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

The Tim Ferriss Show

This bite-sized episode features five podcast alumni sharing practical strategies for cutting through modern overwhelm and simplifying daily life. Chip Conley,

Key takeaways

• Chip Conley describes 'mindful decoupling' after a near-death experience and cancer diagnosis, explaining how he let go of his CEO identity to embrace midlife curiosity and now practices 'social eulogies' with close friends.
• Greg McKeown illustrates the endowment effect using his own 30-year pursuit of a stormtrooper costume, showing how we overvalue possessions or opportunities simply because we already own them or have invested time in them.

Main topics

• Midlife identity transition & mindful decoupling
• The endowment effect & letting go of outdated goals

Notable quotes

Wisdom is something you distill, you simplify.

Conclusion

The episode delivers actionable, psychologically grounded strategies fo

Transcript preview

Speaker 6 (0:00) 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. Speaker 4 (1:20) I'm a cybernetic organism living tissue over metal endoskeleton. Speaker 6 (1:32) First up, Chip Conley. Speaker 5 (1:36) 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 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 in 9-11, and then we were going through the Great Recession, and I didn't want to be doing this anymore. I ended up having an NDE, a near-death experience. And an 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. 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 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. You know, 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 it at 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 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 that an atrium is 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 52, 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 40s, 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 fun was 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 non-profit. 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 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 Speaker 6 (6:57) 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. Speaker 5 (7:05) 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. 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 actually be more magical in my approach to my calling, 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. You know, 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 password is Steve. And chip off the old block, I'm Steve Jr. 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 social eulogies. One in San Francisco, where 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 in 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. Speaker 5 (11:11) 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