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

Chip Conley begins by admitting that he is usually inclined to complicate his life, but says health crises forced him to simplify twice. In his late 40s, he was running Joie de Vivre, the boutique hotel company he founded in San Francisco, which had grown to 52 California hotels and 3,500 employees. After the dot-com bust, 9/11, and the Great Recession, he no longer wanted the life he had built. While giving a speech in St. Louis, he had an allergic reaction to an antibiotic, flatlined nine times over 90 minutes, and spent three days in the hospital. The experience made him realize that his founder-and-CEO identity and VIP status mattered less than his health. Conley calls the resulting process “mindful decoupling,” distinguishing it from Gwyneth Paltrow’s “conscious uncoupling.” He did not know what he would do next, but knew he could not continue doing what he was doing. He sold the company at the bottom of the recession, changed habits, ended a romantic relationship, and altered friendships. He describes the resulting period as a chrysalis or “midlife atrium,” a space with light and air in which something new can emerge. From ages 50 to 52, he read, explored hot springs, studied emotions, and eventually wrote the New York Times bestseller Emotional Equations. He also visited 36 festivals in 16 countries in one year, served as an early Burning Man board member, and brought Tim to his 50th birthday celebration at Burning Man.

Conley says the space created by simplifying eventually led to an invitation from Airbnb’s three founders, when the company was still little known. He joined at age 52 and spent seven and a half years helping turn the startup into what he calls the world’s most valuable hospitality company. For him, simplifying did not mean withdrawing permanently; it created the conditions for curiosity, pleasure, and a better opportunity to emerge. He then describes a more recent and more difficult simplification challenge. When he spoke with Tim in 2019, Conley had stage-one prostate cancer. Over the following seven and a half years, it progressed to stage two and then stage three. He feels a powerful calling to keep working while he does not know how much time remains, but calls the resulting intensity “holy urgency,” which can make him manic. His current task is to turn “manic” into “magic.” His practices include taking a Sunday sabbatical: going offline, meditating for longer periods, walking, and allowing his nervous system and creativity to recover. He also plans a February sabbatical called “the month I died.” He will use the name Steve, his legal first name, carry a burner phone, avoid email, keep nothing on his calendar, and largely disappear. Beforehand, he plans three “social eulogies” in San Francisco, Santa Fe, and Baja, where friends will give one another the eulogies they would otherwise hear only after death. Conley’s larger lesson is to combine slowing down with urgency, because slowing down helps him see beauty, have better conversations, and generate his best ideas.

Greg McKeown uses a closet to explain how people accumulate unnecessary physical and psychological clutter. Someone once told him her closet was organized by decade; McKeown replied that she did not have a closet but a museum. The same problem applies to the “closet of our lives”: people retain goals, opportunities, roles, and possessions simply because they already have them. He explains the endowment effect as the brain’s tendency to value something more because it is owned or has been endowed to us. This can be useful—for example, homeowners often care for their homes more than renters care for rental properties—but it becomes harmful when ownership causes us to retain something that is no longer useful. He illustrates the point with a stormtrooper costume. As a child, McKeown absorbed his older brother’s enthusiastic suggestion that owning a screen-quality Star Wars costume would be wonderful. Thirty years later, he found himself trying one on in a Halloween store and realized that no current part of him actually wanted it. His wife now asks whether a goal is “a stormtrooper” when he is pursuing it because he once wanted it rather than because it serves him now. McKeown recommends reversing the usual questions. Instead of asking how much he values something he owns, he asks how much he would pay to acquire it if he did not own it. For an opportunity, instead of asking how he would feel about missing it, he asks how much he would sacrifice to obtain it from scratch. The same test can be applied to a business: if the company were not already in a line of business, would it choose to enter it now?

David Allen says his first step with an overwhelmed but high-functioning person is not to explain a complicated productivity system. After establishing rapport and asking what the presenting issue is, he creates a physical “in-tray”—a clear place where material can be collected before decisions are made. He gives the person paper and a pen and asks, “What’s on your mind? What has your attention?” Items might include buying cat food, hiring a vice president of marketing, planning a vacation, replacing a broken phone, or fixing a printer. Each item goes on a separate sheet and into the in-tray. Allen says that simply capturing everything usually takes one to six hours for the mid- to senior-level professionals he coaches. This is not yet about organizing or prioritizing; it is about identifying the commitments competing for attention. Tim connects this to a passage in which Allen says that unfinished items represent “agreements you haven’t kept with yourself,” producing grief as well as relief. Allen explains that the problem is keeping those agreements in the head. The subconscious part tracking them has no meaningful sense of past or future, so it behaves as though the person should be buying cat food or hiring the VP twenty-four hours a day—and may wake the person at 3 a.m. to remind them. Allen says breaking an agreement automatically erodes trust with oneself, other people, or both. There are three ways to avoid a broken agreement: do not make it, keep it, or renegotiate it. A person does not have to finish every task to preserve trust, but must get the commitment out of their head and consciously decide what will happen. As he puts it, people can feel good about what they are not doing only when they know what they are not doing.

Elizabeth Gilbert says declining requests is difficult, especially when the person asking is close to her. The intimacy increases the stakes because she wants to hurt loved ones least, even though honesty should theoretically be easiest with people she loves. She now treats her inbox as an extension of her home. If strangers enter her home uninvited and ask for something, she does not owe them coffee or even a polite response; similarly, she deletes unsolicited emails when she feels the sender has taken an unauthorized liberty. She enjoys deleting repeated “just circling back” messages and compares the process to whack-a-mole. For an invitation from someone she likes or an opportunity she finds interesting but does not want to accept, Gilbert uses a short response: “Thank you 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.” She says an explanation is often counterproductive because a skilled manipulator can treat every reason as a problem to solve. She credits Byron Katie’s School for the Work with teaching her the “simple no,” which begins with “thank you,” contains no “but,” and can be as concise as “Thank you and no.” If someone pushes, Gilbert might say, “I hear that,” “I understand you,” or “You might be right about that,” followed by “and no.” She can also add, “If I change my mind about this, I’ll let you know.” She gives a recent example in which a professional contact asked for a one-hour promotional video. After the person explained that COVID-19 had made sales difficult, Gilbert replied, “I hear you and I understand you and no.” She says requests usually stop after that, but emphasizes that the practice is hardest with family; she often rehearses family-related refusals while walking.

Oliver Burkeman begins by challenging much conventional simplicity advice. He has tried many methods that were supposed to simplify life but instead created maintenance overhead. Barack Obama’s limited wardrobe illustrates the issue: wearing only two shades of suit may reduce decision fatigue for a president with staff maintaining the clothes, but for most people, keeping a full supply of clean, uniform outfits may create more work than simply choosing something clean from an ordinary wardrobe. Burkeman makes the same point about scheduling systems. He has tried reserving specific time blocks for calls, podcasts, and writing. Although this reduces some decisions, it creates new difficult moments: he must reject requests outside the blocks or decide whether an important person justifies breaking his own rule. A minimalist home can have the same hidden complexity. Keeping every surface stark and clear may require constant attention and can make a person anxious whenever the room is messy. His conclusion, influenced especially by Zen Buddhism, is that practical simplicity is not mainly a collection of techniques. It is an attitude toward reality: less attachment to how external circumstances must be, less anxiety when the home is messy, and less dependence on perfect systems before beginning important work. Instead of rigidly preventing interruptions, he tries to return fluidly to focus after they occur. Burkeman describes this as entrusting things to nature or reality, letting go of the idea that reality needs him to operate it, and “not minding what happens,” a phrase he attributes to Krishnamurti. This does not mean passivity; it means accepting what is true so he can take vigorous, bold action on what matters.