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

Hello boys and girls, ladies and germs. I wanted a short, practical episode for those of us buried under complexity. So I asked past guests: what one to three decisions could make life dramatically simpler in 2026?

My God, I’m funny to ask; I’ve complicated my own life. But after I flatlined from an antibiotic reaction while running a fifty-two-hotel company, being founder and CEO mattered less than being well. I practiced mindful decoupling—not that Gwyneth thing. I sold the company, changed habits, friendships, and a relationship, and made room for an unfamiliar self.

That space led me to Airbnb at fifty-two. Now, with stage-three cancer, I feel holy urgency, which can tip manic. My work is turning it into magic: offline Sundays, walks, meditation, silent retreats, and a month nearly disappearing as Steve, my passport name. I’m holding social eulogies now: say the loving things before somebody’s gone. Knowledge accumulates; wisdom distills. That’s simplification.

Think of your closet: organized by decade, it can become a museum. The endowment effect makes us overvalue what’s ours—opportunities, ambitions, obligations. I tried on an expensive stormtrooper outfit and realized no present version of me wanted it. Ask: is this a stormtrooper opportunity, inherited from an old self?

Try this reversal: if I didn’t already own this, what would I pay or sacrifice to get it? Use it for a sweater, a job, or a business line.

With overwhelmed people, I don’t start with priorities. I start with an inbox—a physical place for everything demanding attention: cat food, a broken printer, a vacation, hiring a marketing VP. Your head has no calendar; get it out, then decline it, complete it, or renegotiate it.

Deleting. Goodbye. My inbox is part of my home. If a stranger barges in asking for something, I don’t owe them coffee—or a response. With family, lengthy reasons invite negotiation. My teacher Byron Katie’s version is: “Thank you. No.” No “but.”

Plenty of simplification systems create maintenance burdens. A pristine wardrobe or rigid call blocks can mean more setup and stress than adapting to the day. Real simplicity is an attitude: less clinging to how reality ought to be. Accept what’s here, then take the bold action that matters.