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The Tim Ferriss Show
#857: How to Simplify Your Life in 2026 — New Tips from Maria Popova, Morgan Housel, Cal Newport, Craig Mod, and Debbie Millman
00:42:54
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Hello boys and girls, ladies and germs, this is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show. I'm recording this intro on the road. I have a bunch of very unusual stops around the world that I'll fill you in on another time. But right now let's get down to brass tacks. We have a different format from my long form interviews. Many of us, and this includes me, sometimes feel like we're drowning in complexity. Whether that's inboxes, oh my God, another app, another this, another that, or decisions, decision fatigue. Perhaps you're even slipping in and out of overwhelm. It happens. Maybe you're over committed, you need to renegotiate. I have been there yet again. So I wanted to hit pause and ask a question. This was for me, but I thought it might also be helpful for many of you listening. What are one to three decisions that could dramatically simplify my life in 2026? How can I simplify, simplify, simplify. And to explore that, I invited five listener favorites, Maria Popova, Morgan Housel, Cal Newport, Craig Maud and Debbie Millman to chime in and to describe how they have simplified their lives. And you can find previous editions of this series people sharing their simplification strategies. For instance, Derek Sivers, Seth Godin, Martha Beck. That's 837 and if you like this, we'll keep doing it. I am using a lot of what has been shared and I'll continue to do that. So without further ado, please enjoy a few steps towards simplification.
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Optimal Minimal at this altitude I can run flat out for a half mile before my hands start shaking.
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Can I ask you a personal question?
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Now would have seen the perfect time.
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I'm a cybernetic organism, living tissue over a metal endoskeleton.
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Ferris Show.
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My name is Maria Popova and I am a writer. Here are two things I have done to Anneal my life. Simple, practical behavioral changes that have had profound existential benefits. The first is that at some point I realized I was giving my time to people I perfectly like. Respect can spend a passable hour with conversing about things of some interest. But it was always leaving me malnourished, wishing I had spent that hour writing or down a rabbit hole about the anatomy of the eye of the scallop or talking with one of my closest friends about her work on exoplanets. And so I adopted a kind of, I guess you could call it the cherish quotient. I decided to stop giving my time to people whose company and conversation I don't absolutely care. Cherish. Not just like or appreciate or admire or feel kinship with, but cherish. Because as Annie Dillard so memorably wrote, how we spend our days is of course how we spend our lives. And so every middling hour is a step toward a middling life. Life is wasted on the lukewarm. Anything you give your time and attention to should roil with the magma of yes. And the second thing is very kindred to the first. Some years ago I emailed a poet I know who is also an ordained Buddhist and got an autoresponse detailing her over commitment. And as I was reading it I got a text from a physicist friend with an elaborate breakdown of his travels and his relationship troubles to explain why it had taken him three days to get back to me. And I thought, holy stardust. Here are people of extraordinary intelligence, creativity, accomplishment and work ethic who think they are accountable to others for how they spend their time, which is the fulcrum of their life. And I thought how sad, how necessary that we train each other in a kind of basic faith that everyone is doing the best with the equation between the resources they have and which we tend to overestimate, and the demands their life places upon them, which we tend to underestimate because most of them are invisible to us. And so I stopped using autoresponders or apologizing for how long it takes me to return a text. Because the moment you begin apologizing for how you manage your time, you are essentially apologizing for your priorities, which means apologizing for your life.
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Hey Tim Ferriss listeners. Thanks for having me. My name is Morgan Housel I'm the author of three books, the Psychology of Money, Same as Ever, and the Art of Spending Money. And I want to share with you a couple of things that I've done in the last 10 or 20 years that I think had a big positive impact on my life that were both just around the philosophy of making everything as simple as I possibly could. And the first is how I invest and manage my own money. My entire net worth is a House, cash, Vanguard index funds and shares of Markel where I'm on the Board of Directors. It is hard to imagine a more simple investing asset allocation philosophy and I've done it for a few reasons. I think there are smart investors out there who have and will continue to to outperform the market and I know some of them and could invest with them. I'll tell you why I don't do it though. I think there is so much evidence throughout history that the fewer decisions you have to make as an investor, the better you're going to do over the course of your life. And so there may be, given years, maybe even given decades, when smart people ride a trend spot, an opportunity, of course that exists. But the fewer chances and opportunities and decisions that I have to make of what are the trends going to be? Who are the investors that I need to go with? When have they lost their touch and get out, the fewer of those decisions I have to make, the better. So much of the decisions that we make and the forecasts that we make in the economy and with investments are less about truly objective views of trends and where we think the world is going, and more to do with what we want to happen in the future. When you make a prediction about where the US Economy is going, where AI is going, whatever it might be, it's less about what you truly think is going to happen, given the evidence, and more about what you want to happen given the biases and the lens of your own history and your own life and your own incentives, that kind of thing. And nobody is immune to that. Everybody has that. The fewer decisions that I have to make and anyone can make, the better we're going to do as investors. I think that is true for 99.9% of people. The other reason I do it, and I think this gets lost, is there's a lot of evidence that how well you do over your lifetime as an investor has less to do with the returns that you earn in any given year or any given decade, and more, just how long can you do it for? If your goal is to not outperform your peers this quarter or this year, if your goal is to maximize wealth over the course of your life, pretty much the variable that matters more than anything is just how long you do it for. And I know that if I can be an average investor for an above average period of time, I'm going to outperform the huge, huge majority of investors. If I could be a Passive Investor for 50 years, you will probably, after taxes and fees, end up in the top, I don't know, 2 or 3% of investors, maybe the top 1% of investors, just by doing nothing. And maybe that last point is the most important. You're getting all this for doing nothing, for just sitting back and passively owning a slice of capitalism. How do you factor in that ease? And so if, like, let's take an active investor who is working 40, 50, 80 hours a week tracking markets and maybe they love it and they enjoy it, it's their hobby. But let's say they do that and they outperform me by 50 basis points per year, whatever it might be. How do you factor in the fact that I got my return for doing nothing and somebody else got it for lots and lots of work and stress and whatever it might be? And so I think when you put all that together, I want to minimize the biases that I and everybody has in the world. And I think if I can do that, I'll actually end up in the top 1% of investors over the course of my life. And I'll do it for virtually no effort. There's a psychological cost of putting up with the volatility. But I can spend the time that I would have spent trying to track the global economy and trends and use that time in my career, if that's outside of investing my family, my health, my hobbies, those kind of things. The second thing I've done has to do with my relationship with the news. And I would sum it up like this. I think a really good heuristic for your relationship with information is read more history and fewer forecasts. As simple as it gets. Now if you were to scroll most people's social media timeline if they're interested in the news, whether that is business news, economic news, political news, science news, whatever it might be, the vast majority of it is forward looking predictions. It's maybe here's what happened today and here's what that means is going to happen tomorrow. It's very predictive. And of course, if you're even a loose amateur student of history, you know how difficult the history of predictions are. It's just a very difficult thing to do. The world is so much more complex than we want to make it out to be. And so when we're trying to predict what's going to happen next, it's very, very difficult. A little side note because I just watched it and just finished it this week. If you watch or read the book, it's called 1122 63. It's a book written by Stephen King. Unbelievable book about a guy who basically finds a time machine and goes back in time to prevent JFK from being assassinated. And he does this, he goes back in time, he prevents it, he thinks he saved the world and there's going to be no Vietnam war and whatever. And then he comes back to the present day and realizes that because he screwed with a little bit of history in 1963, the present world completely fell to pieces. And so when he comes back in time, it's like a Mad Max scenario. And I think that general idea that trends are very, very difficult to extrapolate and to figure out what's going to happen in the future, particularly if we're talking about long periods of time, is very difficult. And so I don't spend a lot of time doing it or reading it. What I do want to spend a lot of time doing in my life is reading history. And I think if you immerse yourself in history, any kind of history, business history, political history, military history, whatever it might be, even if you're looking at just the last hundred years, just in your own country, you become familiar with a lot of the psychological trends that repeat and you see over and over and over again. And so if you spend time doing that, you understand how people are influenced by incentives, how whole cultures fall into traps of greed and fear and blindness to the problems that they're causing themselves and the problems they're causing them in the world. You become very familiar with big, broad trends. And once you become familiar with those and spend most of your time studying that stuff, your ability to filter the news, the current news, is much stronger. And you can read the news in a much more simplified manner. You can run through the headlines and very quickly tell, that headline's not important. I'm not going to care about that six months from now or a year from now. It's not important in the slightest. This thing about this new technology or whatever this might be, or this example in the news of people falling for the traps of greed and fear. That's pretty interesting. Let me read that and wrap my head around it. Contextualize within the big models that you've learned from history. I think it's made my relationship with the news simpler and healthier. And I think if you don't have those big trends of human behavior in your head that you learn from history, it's very easy to get stuck in these wormholes of reading the news of every headline seems like it's a disaster. And every headline seems like it's something you need to pay attention to that's going to change the rest of your life. And there's a great quote that I love from an author named Kelly Hayes. And she says, when you haven't engaged with history, everything feels unprecedented. I think that's a great way to summarize that. That's what I got for you. Thanks so much for listening, and thank you for Tim and the rest of his team for doing this.
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Hi, I'm Cal Newport. I'm a computer science professor and a technology theorist. I write and podcast about seeking depth in an increasingly distracted world. What I want to talk about here is simplifying. Now, I want to establish something right off the bat. The entire reason why I'm a professor and a writer for my job and not, say, like a technology executive or a startup founder who's made a bunch of money, is that my body cannot handle busyness. When I have too many things to do and my calendar is filled with appointment after appointment. This does not energize me. This does not excite me. I get anxious, I get stressed out. What I need in my life is autonomy and space to work on my own terms, to produce cool things over a long amount of times, not to do a lot of stuff in the short term. This has caused me to have to continually readjust what's going on in my life to make sure that this busyness does not get out of control. I have to continually simplify to keep my lifestyle something that I can actually tolerate. So I want to give you two examples about this from my actual life. The first has to do with the opportunities that I get offered because as a writer and a podcaster, I'm relatively successful at what I do. As the years have gone on and I've gotten better, so have the opportunities and offers that come my way. I'm talking about like traveling to really cool places, chances to hang out with famous, really interesting people, stupid amounts of money being thrown my way. I mean, I'm talking about like a two day trip that they're offering you healthily, more than, you know, my annual professor salary. What I've learned over the years is that I basically have to make no my default answer. Because here's the problem. If you try to put in a triage rule, here's how I evaluate if something is good enough for me to actually spend time doing it. I found that whatever rule I came up with, too many things actually satisfied that rule. There are too many good enough offers coming my way that I would end up becoming busy anyways. And I would go into a cycle where I'd be completely overloaded. I get anxious and resentful. And then in reaction, I'd angrily say no to everything else. And I would tell people they don't care, but I would tell them I am so busy, I can't possibly do this. Like they care, like they need to know why you can't do something. And then I would cycle down to doing nothing. Then I would cycle up to being too busy again and anxious and upset. And this was not healthy. So I realized no just has to be more or less my default answer to keep my life at the level of simplicity that I personally need to thrive. So now I basically, when it comes to these type of offers, I'm really only agreeing if it's something I can bring my family to, and it's basically funding a vacation that we want to do otherwise, or if it's something that's cool and super convenient. Now, here's the thing. In addition to, like, you know, missing out on money and contacts and book sales or whatever, I'm also clearly missing out on cool experiences by doing this. Like, I'll give you an example. For over a year, masterclass was asking me like, hey, will you do a masterclass? We think your topic is well matched to our audience. And my default answer was no. Like, that sounds like a hassle. And it would be cool, but I don't want hassle. No, no, no, no. But eventually we found a way to make it work. I mean, they were really accommodating. Like, look, we could just do this in dc. It's not going to be a big deal. I talked to some other people who had done masterclasses. I was like, you know what? Maybe I'll do this. This is convenient enough. And I did. You know what? It was really cool. They rented a house. They had a crew of 20 people. It was like a movie set where the only talent. And I'm putting ferocious air quotes around this was me. So you got to meet interesting people. The director had worked on a bunch of television shows. I know the makeup artist had just been working on Ryan Coogler, Sinners. The class which actually just came out is really good. I probably should have just done this originally. And who knows how many other things like this that are pretty cool that I'm missing out on. But here's the thing. I realized over time, that's okay. The goal with me simplifying the things I say yes to is not to try to avoid bad things. Not like, I need to get rid of these bad things out of my life so I can focus more on the things I really like. It's instead trying to hit an ideal lifestyle. And for me, my ideal lifestyle isn't too busy. All right, let me give you another example. This has to do with my academic life. This was a complicated one for me. I'm a computer scientist by training. I got my doctorate at mit. I worked under Nancy lynch in the theory of distributed systems group. I specialize in distributed algorithm theory with a focus on shared channels. And really my subspecialty, because you all care about this, is lower bounds for randomized algorithms, and that's what I do. And I was pretty good at that. And I became a professor at Georgetown to work on doing distributed algorithm theory, Supervising grad students, getting grants, writing papers, trying to win awards, etc. So this is what I did. I also was always a writer. I wrote my first book when I was an undergraduate, and so I sort of had writing going on, but it was on the side. And these weren't, at the time, major books. And it was just something I started as an undergraduate, as a grad student to make some extra money. And I kept going. These two worlds collided in 2016. This is right around the time I was about to go up for tenure as a professor, and I published my book Deep Work, which was actually my fifth book, because I started early. I published this book, Deep Work, and it did really well. I mean, it wasn't meant to be some major launch or whatever. It wasn't meant to be the big book of the year, but it's something about it hit a chord, and that book started to do really well. Like 2 million copies, 45 languages, type of. Well, that began to change things for me, especially as I kept writing books and I started podcasting. That part of my life shifted from being almost like a hobby to something that I was really well known for. And now I had two major lives going on at the same time. Wrangling my career as a writer, while also wrangling my career as a professor and a theoretician. And it was a lot to try to do both of these things because there's a lot of logistics and overhead involved with both of those worlds. There's a lot of work involved with both of those worlds. A lot of thinking goes into proving theorems, and a lot of thinking goes into trying to write a book. And you have to do these things at the same time. It also created really sort of schizophrenic experiences where you would go from a small computer science conference where you're essentially taking the super shuttle over to present the paper, and there's like 20 people there. And then you would fly to Malibu and a driver is taking you to your Oceanside suite where you've been, a handler brings you to stage to give this one hour talk. It really became this weird, mixed world, and it was too complicated. But I didn't know what to do. I Love being a professor, right? I've been in academia my entire life and I love writing. I just love thinking, like, what was I going to do here? And the key was simplify what's going on with unification. So the discovery I had is like, well, wait a second. This book I wrote, Deep Work, which is at its 10th year anniversary. That book was about technology disrupting our ability to work well and what you should do about it. My next book was called Digital Minimalism. That was about technology. My next book after that was called A World Without Email. That book was about technology. A lot of what I was doing on my podcast was technology. I started writing for the New Yorker. A lot of what I was covering for the New Yorker was technology. And then around this time, as if the point wasn't being made clear enough to me, the university where I work started a focus on digital ethics and they created the center for Digital Ethics and asked me to be involved. And I realized, wait a second, these aren't two different worlds. I'm a computer scientist and I'm writing about the impacts of the type of technologies that computer scientists create and what we should do about it. Oh, this is the same world. I could be an academic that focuses on technology and its impacts, the ethics of technology. And this is a more recent change I've made and it's brand new and I'm still trying to adjust to it. But at least for now, I have put a pause on doing distributed algorithm theory and supervising doctoral students working on distributed algorithm theory and going to distributed algorithm conferences and getting grants to fund students to work on distributed algorithm theory. I put a pause on that to say all of my effort is aimed at the same thing. Thinking and writing about technology and its impacts on humans, flourishing and depth and what we can do about it. And that simplified everything. That's a completely reasonable thing. I'm now a full professor, so I'm at a stage of my career where I have flexibility and I should be exploring other intellectual avenues now. My writing, my podcasting, my article writing, all of this is now unified towards a common topic. I simplified what was going on in my career. Now again, this involves cutting off options. It involves cutting off opportunities. It also means, you know, I could be doing one thing maybe even better. To me, the right way to think about simplifying is lifestyle design. I'm going to use Tim's word here, lifestyle design. You know, what conditions of your day to day existence are best for you? The conditions in which you, your, you as an individual are going to thrive and what your the whole game is designing a lifestyle that matches that. And for me that required a high level of simplicity. I needed autonomy and I needed a lack of busyness. And so I don't think about any of this in terms of what's being left on the table. I think about it in terms of like how much I get to enjoy my day to day life when I'm successful with these efforts. So I still struggle with this. I constantly have to cycle and resimplify. Sometimes I go too far. But it's something I think about a lot. It's probably something you should think about a lot as well.
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Just a quick thanks to our sponsors and we'll be right back to the show. As many of you know, for the last few years I've been sleeping on a midnight luxe mattress from today's sponsor, Helix Sleep. I also have one in the guest bedroom downstairs and feedback from friends has always been fantastic. It's something they comment on without any prompting from me whatsoever. I also recently had a chance to test the Helix Sunset Elite. The Sunset Elite delivers exceptional comfort while putting the right support in the right spots. It is made with five tailored foam layers including a base layer with full perimeter zoned lumbar support right where I need and middle layers with premium foam and microcoils that create a soft contouring feel. Helix offers a 100 night sleep trial, fast free shipping and a 15 year warranty. So check it all out. And now you can get 27% off anything on their website so site wide. So just go to helixsleep.com Tim one more time. Helixsleep.com Tim with Helix, better sleep starts now. Not to be a salty old dog, but in the early 2000s, back in the day when I was running my own e commerce business, the tools were atrocious. They tried hard, but man was it bad. You had to cobble all sorts of stuff together. I could only dream of a platform like Shopify. Shopify is the commerce platform behind millions of businesses around the world and now 10% of all e commerce in the US is on Shopify. Now back to the early 2000s, then nobody even thought of AI. Who could have predicted even in the last 24 months the magic that is now possible with AI? Shopify has been ahead of the curve and they are packed with helpful AI tools that will accelerate everything. Write product descriptions, page headlines, even enhance your product photography. Best of all, Shopify expertly handles everything from managing inventory to international shipping to processing returns and beyond. If you're ready to Sell. You're ready for Shopify. Sign up for your $1 per month trial and start selling today at shopify.com Tim one more time. That's shopify.com Tim in 2026, stop waiting and start selling with Shopify.
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Hi, I'm Craig Mod, writer, photographer and long haul walker who has lived most of his adult life in Japan. Actually pretty much all of it. My most recent book is called Things Become Other Things. It was published by Random House last year. I did a book before that called Kisa by Kisa. These are both books about huge walks across Japan. I've walked from Tokyo to Kyoto three times. I've walked the Ki Peninsula a bunch, the Hagiokan, the Rokuju, Ryukoi, Kaido, all sorts of different routes all over Japan and actually all over the world at large. But in Japan, I'm mostly looking at how the country is changing and just trying to understand things. So three decisions I've made to simplify my life. Number one, cutting out alcohol. Easily the lowest energy in biggest impact out simplification of my life has been to drop alcohol by the side of the road like a sack of dead cats. Stinky dead cats. I struggled mightily with alcohol abuse in my 20s and looking back, nothing made things more complicated than this very stupid, very destructive relationship between me and drinking. Everything I perceived as complex in my life, trying to figure out who I was believing in that person, that that person could even exist, wanting to find a strong, meaningful partnership, was made exponentially more complex by the presence of alcohol. If I could just go back and whisper in my 19 year old ears, hey dude, just don't drink. And if I could have followed that, a lot of things would have been simpler. Almost Nothing in my 20s was made better by alcohol. And now the big question is of course if you're struggling with alcohol is how do you cut the cord? That's the big conundrum with a habit, an addiction like that. And for me it was finding deep meaning in my work. It was also sort of about hitting rock bottom. That was definitely a catalyst. Waking up one night and just being like really feeling like I was at the bottom of a terrible well. But just being at the bottom of that well I don't think is enough to motivate you to really kick the habit. You need some kind of almost spiritual, higher power experience, I think to really get over an abusive relationship, I mean alcohol or otherwise. For me, that was my work. I was really lucky in the sense that I had this internal compass that I've Felt for my entire life that was drawing me towards a certain kind of work, the writing, the walking I started doing. And I could see, once I acknowledged that kind of higher power in the work, every drink I took, I saw and I felt in my bones as taking away from that work. And that alone was enough for me to be able to say no easily, consistently, and ultimately over the long haul. That was about 18 years ago that I really decided to, okay, let's cut this out. But I think if you don't have that purpose, it's almost impossible to cut the habit. The second big decision I made, or tiny decision or whatever to simplify my life is therapy. At the risk of sounding like a cliche, starting therapy in earnest almost nine years ago now, it was funny, it was about nine years after I quit drinking was one of the simplest decisions I've made. That's probably had one of the biggest impacts on my life. And in simplifying my life through clarification, I believe that's very difficult. To achieve simplicity in life and to feel purpose strongly and clearly with a muddled mind kind of makes sense. And the man who doesn't know who they are can't be expected to perform at the best or to simplify their life or to make the right decisions if purpose itself feels mystical and forever off on some impossibly elusive horizon. I find that therapy, when it's done really well, it cuts to the bone in a really clarifying, interesting way. It just calls out all the bullshit addled voices that you carry around in your head that you've probably been carrying around your whole life. And it just kind of calls bullshit on this, hey, okay, let's really figure out what this voice is saying. And most of the time, you realize that voice is responding to something that either hasn't been a part of your life ever or hasn't been a part of your life in, say, 30 years. In demystifying yourself and then thereby clarifying who it is you really are and why you are the way you are, you are, paradoxically, I find, more freer, less limited than ever. To use a dope metaphor, we're all swimming. Some of us are swimming in clearer waters than others. Fundamentally, you're not going to change the creature that you are in the water. But I do find that therapy cleans the waters quite a bit. And in those muddy waters, you just find yourself swimming in circles like an idiot. And I certainly found that to be the catalyst for reaching out nine years ago, and wanting to begin therapy in earnest was even Though I had achieved a certain amount of clarity and I felt a certain kind of purpose, I was still doing some dumb things in my life that felt just irreconcilable based on the purpose that I also felt. And so these sort of circles that I found myself moving in for certain aspects of my life, in order to demystify, to clarify them, I thought, okay, third party help is probably required. I don't think we can carry this weight on our own. And I did. And actually immediately I found within the first couple of weeks of therapy, this incredible sense of clarity and also this vision of a better version of myself, an even better version of myself that I felt like I could become. And every week in therapy, I find myself stepping up and becoming that person. And over time, it's not just been an hour of therapy a week, that becoming that person leaks out onto the sides of it. And I find that I'm more able to readily inhabit that version of myself that I want to be. So therapy just cleans the waters, clarifies things, simplifies all of that, the act of living. And it allows you to move forward in ways that I think would be impossible on your own. And those paths that you can move forward on are much simpler than the ones I found I was moving on without therapy. And then the third decision I've made to simplify my life has been to commit to craft. Almost nothing in my life has paid bigger dividends than stopping my waffling around trying to figure out if I was an artist or a musician or a technologist or a writer or programmer or publisher or photographer. No, I'm a writer. The end. And the more I've doubled down on that choice, that commitment to the craft of writing, the simpler my life has become and the more vast my connections to beautiful, inspiring people. Everyone that I have in my life, that I love and respect can be traced back almost one to one, to the commitment to the craft of writing and the act of writing itself and publishing, getting things out there in the world. The more I write and the more people I reach, I find the bigger the impact of not only my present writing, but also stuff I've written in the past. It sort of pays, compounding dividends. And the more all of that is happening, the more inspiring people enter my orbit. And when I say craft, committing to that craft of writing is not just dashing things off here and there. It is a full sort of almost maniacal pathological commitment where you'll spend weeks and months and years working on certain texts and it involves a lot of reading, editing, conversations, engagement with the world of literature as a whole. That's what it means in my mind to commit to craft. Because you're not just committing to hiding in a cave typing, you're engaging in the case of writing. In the case of writing that I like to do. Case of writing that moves me, that I feel most drawn to this literary nonfiction, literary fiction universe of writing in my mind. Look, I'm still a photographer and I love technology and following how it's changing the world and thinking about its impact on society. But these interests and identities that I've carried all throughout my life, to a certain degree or another, are all mediated now through writing. And instead of trying to be a jack of 50 trades, especially as I was in my teens and 20s, which I kind of had to be to a certain degree, I chose one trade to commit to, which is the craft of writing. That's it. I mean, of course friends and family are omnipresent big part of things. But the foundations that allow me to be present for them and to be the best version of myself for them and for everyone else out there lies in the three decisions that I've outlined here. They've made things simpler and goddamn, they've made things better.
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The Four Month Decision by Debbie Melman In 2016, I turned down a job offer to become the CEO of the company where I had been working for over 20 years. At the time, I was president of the firm. My partners and I had sold the company to Omnicom. In 2008. I had a five year earn out, which meant I was obligated to stay there through 2012. After that, I was free to leave. And that is exactly what I was planning to do. For years, I'd been fantasizing about a different life. A life with more writing and creativity, more teaching, more experiments. A life that felt simpler and less operational, less quarterly. But when the earn out ended, I didn't leave. I told myself at the time there were many reasons. Money, security, status, fear, power, identity. I acknowledged it was hard for me to walk away from something I had helped build. It was scary to leave a place where I could see the evidence of the biggest successes of my life all around me. And it was difficult to disentangle what I was running day to day from what I wanted to run towards. So I stayed. Three years went by, but by 2015, I finally mustered up the courage to make my move. It wasn't particularly dramatic. It really was just time. And then I was offered an even bigger job. My existing CEO, a man I worked with for the entirety of my 20 years at the firm, was looking to transition to chairman. And then he offered me his job. CEO, the chief Executive officer. On paper, it was extraordinary. I would be one of a small number of female CEOs within Omnicom. I would be one of the few openly LGBTQ leaders helming a branding consultancy. I would have full authority to shape the future of the agency I loved. It felt like an honor. It felt historic and powerful. But it also felt heavy. I told myself I should want it. It was the opportunity of a lifetime. I told myself that declining it might mean I lacked ambition or courage or vision. As I considered what to do, I wondered. If I turned it down, I would regret it forever. If I would disappoint people, if I would disappoint myself. And then I couldn't decide. For four months, I vacillated. I made spreadsheets and pro con lists. I sought advice. I talked to friends. I consulted with my mentors. And every time I tried to land on a yes, something in me resisted. And I continued to vacillate. One afternoon, after yet another conversation about my indecision, my very patient CEO said something to me that changed everything. He said, debbie, anything that takes you four months to decide might mean you really don't want to do it. And suddenly, it was as if someone had opened a window in a sealed room. I had been framing my decision as bravery versus fear, as ambition versus retreat, and as successful versus surrender. What if the four months weren't indecision, but rather clarity Trying to surface his sentence gave me the permission to admit what I didn't want and permission to prioritize alignment over advancement. And so I turned the CEO job down. I remember the moment distinctly, but it wasn't cinematic. There was no swelling music. There was no dramatic speech. But there was immediate, unmistakable relief. And yes, it was also bittersweet as I went through the realization that when you close one door, you're closing a version of yourself. But I have never once regretted it. Not once in the 10 years since I made the decision to step into the life I now lead. Turning down that job simplified my life in ways I couldn't have predicted. Instead of scaling an organization, I began expanding my ideas. I continued my writing and my podcast, taught more intentionally, and began taking my illustration work more seriously. And I invested in doing projects that felt like extensions of my values rather than my title or my portfolio. Something else happened, too. My ambition changed shape. For much of my career Ambition looked like a scent. More responsibility, more authority, more achievement, more recognition. Becoming CEO would have been impressive to who I was, but it would not have been aligned with who I wanted to be. There's a particular kind of simplicity that comes not from doing less, but from doing what feels really true. Simplicity isn't only about minimalism. I think it's also about coherence. I often think about how seductive power can be, especially for women, especially for queer people, especially for anyone who has had to fight for legitimacy. When an institution offers you the top seat at the table, it's heady, feels like validation. But validation is not the same thing as fulfillment. And power is not the same thing as purpose. Simplifying my life didn't mean shrinking it. What I wanted, though I didn't fully have the language for it at the time, was not more control. I wanted more freedom. That freedom has allowed me to build a very different kind of life. This meant removing the parts that no longer fit so that the parts that did could expand. And to me, that has been the greatest simplification of all.
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Hey guys, this is Tim again. Just one more thing before you take off, and that is five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between 1 and a half and 2 million 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. Not to be a salty old dog, but in the early 2000s, back in the day when I was running my own e commerce business, the tools were atrocious. They tried hard, but man, was it bad. You had to cobble all sorts of stuff together I could only dream of a platform like Shopify. Shopify is the commerce platform behind millions of businesses around the world and now 10% of all e commerce in the US is on Shopify. Now back to the early 2000s, then nobody even thought of AI. Who could have predicted, even in the last 24 months the magic that is now possible with AI? Shopify has been ahead of the curve and they are packed with helpful AI tools that will accelerate everything. Write product descriptions, page headlines, even enhance your product photography. Best of all, Shopify expertly handles everything from managing inventory to international shipping to processing returns and beyond. If you're ready to sell, you're ready for Shopify. Sign up for your $1 per month trial and start selling today at shopify.com/tim one more time. That's shopify.com Tim in 2026, stop waiting and start selling with Shopify. As many of you know, for the last few years I've been sleeping on a midnight luxe mattress from today's sponsor, Helix Sleep. I also have one in the guest bedroom downstairs and feedback from friends has always been fantastic. It's something they comment on without any prompting from me whatsoever. I also recently had a chance to test the Helix Sunset Elite. The Sunset Elite delivers exceptional comfort while putting the right support in the right spots. It is made with five tailored foam layers including a base layer with full perimeter zoned lumbar support right where I need it and middle layers with premium foam and microcoils that create a soft contouring feel. Helix offers a 100 night sleep trial, fast free shipping and a 15 year warranty so check it all out. And now you can get 27% off anything on their website so site wide so just go to helixsleep.com Tim one more time helixsleep.com Tim with Helix better sleep starts now.