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

Tim Ferriss (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.

David Allen (1:08)

Optimal minimal.

SPEAKER_3 (1:09)

At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

Tim Ferriss (1:33)

First up, Chip Conley.

Chip Conley (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 hotel in the US. But in my late 40s, my life was really complicated. We were going through the dot-com bus to 9-11, 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 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 on to it at difficult time.

I made space in my life. And what I want to just 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 Bates and Margaret Mead's daughter would call the midlife atrium. So what we know about an atrium is in an atrium, 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 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.