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

Why does it matter? Because the simplest life you could live is probably more complicated than the one you already have.

Barack Obama's famous two-suit wardrobe — held up everywhere as the gold standard of decision minimalism — would make most people's lives harder, not easier. Oliver Burkeman points out the obvious: Obama had a team maintaining that wardrobe. Without one, you've just built a uniform-management system on top of everything else. That contradiction is the key. Simplicity is not a technique. It's an attitude.

• Any simplification system creates overhead to maintain — and that overhead often costs more than the original problem
• Your stale commitments feel valuable only because you already own them; the endowment effect keeps you chasing goals your past self wanted
• Every unprocessed task in your head is a 24-hour broken agreement running silently, eroding your self-esteem
• The cleanest "no" has no explanation — every word you add after it becomes a weapon you hand to the other side

Every system you build to fight complexity will eventually fight you back

The Obama suit story is a trap. Burkeman — author of Four Thousand Weeks — notes that Obama had a team maintaining that wardrobe. Without one, you've just added a uniform-management system to your existing cognitive load. "Pretty much any system, as we all know, creates overheads to maintain."

Time-boxing your calendar to protect writing time? In practice it generates decisions: is this person important enough to break the rule? The minimalist apartment — all clean lines, bare surfaces — is "actually pretty high maintenance, which in the important sense here, I think, is the opposite of simple."

His alternative isn't another system. "True simplicity, the simplicity that actually practically helped me in life, is not a question of technique. It is an attitude." Specifically, learning — as Krishnamurti put it — "to not mind what happens." Not passivity: unclenching enough from external conditions that you can take vigorous, bold action on what actually matters, rather than endlessly managing the environment.

The test for any new system: does its maintenance cost exceed the problem it solves? If yes, you've traded one kind of clutter for another.

You are probably pursuing at least one stormtrooper suit right now — a goal your past self wanted that your current self would never choose fresh

Greg McKeown stood in a Halloween store, fully dressed in a stormtrooper costume, and realized he'd been thinking about owning one for thirty years — because an older brother once offhandedly said it would be cool. He had no actual interest in it now. He just couldn't put down the idea.

That's the endowment effect: "we value things more because we have them." It's why nobody in the history of the world has ever washed a rental car — and why the career track, side project, or relationship dynamic you can't quite leave might be one of these suits. Goals a past self wanted, preserved by the texture of ownership.

McKeown's fix is one question: "if I did not own this item, how much would I pay to obtain it?" For commitments: if I didn't already have this, how hard would I fight to get it now? The question bypasses ownership inflation and forces a fresh evaluation.

Andy Grove ran the same test at Intel: if we weren't already in this business, would we enter it? The answer was sometimes no — and that clarity freed up everything. "Is that the stormtrooper that you're pursuing?"

Your to-do list anxiety isn't a character flaw — it's a structural problem with a structural fix

A part of your brain thinks you should be buying cat food 24 hours a day. David Allen's diagnosis is precise: the part of the mind that tracks open loops has no concept of past or future. Every uncaptured task lives in it as something you must be doing right now, continuously. Three in the morning: cat food. Cat food. Cat food.

The guilt that comes with a long to-do list isn't laziness. Allen reframes it as broken agreements with yourself. "What happens when you break an agreement with yourself is that your self-esteem plummets." The low-grade exhaustion and shame people carry around isn't a personality trait — it's the compounding cost of thousands of open loops.

The fix is structural, not motivational. Get every item out of your head and into an external system. Critically: "you don't have to finish the thing to keep your agreement. You do need to get it out of your head." Then renegotiate each item — cancel, defer, or commit. The relief doesn't come from doing more. It comes from stopping the loop.

Allen notes it takes mid-to-senior-level professionals one to six hours just to capture what has their attention — not to organize, prioritize, or decide, just to identify it. Making the list produces a mixture of grief and relief. The loop, finally, is closed.

Give a reason when you say no, and you hand the other person a weapon

Elizabeth Gilbert learned this from Byron Katie: someone offered Byron her own written book. Katie said, "Oh sweetheart, I'm never going to read that." No apology, no qualification, total warmth. Gilbert's reaction: "I didn't know you could say that."

The formula is exact. "It always begins with thank you. And there's never a, but." The complete sequence: "Thank you, and no." If pushed: "You might be right about that. And no." If pushed harder: "If I change my mind, I'll let you know. And no."

Stripping out the explanation is tactical, not cold. "If that person is an expert manipulator — as many of us are — that explanation will not suffice." Every word after the refusal opens a new angle: an offered workaround, a reframe, a guilt lever. The wordless no gives them nothing to grab.

Gilbert tested this on a professional contact who pushed twice, citing mounting need each time. She wrote back: "I hear you and I understand you and no." The third message never came. "The more words you add after that, more entangled you get."

The hardest version is with family. Gilbert practices the words on long walks before difficult conversations. The formula doesn't change. The preparation does.

Holding onto an identity past its expiry date is what makes a life complicated — not busyness

Chip Conley flatlined nine times in ninety minutes on stage in St. Louis — an allergic reaction to an antibiotic, 47 years old, 52 hotels, 3,500 employees, the second once-in-a-lifetime recession of the same decade. The near-death experience delivered one message. "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."

He sold the company at the bottom of the Great Recession, ended a relationship he was holding like a life preserver, and spent two years in a hammock. Thirty-six festivals in sixteen countries in a single year. "I don't know what I'm supposed to do next, but I know I'm not supposed to do this anymore."

Two years later, the founders of Airbnb called.

The name for what he entered: the chrysalis. "Between caterpillar and butterfly, there is a chrysalis. In the chrysalis, the transformation happens." Midlife is where the old identity has to dissolve before the new one can emerge — but most people rush through that dissolving, grabbing the next role immediately to fill the void. The uncomfortable not-yet-knowing isn't the problem. It's where growth actually lives.

Most people will say what they truly feel about someone exactly once — at the funeral, when it can no longer be heard

Chip Conley has stage 3 prostate cancer and is not willing to wait for that.

This February, he's hosting three social eulogies — small dinners in San Francisco, Santa Fe, and Baja where his closest people say to his face what they'd say if he were gone. "We do a very poor job of telling people how much we love them while they're living. I want to hear that while I'm still living."

He also has what he calls "holy urgency" — a sense of calling so sharp it tips into mania. "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." The flatline birds gave him the counter-instruction: "You can't see beauty in awe unless you slow down." He's trying to hold both at once — urgency and stillness, purpose and presence.

Stanford's Laura Carstensen has documented the dynamic: less perceived time left means sharper focus on what's important, greater happiness. The constraint doesn't diminish life. It focuses it.

The only simplification that sticks is the one urgency forces

The through-line across all six isn't technique — it's urgency forcing clarity. Conley's stage 3 cancer manufactures what most people never impose on themselves: the recognition that time is finite, which suddenly makes everything that doesn't matter easy to shed. You don't need a diagnosis to access that lens. The Stoics called it memento mori — not as a morbidity exercise, but as a simplification tool. Everything looks different when you stop pretending the default horizon is infinite. The question isn't how to simplify. It's how long you're willing to wait for urgency to do it for you.

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Topics: simplicity, productivity, identity, midlife transitions, decision-making, saying no, minimalism, endowment effect, GTD, life philosophy, mortality, mental clarity