entry you'd be surprised by the way first of all how many people don't have an entry or if they do have one it's petrified because it's just been sitting there with you know crap in it for weeks we need to have some sort of clear space to just collect all that stuff to begin with that process tim takes you usually in my experience over all these years for the mid to senior level professional that we actually coach with this process it takes one to six hours just to capture what has their attention not to organize it not to prioritize it not to make decisions about it just to identify it yeah it's so impressive and horrifying at the same time and i was doing prep for this conversation i found one paragraph that struck me as important that's related to this i think in in some capacity this is from an older piece in wired but it reads as the following so at a seminar alan asked the audience to try to capture all their stuff by writing a list at the end of a few minutes tells us to look at the list and think about the way it makes us feel he guesses that our feelings include and feel free to fact check any of this by the way a mixture of grief and relief the relief he suggests comes from the simple fact of making the list but where does the grief come from and this is the quote that really caught my attention these items represent agreements you haven't kept with yourself alan says what happens when you break an agreement with someone with yourself is that your self-esteem plummets could you speak to this a bit because i would imagine a lot of folks would say i feel guilt perhaps about all the things i haven't done for myself or for other people but this grief and agreements that you haven't kept with yourself struck me as important at least got my attention could you speak to that well i'm going to reverse engineer it a little bit and come back to the fact that you're breaking of the agreement is because you're keeping track of it in your head and where you keep track of that has no sense of past or future so that part of you that little sublime part of you think you should be buying cat food 24 hours a day vice president 24 hours a day that's why it wakes you up at three o'clock in the morning oh shit cat food oh because that thing has no sense of past or future so because it doesn't you can't do more than one thing at a time and so there's a part of you that thinks you should be doing all of that all the time so talk about a ton of broken agreements yeah but you don't have to finish the thing to keep your agreement you do need to get it out of your head agreements and this is one of the things i learned back in their old personal growth days you know agreements there's an automatic price you pay when you break an agreement is you disintegrate trust either with other people or with yourself or both if you don't want to have a broken agreement you have three options one is don't make the agreement called no i'm not going to do that right move it to someday maybe or something keep the agreement go buy the cat food go hire the vp go finish the thing or most importantly for most people is renegotiate the agreement if i made an appointment you know today for instance tim as people may hear ambient noise out there there's construction going on if that was too loud i would probably have to try to renegotiate and reschedule this talk with you and then i don't have a broken agreement if i don't do it but you can only feel good about what you're not doing when you know what you're not doing so most people just have just made so many more agreements than they're aware of so all we do in our coaching is get people aware of what are all the agreements you've made what are all the would could should need to solve twos and that's one of the reasons people feel good when they make a list if they look at and go well gee i can't do all this right now no kidding right and so that's the it comes back to externalizing stuff out of your head that's why it's so critical to do that and most people i don't think have really understood or certainly managed themselves with an understanding of that dynamic many of you know that i've battled sleep for decades i've i've had onset insomnia i'm constantly hot because i'm a little meat cube and the list goes on but i've used eight sleep for many years now since the beginning and man it is a godsend people have experienced up to 34 percent more deep sleep and by people i mean customers hrv improvements of 13 on average they've transformed more than one million nights of sleep for their customers each sleep just released the pod six i'll explain what it is and it is a major upgrade but first things first right the pod is a cover that fits over your existing mattress kind of wraps it cools or heats each side of the bed independently as i mentioned i run super hot my lovely partner tends to run cold with the pod we each get the temperature we want and need for good sleep no more fighting over the thermostat no more pulling the blanket off putting the blanket on sticking one leg out all that nonsense fixes all of it now to the upgrades the pod six hub latest and greatest that runs the temperature system is 50 smaller than the pod 5 and fits under most bed frames the thermal engine reaches your set temperature 20 faster so the bed is ready whenever you are and the cover embeds nine times the number of biometric sensors tracking things like heart 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age you may be that age maintaining lean muscle becomes priority number one and ag1 pro is formulated to support exactly that it includes hmv a clinically studied compound that supports protein synthesis and helps reduce muscle breakdown plus zinc carnosine to support the gut lining so remember training is only half the equation you have to feed the machine and as you get older there's certain things that can help turn the dials just a bit in your favor recovery is where the work compounds and ag1 pro is built to support it it's nsf certified for sports so what's on the label is what's in the pouch get your free ag1 pro yeti shaker in the welcome kit at drinkag1.com tim that's drink ag1 the number one so d-r-i-n-k-a-g the number one dot com slash tim next up elizabeth gilbert when you do say an integrity check and i had read that when raya was sick for instance you began deleting or archiving emails without responding as a bit of a treat to yourself and not archiving okay deleting goodbye and when you say now check in with yourself and decide to say no to something let's just to make it easy or make it concrete via email you get an invitation from a friend you do actually really like with something that could plausibly advance your career or be fun but you check in with yourself and it's like no this isn't a yes how do you phrase your no's or declines do you have any particular go-to language that you like to use i just want to make sure everybody knows that this is not easy i don't want to have any illusions for anybody that this is simple and the closer the relationship the harder it is the closer and more intimately i'm involved with somebody the more stakes there are for me and the harder it is for me to tell the truth and that feels like it should be there's a paradox the people you love the most should be the people that you are able to be the most honest with well no because they're the people who you want to hurt the least that's that's where it's really really hard there's a couple layers of it right so i now treat my inbox like it's my home because i think it's an extension of my home so if somebody walks into my home uninvited and announces themselves and doesn't say how they got a key and asks for something, I delete that email. I'm just like, I didn't invite you in. There are proper channels, you know what they are. I don't know how you got my personal email and I just delete it. And if I feel a sense in my sternum of a sense of feeling like this person has taken a liberty, I don't believe that I owe them anything. I don't believe that I owe them anything any more than if I came down to my kitchen and saw people sitting at my table who I didn't know eating breakfast, I wouldn't believe that I owed them to make them a cup of coffee. I'd be like, get out of my house. You're not supposed to be here. I don't even think I owe them a polite response. I owe them nothing. I didn't ask you to come into my house. I don't owe you anything. So that's the easiest. Those are ones are easy. And I now treat myself to doing that. I mean, I do that every day. I clear my inbox out very quickly that way. I'm entertained when they come back later and they're like, just sort of. Circling back. And I'm like, yeah, just deleting you again. Circle back as many times as you want. You are not coming in. So that's simple. Just bumping this up because I know you. Yeah. I'm just bumping you back. And I'm just, it's like whack-a-moles. It's like, I can do this all day. Delete, delete, delete. If it's somebody who I care about, if it's something that I'm interested in, but I'm just not going to do it because I don't want to, I will write back and say, so much. I'm really honored that you invited me to this, but I'm not going to be able to do this at this time. And I don't feel the need to give a reason. I think a simple no is really, really good. And the reason sometimes the reason it's good not to give an explanation is that if that person is an expert manipulator, as many of us are, that explanation will not suffice. So it won't matter what you give as an explanation because they can come back and be like, well, we can do it by audio. You know, we can do, oh, well, we can do it a different weekend. Just no. And I learned a lot about this from my teacher, Byron Katie, who teaches an amazing thing called the school for the work. She's a whole nother, another being who's not, not at all living by the rules. Extra terrestrial, for sure. She is extra terrestrial. She is the only fully enlightened human being I can, I believe I have ever met. And as such, she does not have any trouble saying an honest yes and an honest no to people. And just to underscore that, because I did a, an in-person training with her. I mean, literally no hesitation, no struggle, no conflict. It's bizarre and just mesmerizing to watch. And she loves you. And she loves you. There's also no hostility. Somebody came up to her at an event, handed her a book that they'd written, which people do to me all the time too. So I really marveled at this. And they said, I wrote this and I want to share it with you. And she said, oh, sweetheart, I'm never going to read that. It's just true. I'm never going to read that. And I'm like, oh my God, I didn't know you could say that. Right. It's so, that's amazing. And she said it so lovingly, like, oh, oh no, I have no interest in reading that. So, so she teaches, I don't know if you did, when you took her training, did you do where she teaches a simple no? And she does the training on how to give a simple no. I don't think we actually spent much time on that. So I would love to hear you say more. We worked on the emotion. The emotional one pages and the turnarounds. We did a lot on the turnarounds, which is probably, we could do a whole episode just on that. But you look up Byrie Fady, she's amazing. And if you have the means, and if you have the chance to ever take her nine day school for the work, it's the most important thing I've ever done for myself. So say that quite simply. But she has a whole day in the nine day school for work, which is about the simple no. And the simple no is ways to say no. And it always begins with thank you. And there's never a but, because she feels that the word but is very cruel. And it's just an and. So it's thank you and no. And that's it. That's a simple no. And then if they come back, you can say, well, hold on, just to pause for a second. Is that literally the phrasing? Or is it just? Yeah. Thank you and no. Yeah, that's it. That's it. That's simple no. And it just, it still makes my stomach ache because I'm like, oh my God, you can't just do that. You've got to give, you've got to like do the dance. And she's like, you don't have to do the dance. And she's the one who taught me if the person is a good enough manipulator, it doesn't matter. It doesn't matter what you bring. They're going to manipulate it. And the beautiful thing about a simple no is that it gives, in the jujitsu game, it gives somebody no weapon that they can take and bring back at you. They can say, you're being incredibly selfish. And you can say, I hear that. And you might be right about that. That's another one. She always says, you might be right about that. You might be right about that. And no. And you just keep adding and no after the statements. But you know, I really, I need you to do this. I'm desperate. And you say, I see that. I see your desperation. And no. And one other thing she'll add is you can say, if I change my mind about this, I'll let you know. And no. And that's been a game changer for me. So I just did one last week. Somebody who I have a professional relationship said, I want you to do this one hour video interview to promote this thing that I'm doing. And old Liz would have thought I owe her that because she did this other thing for me that time. And I checked in with my inner compass and I was like, nothing in me wants to do this. And so I just wrote back to her. I said, I'm sorry. And I'm not going to be able to do this at this time. And she wrote back and pushed in and said, oh, let me clarify. I wasn't clear about why we need it. We really need it because right now it's really hard for us to sell things because we don't have because of COVID-19. And that's why we need it. And I wrote back and said, I hear you and I understand you and no. And it goes away. They don't tend to come back a third time. It really does just stop and let it sit at the no. The more words you add after that, the more entangled you get. But again, I want to make clear it's hardest closest to home and it's hardest with family. And with family, I find if I anticipate that I'm going to be asked something, I really have to practice because it's scary. And I have to really practice saying, I'm not doing that right now. I'm not coming this year. And I'll say it a thousand times. I'll just go for a long walk and I'll just practice it and practice. Because as I say, the closer the people are to you, the more difficult it is. Last but not least, Oliver Berkman. Hello, I'm Oliver Berkman. I'm the author of books, including 4,000 Weeks and Meditations for Mortals and the Imperfectionist Newsletter. So I have to answer this question about simplicity and simplifying my life, honestly, I think, and say that I have tried so many ways to simplify my life. I've tried so many ways to simplify my life. Only to discover that in subtle ways, they've actually had the opposite effect. So I'm going to tell you what has truly simplified my life in a moment, but I want to get there by way of explaining what I think the downside is with quite a lot of simplification advice. It's just that pretty much any system, as we all know, creates overheads to maintain. So it becomes all too easy for some supposedly pro-simplicity practice to make things more complicated. One random example I would like to share with you is when Barack Obama was running for president. Obviously, Barack Obama only wore, I think, two shades of suit in order to reduce decision fatigue. He didn't have to worry about what range of suits he was going to choose from so that he could make more important decisions later in the day. I always loved this example, but of course, Barack Obama was president and he had a team of people to keep his wardrobe of suits in perfect condition. Whereas for me, for most of us, a wardrobe full of clean iterations of a work uniform, making sure that I always had everything I needed in order to only make a small number of choices, that's actually going to be quite likely to add to my overheads. It might be a good idea for other reasons, but I'm going to have to think about it, going to have to put in the upfront work to setting it up, and then a lot of maintenance work to make sure that it's always ready. And actually, for me, it's probably easier and simpler to just look inside my wardrobe. So I'm going to have to think about it, and I'm going to have to pick something that's there and that's clean and that basically works. There are some other systems I can think of that are equally kind of great in a way, but I do question if they make life simpler. So for example, I try to nominate specific time boxes during the week for calls and doing podcasts and things in order to safeguard time for writing. This is often described as a way of simplifying your life, a decision filter. And it's true, it stops me having to think so much maybe about whether I can fit in another call outside of those predetermined boxes. But in fact, it actually makes for many more tough moments where I either have to tell someone no because I can't fit them in, or alternatively have that time where I'm thinking, well, is this an exception? This guy's quite a big deal. I should probably alter my rules to make time for him. So it doesn't actually end up simplifying my life to try to impose this alleged simplicity on it. You know, I think about the image of the obsessive minimalist in interior design who lives in a sort of perfectly simple apartment, all clean lines and stark bare surfaces. So that might be your idea of beauty, and that's fine. I think I can really see the appeal. But it's not actually very simple in the psychological sense of reducing the thought and cogitation and stress that has to go into keeping it that way. It's actually pretty high maintenance, which in the important sense here I think is the opposite of simple. So to stop being so negative and say something practical and positive instead, I think what all this is leading up to, and this is something that I've really taken from Zen Buddhism especially, is that I think true simplicity, the simplicity that actually practically helped me in life, is not a question of techniques. It is an attitude. It's a kind of a relationship between me and my reality. It's the kind of relationship in which I'm just not so attached and clinging to how things are in the external world, in which I can pass through my days less bothered by whether things are one way or another. So, you know, for example, it's less about keeping a really minimalist home and more about not being made anxious because the home is a bit messy, not feeling that I can't get down to work or to something else important until I've done every little bit of clearing up. It's less a case of not being able to get down to work or to something else important until I've done every little bit of clearing up. It's less a case of rigidly time-boxing my day in order to reduce interruptions, though again, I think that can have a role, and maybe more about being able more fluidly to drop back into work and to focus after an interruption has happened. I've seen this attitude described variously as entrusting everything to nature, entrusting everything to reality, letting go of the idea that reality needs me to help operate it, just sort of unclenching, withdrawing my claws from things and learning, as Krishnamurti put it rather wonderfully, to not mind what happens. I don't think that means to be a doormat or a pushover or to be passive, far from it, the opposite. I think it is to be able to say, okay, look, well, reality is as it is, and that's fine. I mean, it better be fine because it's the truth of the matter, and now I can just be okay with that situation, and take action, vigorous, bold action on the things I really want to do. So that is, after many learning experiences, what simplicity has come to mean for me. I hope it's useful. Thanks. People subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums, perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange, esoteric things end up in my field, and then I test them, and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to tim.blog/friday, type that into your browser, tim.blog/friday, drop in your email, and you'll get the very next one. Thanks for listening. This episode is brought to you by AG1, which I have taken for more than a year. I hope you enjoyed this episode, and I look forward to seeing you next time. Bye! I am a young 48 years old, and I've noticed that change. So past a certain age, you may be that age. Maintaining lean muscle becomes priority number one, and AG1 Pro is formulated to support exactly that. It includes HMB, a clinically studied compound that supports protein synthesis and helps reduce muscle breakdown, plus zinc carnosine to support the gut lining. So remember, training's only half the equation. You have to feed the machine, and as you get older, there's certain things that can help. Turn the dials just a bit in your favor. Recovery is where the work compounds, and AG1 Pro is built to support it. It's NSF-certified for sports, so what's on the label is what's in the pouch. Get your free AG1 Pro Yeti Shaker in the welcome kit at drinkag1.com/tim. That's drink, A-G, one, the number one. So D-R-I-N-K, A-G, the number one.com/tim. Many of you know that I've battled sleep for decades. I've had onset insomnia. I'm constantly hot because I'm a little meat cube, and the list goes on. But I've used Eight Sleep for many years now, since the beginning, and man, it is a godsend. People have experienced up to 34% more deep sleep. And by people, I mean customers. HRV improvements of 13% on average. They've transformed more than one million nights of sleep for their customers. Eight Sleep just released the Pod 6. I'll explain what it is, and it is a major upgrade. But first things first. The Pod is a cover that fits over your existing mattress, kind of wraps it, cools or heats each side of the bed independently. As I mentioned, I run super hot. My lovely partner tends to run cold. With the Pod, we each get the temperature we want and need for good sleep, no more fighting over the thermostat, no more pulling the blanket off, putting the blanket on, sticking one leg out, all that nonsense. It fixes all. Now to the upgrades. The Pod 6 Hub, the latest and greatest, that runs the temperature system is 50% smaller than the Pod 5 and fits under most bed frames. The thermal engine reaches your set temperature 20% faster so the bed is ready whenever you are. And the cover embeds nine times the number of biometric sensors, tracking things like heart rate, HRV, and sleep stages with no wearable. The Pod 6, check it out, starts at $1,999, the lowest starting price Eight Sleep has ever offered. Use code TIM at eightsleep.com/TIM for up to $200 off of the Pod 6. Spell it all out. 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Podcast Summary

Key Points:

  1. Chip Conley emphasizes mindful decoupling as a midlife practice to let go of identity and roles, creating space for transformation and new possibilities.
  2. He links simplification with deep personal experiences, such as near-death events and cancer diagnoses, which trigger a shift toward slowing down and embracing present-moment awareness.
  3. The "month I died" experiment involves a radical social eulogy retreat to confront mortality and prioritize meaningful connections over busy commitments.
  4. David Allen advocates capturing all attention-grabbing items in a physical list to externalize mental clutter, revealing broken self-agreements and helping people recognize what they’ve been avoiding.
  5. Elizabeth Gilbert promotes a simple "thank you and no" response to declining requests, especially from close relationships, to protect boundaries without guilt or manipulation.
  6. Oliver Berkman argues that true simplicity is an attitude—less about rigid systems and more about psychological detachment and fluidity in response to life’s unpredictability.
  7. The endowment effect is illustrated through personal stories, showing how ownership inflates perceived value and making it harder to let go of unused items or opportunities.
  8. The episode collectively demonstrates that simplification is a process of distillation, rooted in self-awareness, boundaries, and alignment with one’s core values.

Summary:

This episode explores how to simplify life through personal, practical insights from key figures. Chip Conley shares how life-altering experiences—like a near-death incident and cancer diagnosis—led him to embrace mindful decoupling, where he let go of identity and roles to foster personal growth. He introduces the "month I died" experiment, where he disconnects from technology and society to deliver social eulogies, reinforcing the importance of present-moment focus and emotional honesty.

David Allen emphasizes the value of externalizing mental clutter through physical lists to reveal unmet personal agreements and reduce internal stress. Elizabeth Gilbert advocates for a simple, boundary-setting "thank you and no" response to protect relationships and self-respect, especially in close connections. Oliver Berkman challenges common simplification techniques, arguing that true simplicity lies in an attitude of acceptance and detachment rather than rigid systems.

The endowment effect is illustrated through personal stories, showing how ownership distorts value and makes letting go difficult. Collectively, these perspectives highlight that simplification is not about reduction but about deepening self-awareness, creating space for authenticity, and aligning actions with core values—especially in midlife and in the face of uncertainty.

FAQs

Mindful decoupling is the intentional letting go of identities and roles you've relied on, such as being a founder or CEO, to allow for personal transformation. It creates space for new possibilities, especially in midlife, and helps reduce stress by shifting focus from past roles to emerging potential.

The endowment effect makes us value things more because we own them, even if they're unnecessary. To counter this, ask yourself: 'How much would I pay to obtain this if I didn't have it?' This reframing helps detach emotional value from ownership and leads to more rational decisions.

A simple no begins with 'Thank you and no,' without adding explanations or 'but' statements. This approach maintains boundaries without conflict, reduces manipulation, and helps preserve self-respect, especially when dealing with close relationships or high-stakes requests.

Chip Conley recommends taking a 'Sunday sabbatical' to disconnect from technology, meditate, and walk—activities that nurture creativity and mental clarity. He also plans a 'month I died' where he disconnects entirely, focuses on present-moment awareness, and gives social eulogies to loved ones.

True simplicity isn't about rigid systems or minimalism; it's an attitude of letting go of attachment to outcomes. It means being comfortable with imperfection, allowing interruptions, and focusing on action rather than control, which reduces mental stress and increases psychological freedom.

By reducing clutter in daily routines and mental load—such as through digital detoxes or focused time blocks—people create mental space for deeper thinking. This aligns with the idea that curiosity and creativity thrive in stillness and simplicity.

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