Please enjoy this transcript of a special episode of The Tim Ferriss Show, featuring four listener favorites—Anne Lamott, Claire Hughes Johnson, David Yarrow, and Diana Chapman—whom I invited to answer the question What are 1–3 decisions that could dramatically simplify my life in 2026?
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David Yarrow: My name is David Yarrow. I’m a British photographer that works principally in America. We sell our art through the fine art market around the world, but principally in America. I think the number one thing that I did to simplify my life was not to get remarried after I got divorced at a very young age of maybe 40 years old. My wife had given me the two most important things in my life, my two children. And it would’ve been easy at that stage of enormous self-doubt to jump into a new life with someone else and that could only have made life more complicated. I’ve got massive respect for people to choose to take that path. But for me, I had my family and I didn’t want it to get more complicated. I just hoped that the reasons why we’d separated would, over time, heal as we matured as individuals.
And that, luckily, is exactly what happened. And we’re far better friends. We spend a lot of our lives together now, and we often think about how different it would’ve been if we’d both gone and remarried and started new families. As it is, the four of us now spend an awful lot of time together as a unit. It’s abnormal, probably, for outsiders. But I think because we’ve been through pain and seen from the outside the issues that perhaps others can have when stepchildren are introduced into things, we recognize that it was right for us, not right for everyone, but it’s certainly allowed us both to focus on our jobs and the other parts of our lives without the stress and complications of complicated families. I think complicated families can lead to complicated lives. And I think if you’re single, but you have the mother of your children as close to you as you possibly can, it does allow you to be not selfish, but self-indulgent and appreciative of your goals. And I think it’s led to a far stronger relationship with my children than otherwise would be the case. And if you have a strong relationship with your children, I think it makes it much easier to be productive in other parts of your life.
That is not to preach to anyone else. I’ve made more mistakes than most people, but I do know that the simplification of my life born out of the decision not to seek comfort in a second marriage was key to the happiness in my life.
I think another tenet of the simplification of my life, which has been very, very necessary, is to have a perpetual filter in my address book. And specifically in terms of the number of close friends that someone in the late summer of their life can have. And when I was young, I used to believe that it was an asset to have 60 or 70 people that you could call close friends.
I think that’s impossible. It’s almost an oxymoron to say you can have 60 close friends. I think that principle holds true at 30 close friends or 20. I think I probably have now outside my immediate family, seven or eight people that I’d consider very close to. I had a bereavement in the family recently and with my brother, and ultimately, I didn’t want to speak to too many people. It was too emotional. And I just spoke to the people that I was closest to.
I’m a person that likes to give energy to any relationship, and I think energy is a luxury brand. And like any luxury brand, it’s got to be fairly elusive at times. You need to invest in yourself. And I’ve been very guilty of investing too much in people that perhaps don’t deserve it or won’t reciprocate it. That’s not to be mean, it’s just common sense.
I think in business as well, a corollary of this is I don’t have an agent. I’ve never had an agent. I know there’s very good agents in the world that earn every penny, but I found a lot of them to be slightly financially thirsty and slightly goal hungry when it comes to taking the acclaim. And the lack of an agent has meant that there’s been a lot of direct contact one-to-one with me. Will you do this? Will you do that? And the ability to say no comes with age. I think I was far too willing to say yes to things where every sinew of common sense suggested that was a suboptimal use of time. I think the idea of going out seven nights a week is totally exhausting and it impinges on the two nights where you do have to give good energy. I don’t think I’ll reverse this trend. I might end up with no friends, but I think having 10 friends is the right number for me and it has ultimately simplified my life.
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Claire Hughes Johnson: Hello, Claire Hughes Johnson here. I’ve spent over 20 years scaling tech companies first at Google, and then as the Chief Operating Officer of Stripe for many years. And I guess I’m best known for writing a book called Scaling People: Tactics for Management and Company Building, and that is how I met Tim.
I’ll be honest, I’m surprised Tim asked me to talk about simplifying my life because that is not something that I think I’m particularly good at. In fact, I think in my interview with Tim, he ended up advising me, and I think the advice he shared was there’s a point in your career when you switch from default yes, which is a great position when you’re trying to meet people and learn new things and build your connections and your network and your career, to default no. And that was one of my big lessons from our conversation. But with that, maybe not confidence-inspiring introduction, I’ll share some thoughts on simplifying my life.
I think the first, actually, thought for me is I needed to understand why I said yes to too many things. And that involved doing some introspection and some work, and yes, getting some help in talk therapy, which is not something I’ve had a lot of success with. But for some reason, I feel like I need to be needed, and that I earn love and affection by saying yes and being of use to people as opposed to just being me. And I’m still working on that. So that’s number one to simplifying your life is why is your life complicated? And mine has always been complicated because I say yes to too many things.
All right. So second lesson is, I think I mostly borrowed this from Arthur Brooks’ book From Strength to Strength, but you’ll find it in a few different “prioritize your life” advice books. And that is, I think we sometimes get too oriented toward tasks, jobs, things we need to do with our time. And if you flip it and think about people, it’s easier to see your priorities. Who are the people that I most want to spend time with? The easiest one for me is my children.
But instead of thinking, well, I want to do this thing, like go see this soccer game or go to my friend’s book event, I think, well, who’s the person involved? And I start the year with who are the most important people in my life to spend time with. And if it’s one of the people on that list, I’m going to say yes, and it doesn’t matter what we’re doing. It’s helped me to make sure I’m spending time with the most important people. It’s really easy now when someone asks me to do something that compromises time with my children, I just say no, because they’re the most important. I left an event today early to come home to have dinner with my son. So that’s the people flip.
When I do say yes, I’ll also mention that I’ve learned to be better about understanding, okay, why did I say yes? What’s my goal? What’s my job at this thing that I said yes to? And sometimes you get into a situation, you think, well, I should be networking, I should be meeting people, but maybe I just went to give a talk and I’m going to give a talk and then I’m going to leave. Or I went to meet just one person who I wanted to catch up with and I go and spend time with them and then I can leave. But keeping your eyes on your mission for how you’re spending your time can help not feel so guilty about not doing the other things that might be in front of you with your yes.
The final way that I’ve simplified my life is I’ve built some things into my, again, my calendar and my time, that I think people think of as extracurricular that I’ve realized are just too important to skip. The most notable of those is time to exercise. I am not a big athlete. I wasn’t a super successful athlete in high school. I worked out a little bit in college, but I came to understand that exercise is important to my mental health, and just feeling good in my body and being a confident person and a well-balanced leader, getting sleep is also very important to me and my success.
And once I realized that I wasn’t as effective, certainly when I started at Stripe, I was compromising on sleep, I was compromising on exercise. I didn’t compromise on having dinner with my kids most nights when I wasn’t traveling, but I was compromising myself. And I had this realization that to be the best leader, I needed more sleep and more exercise, and I made it part of my job. And I told Stripe CEO and founder Patrick that I was going to embark on a retention exercise, meaning retain myself at the company, and that meant I was going to come in a little late one or two mornings, leave early one day, and I booked time with a friend to work out. And I just, instead of just doing it on the weekends, I made time during the week to get enough exercise. And I also started to have rules for myself about when I would shut the laptop and get to bed, and that probably did retain me for a few more years. I guess I still work part-time at Stripe, so maybe it’s a long-term retention.
Nobody knows, you don’t know what that thing is for other people, but if you think about if your energy is these scales and on balance — am I getting energy from how I’m spending my life or is it being taken away? Try to measure what it is. It might be spending time with an elderly parent, it might be time with your kids, it might be exercise.
It might be having a deep conversation with someone once a week about a topic that’s not your work. But look for what those things are and track them and then make sure you’re booking time for those things into your calendar as if it’s a job. And don’t be apologetic. Don’t compromise that thing unless it’s an emergency. Really don’t compromise it and book around it. And I think the people who know me really well are surprised at how much I prioritize getting a workout done. And I no longer feel guilty about that. I feel really good that I’ve decided this thing is important to how I live my life and it’s not negotiable.
***
Diana Chapman: Hi, there. This is Diana Chapman, and I am passionate about Conscious Leadership. I’ve spent the last 20 years disrupting many influential leaders around the globe, teaching them that the thing standing between them and their next level of impact is usually themselves and most often their fears.
So I’ve been asked to talk about decisions I’ve made that have helped simplify my life. And one of the key things I’ve learned is that simple happens when your inner and outer worlds are in agreement.
I call that “a whole body yes,” that every part of me is in alignment inside with what is happening outside. I am congruent. And when that happens, so much complexity drops away.
I’m excited to share these three decisions I’ve made. And the first one is, I made a decision a decade ago that I would no longer live in any obligation. And what that means is I don’t live any more from a should — I should do this; I should do that — because that’s what a good daughter or a good partner or parent or friend does. Instead, I deeply listen. Is this what wants to happen? Would this serve me and them and my aliveness and the world as a whole? So now my choices come from a deep place of trust and no longer from the fear of disappointing people or breaking habits that you’re supposed to do.
I do want to clarify one thing here. Some people ask, “Does that mean you love all the activities you are a part of with the people you do them with?” And the answer is no. My husband might ask me to go to a concert of one of his favorite musicians, and I might not love that music, but what I would really enjoy is being with him, celebrating one of his favorite musicians, and being in all that joy with the crowd. That I have a whole body yes to, and so I go free of obligation. My inner and outer worlds are in agreement.
The second decision I made, and this is a biggie, is that I decided that I wanted to create a relationship contract with every person I spend any meaningful amount of time with in my life. It’s very similar to if I asked someone to come play a game with me and I’d say, “Hey, here are the rules of the game, and I want to ask if, based on those rules, you’d be willing to play with me.” And the value of all of us agreeing to a set of rules is that we have so little drama playing the game.
And so I use that same concept with all of my close relationships and I ask all of them, “Would you join me in a way of doing relationship?” I use the 15 Commitments of Conscious Leadership, which is based on the book of the same name I co-authored. And these commitments I brought to the business world, but they originally were in my personal life and I started them in my relationship with my husband. And these commitments are ways we agree to do life and then we make clear agreements with each other around how to do those.
So for example, in all of my close relationships, I make an agreement with everyone that we don’t blame each other, that instead we each take a look at how we are co-creating whatever it is we would like to change. That way, we’re in a constant state of learning and growing and no blaming. Gosh, that ends so much drama, and low drama makes a very simple life.
When my family and I agreed that we would end blaming in our home, we literally put signs up around in different rooms with the word “blame” with a circle around it and an X through it. So when anybody blamed, any one of us could point to one of the signs and say, “Reminder, you’re in a no blame zone.” And then the agreement was, rather than blame, we would take responsibility for how we were co-creating the thing that we were complaining about and teach a class.
So an example might look like I blame my family for making a mess in the kitchen and instead I say, “I want to take responsibility. I don’t have clear agreements with you guys about how we keep the kitchen clean, and so I’m co-creating a messy kitchen, so I don’t want to blame anymore. I want to take responsibility for how I have a part to play in this, and rather than blame, I want to clean it up and in this case make some clear agreements so we can permanently end this pattern that recycles over and over again.”
I had a client who called and was frustrated because his CEO, who he reported to as the COO, was not giving him the feedback he wanted for his professional development. He was blaming. So I said, “Hey, remember we’ve committed to no blame, so now teach me the class. I too want to have my CEO not give me the feedback I want for my professional development, so teach me how do you make sure you don’t get the feedback you want?”
So my client thought for a moment and said, “Okay, here’s some ideas. Here’s how I do it. Step one, when the CEO cancels one-on-one meetings on a regular basis, don’t complain about it, don’t ask them to get rescheduled, and assume other things are more important than you. Two, don’t ask for feedback. Just sit around waiting feeling entitled, but don’t clarify that it’s important to you. Three, when feedback occasionally does come, don’t appreciate it, don’t value it. Instead, in your own mind, dismiss that it’s not particularly valuable feedback, and therefore don’t encourage the person to give you more of it.” So, I said, “Great. If I did those three steps already, I would probably create the exact same issue that you have.” Then my client agreed to go back to the CEO and say to him, “Hey, I want to take responsibility for how I’m not getting the feedback I want.” And he taught the class to his colleague. That’s how it’s played.
Another thing we agree to is to stay deeply in curiosity and not get caught up in being righteous with one another. And if we do notice righteousness, we just gently invite each other to see that in the game we’re playing, that’s considered a, quote, foul and we recommit to coming back to curiosity.
We also make agreements about letting it be okay to feel our feelings and let the other one have their feelings. A lot of drama comes because we’re trying to control each other’s feelings.
When my son was applying to colleges, he really wanted to go to Berkeley. And the letter came and he and my husband and I were sitting together in a room, and he was rejected. And in that moment he started to cry. And I jumped in and started to say, “It’s fine. It’s fine. You’re going to UCLA. That’s such a great school too.” And my husband interrupted and said, “Sweetheart, let him feel his feelings.” And so, my son let a few tears come through so he could let go of the vision he had of going to Berkeley. Once he did that, which only took about 30 seconds, he was then able to open up and be excited about the opportunity to go to UCLA. I’m so grateful that my husband called out the pattern of how I was trying to control my son’s feelings, really, so that I could control my own. So he asked both my son and me to feel our feelings.
We also make an agreement that we reveal to one another any thoughts we’ve had three or more times so we don’t withhold, because when you withhold, you withdraw, and when you withdraw, things get complex. And then of course, gossip can get started and then you really get complex.
We also agree that we do our best to keep our agreements. We only make agreements that we’re really willing to honor and we do our best to do what we say we’re going to do.
Another one of my favorite agreements is to play with things when they start to get serious. That’s one of my favorite ones to do with the people around me who are willing to do that because, my goodness, can we move through a lot of complexity quickly if we can play. 40 percent faster, it says that kids learn when they’re playing and I think probably the same thing is true for adults.
I’m really lucky that I have so many people that will play with me when things get serious. My friend Grace is one of them. And one day I get a phone call, and I pick up the phone, and on the other end there’s this very playful voice in a Southern accent, and it said, “Hi, my name is Grace Anne. Is this Diana?” And I said, “Yes, it is.” “Well, Diana, I want to let you know Grace, I’ve learned, is real hurt by something you said the other day. Now, she’s not going to call you and tell you that, she’s kind of prideful, but I’m calling, because I thought maybe you’d like to know and give you a little hint about that.” And I said, “Well, Grace Anne, thank you so much. I’m really grateful.” And she said, “You are welcome.” And she hung up.
So, of course, I picked the phone back up and called Grace. And I said, “Hey, Grace, I want to let you know that I have a sense that you might have been hurt by something I said the other day.” And she said, “Yeah, you know, actually, I was.” And we got to have a conversation about it and move through it and come out on the other end close and connected. And I so appreciated that she didn’t know how to reach out, but through play, she was able to learn — and so was I — how to come back into connection.
A third decision that I made in my life occurred at a time where I was working really hard, more hours than I ought to, because it was compromising my health and wellbeing, which has its own kind of complexity. At that time, I believe that the overwhelm came because I really wanted to be right in a story I had that my work in the world really mattered. And because it really mattered, I had to push myself and drive myself, and that wasn’t working.
So I came to a decision in which I wanted to hold two truths equally, and the two truths for me are my work does really matter. The values I hold, the intentions I have, where I place my attention, all of these have impact on others, and that really matters. At the same time, I choose to hold the belief equally that my work does not matter, that the world would be just fine if I was no longer here. This is a wonderfully brilliant, intelligent world, and it can figure itself out without me.
And holding these two truths together offers me the opportunity to live in congruence, listening to what is mine to do, what is not mine to do. How do I do it in a way that is sustainable? Because living unsustainably creates a tremendous amount of complexity, and it’s the kind of complexity I don’t want to live with any longer.
It is my great hope that some of these ideas inspire some of you and that in trying them on for yourself, you discover there is real liberation and aliveness and joy in the experience of having your inner and outer worlds in agreement. I am wishing you all so very well. Cheers to being human. It is not for the faint of heart. And if we can make it a little simpler, amen.
***
Anne Lamott: Hi, my name is Anne Lamott. I’m the author of 21 books. The last one was called Good Writing, which I wrote with my husband, Neal Allen. At the age of 60, 12 years ago, I woke up feeling a heaviness on my chest, a cellular understanding of how much I had been carrying all these decades that were things my parents had told me about myself that were simply not true.
My parents were very progressive, but they started seeing me for my achievements at five or six, instead of for the goofy, loving being that we are all underneath the surface. When I decided on the right to be who I truly was, instead of the person I had always agreed and striven to be, i.e., highly successful, endlessly charming, life got a lot more simple.
I had to do the deep dive into the belief that I needed people’s respect and affection to feel of value, to feel that I was a valuable human being. Once I realized that this feeling wasn’t out there, but that it was rather going to be an inside job, my life got much quieter, and I could slow down and actually live it, savor it, breathe it in. Reclaiming the goofball inside helped me reclaim curiosity, which they had stopped grading for by about first grade, and this made everything so much simpler. I no longer had to keep the same six plates spinning in the air so people would think I was fabulous. I discovered that I didn’t have to keep trying so hard all the time in every way.
My Diocesan priest friend, Terry Richey, once told me that the point is not to try harder but to resist less. Hearing this instantly simplified life for me, seeing the folly of the endless trying to achieve, to improve, to impress, whatever, helped me find my way back each day and in every way to one simple thing I wanted to bring my focus and best self to. I was no longer in the frantic, striving, complex world of needing people to validate my parking ticket, because I was affirming my own worth. I could breathe again, and there is no more simple, profound, enriching change we can make than learning to breathe again. To really breathe gives us an umbilical connection to life, to the universe, our own hearts, and our deepest selves.
Two meditation techniques helped me learn to breathe with consciousness. One was simply to put my hand on my belly and inhale slowly all the way down until I could see my hand rise. I ask you, is there anything more simple than breathing into your hand and watching your tummy go up and down, expand and contract?
The other technique was something I learned from Ram Dass, who taught that we could imagine our hearts as having nostrils and experience expanding our heart in this way. The heart is our spiritual core, and it feels just wonderful to make it bigger.
60 was a significant birthday, because I realized I was starting the third third of my life. Many people I loved deeply had died, and I truly got on a cellular level that we’re all on borrowed time, and it’s good to remind oneself of that. It makes life so much more simple when we stop hitting the snooze button and start being more intentional about how we spend our days and our life force.
I felt like I had been flying around in the little plane of me with all the tense little boxes of no longer meaningful stuff that was so hard to let go of, but that it was keeping me flying too low, metaphorically. So, with the help of wise teachers, I started tossing it out of the airplane and I felt myself begin to rise. Simplicity in life is related to creating spaciousness and greater weightlessness, reclaiming curiosity and spaced outedness, which brings us back into the present moment, the momentous moment, which is home.
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